Welcome back to Career Field Guide: weekly career advice for early-career professionals learning how work really works in the age of AI. If someone forwarded this to you, subscribe here.

This is Part 6 of 10 in the Essential Skills Series: the 10 skills that separate people who advance from people who plateau. Start from the beginning here.

Subscribe now

Writing clearly at work is about helping the reader know what to do next.

A professor reads your whole essay because it’s their job, but at work you’re lucky to get two minutes of someone’s real attention. People scan, so you have to get to the point:

• What happened?

• Why does it matter?

• What do you need from me?

Miss any of these and you’ve handed your work to the reader. Now they have to decode your message before they can do their own job.

Writing Is How Thinking Gets Tested

In the age of AI, anyone can generate a 500-word email in seconds. Because AI has made writing effortless, the market is flooded with long, generic text. Your competitive advantage is no longer just producing words; it’s editing them down to the precise core of what your reader needs to know.

Amazon famously replaced slide decks with written memos in its leadership meetings, a shift Jeff Bezos pushed in 2004 because a narrative forces you to think in complete sentences instead of hiding behind bullets.

I remember the intensity of leading my first doc review at Amazon, sitting in silence while the team read six pages I had written and marked them up in real time. It was punishing to watch my ideas get challenged line by line, but it taught me a critical lesson: writing exposes unclear thinking.

The other lesson from that room was that good workplace writing starts with the reader, not the writer. Before you write anything important, match your message to three things:

1. Audience

2. Moment

3. Action

1. Audience: Who Is Reading This?

You need to understand the altitude of the reader:

• An executive needs the point.

• Your manager often needs to know where you're stuck.

• A new teammate might need you to show them what good looks like.

If I’m writing to an executive, I start with the answer.

Recommendation: delay launch by two weeks to reduce customer risk.

Then I frame the tradeoff:

The issue is not product readiness. It is support coverage. We can launch on time, but the customer experience risk is higher than the schedule risk.

If I’m writing to a peer, I give a little more context.

Can you review slides 4 to 6 by Friday at noon PT? I only need a check on customer accuracy, not design or wording.

If I’m writing to someone junior, I give them the why.

Can you pull three examples of competitor onboarding flows by Friday? The goal is to compare where our sign-up process feels slower. Good output would be screenshots plus 2 to 3 bullets on what each company does well.

Same underlying request, three different altitudes. Writing for the reader is just respecting what that person needs in order to understand and act.

2. Moment: What Does the Situation Require?

Some moments need speed, some need diplomacy, some need a sharper point to cut through the noise.

Picking the right channel is most of the battle:

• Slack when the work needs speed.

• Email when the work needs alignment or a record.

• Docs when ideas need critique or testing.

• Meetings when the team is stuck and the email thread keeps growing.

Channel is also culture, and culture is not the same everywhere. At Amazon, it was considered fine, even expected, to stand up and leave a meeting the moment you were no longer giving or getting value. At Microsoft, doing the same thing could land you in hot water. Communicating well includes reading the company you’re in, not just the message you’re sending. No matter the culture, reading the moment means matching your length and format to the urgency of the situation.

A few habits that have saved me grief:

• Don’t add another email to your boss’s inbox when a quick Slack or a walk to their desk would do.

• Don’t use Slack for something that needs ten rounds of back and forth. Call them or grab fifteen minutes.

• Don’t write a novel or hedge your idea when the reader is asking for a clear yes or no.

• Don’t ask for “thoughts” when you actually need a decision, or worse, when you’ve already decided and are really just informing them.

And please, for everyone’s sanity, stop burying the point of your message under polite filler. “Hope you had a great weekend!” does not need to precede an Asana update. Your coworkers already know you’re friendly. Get to the point.

Subscribe now

3. Action: What Should Happen Next?

Before you write, ask what result you want from the message. Most people feel stressed, fire something off, and ask for vague support without ever deciding what they need from the reader.

These messages tend to go out late on a Friday and end with something like:

• Thoughts?

• Wanted to flag.

• Just putting this on your radar.

Respect your reader enough to know what you want to happen as a result of your message:

• Do you need them to make a decision?

• Are you asking for a review, or just making them aware?

• Do you need a reply by a certain time?

Using precise words so the ask is unmistakable will 10x the impact of your writing.

Another useful phrase at work: no action needed from you yet. Telling people whether they need to act, and when, is half of clear communication, because it lets a busy reader file your message correctly instead of guessing.

Good Writing in Practice

Asking your manager for a decision

Bad:

Hey Boss, just wanted to send over some thoughts on the client issue. There are a few things going on and I’m not totally sure what the best path is, but I wanted to get your thoughts when you have a chance.

Better:

The client is struggling with the new strategy material we presented Friday, especially slides 4-6 (deck attached). We may need to adjust the plan. Can you take a look and let me know?

Best:

We need to decide by Thursday whether to keep the launch plan we showed the client Friday (deck attached) or adjust it based on their feedback (latest email attached). My recommendation is to adjust and incorporate X and Y, which keeps us responsive to their feedback while protecting our new IP. Can you approve the revised plan by 3 p.m. PT Thursday? If you’d rather talk it through, I’ll find fifteen minutes on your calendar.

The best version nails all three. Audience: it gives a manager the decision and a recommendation, not a puzzle. Moment: it names the Thursday deadline. Action: it asks for a specific approval by a specific time.

Giving a status update

Bad:

Just FYI, still working on the project and will keep you posted.

Better:

Quick update: the project is moving, but the vendor is delayed.

Best:

Quick update: we’re still on track for Friday, but the vendor is two days behind on their input. I’m following up today and will escalate by noon tomorrow if they don’t respond. No action needed from you yet.

The best version tells the reader what’s happening, what could go wrong, what you’re doing about it, and whether they need to act. That last line, “no action needed from you yet,” is the one that builds trust, because it tells your boss exactly when to stay out of it and when to step in.

Escalating a risk

Bad:

There might be an issue with the timeline.

Better:

The timeline may be at risk because legal has not reviewed the contract.

Best:

Flagging this as a launch risk: legal has not reviewed the contract, and we need approval by Wednesday at 3 p.m. ET to stay on schedule. I just escalated to legal by email with you on CC. If we don’t have approval by tomorrow at 4 p.m. ET, launch slips by one week.

The best version does not panic, but it names the risk, explains why it matters, shows ownership, and defines the consequence. Your boss needs to know about risks early, and you need to make them as loud as the situation deserves.

Writing to an executive

Bad:

I wanted to provide some context on the customer onboarding work and share a few updates from the team.

Better:

We have an update on customer onboarding and need your input on launch timing.

Best:

Recommendation: delay the onboarding launch by two weeks to reduce customer risk. The issue is tied to a lack of support coverage. We can launch on time, but the customer experience risk is higher than the schedule risk.

One more thing on messaging execs: if you’re messaging a skip-level leader (your boss’ boss or above), run it by your boss first, or at least give them a heads up. If something you send lands poorly, your boss hears about it directly, so keep them in the loop and save yourself the headache.

Asking a peer for input

Bad:

Can you review this when you get a chance?

Better:

Can you review the attached deck by Friday?

Best:

Can you review slides 4 to 6 by Friday at noon PT? I only need a check on customer accuracy, not design or wording.

The best version saves the other person time. It tells them where to look, when you need it, and what kind of feedback you actually want, which is the Action piece in miniature.

The Hardest Case: When You’re Frustrated

Writing when you’re emotional should send alarm bells and cause you to slow down before clicking send.

People who are just trying to make a point will vent, cut others down, and do whatever it takes to look right. People genuinely trying to make a difference are willing to look like they lost the argument if that’s what helps the work move forward. One of the biggest career limiters is being seen as a hot head who dumps on people under stress.

Here is the same situation, handled three ways.

Bad:

We talked about this last week, and you said you’d have it done by Friday. This is now blocking the rest of the work and you’re putting me in a bad position.

Better:

We’re blocked because the input wasn’t ready Friday. Can you send it today?

Best:

We’re blocked on the customer summary and need it today to keep the timeline on track. Can you send your section by 2 p.m.? If that timing no longer works, tell me what’s realistic so I can adjust the plan.

The best version names the issue without turning it into a character judgment, gives a deadline, and leaves room for reality. It moves the work forward. You can always follow up in a one-on-one later to talk about the process and how to work together better. In the moment, the focus should be getting the work across the finish line.

If you’re hot under the collar, write an angry version of your message in a Word doc, delete it, and get it out of your system. If needed, take a walk or sleep on it and then write the version that moves the work forward and doesn’t end with you sitting in HR’s office.

Before sending anything emotional, ask:

• Am I trying to solve the problem or prove I’m right?

• Will this make the next step easier or harder?

• Would I stand behind this if it were forwarded?

Often, maturity means letting it go and getting the job done.

Subscribe now

Your Move This Week

Pick a message you need to send this week that actually matters: a request to your boss, an update to your team, a flag to someone senior. Before you send it, run it through the three questions:

• Audience. Am I writing at the right altitude for who’s reading this?

• Moment. Is this the right channel, and does the tone fit what the situation needs?

• Action. Have I made the one thing I need unmistakable, and said when I need it?

Then delete every sentence that isn’t doing one of those three jobs. Most first drafts are twice as long as they need to be, and the cutting is where the thinking actually happens.

If you want the real version of what made me better at this, send the draft to one person whose judgment you trust and ask them to mark it up. Not “does this sound okay” but “where do you have to stop and figure out what I mean?” A chatbot can tell you if a sentence is clear, but a person who knows the work can tell you if you’re solving the right problem so use both to refine your writing.

Use your communication to move the work forward and build the culture you want to see in your workplace.

If this series is hitting home, send it to someone who needs it.

Share

P.S. I work with a small number of readers one-on-one to help them apply these frameworks to their own career. If you are at a moment where you need more than a newsletter, book a one-off or ongoing session here.

If you enjoyed this, here’s what to read next:

Welcome back to Career Field Guide: the weekly newsletter for people who want to build a career that holds up in the age of AI. If someone forwarded this to you, subscribe here.

This is Part 5 of 10 in the Essential Skills Series: the 10 skills that separate people who advance from people who plateau. Start from the beginning here.

Subscribe now

I learned one of the most useful career lessons at Amazon by frustrating my manager.

Before Amazon, I worked in environments where it was normal to run a lot of things through your manager before acting. That was comfortable for me, and I was trying to stay aligned, avoid mistakes, and make sure I was doing the right thing.

Then I got to Amazon, and my manager started getting frustrated that I was not moving fast enough. The issue was that I was asking for approval on decisions in an environment that valued a bias for action, experimentation, and iteration.

That was a turning point because it forced me to learn something school does not teach very well: not every decision deserves the same amount of process.

School Trains You to Wait for Permission

In school, the assignment, deadline, and rubric are given to you with clear instructions. Submitting early or innovating outside of the original ask is usually treated with ambivalence or penalty (”Points will be deducted for papers over 5 pages in length”).

At work, the assignment is often unclear, there are multiple decision-makers evaluating your work, and the constraints are not always visible. The expectation is not always, “Come clarify with me before you do anything.” Often, it is “use good judgment and keep making progress.”

That gap is uncomfortable, especially when you are early in your career or at a new company. Will I look arrogant if I overstep? What if I get it wrong? If I make the call without consulting my manager, will it look like I went rogue? If I do not make the call, will it make me look too junior?

Most people default back to what feels safe. They ask for feedback, ask again, and the work waits. Meanwhile, the manager feels like they have to manage you and your work.

Last week, we looked at how to ask for and receive feedback. Asking first can be the right move, but it is often a sign that you have not yet learned what kind of decision you are making.

One-Way Doors and Two-Way Doors

One of the most useful frameworks I learned at Amazon is the difference between one-way door and two-way door decisions.

• A one-way door decision is hard to reverse. Once you walk through, it is expensive, painful, or impossible to go back.

• A two-way door decision is reversible. You can try it, learn from it, and walk back through the door if it does not work.

If the decision is hard to reverse (one-way door), then slow down, get context, understand the risks, and build support for your recommendation (including your boss) before taking action.

If the decision is reversible (two-way door), low-risk, and within your role, move forward. Make a reasonable call, communicate clearly, and adjust if it does not produce the outcome you wanted.

The mistake most people make is treating both kinds of decisions the same. Early-career people over-process small decisions and under-prepare big ones. They turn reversible decisions into group projects because they want everyone to agree. Then they launch bigger ideas cold because they assume the quality of the idea should speak for itself.

If you make small decisions too heavy, people stop trusting you to move work forward. If you make big decisions too light, people stop trusting your judgment. Professional judgment is learning the difference.

Move Fast on Reversible Things, Not Risky Ones

To be clear, I am not saying you should stop asking questions or ignore your manager. Nor should you move fast on things that are risky, political, expensive, unethical, customer-facing, legally sensitive, or hard to reverse.

A lot of early-career professionals hear “take initiative” and think it means acting like they own the company. The right move is learning how to carry the right-sized decision. Your manager should not have to approve every tiny step, and they should not find out after the fact that you made a decision with real blast radius.

The goal is calibrated action, which takes insight, wisdom, and a few scars after you step in it.

The Decision Spectrum

Not every decision has the same weight. The riskier the decision, the more context, trust, and support your idea needs. Here are four points to consider for each decision.

1. Taste Decisions

Taste decisions are small, low-stakes, and easy to reverse.

• Where should we go for lunch?

• What should the happy hour plan be?

• Should the update be a table or a few bullets?

• What time should we meet?

These decisions need someone to make a useful recommendation.

A bad version sounds like:

“Where does everyone want to go? I’m good with whatever.”

Now ten people are debating restaurants in Slack for 45 minutes.

A better version sounds like:

“How about tacos at 6? It’s close to the office, has space for the group, and I can make the reservation. Any food allergies?”

That sounds small, but it shows natural leadership and is massive in moving people forward. It is also where people learn whether you make things easier or harder.

2. Process Decisions

Process decisions are about how work gets done.

• How should we run the weekly staff meeting?

• How should we track action items?

• What should the project update include?

• How should the team handle handoffs?

• What recurring friction could be made easier?

These decisions are usually reversible, but they touch other people’s habits, so tone matters. The goal is to be winsome, not critical.

Do not walk in with:

“This meeting is a waste of time.”

Try:

“I noticed we sometimes run out of time for decisions because the updates take most of the meeting. Would it help if I drafted a simple agenda that starts with decisions needed, then blockers, then updates?”

Same idea, completely different effect. The first makes people defensive, while the second makes you useful. You earn influence by making things better without making people feel stupid for the way it worked before.

3. Project Decisions

Project decisions have real tradeoffs.

• What should we prioritize?

• What should we delay?

• Which path should we take?

• What risk should we accept?

• Who needs to be involved?

• What does “good enough” mean here?

This is where a lot of early-career people get frustrated because they assume the better idea should automatically win. Most project decisions are shaped by timing, capacity, budget, stakeholder trust, technical constraints, leadership priorities, and the people who will have to do the work after the meeting ends.

For project decisions, do not just bring an opinion. Show that you understand the context. Before advocating for a path, ask:

• Who owns the decision?

• What constraints matter most?

• Who will have to support this?

• Who will have to do the work?

• What risk is the team trying to avoid?

• What would make this easier to say yes to?

That is the difference between having a point of view and helping the group make a decision. A point of view without context is just a preference.

4. Business Decisions

Business decisions are the highest-stakes decisions most people encounter at work. They touch money, customers, strategy, headcount, risk, quality, growth, or future capability.

• Where should we invest?

• What should we stop doing?

• What customer problem matters most?

• What capability should we build?

• What risk is worth taking?

• What tradeoff should the business accept?

The bigger the decision, the less cold your idea should be when it enters the room. Important ideas move through people. People need context, time to react, a chance to improve the idea, and to know whether they are being asked to approve, support, implement, or simply be informed.

If the first time people hear your idea is in the meeting, you are making the meeting do too much work.

Good Ideas Do Not Travel by Themselves

At Microsoft, some of the best support I ever built for ideas did not happen in the formal meeting. It happened in lower-stakes conversations, over coffee, a 1:1, or a happy hour where the topic came up naturally.

The idea still had to be good, but by the time it reached the meeting, it was not landing cold. People had already pressure-tested it, challenged parts of it, and understood why it mattered. I also knew that I had supporters in the room who would back my idea.

That meant the meeting was about alignment, not about debating the value of the idea itself. People early in their career try to win the room from zero. Leaders bring forward something that already has fingerprints from the people who need to support it.

Even the best among us can be territorial or political at work. Asking for feedback, improving your idea with others, and respecting people by running things by them before their boss is in the room is how you show respect and build influence.

Subscribe now

Your Move This Week

Pick one decision at work, in an internship, on a class project, in a club, or on a team this week.

Start by asking: what kind of decision is this?

• If it is a taste decision, make a useful recommendation. “Let’s do this. I’ll take care of it.”

• If it is a process decision, suggest a small test. “I noticed this part is creating friction. Want me to try a simple version next week?”

• If it is a project decision, pressure-test before the meeting. “I’m thinking about recommending this path. Before I bring it to the group, what am I missing?”

• If it is a business decision, build the support map. Who owns it, what constraints matter, who needs to support it, who will worry, what would make this easier to say yes to.

Then ask yourself one more question:

Am I asking for permission because this decision truly needs approval, or because I am nervous to act and potentially get it wrong?

Sometimes you should slow down, but most days the right move is to make a reasonable call, communicate clearly, and keep iterating. School trains you to wait for permission, but work rewards people who know when permission is no longer the point.

Your job, especially earlier in your career, is to become trusted. Trust comes from learning which doors you can walk through, which ones need support, and which ones deserve a slower hand on the knob.

Share

What else?

Hi! I’m Justin. I share weekly articles to help you improve your career after 15 years of working and managing teams at Amazon, Microsoft, and Starbucks. You can follow along by subscribing below:

Subscribe now

I also work with a small number of readers one-on-one to help them apply these frameworks to their own career. If you are at a moment where you need more than a newsletter, book one off or ongoing sessions here.

If you enjoyed this, here’s what to read next:

Welcome back to Career Field Guide: the weekly newsletter for people who want to build a career that holds up in the age of AI. If someone forwarded this to you, subscribe here.

This is Part 4 of 10 in the Essential Skills Series: the 10 skills that separate people who advance from people who plateau. Start from the beginning here.

Subscribe now

I recently spoke with graduate students at the University of Washington about AI, careers, and what organizations may look like five years from now. One of the questions students always ask me is something like:

“What’s the thing you wish someone had told you in your first job that you had to learn the hard way?”

I gave a fine answer in the moment, but a better answer came to me later in the Uber: Feedback is not a grade.

Are You Worth Investing In?

Feedback is not a grade. At school, feedback tells you how you did; but at work, feedback tells you what to improve next.

That sounds simple until you are sitting in a 1:1 and your manager pulls up a doc you sent them on Monday. They tell you the structure is unclear, the recommendation is buried, and the analysis does not quite hold up under the question they expect leadership to ask.

In the next three seconds, one of three things happens.

1. You defend. “Right, but the reason I structured it that way is...” You start explaining your thinking before they finish theirs. You’re not being aggressive. You’re trying to demonstrate that you thought about it. They watch you do it.

2. You deflate. Your face changes. You go quiet. You write things down without responding. The rest of the meeting feels heavy. They notice and start softening the next piece of feedback before it leaves their mouth.

3. You nod and ignore. “Got it, makes sense, I’ll fix it.” You don’t ask a single clarifying question. You walk out, change two sentences, and send it back. They read it and realize you didn’t actually take in what they said.

All three reactions are understandable, but they’re incomplete and can make feedback more expensive to give next time.

Your manager is not only reacting to the work in that conversation, they are updating a different file in their head: how much honest feedback can I give this person before it costs me more than it’s worth? The answer determines how much of their time, attention, and political capital you get for the rest of the time you work for them.

Feedback Is a Flywheel

Giving honest feedback is uncomfortable. Most managers, peers, and senior colleagues run an unspoken test the first few times they give you anything sharp: Did this land? Was it worth it? Will I do this again?

If the answer is yes, you start getting better feedback, earlier feedback, and more direct feedback. The people around you begin treating you like someone they can be honest with, which is one of the most valuable things a workplace can offer you in your first ten years.

If the answer is no, the feedback gets quieter, more diplomatic, and eventually stops. You may not notice this happening because the absence of feedback can feel like things are going well, even when they are not. The reality is that you’ve just been moved into the category of people who are hard to coach and the people in that category are often the same people who get blindsided by performance reviews or surprised when they do not get promoted.

The reason feedback feels so charged in the moment is because your brain often hears it as danger before it hears it as information. Your competence, reputation, and belonging all feel tied to your work, so the self-protection instinct is to explain, retreat, or protect yourself before you’ve fully processed what was said.

When that happens, remind yourself: Feedback is not proof that you’re failing. It’s proof that someone still believes your improvement is worth the effort.

That said, it doesn’t mean rolling over either. The mistake almost everyone makes is treating “receive feedback well” and “agree with feedback” as the same thing. The people who handle feedback best are often the ones who eventually push back on it. They just push back at the right time, in the right way, on the right things. That is the difference between being coachable and being endlessly agreeable.

Receive in the Room. Evaluate Out of It. Close the Loop

There are three moves that make feedback useful:

1. Receive in the room

2. Evaluate out of it

3. Close the loop

1. Receive in the Room

In the room, your job is not to decide whether the person is right.

Your job is to take the feedback in cleanly enough that you can think about it later when your ego is not sitting at the table. That does not mean you have to agree with everything but at least get clarity on what’s been critiqued.

Concretely, that looks like this:

• Listen all the way through before responding. Most people start formulating their response at the first sentence, which means they’re too focused on responding and miss what’s being said.

• Ask clarifying questions instead of explaining. “Can you give me an example of where you saw that?” is a hundred times more useful than “Well that’s because...”

• Acknowledge specifically. “That makes sense, especially the part about the recommendation being buried” tells the person you actually heard them. “Got it, thanks” tells them almost nothing.

• Buy yourself time to evaluate. “I want to think about this and come back to you with how I’m going to adjust” is a complete sentence. You don’t have to commit to action in the room.

Whatever you do, don’t go to “got it, makes sense” too fast. That is often the tell of someone who has already mentally left the conversation. Senior people will clock it immediately.

2. Evaluate Out of It

Out of the room, your job changes. Now you have to figure out whether the feedback is right.

Not all feedback is right. A lot of it is partially right, some of it is wrong, and some of it is wrong in ways that would actively damage your career if you implemented it.

Your job is to figure out which is which, and you can’t do that while you’re still emotionally activated from the conversation.

This is where the open-hand / closed-hand distinction matters.

Open-hand feedback is feedback about how you work:

• Your structure.

• Your communication style.

• Your approach to a project.

Hold these loosely and be willing to pivot quickly.

If someone tells you your recommendation is buried, your update is too long, your stakeholder management is unclear, or your project plan is hard to follow, default to curiosity. These are working habits, not sacred truths.

Closed-hand feedback is feedback that touches who you are and what lines you will not cross:

• Your ethics.

• How you treat people.

• Whether you tell the truth.

• Whether you take credit for someone else’s work.

Hold these tightly and stand firm in your convictions.

Most early-career people get this backward. They defend habits like values and compromise values like preferences. The first can slow your growth, but the second can change who you become.

As a first-generation college student walking into a Fortune 500 office for the first time, my default was to take everyone’s feedback at face value. I thought everyone must be smarter than me and I assumed the people above me knew more than I did about everything. That was true on some things, but very much not true on others.

That instinct helped me get through the door, but eventually it started working against me. I was well-liked, but I was not always well-respected. I had to quickly pivot after being hired at Amazon. The culture there has strong personalities and strong opinions. The people who succeed are the ones who can hear “you’re wrong” without flinching, defend their point of view when needed, evaluate whether they actually are wrong, and then either change their position or hold it with calm conviction.

Standing my ground in a way that was clear, thoughtful, and not performative was a skill I had to build deliberately. Nothing in my upbringing had taught me that disagreeing with authority was an option, let alone an expectation. The shift was learning that receiving feedback cleanly did not mean surrendering my judgment.

Out of the room, run feedback through a filter:

• Does this person understand me and my work well enough to have a useful opinion?

• Do I respect this person’s judgment in the area where they are giving feedback?

• Have I heard this pattern before, or is this the first time?

• Is this person invested in my growth, or are they just reacting?

A critic is not the same as an enemy. Plenty of advocates will criticize you, often more sharply than anyone else. The question is not, “Did this hurt?” The question is, “Is this useful, true, and worth acting on?”

3. Close the Loop

This is the move almost nobody makes, and it compounds more than any other single thing in this article.

A few weeks after you implement something based on someone’s feedback, go back and tell them what changed.

Something like:

“You told me a few weeks ago that I was burying the recommendation. I rebuilt the structure of my last memo around leading with it, and the response was completely different. Thank you for that.”

That small follow-up does a lot. It tells the person their feedback mattered and shows that you can turn input into better work. It makes the next hard conversation easier and teaches them that giving you feedback is high leverage. They invested a few minutes, and you came back with proof that it changed something.

This is how you get busy, sharp people to keep investing in you. I have built some of the strongest advocates in my career not because I was brilliant in every room, but because I was willing to listen, act, and come back better.

The irony is that over time, the same people who once gave you feedback may start asking you for yours. At this happens, it means you are not just someone who can receive judgment, but are becoming someone whose judgment other people trust.

First Drafts Are Cheap, Iteration Is the Job

This matters more now than it did ten years ago because AI has made first drafts cheap. Anyone with a laptop and a decent prompt can produce a memo, an analysis, or a deck. Execution stopped being the differentiator.

The advantage is shifting to people who can improve the work faster. People with judgment, taste, and clarity who can incorporate feedback to make the next version better. Someone early in career may think that the win is completing an ask, whereas a seasoned leader knows the win is making the deliverable impactful. Feedback receptiveness and iteration is how you compound past people who are using the same LLMs as you.

Your Move This Week

Think about a piece of feedback you’ve received in the last 90 days that stung. Could be from your manager, a peer, a stakeholder, anyone.

Run it through the four-question filter:

If the feedback survives the filter, do something about it this week and then close the loop with the person who gave it to you within the next month. If it doesn’t survive the filter, let it go. Stop carrying around feedback that was never useful in the first place.

Then ask yourself the harder question:

• What feedback have I been defending that should be open-hand?

• And what feedback have I been absorbing that should be closed-hand?

Feedback is not a grade. It is not a verdict or proof that you failed. It is the loop that makes your work better and if you learn how to receive it, evaluate it, and act on it, you become the kind of person people keep investing in.

If this series is hitting home, forward it to someone in their first few years of work. It’s free, and it might be the thing nobody’s told them yet.

Share

Leave a comment

P.S. — I work with a small number of readers one-on-one to help them apply these frameworks to their own career. If you are at a moment where you need more than a newsletter, book one off or ongoing sessions here.

If you enjoyed this, here’s what to read next

Welcome back to Career Field Guide: the weekly newsletter for people who want to build a career that holds up in the age of AI. If someone forwarded this to you, subscribe here.

This is Part 3 of 10 in the Essential Skills Series: the 10 skills that separate people who advance from people who plateau. Start from the beginning here.

Subscribe now

The Communication Trap

No matter how smart you are, it’s almost inevitable that you’ll get this feedback at some point in your career:

“You need to work on your communication skills.”

What do you do with that?

Their first reaction is usually confusion, especially for folks who are used to succeeding throughout life, so they assume the feedback means they need to be more confident, polished, or concise. They might watch a few TikToks on communicating well, but they’re still not sure what it means to “work on your communication.”

Here is what the feedback actually means: the way you communicate works perfectly in one room and completely fails in another. You’re probably not bad at communicating overall (we all communicate well throughout our life), but you’re likely stuck in one mode, and each workplace has (at least!) four layers of communication.

Most people never learn to switch between layers, but the ones who do have an uncanny ability to accelerate their career.

The Scene You’ve Either Lived or Watched

A 26-year-old analyst gets her first chance to present directly to a VP. She has done the work, prepared well, and has a defensible recommendation.

The VP joins the Zoom three minutes late, apologizes, and says he will have to leave early for another call. The analyst skips her intro, starts at slide one (of 27), and provides baseline context. The VP nods politely, but interrupts by slide three:

“What’s the one thing I need to know? Are we on track or not?”

She freezes. The one thing she needs to tell him is on slide nine. She tries to explain that it requires the context from slides four through eight to make sense. The VP says, “Okay, let me come back to this. Send it and I’ll read it later.” He drops off (and does not read it later).

Weeks of work, evaluated in a few minutes, and the evaluation is not about the analysis. It is about whether this person is able to effectively communicate with senior leadership. In this case the answer is no, because she wasn’t able to communicate effectively with the VP. She hasn’t learned how to communicate at this level.

I’ve Been on Both Sides

I spend a lot of my week at Zero100 translating between levels. I sit with factory leaders in the morning, hear what is actually happening on the floor, and by the afternoon I am in front of a COO compressing all of it into three sentences they can act on. My entire job is closing other people’s compression gaps and it took me twenty years to get good at this, but I learned it the hard way.

The first time I presented to a general manager at one of my early corporate jobs, I fumbled it badly. I had not prepared the way I should have and I ended up rambling and burying the point. When the GM asked me what the “so-what” was, I gave him a meandering answer that was really a confession that I did not know. He was polite, but my boss sidelined me and it took a lot of reps before he let me present again at that level (rightly so).

I did not lose that opportunity because my work was bad. My work was fine for my level and experience. I lost it because I had not yet learned that the work and the compression of the work into a clear executive message are two different skills. Senior leaders evaluate you on the second one long before they trust you with more of the first one.

Why This Is Getting More Brutal, Not Less

Standard career advice has not caught up to how AI is changing communication. Anyone with a laptop and a good prompt can produce a memo, a model, a first draft, or an analysis. The raw output that used to take a team of analysts a week now takes a single person an afternoon. That may sound like good news for early-career professional, but it changes what you are being evaluated on.

Execution is a commodity now. Compression is what is left. That is the skill AI amplifies rather than replaces, and the people who develop it early are going to succeed in the AI era.

The Four Translation Layers

The ability to translate between layers is not one skill, it’s four: in a workplace you are constantly translating in four different directions depending on who you’re talking to.

Translating Down (to people earlier than you)

• The job: Transfer hard-won context into patterns they can actually use.

• The failure mode: Assuming they already know what you know. Explaining the mechanics without explaining why any of it matters. Being so eager to sound senior that you talk past them.

• The mastery signal: They make a decision on their own that you would have made yourself. Without calling you.

Subscribe now

This one starts earlier than you think. If you’re a junior in college, the person you are translating down to is the sophomore on the group project. If you are two years into a job, the person is the intern. Every time you help someone one step behind you get unstuck, you are building the muscle you will use with your own team later. Because you’re explaining a topic to someone with less experience, you may need to go more in-depth and take your time. Don’t compress information at this level because you risk creating confusion.

Translating Across (to peers)

• The job: Coordinate without hierarchy. Make your context portable.

• The failure mode: Treating peers like they’re managers or subordinates. Looping in your manager on peer conflicts before doing the work of influence yourself. Communicating like you are trying to win instead of trying to get the work done.

• The mastery signal: When a new project starts, someone from another team asks if you can be on it because you make the work easier.

This is the layer most junior people ignore completely, and it shows up later as the invisible ceiling. How you communicate with your peers affects how they feel about you.

If you treat everyone like they’re your manager, you aren’t going to be helpful. You defer, avoid pushing back, and fail to offer real input because you’re trying to be agreeable. If you go the other direction and try to assert authority that you don’t have, you create friction. You push too hard, overstep, and turn collaboration into something people have to manage instead of benefit from.

How you treat your peers is important because a strong peer network built in your first five career years is the single biggest hedge you have against a bad manager, a bad market, or a bad economy. Only compress information at this level when you’re clear that both you and your peer have the same context and understanding of the topic.

Translating Up (to your manager and their peers)

• The job: Reduce your manager’s cognitive load. Convert complexity into decisions they can make quickly.

• The failure mode: Dumping information and calling it an update. Asking for direction when you should be asking for calibration. Sending a weekly status that buries the three things that actually matter under nine things that do not.

• The mastery signal: Your manager’s manager knows who you are and knows one specific thing you are working on because your manager keeps mentioning you.

This is where the skill really starts to really show up. A manager who has to work hard to extract the point from you will not bring you into the next opportunity. A manager who can walk into their own boss’ office and cleanly represent your work will find more ways to give you visibility. It’s the same work, but with wildly different outcomes. You need to compress the information and provide a little context.

Translating to Altitude (to executives two or more levels up)

• The job: Fit your work into a narrative they are already telling themselves. Get to the point in thirty seconds.

• The failure mode: Explaining what you do when you should be explaining why it matters for their agenda. Taking three minutes to get to the headline. Bringing fourteen slides when the decision can be made from one to three.

• The mastery signal: Someone two levels up references your work in a meeting you were not in.

Nobody teaches you how to do this because most of your managers are not great at it either. The entire executive communication skill is built on this: can you see the big picture, pick what matters, and present it clearly.

If you’re presenting to senior leadership, they already trust your analysis so no need to waste time explaining how you got to your conclusion; present just the details that leadership needs. Executives are drowning in information and they don’t need more. They need someone who can look at all of it and hand them the one sentence that allows them to make a decision. Compress information to the essentials; if leadership wants more info, they’ll ask.

This is the altitude where this skill either makes or breaks careers. It’s also the altitude where AI has raised the bar because most executives are now getting more AI-generated material than ever (noise) which means the human who can compress reality clearly (signal) stands out more than ever.

From the Executive Floor

A CSCO recently shared with me: “I may not remember everything my team said in a meeting. I remember the one slide they put in front of me that synthesized the issue, the solution, and the next steps with clear time-based outcomes that I could easily use with my boss. That’s the value.”

Three months of work judged on one slide. That’s why it’s important to understand what the other person will take away based on how you translate it for them.

Your Move This Week

Below are four questions, one for each translation direction. Answer them honestly. Wherever you flinch or have to guess, that is your skill gap right now.

• Down: Who have I made more capable in the last 90 days?

• Across: Who on another team would describe me as the easiest person to work with on mine?

• Up: Does my manager’s manager know one specific thing I am working on right now?

• Altitude: Has anyone two or more levels above me ever referenced my work in a room I was not in?

If the answer is “no” or “I don’t know” for any of these, pick one, and make that your focus for the next 30 days.

If you are in college, Translation 1 and 2 are your first real test. Communicating well with your junior and equal peers gives you practice for the workplace.

If you are a few years in to your career, Translation 3 is the wall most people hit. You are doing the work, but you have to learn how to hand it up.

If you are ten years in, Translation 4 is where careers plateau. The audiences got more senior and the thirty-second test got harder. Nobody ages out of developing these skills, you just meet it at higher altitudes. Learn how to communicate quickly within the high-level context of senior leaders and you will be well on your way to building a great career.

If this series is hitting home, forward it to someone in their first few years of work. It’s free, and it might be the thing nobody’s told them yet.

Share

Leave a comment

P.S. — I work with a small number of readers one-on-one to help them apply these frameworks to their own career. If you are at a moment where you need more than a newsletter, book one off or ongoing sessions here.

If you enjoyed this, here’s what to read next

Welcome back to Career Field Guide: the weekly newsletter for people who want to build a career that holds up in the age of AI. If someone forwarded this to you, subscribe here.

This is Part 2 of 10 in the Essential Skills Series: the 10 skills that separate people who advance from people who plateau. Start from the beginning here.

Subscribe now

Busy Isn’t the Same as Productive…And Your Manager Can Spot the Difference

It’s Tuesday afternoon. You have fourteen things on your list, three Slack threads you haven’t answered, and a 1:1 with your manager in the morning.

You’ll spend tonight trying to make progress on all of it. You’ll show up tomorrow with a status update that covers everything. Your manager will nod, ask a few questions, and move on. And then you’ll leave the meeting with a sense that something isn’t landing, even though you worked hard all week.

Here’s what’s actually happening: your boss is getting a sense for whether you have good judgment or not.

Promotion decisions rarely go to the hardest worker in the room. They go to the person whose work is most aligned with what leadership actually cares about, which is why learning to prioritize your work is one of the most important skills you can build early in your career.

School Taught You Perfection. Work Grades You on Impact.

School has one rule: finish everything well. Every assignment matters equally and leaving something incomplete is a failure. That rule gets you through sixteen years of education, but then you enter the workforce and nobody tells you it stops working.

At work, output is judged on impact, not completeness. A task finished on time that moves nothing is invisible. A task left imperfect that moves the right metric gets you in the room for the next exciting project or opportunity. Your manager isn’t grading your completion rate. They’re asking two questions: does this person know what actually matters, and are they doing those things well?

The trap is applying school logic to a work environment where the list never gets shorter and the stakes on each item are wildly unequal. The reality is that most emails don’t need a response and most tasks won’t move your career or your team forward. The challenge is learning which ones will and then doing those items with excellence.

Steve Jobs said focus means saying no to a hundred good ideas and Warren Buffett called everything outside his top priorities his “avoid at all costs” list. They were talking about running companies, but the same logic applies to running your week.

The fix isn’t working harder; It’s knowing what’s actually impactful.

Companies Don't Reward Busy Work. They Reward Aligned Work.

Every company, regardless of size, runs the same way at its core. Leadership sets strategic goals — grow revenue by 20%, reduce cost by 15%, enter a new market, ship a product by Q3. Those goals get broken into team objectives, which filter into individual priorities. The cascade goes all the way down to your weekly task list. This means your work is always being evaluated against something above it, even when nobody tells you what that something is. The best managers make this explicit and reinforce it regularly.

At the highest levels, companies judge performance on three things: metrics that move, profit that compounds, and evolution that keeps them competitive. The number of emails you answered, your Slack response time, or tasks you checked off before lunch will never make leadership’s radar. Ironically, being great at those things is usually the easiest way to spot a junior person versus a more senior one. The junior person optimizes for activity whereas the senior person optimizes for outcome. The gap between them is understanding which game is actually being played.

The early-career trap is operating at the bottom of that cascade without understanding it. You complete tasks because they’re on your list, not because you’ve traced them back to something your organization actually needs.

The reason that this matters is because you can’t possibly do everything at work. There will always be more work than hours in the day, so the way your prioritize tasks indicates your understanding of the business. The professionals who advance fastest are almost always on teams that can draw a straight line from their daily work to their leader’s strategic goals because they understand the cascade and point their energy at it. When budgets get cut, those teams get protected. When opportunities open up, those people get called.

This is why prioritization isn’t a time management skill, it’s a strategic one. Even if you could pack every task into your day (you can’t), you’d still be spending precious time on unnecessary busy work. Before you sort your task list, the most important question isn’t “what’s urgent?” It’s “what does my manager’s leadership team care about most this quarter, and am I pointed at it?”

The practical move is simpler than it sounds. In your next 1:1, ask your manager one question: “What does leadership care most about this quarter, and how does our team’s work connect to it?” A few managers might be vague, which is also useful information, but most managers are excited to hear someone who wants to understand the strategic landscape and help them with strategic goals.

If you can understand your org and team’s strategic goals, prioritization gets significantly easier. If you can’t, no framework will save you.

How High Performers Actually Prioritize

Start with the Eisenhower Matrix

Before your next 1:1, sort everything on your plate into the four quadrants below from the Eisenhower Matrix.

After doing this you'll find that a surprising portion of your week lives in the bottom half. The matrix doesn't give you a perfect answer, but doing it forces you to make a judgment call about how you’ll use your time before someone else makes it for you.

Then pressure-test with four questions

The matrix tells you where tasks land. These questions tell you whether you sorted them correctly:

• Does my manager’s manager care about this? If yes, it’s almost certainly high-impact. If you don’t know, find out — that gap is worth closing on its own.

• Does this unblock someone else? Work that holds up a colleague or a downstream process compounds in both directions. Doing it fast creates momentum. Sitting on it creates drag that’s visible to more people than you think.

• Is the deadline real or social? Some deadlines are attached to business outcomes — a launch, a client commitment, a board review. Others exist because someone asked and it felt awkward not to give a date. Treat these deadlines differently.

• Would skipping this be noticed in 30 days? If the honest answer is no, it belongs in the bottom half of the matrix regardless of how urgent it feels today.

Here’s what this looks like in practice

Early in my time at Microsoft, I was preparing for a weekly 1:1 with my manager and I felt buried by the workload. I had twelve things on my list, all of which felt real and critical. Two were reports I’d been asked to pull, one by my manager, one by a colleague who needed it for a presentation the following week.

Running the four questions changed my read on both. The colleague’s report was urgent and felt important, but my manager’s manager had no visibility into it, it didn’t unblock any cross-functional work, the deadline existed because someone had put a meeting on the calendar, and nobody above my manager would have noticed if it slipped a week so it went in the bottom half. The report my manager had asked for connected directly to a metric their leadership team reviewed monthly. It belonged in the top half and I needed to lead with it.

I showed up to that 1:1 with three things ranked, the rest explicitly deprioritized, and one open question. My manager spent the first ten minutes on the thing that actually mattered and appreciated that I was focused on the critical few items. He was also able to provide quick feedback on rearranging my list so that I can deprioritize a few items that had seemed critical to me, but not to him.

Bring the ranked list, not the full list

My 1:1s with my manager felt like working with a partner when I started showing up with a ranked view and my manager appreciated that I was able to quickly articulate what I think matters most this week, what I’m deprioritizing, and one thing I want his read on.

Your manager can affirm, redirect, or catch something you missed, but you need to do the work of organizing if you want to be seen as a leader. It’s a big difference between asking for direction and asking for calibration. One puts the work on them, the other shows you’ve already done it.

Say out loud what you’re cutting

Don’t quietly drop low-priority work. You need to state it to the others involved: “I’m pushing the vendor report to next week to stay focused on the launch.” The sentence builds trust and ensures that you’re not accidentally missing something critical. It also signals judgment, not avoidance. You want your boss to see you as strategically prioritizing your work, not dropping the ball.

Use AI to Build the Judgment, Not Just the List

Before your next 1:1, run this prompt:

“Here’s my task list: [paste it - don’t include anything confidential]. My manager’s current focus is [one or two sentences]. Our team’s top priority this quarter is [one sentence]. Rank these by likely impact on what my manager cares about most, flag anything that looks low-value given those priorities, and for the top three items explain specifically why they rank highest. I want to understand the reasoning, not just the ranking.”

That last sentence is the important one. You’re asking for the logic behind the sort so you evaluate it; if it’s good, internalize it and apply it yourself next time without needing the help.

Use AI to develop your thinking, don’t blindly follow its outputs.

Your Move This Week

Before your next 1:1: write down everything on your plate, sort it with the Eisenhower Matrix, run the four questions on anything you’re unsure about, and bring the ranked list. Then run the AI prompt above and adjust if anything surprises you.

Your manager doesn’t need you burned out over tasks; they need to know that you understand what matters and that you’re committed to getting it done.

Share

Leave a comment

P.S. — I work with a small number of readers one-on-one to help them apply these frameworks to their own career. If you are at a moment where you need more than a newsletter, book one off or ongoing sessions here.

If you enjoyed this, here’s what to read next:

Welcome back to Career Field Guide: the weekly newsletter for people who want to build a career that holds up in the age of AI. If someone forwarded this to you, subscribe here.

This is Part 1 of 10 in the Essential Skills Series: 10 skills to become the person who knows what they're doing at work

Subscribe now

Your first few weeks at a new job feel productive. There’s onboarding, training modules, and a buddy. Then one morning your manager sends you a Slack message: “Can you take a look at this and come back with a recommendation?”

In this interaction, and the hundreds of others like it, you’re either going to show that you know what to do when there’s no rubric or that you’re still too green to be trusted with real responsibility.

I was in New York this week leading a keynote on agentic AI with a room full of supply chain executives. Even with such a technical topic, we spent a significant amount of time discussing the challenge of getting teams to take ambiguous problems and run with them instead of freezing. This isn’t an entry-level problem. It’s a career-long skill, and the earlier you build it, the faster everything else compounds.

The moment it breaks down

“Our customer churn has been creeping up the last two quarters. Can you dig into what’s going on?” -Your Boss

You nod and sit down, but your chest tightens. How deep should you go? Who should you talk to? Is this a priority or a test? Two days later you’re back at your manager’s desk asking for more direction. They give you something half-formed because they’re mentally already in their next meeting. You leave with less clarity and an annoyed boss.

Your manager isn’t frustrated because you have questions, but because every question puts the work back on them. They wanted you to take the ambiguity off their plate, not return it with a Post-it note attached.

Here’s what nobody told you:

The vague assignments from your boss aren’t just tasks, they’re auditions.

Promotions aren’t rewards for past performance. They’re bets on the future and the people in promotion meetings are asking one question: “Do we trust this person to handle what comes next?” Vague assignments are where they start to gather the evidence.

Why this feels so hard

You spent 16 years in school learning that good work means following instructions. Every assignment had a rubric, tests had a prompt, and every project had a due date with a well-defined format.

Then you enter the working world, someone hands you something open-ended, and the instinct that’s worked your whole life stops working. In school, you succeed by asking for more information, dropping in on teacher office hours, and scrutinizing the rubric. But at work, that’s creative stalling and your manager can see it even if they don’t point it out.

The difference between school and work is that your manager doesn’t need you to get it right on the first try. They need momentum and ownership. An 80% answer timely delivered is worth more than a 100% answer they had to pull out of you. Your job is to take crap off your boss’s plate, not add to it.

If you’re a manager reading this, I’m sure you’ve watched this pattern on your own team. You’ll commonly see it in the talented new hire who keeps asking what exactly you want until you start wondering if they can operate without a script. It’s helpful to recognize that it’s rarely a motivation problem. Instead, they’re probably an over-achiever who thinks the goal is perfection. They’re still playing the school game becasue nobody told them the rules changed. Tell them in your next 1:1.

What actually works

Follow this decision flowchart as soon as you feel stuck:

I’ve been on both sides of this. I’ve been the person sitting at my desk not knowing where to start, and I’ve been the manager waiting for someone to come back with a direction instead of another question.

• If you don’t understand something, ask immediately. Not later or in a follow-up email. Ask in the conversation. The moment your manager finishes explaining and there’s a piece you don’t fully get, say so. “I want to make sure I understand. When you say, ‘take a look at onboarding,’ are you thinking about the first week or the first 90 days?” The longer you wait to clarify, the more work you do in the wrong direction. Asking in the moment signals confidence and treating your boss like a peer, while waiting three days to ask the same question signals that you’ve been spinning. It gives rookie vibes.

• Ask who’s done this before. One of the most underused questions in any workplace. “Has anyone tackled something like this recently? Is there someone I should talk to?” Junior folks perceive this as admitting weakness, but leaders do this instinctively: finding existing knowledge before building from scratch. Most organizations have someone who tried something similar six months ago. Their work, even if it was imperfect, gives you a starting point that saves you days.

• Find someone to partner with. The assignment landed on your desk, but that doesn’t mean you have to figure out every piece alone. “Is there someone on the team who would be a good thought partner on this?” This gets you help and it shows your manager you’re thinking about how to get the best result, not just how to survive the assignment. Bonus points if you succeed while working collaboratively and sharing the kudos with a peer.

• Vibe check your boss. Before you decide how to approach the work, figure out how your manager likes to work. Some managers want to brainstorm with you, think out loud together, and shape the direction as a team. Other managers want you to go away, come back with something, and only then engage. If you bring brainstorming energy to a manager who wants a finished draft, you’ll look unprepared. If you bring a finished product to a manager who wanted to shape it together, they’ll feel cut out. You can figure this out by watching how they work with other people, by asking directly, or by paying attention to how they respond when you check in. Their body language and energy will tell you everything.

• Write your own problem statement. Before your next check-in, write two or three sentences describing the problem as you understand it. What you think the goal is, who it affects, and what a good outcome looks like. You’ll be wrong about some of the framing, and that’s fine. A wrong problem statement that your boss or a senior peer can correct is ten times more useful than no problem statement at all.

• Do 25% of the work, then check in. Don’t wait until the project is 80% done to find out you went the wrong direction. Get a rough draft, a first pass, or an initial outline together and bring it to your next regularly scheduled one-on-one. “Here’s where I’m headed. Does this direction make sense, or should I adjust?” You’ve done enough work to show initiative, but not so much that changing course feels like a loss. Important: The key words are “regularly scheduled.” Use your next one-on-one that already exists on the calendar to check in. Don’t create new meetings for status updates on one assignment. Your manager’s time is a scarce resource and how you treat it tells them everything about how you think.

• Frame the check-in as partnering, not feeding. There’s a difference between “I’m stuck, can you help?” and “Here’s what I have so far. I’d love your input on the direction before I go deeper.” The first one creates drag while the second creates momentum. Even when you feel completely lost, lead with what you’ve done, not what you haven’t.

• If you’re really stuck, talk to a senior coworker. Not your manager, but someone you trust who’s a level or two ahead of you. They’ve been where you are and know which parts of the ambiguity are real problems. Sometimes you don’t need direction from your boss. You need perspective from someone who remembers what it felt like to be in your shoes. Even better if you can build a relationship with a peer of your boss. They can advocate for you directly, and that kind of lateral visibility is how careers accelerate.

• Use AI as a sparring partner. Drop in what you know about the problem, your assumptions, and your initial thinking. Use it to stress-test your direction, identify gaps, or generate a rough framework you can react to. Use AI for thinking, not for copy-pasting. If you hand your manager an AI-generated document that you haven’t actually processed and made your own, it will be obvious, and it will undermine exactly the trust you’re trying to build.

What will kill your credibility

I’ve managed enough people to know what this looks like from the other side. These are the things that will erode your manager’s confidence in you, even if they never say it directly.

• Don’t outsource the work and call it collaboration. Partnering with a colleague means you’re both contributing. Handing the hard part to someone else because you’re uncomfortable with ambiguity means you just transferred the test your manager gave you. They’ll notice, and the person you handed it to might get the credit for doing the work you couldn’t. Even worse, don’t hand in work without acknowledging who you worked with and how they supported you. Lone rangers are cool in movies, not in offices.

• Don’t paste AI output and present it as your thinking. Again, I can’t repeat this too many times: your manager will recognize AI slop, no matter what the AI detector may say. It reads differently and lacks the specificity of someone who actually wrestled with the problem. Once they suspect you’re pasting AI output, they’ll question everything you hand them going forward. Better approach: frame AI usage as part of your process. “I used ChatGPT to benchmark what others have done. You can see how I incorporated some of that thinking here and then refined it based on what I know about our business.” If you acknowledge it, you look innovative and resourceful. If you don’t, it makes you appear untrustworthy.

• Don’t go dark for two weeks and then say you’re stuck. This is the most common version of the problem and the most damaging. Silence isn’t neutral. When your manager doesn’t hear from you, they’re not thinking “they must be heads down working.” They’re thinking “I wonder if this is going to land.” Two weeks of silence followed by “I’m stuck” tells them you sat with the discomfort instead of doing something about it. Quick note: If you’re already in this spot, own it directly: “I want to be straight with you. I haven’t made the progress I should have on this. I should have asked for clarification earlier, and I didn’t. Here’s where I am and here’s what I’m planning to do next.” A good boss will respect the honesty. If your boss punishes you for that kind of directness, it might be time to start looking for your next role.

• Don’t ask for feedback on every micro-decision. Check in once or twice, but not daily or on every detail. If you’re coming back to your manager every day with a new clarifying question, you’re not reducing ambiguity. You’re creating a new kind of it. They start spending their time managing you instead of managing their own work.

Why this matters at every level

If you’re in college or just starting out, this is the gap between you and the intern who gets the return offer. It’s not grades or technical skills, it’s the ability to take a vague project and say, “here’s how I think we should break this up” or notice that no one taking notes in an important meeting and say, “I’ll take notes and send out next steps for everyone.” They’re driving clarity, which screams leadership material. Again, it’s doing the actions that prove they’re ready for the next role.

If you’re a few years into your career, this is the invisible wall between you and your next promotion. The people who get promoted fastest aren’t the ones with the best answers. They’re the ones who reduce ambiguity for the people around them. Every time you walk into your manager’s office with a defined problem, a proposed direction, and a list of assumptions, you’re doing what most of your peers won’t do for years. This is a key element of executive presence.

If you’re ten years in, you’ve noticed that the ambiguity doesn’t go away—it got bigger. The questions stopped being “what does my manager want?” and started being “what should this team be doing that nobody has asked for yet?” At senior levels, it means having the humility to be a beginner in emerging technologies that no one has brought to the team yet, like AI, and asking questions of junior peers or colleagues who have valuable insight.

Your move this week

Next time you get a vague assignment, before you ask your first question, write down three things: the problem as you understand it, one assumption you’re making, and a first step you’d take. Bring that to your manager instead of a question. It takes five minutes and it will change how they see you.

If this series is hitting home, forward it to someone in their first few years of work. It’s free, and it might be the thing nobody’s told them yet.

Share

Leave a comment

P.S. — I work with a small number of readers one-on-one to help them apply these frameworks to their own career. If you are at a moment where you need more than a newsletter, book one off or ongoing sessions here.

If you enjoyed this, here’s what to read next:

Welcome back to Career Field Guide: the weekly newsletter for people who want to build a career that holds up in the age of AI. If someone forwarded this to you, subscribe here.

AI Is Not Going to Take Your Job (But Here’s What Will)

It’s Sunday night and you’re doomscrolling again when another headline pops up: “Company X to cut 4,000 roles as AI adoption accelerates.” It feels like it’s only a matter of time before you become the headline.

The worst part is not the fear of being fired, it’s the fog of not really knowing what to do about it while you wait for the shoe to drop.

You’ll hear it a lot: “AI won’t replace you, a person using AI will,” but what do you do with that? At the heart of AI-related anxiety is the growing suspicion that the people around you are becoming that person using AI while you are falling behind.

I'm a researcher who helps some of the largest companies in the world navigate these decisions, and this past quarter I've traveled across the US and Europe to understand where AI is actually being implemented. I want to share what I'm seeing, but first, let's talk about you, because there are three mistakes I watch people make over and over again when the ground starts shifting underneath them.

Three Mistakes People Make

Most people respond to technological disruption in the same way, but I see this playing out specifically with AI anxiety in three ways:

Denial. "My job requires human judgment. AI cannot do what I do." The reality is that nearly 30% of the Fortune 500 are now live, paying customers of a leading AI startup. These are not historically early adopter companies. If the Fortune 500 is moving this fast, the "my industry is different" defense is collapsing. Sticking your head in the ground doesn't just cut you off from the opportunity, it builds a reputation as someone unwilling to grow.

Panic-skilling. On the other end, some people start signing up for every AI course, chasing a prompt engineering certificate, learning to code at midnight, and watching endless hours of AI content. This feels productive but rarely translates into anything your employer actually values. According to the World Economic Forum’s Future of Jobs Report, 81% of employers now prioritize demonstrated work experience over a degree when evaluating candidates, and only 14% view short courses or online certificates as meaningful hiring signals on their own. The skill gap employers care about is not “can you use AI” but “can you apply AI to real business problems in your domain.” Everyone should develop a base understanding of AI, but you need to be intentional before jumping into every shiny opportunity.

Freezing. Doing nothing while recognizing that things are truly changing. This is the most common response and the costliest, because the learning curve advantage compounds. Every month you wait, the gap between you and the person who figured it out widens. Unless you plan to retire in the next five years, AI will become a critical part of your work, so it is best to deal with it head on.

Now let’s look at what’s actually happening so you can make better decisions about what to do next.

How AI Is Transforming Companies

Before AI comes for your job, it's coming for your tasks. AI is not ready to massively displace humans, at least not yet. What's playing out is a more specific and useful story if you know where to look.

The data work is being automated first. Entry-level roles have historically been allocated to the unglamorous work of cleaning, validating, and making sense of data. Questions like “is this data right” and “do we trust these numbers” are increasingly being answered by AI. One of the clearest examples is in customer support, where AI agents are already handling higher ticket volumes, improving resolution rates, and raising customer satisfaction scores, all at lower cost than the status quo. There has also been a “TikTokification” of customer signals where a product goes viral and a company’s supply chain is not ready to capitalize. AI is built to find the needle in that haystack long after your entry-level analyst has left for the day. This is one of the most immediate areas where you will see a labor impact as companies simply need to hire fewer people for this type of work.

The talent question is wide open. Regardless of what you hear online, no one really knows what AI is fully capable of yet. Leaders are desperate for people in their companies to find ways to be meaningfully better at their jobs using these tools, but this is uncharted territory for most people. The best engineers at top companies are reporting productivity gains of 10 to 20x with AI coding tools. That number resets what "good" looks like for everyone. Executives are not eager to remove people because of AI (the technology is not ready, even if they wanted to), but they are having intense conversations about upskilling their people with AI so they can leverage these tools. There will also be an expansion of scope as these tools allow people to do things like write code with natural language, even if they are not on an engineering or data team.

Agentic workflows are moving from science fiction to production. The biggest unlock is not headcount reduction. It's taking a process that has always required five people managing multiple spreadsheets and redesigning it so an AI agent handles the data gathering and pattern matching while a human applies judgment at the decision point. This puts human attention where it actually matters and lets the machine handle the parts that never needed a person in the first place. Model capabilities are improving fast, with some domains showing 20 to 30 percent jumps in benchmark performance in just four months, and every major lab is investing heavily in long-horizon agents and computer use that opens up entirely new classes of work. The most valuable person on your team will be the one who can work with these tools while applying sound business judgment and finding novel applications across the business.

You're Not as Behind as You Think

If you feel like you've missed the moment on AI, you probably haven't. We are still early. But "early" does not mean "plenty of time." This is a great graphic from Ruben Hassid over at How to AI to remind us that there is a ton of opportunity still available.

The reality is that we’re early on AI, but it can feel like you’re behind when you’re constantly scrolling on TikTok or X and following people on the bleeding edge of OpenClaw or constantly analyzing Claude’s latest feature drop.

The real shift is that AI raises the baseline expectation for how fast you learn, how fast you adapt, and how quickly you deliver value in a new context. The people who cannot keep up with that new speed or who completely disengage are the ones who become expendable, not because a bot took their job but because someone else figured out how to ramp faster, upskill continuously, and operate at a level that used to take five years of experience to reach.

The photo above is of a room full of human computers. According to NASA, this team of women had been around since the Jet Propulsion Laboratory’s beginnings in 1936 and were responsible for the number crunching of launch windows, trajectories, fuel consumption, and other calculations that helped make the U.S. space program a success.

We have moved from human computers in the 1930s to agentic AI applications in 2026, but the reality is that ambitious people have always had to navigate technological disruption. The challenge is the same as it has always been: minimize mistakes and determine where to invest your limited time, capabilities, and resources.

What to Do Next

The executives I work with are not looking for all of their people to become software engineers. They are looking for people who learn fast, can translate between the technical and the human, and reduce the time between "we have a new tool" and "we are getting value from it."

Here is how to become that person.

Step 0: Build a foundation. Start with NVIDIA CEO Jensen Huang’s “AI is a 5-Layer Cake” to understand the essential infrastructure behind AI. In parallel, bookmark Anthropic Academy and sign up for a free course like this one on AI Fluency. You can also subscribe to their AI Fluency newsletter at the bottom of the academy homepage. These are free and give you a real foundation, not just buzzwords.

Step 1: Name your 90-day problem. Every role has a version of the onboarding question: what takes too long to learn or ramp up on? Maybe it is a new system, a new client’s business, a new market, or a new regulation. Name the thing that, if you could learn it twice as fast, would make you materially more valuable. If you are still in school, pick a topic or research area and run the same process.

Step 2: Use AI to compress your learning curve right now. Instead of investing thousands of dollars in an AI certificate, take the 90-day problem you just named and use AI to cut your ramp time in half this month. Upload a complex document you have been meaning to read and have AI break it down. Build a custom prompt that helps you prep for meetings in a domain you are still learning. Use AI to simulate a conversation with a stakeholder before you have the real one. The point is not to learn AI as a skill, but to get in the practice of using AI as a tool.

Step 3: Make your learning speed visible. It is not enough to get faster. Your manager and the people above them need to see it. This matters more than you think: research from Wharton’s Ethan Mollick found that while over 40% of workers are using AI at work, most are doing it secretly because they are unsure whether revealing it will be rewarded or punished. When you compress a workflow that used to take a quarter into a month, say so. When you use AI to prepare for a meeting and it goes well, mention the prep process. You are demonstrating that you are the kind of person who figures things out fast, and that is exactly the signal that gets discussed in promotion conversations and encourages others to mention your name to their network. Most of your peers are too cautious to step into that space, which is why it is an advantage.

Step 4: Become the person who makes AI work for your team. The biggest bottleneck in AI adoption inside large companies is not the technology. It is the need for someone to sit between the tool and the team and say, “here is how this actually applies to what we do.” That person becomes indispensable, not because they are technical, but because they reduce the learning curve for everyone around them. If you can be that person, it immediately increases your opportunities for promotion, interesting projects, and influence across your organization. This is also great content to share on LinkedIn. If you need help getting started on LinkedIn, I wrote here about how to find your voice and build your network.

A Prompt You Can Use this Week

Here is a prompt you can use today with ChatGPT or Claude to start compressing your learning curve:

You are a world-class executive coach and domain expert. I work as a [YOUR ROLE] at a [TYPE OF COMPANY]. I am currently trying to get up to speed on [THE THING YOU ARE LEARNING OR RAMPING UP ON]. I have about [TIME AVAILABLE] per week to dedicate to this.

Help me build a 30-day learning sprint. I want you to:

1. Identify the 20% of knowledge in this area that drives 80% of the value in my role

2. Create a week-by-week plan that prioritizes the most high-leverage concepts first

3. For each week, suggest one concrete action I can take to apply what I learned in a visible way at work (in a meeting, in a deliverable, in a conversation with my manager)

4. At the end, give me three questions I should be able to answer confidently after 30 days that would signal to my team that I have ramped up faster than expected

Be specific to my industry and role. Do not give me generic advice.

Use this on whatever you are ramping up on right now, whether it is a new system, domain, stakeholder group, research project, or market.

Subscribe now

The Bottom Line

The AI conversation is going to keep getting louder. The headlines are not going to stop, but the people who build careers that hold up are not the ones who panicked the loudest or upskilled the fastest. They are the ones who figured out how to learn faster than the world changed around them.

That skill will never go out of date, regardless of the technology.

P.S. — I work with a small number of readers one-on-one to help them apply these frameworks to their own career. If you are at a moment where you need more than a newsletter, book one off or ongoing sessions here.

Leave a comment

Share

If you enjoyed this, here’s what to read next

The first time I had a seat at the table deciding who gets promoted, I was surprised. I expected the conversation to be about goals and OKRs, but excellent work is table stakes. The real debate was about something else.

What became clear over the years is that promotions recognize two things:

1. Excellent work

2. Who we trust to handle what comes next

People are spending far too much time focusing on #1 as the way to get promoted when it really comes down to #2.

When someone is promoted, leaders are placing a bet that the person they're recommending will not make them look stupid amongst their peers and their boss. That means the person has to have already proven they can operate at the next level, not just perform well at the current one.

This is why so many high performers hit a ceiling they can’t explain. They’re doing everything right and watching someone else get the opportunity.

Subscribe now

The people who get promoted aren’t always the best performers. In fact, they’re likely top-half in performance but they’ve built relationships with the people making decisions, made their work visible to the right audiences, and positioned themselves as the obvious choice for the next opportunity. They demonstrated capability for the next level before they were given it.

The question isn’t “am I doing good work?” The question is: “what level am I operating on, and how do I demonstrate the next one?”

I built the Leadership Ladder to help you answer that question.

The (Invisible) Leadership Ladder

Level 1: Lead Yourself

Do your job well.

Leading yourself means you deliver reliably. You manage your time, your energy, and your commitments without someone standing over your shoulder. People trust you to do what you said you’d do, when you said you would do it, with excellence.

In the AI era, it also means you use AI tools to amplify your own output. Jensen Huang said it on Lex Fridman’s podcast: if he had to choose between two new graduates — one with no AI knowledge and one who’s an expert — he’d hire the AI expert every time.

• Technical Fluency at Level 1 means you’re aware of and using AI tools naturally. You know when to trust them and when to question them. You’re not afraid of the technology, and you’re not naive about it either.

• Business Judgment means you understand your role, you understand what success looks like for your team, and you make good decisions within your defined scope.

• Relational Depth at this level means people want to work with you. You're reliable, you're pleasant, and you raise the energy in the room.

At Level 1, grit matters more than genius. Most people think they’ve mastered this level, but many haven’t. If you can’t use AI to meaningfully improve your output, if people have to follow up with you to make sure things got done, or if your manager is still telling you what to do instead of trusting you to figure it out, you’re still working here.

Level 2: Lead Critical Work

Do work that impacts critical parts of your company.

Leading critical work means you own outcomes that matter beyond your own role. You're not only executing your tasks well but also taking ownership of problems that cross boundaries. You're trusted with your boss's work and leading efforts that are cross-functional.

• Technical Fluency at Level 2 is about driving productivity beyond yourself. You're the trusted human in the loop who is accelerating AI across a team or function. When an agentic system makes a bad call, the person who catches it needs to understand both the technology and the business context. That combination barely exists in the workforce right now, and it's highly coveted.

• Business Judgment means making good decisions with incomplete information. You’re not waiting for someone to tell you what to prioritize. You’ve built an ability to read a situation, understand the stakes, and act. This can’t be automated because it requires context, accountability, and the willingness to be wrong.

• Relational Depth shows up as earned trust, internally and externally. You influence people who don't report to you and raise the credibility of your team beyond its walls. You've built enough trust with the people making decisions that when a room is deciding who gets the next opportunity, your name comes up.

This is what separates the person who gets promoted from the person who gets a great performance review and nothing else.

Level 3: Lead The Organization

Shape the system that everyone else operates inside.

Leading the organization means your decisions set the conditions for hundreds or thousands of other people’s work. You’re accountable not just for outcomes, but for the structure that produces them. There are two sides to Level 3, and both have to be working.

The Internal Side: Building the Machine

Most people think leadership at this level is about strategy decks and executive presentations. It’s really about building the systems (teams, incentives, processes, and culture) that produce results when you’re not in the room.

I learned this at Amazon. The best senior leaders I worked under didn’t make better decisions than everyone else. They built organizations where good decisions happened without them. They hired people who were smarter than them in specific domains, created mechanisms that surfaced the right information at the right time, and spent their energy on the two or three bets that would change the trajectory of the business. Senior leaders are phenomenal people coordinators.

• Technical Fluency at Level 3 means you’re shaping how the organization uses technology, not just using it yourself. You’re making investment decisions about AI capabilities. You’re deciding which workflows get automated, which get augmented, and which stay human, and you’re accountable for those calls. The executives I talk to every week are making exactly these decisions right now, and most of them are flying partially blind because they don’t have enough leaders who understand both the technology and the operations.

• Business Judgment at this level is about allocating resources across competing priorities with long time horizons. You’re making trade-offs that won’t pay off for two years, and you’re building the case internally for why the organization should follow you there. This requires a combination of analytical rigor and storytelling that very few people develop.

• Relational Depth internally means you can move an organization. Not through authority, as anyone with a title can do, but through trust accumulated over time. The people three levels below you know what you stand for. Your direct reports run through walls because they believe you’ve got their back. When you reorganize a team or kill a project, people may not love the decision, but they trust the process.

The External Side: Representing the Enterprise

I once watched one of our executives resolve an urgent operations issue that our team had been navigating for days with a single text to a supplier’s CEO. That's what Level 3 relational depth looks like from the outside. Years of being credible, generous, and consistent in your industry, converted into a two-sentence text that solved in minutes what process couldn't solve in a week.

Level 3 also means you’re a face of the organization to the outside world. Customers, partners, regulators, investors, media, and talent you’re trying to recruit. You are trusted and expected to represent the company’s point of view in rooms where the stakes are real.

• Technical Fluency externally means you can translate what your company is doing into language that customers, partners, and the market understand. You’re the person a journalist calls for a quote, or a conference organizer invites to keynote, because you have a point of view informed by real operational data, not just opinions.

• Business Judgment externally means you understand how your company fits in the broader ecosystem (competitors, regulators, market shifts) and you position accordingly. You’re shaping how your company shows up in the broader business landscape.

• Relational Depth externally means your network creates value for the organization. A phone call from you opens a door that a cold email from anyone else wouldn’t. Customers trust your word and partners want to work with you specifically. Talent joins because of your reputation. Your network is the compounding return on years of showing up the right way in your industry.

The best leaders at this level are building something that outlasts their tenure. They’re developing the Level 2 people below them, creating conditions for the next generation of leaders, and making the kind of long-horizon bets that define what an organization becomes.

Why Performance Alone Won’t Get You There

If you’ve been reading Career Field Guide, you know that a great career requires two things working together: Performance and Optionality. (If you’re new here, the One-Pedal Trap is worth reading.)

Performance is doing your current job excellently. Optionality is building the skills, relationships, visibility, and positioning that create future opportunity. Most career advice focuses only on performance, which is like riding a bicycle with one pedal.

The Leadership Ladder explains why you need both. Performance keeps you at your current level. It earns you good reviews and trust, but it doesn’t earn your promotion because promotion isn’t a reward for the past. It’s a bet on the future and the people making that bet are looking for signals of the next level.

Those signals come from Optionality. The cross-functional project you volunteered to lead. The relationship with the VP who now knows your name. The time you made a judgment call on something ambiguous and it worked. The presentation you gave to a room above your pay grade. None of those things are your job, but all of them are evidence that you can operate at the next level.

Where Are You on the Ladder?

Here’s why this matters now: AI is compressing entry-level work across every industry simultaneously. Anthropic’s labor market data shows that the rate of young workers entering AI-exposed occupations has already dropped 14% since 2022. The executives I talk to every week aren’t waiting to see how this plays out. They’re restructuring teams, hiring differently, and asking “who can operate at the next level?” The gap between what AI can theoretically do and what it’s actually doing is massive right now. When that gap closes, the people who already climbed the Ladder will have a compounding advantage that’s very hard to catch. The window to move is open, but it won’t stay open forever.

Here are three questions to get an honest self-assessment:

1. Can you use AI to produce work that’s measurably better than what you’d produce without it? Not “I’ve tried ChatGPT a few times.” Can you sit down tomorrow, use AI tools as part of your actual workflow, and produce something faster, sharper, or more complete than you could alone? If the answer is no, you haven’t finished Level 1.

2. Have you owned a project or problem that crossed beyond your defined role where you had to coordinate with people who don’t report to you, make a call without being told what to do, and take accountability for the outcome? If the answer is no, you’re performing well at Level 1 but haven’t demonstrated Level 2. That’s the gap your manager sees, even if they can’t name it.

3. If your name came up in a room where you weren’t present, would someone advocate for your promotion? Not your direct manager doing their job. Someone else — ZAa VP, a peer leader, a cross-functional partner — who would say “that person is ready.” If you don’t know the answer, or if the answer is no, your Optionality pedal isn’t turning.

Pick the question where you answered no and spend 30 minutes this week doing something about it. Open an AI tool and build something with it. Volunteer for the project no one wants. Send a message to a cross-functional partner to understand more about their role. Even better, bring these concepts to your boss in your next 1:1 and ask them which level they see you operating at and how to improve.

The career ladder used to be something you climbed by showing up and doing good work for long enough. That ladder is being replaced and the one that’s taking its place rewards people who can operate at higher levels faster, who pair technical fluency with real business judgment, and who build the kind of relationships that make other people want to bet on them.

That’s the Leadership Ladder. And right now, the barrier to climbing it has never been lower — if you’re willing to put in the work.

Start building.

Inspired to keep reading? Bookmark this for your next interview!

In my years as a hiring manager, I saw the same thing happen over and over again.

Candidates would show up fifteen minutes early, dressed sharp, and walk me through a polished summary of everything they had accomplished, then go completely blank when I asked them about our company, our team, or the actual role they were interviewing for that day.

At Amazon and Microsoft, where a few hours of research online would have told you almost everything you needed to know, this was an immediate disqualifier. In a competitive process where interviewers are actively looking for reasons to cut the list, you just can’t afford to send such a costly signal.

Skills get you in the room, but preparation is what gets you the offer.

The good news is that looking unprepared is completely avoidable. Before your next interview, you need to be able to answer three questions that every hiring manager is asking, whether they say them out loud or not. Hiring managers aren't just testing your answers. They're testing your preparation, because how you prepare for an interview is usually how you prepare for everything else.

The Three Questions

01: Why this Industry

What they're really asking: Do you understand the world this company operates in, or are you just here because we were hiring?

This question gets fumbled constantly because candidates reach for something safe rather than something true. When I was hiring for a renewable energy developer, candidate after candidate told me they wanted to help the environment. After hearing such a generic answer continually, it stopped sounding like a reason and started sounding like a lazy placeholder for deeper thought. Experienced interviewers have heard enough of those that they function almost as a red flag.

The fix is simpler than most candidates think. Spend thirty minutes before your interview reading 2-3 recent industry news pieces and identify something happening in the space that you find genuinely interesting. Something interesting enough that you could talk about it for five minutes without running out of things to say. When you can tell an interviewer something specific about the industry they’re operating in, you’ve already separated yourself from most of the candidates who walked in before you.

02: Why this Company

What they’re really asking: Did you spend time learning about us (our website, our podcast, our press releases) or are you mass-applying to every company?

Start with the company website and read it like you’re preparing for a conversation, not skimming for keywords. Understand their mission, their current priorities, anything notable in their recent news. If they have a podcast or a founder who speaks publicly, spend an hour there and you will hear things that don’t appear anywhere in the job description. Referencing those learnings in an interview signals a level of genuine interest that almost no other candidate will match. If the company is publicly listed, ask Claude or ChatGPT to summarize their last earnings call and what has recently impacted their stock price.

Research the specific team you’d be joining. At larger companies especially, understanding the team’s function and current priorities is an entirely different preparation from understanding the company broadly.

Look up your interviewers on LinkedIn as soon as you know their names. LinkedIn notifies people when you view their profile, and checking five minutes before the interview communicates exactly the kind of last-minute scramble you’re trying to avoid.

Prepare two or three questions that couldn’t have been answered by a quick Google search. The questions you ask at the end of an interview reveal as much about your preparation as anything you said during it. The ones that stick are the ones that reference something specific: a team priority, a recent company move, something from your research that you’re genuinely curious about. Interviewers remember those questions after you’ve left the room.

Subscribe now

03: Why this Role

What they're really asking: Can you connect your story to this job in a way that makes sense or are you just looking for any job?

Most candidates can tell you what a role does. What they can’t tell you is why they want this role specifically, and not just any role at this company.

I’ve interviewed plenty of supply chain candidates who could tell me they wanted to work in our organization. Almost none of them could tell me why sourcing over planning or logistics, and what in their background made them the right fit for that function specifically.

Before your next interview, go back to the job description and read it differently. Instead of scanning for keywords that match your resume, ask yourself why this role exists. Is it a new capability being built from scratch, a team scaling into new territory, or a function being restructured around changed business priorities? Understanding the purpose behind the posting gives you a positioning angle that generic candidates never find. More importantly, it forces you to answer the harder question: given everything you know about this role and why it exists, why are you the right person for it and not just someone with relevant experience?

Then prepare your stories. Identify five to seven specific examples from your experience that demonstrate the skills this role requires and write them out, because writing forces the clarity that mental rehearsal doesn’t. Know your results specifically since hiring managers remember numbers and forget adjectives. The difference between “we significantly improved delivery performance” and “we reduced fulfillment delays by thirty-one percent over two quarters” is the difference between a story that lands and one that evaporates. We’ll dive deeper into how to prepare these stories next week.

After the interview, follow up within twenty-four hours with a short, specific note to each person you spoke with. Reference something real from your conversation, not a summary of your qualifications. If you don’t have their emails, send the notes to your recruiter and ask them to pass them along, then connect with each interviewer on LinkedIn with a brief message. It takes fifteen minutes and most candidates don’t do it.

Using AI to Prep for Interviews

There’s a line going around that says some people use AI to improve their thinking, and some people use AI so they don’t have to think.

AI genuinely earns its place in interview prep when you use it to compress research. Feed Claude or ChatGPT a job description and ask it to surface the company’s recent strategic priorities, the industry pressures the hiring manager is likely navigating, or the questions a smart executive in that role is probably asking themselves at night. What used to take three hours of LinkedIn rabbit holes and earnings call transcripts can now take twenty minutes.

The lazier version is generating polished answers to likely interview questions and memorizing them. That works right up until your interviewer does what every good interviewer does and pushes on a decision, asks you to go deeper, or follows a thread you didn’t expect. If the answer came from AI and not from your actual experience, you’ll go quiet at exactly the wrong moment.

The rule is simple: use AI to understand the company and its context. Use your own thinking to answer questions about what you’ve done and why. Those are the only answers that hold up under pressure because they’re the only ones that actually belong to you.

The Bar Just Got Higher

AI has made applying nearly frictionless, which means hiring managers are wading through more candidates than ever, most of whom spent thirty seconds submitting a resume and assumed the interview would take care of itself.

When you finally get the interview, take the time to prepare well and then knock it out of the park.

Leave a comment

Know Someone Interviewing or Looking for a Role?

Forward this article to them and encourage them to subscribe for weekly posts on career building in the age of AI disruption.

Share

Inspired to Keep Reading?

It was great to be at SXSW this week. It took being in the back of a Zoox autonomous vehicle to be reminded that we are living in unprecedented times.

Now, maybe more than ever, you’ve got to have a plan for your career.

Three Doors into Every Job (And Why Everyone's Crowding the Wrong One)

Right now, somewhere, a smart and hardworking person is being told their resume isn’t optimized enough. They’re paying someone to rewrite it, or watching TikToks on ATS keyword matching, or spending their Saturday writing cover letters for roles they’ll never hear back about because the hiring manager already knows who they’re going to call.

This is the junk that passes for career advice in 2026.

There are three doors into every job. Nobody tells you this, but here’s what they are, how they work, and which ones are worth your time.

The Front Door: Why the Job Posting Is a Lottery Ticket

The front door is the job posting — the lottery ticket that everyone keeps buying.

It used to be a reasonable bet, but AI and mass applying (thanks, LinkedIn) has made it nearly worthless.

When applications cost nothing to produce, everyone applies everywhere. A motivated candidate and a disengaged one submit identical-looking resumes in the same thirty seconds, and hiring managers end up drowning in hundreds thousands of polished, tailored submissions that are functionally indistinguishable from each other. The resume stopped being a signal a long time ago, and AI finished it off.

What that means practically is that spending hours improving your resume to compete through job postings is optimizing a lottery ticket. In mass-applying to hundreds of jobs, you’re not improving your odds in any meaningful way. The people who understand the other two doors are building their careers in a way that actually works.

The front door isn’t closed, it’s just the most crowded, lowest-signal entry point that exists and it’s getting worse every month.

The Side Door: The Humble Path That Actually Works

The side door is the role that gets you close to the one you actually want, even if it isn’t the one you’d choose if you had a choice.

Early in my career, my target was a corporate supply chain role at Starbucks. What I had was a job at one of their manufacturing facilities, working early shifts leading a team on the floor. Most people in that situation put their heads down, perform well, and wait for something to open up. I did something different with the interactions I was already having.

Supply chain planners, operations managers, people I exchanged emails with in the normal course of work, I started treating those transactions as the beginning of something rather than just getting the task done. After my shift, I’d send a short note:

“I’ve enjoyed working with you on this and would love to connect over coffee sometime.”

A lot of people said yes, and one of those conversations eventually led to a sponsor who opened the door to the corporate role I’d been working toward. None of it happened during work hours, but in my “off” time I could have spent doing something else.

The side door requires patience and some ego management. The role you take to get inside might feel beneath your experience, and that’s fine, because what you’re actually buying is proximity, visibility, and the chance to prove yourself to people who make real hiring decisions. Internal candidates succeed at dramatically higher rates than external applicants for the same roles because trust is already established and your name is already known. You’re not compromising on your goals by taking the side door. You’re taking the smarter path to them.

The Back Door: The Role That Finds You

The back door is the role that finds you before you go looking for it.

No application, no posting, no competing against four hundred other people. Someone already inside the organization thought of you when a need arose, reached out directly, and the conversation became an offer. This isn’t luck, even though it can feel that way from the outside. It’s the result of years of consistent, visible presence in the right circles — sharing your thinking on LinkedIn, building genuine relationships before you need them, and being useful to people in rooms you want to eventually be in yourself.

Your network works like concentric circles, and the most valuable connections are often already around you. Former colleagues, classmates, alumni networks, people you work alongside every day. You don’t need to cold-email executives to start building. You start with the people already in your orbit and work outward from there over time.

The back door is rare, but it is never accidental.

The Question You Should Be Asking Before You Need a Job

At some point you will be laid off, restructured, or simply ready to leave. When that day comes, you’ll have one of two things: a network that already knows your name, or a resume and a stack of applications.

Most people only have the resume, and not because they’re lazy or unambitious. Nobody told them the other doors existed. The career advice industry is built entirely around the front door, and the courses and services and career centers optimizing your keywords all assume that the job posting is the game. It isn’t. It’s the most competitive, lowest-return version of the game, and technology is making it harder every month.

The resume gets you a ticket to the lottery. The side door takes patience and hustle as you actively build your network. The back door takes years and the best time to start is before you need the help. Both of them build something that the front door never will, and both of them start with decisions you make long before you need a job.

You already know which one you’ve been building toward. The more useful question is what you do differently starting now.

Why Most Careers Run on One Pedal

There’s a framework I come back to constantly when I think about this. A great career runs on two pedals working together. Pedal One is performance — doing your current job well, delivering results, being someone people can count on. Pedal Two is optionality — building the skills, relationships, and visibility that create future opportunity.

Most people only focus on performance and end up stuck in the one-pedal trap. They perform, and they wait. They assume the work will speak for itself and someone is paying attention. Sometimes that’s true. More often it isn’t, and they find out the hard way in their forties when the layoff comes and the network they never built isn’t there.

The three doors are Pedal Two made concrete. The side door and the back door don’t open by accident. They open because someone spent years building relationships, showing up in the right rooms, and making themselves visible to the right people.

The resume is Pedal One on a job application. It matters, but if it’s the only thing you’re building, you’re riding a one-pedal bike and wondering why you keep falling over.

Subscribe now

Inspired to keep reading?

This past week I was in Scottsdale with a room full of Fortune 500 COOs and Chief Supply Chain Officers. Executives managing billions in operations, thousands of employees, and supply chains that touch every product you’ve bought in the last week.

The conversation wasn’t abstract. Thirty years of globalization are being unwound in real time, AI is moving faster than governance can keep up, and behind closed doors, the people doing the hiring were asking the same question out loud: where are the people who can actually navigate this?

That question has a direct answer and if you’re building your career, it’s the most important thing you can understand right now.

The Market in Splitting in Two

There’s two competing versions of what’s happening for people in the job market right now:

1. Catastrophe: AI is coming for everything, your degree is worthless, learn a trade or drive for Uber (until they’re all autonomous too).

2. Optimism: Don’t worry, new jobs always emerge. Technology creates more than it destroys. It will be fine.

Neither is quite right. The more accurate version is that the job market is genuinely difficult1 and a specific kind of person is thriving.

Hiring for college graduates is down 16% compared to last year and 44% below 2022 levels2. Companies are pausing hiring not because they don’t need output, but because AI and digitization is making it cheaper to get output without headcount.

At the same time, according to The Wall Street Journal, base salaries for AI-skilled workers with zero to three years of experience grew 12% from 2024 to 2025, the largest gain of any experience group. At companies like Scale AI and Databricks, 22-year-olds are making $200K base before equity. Databricks CEO Ali Ghodsi told the Journal: “Under 25, you can be making a million.3”

The market isn’t collapsing: It’s bifurcating and the divide isn’t really about age or even technical skill, it’s about something harder to name and harder to fake.

What the people doing the hiring decisions are actually saying

Every executive I spoke with in Scottsdale is wrestling with the same gap.

They can’t find people who are technically fluent and have real business judgment. They also can’t find experienced operators who are genuinely excited about embracing new AI tools. The person who sits comfortably in both places barely exists.

This isn't a small problem. When an agentic system makes a bad call, it can ripple into hundreds of millions of dollars of disruption before anyone catches it. The human in the loop isn't a formality; they're the last line of defense. That person needs to understand the technology well enough to question it, and the business well enough to know when something is wrong.

That person is extraordinarily rare, every executive I know is looking for them, and you can become that person: the full-stack worker.

The Full-Stack Worker

A full-stack engineer works across an entire system, not just one layer. The Full-Stack Worker is that idea applied to being human at work.

Three qualities that function as a system with each layer making the others more powerful:

1. Technical Fluency. Not necessarily a CS degree, but genuine comfort with AI tools, data, and the systems shaping your industry. Enough to use them, question them, and improve them. The bar here is curiosity more than credentials, but those who go technically deep will be rewarded with pay and opportunities.

2. Business Judgment. The ability to read a situation, understand what’s actually at stake, and make a call when the data is ambiguous, which it always is. This is what executives mean when they say they can’t find good people. Judgment can’t be automated because it requires context, stakes, and accountability.

3. Relational depth and grit. The ability to make people want to work with you, follow you, and bet on you combined with the stubbornness to do hard things without being asked. Not charm as a substitute for competence, but as a multiplier of it.

An AI agent can execute, generate, and optimize. It cannot walk into a room, make a judgment call under pressure, and make people want to follow them. That’s still a human thing. In 2026, make it your thing.

🤖 Bookmark this article for a step-by-step guide to build AI fluency and create portfolio-ready proof you can bring to your next interview or annual review.

The Window is Open

Nobody has ten years of AI experience yet. The ceiling on how fast you can close the gap on a 45-year-old with decades of institutional knowledge has never been lower. Most Fortune 500 companies are still figuring out how to move past AI pilots, which means the people who can bridge technical fluency, business judgment, and relational depth are needed right now, not in five years.

This window won’t stay open indefinitely. The people who get after it in the next two or three years will have a compounding advantage that’s very hard to close later.

The executives in that room in Scottsdale are looking for someone. That someone could be you. Start building.

Career Field Guide is a newsletter for early-career professionals building AI-resilient careers. If this resonated, forward it to someone who needs it or subscribe below.

Subscribe now

Week 4 of a four-part series on building career resilience.

• Week 1: You vs the Robot

• Week 2: “I’m Comfortable With AI” Is the New “I Know Excel”

• Week 3: Stop Waiting to Be Discovered

• Week 4: Developing Cross-Domain Fluency

Subscribe now

I was recently in Paris for work and was reminded how disorienting it is to move through a place where you do not speak the language. Even small tasks, like ordering a coffee, suddenly require a lot of effort when you can’t easily communicate in a common language.

Inside companies, cross-functional work often works the same way. Each department speaks its own strategic language, so when different teams work on the same project they end up talking past one another. Progress, therefore, depends on the people who can translate between them.

When I joined the Amazon team building Project Leo, I might as well have been in Paris. Sitting with engineers planning component procurement, staring at intricate design documents, and watching CAD files update in real time, it quickly dawned on me that I needed to learn their language or the project would stall. In other words, I had to become the Rosetta Stone who could translate between supply chain and engineering.

The shrinking value of one good skill

AI is getting excellent at executing tasks. What it still struggles with is asking the right question and making sense of the answer in context.

The analyst who built better Excel models than anyone on the team lost that edge the day everyone got Copilot. The same thing is happening across every domain, faster than most people realize.

This is already happening at the organizational level. Jason Calacanis — one of the besties on the All-In podcast — published a post last month announcing that his firm won’t hire another human employee for at least a year or two. His AI agents handle 20% of the firm’s tasks and improve 10% every week. His conclusion: adding a human to the team has become a “luxury spend.”

He also noted that at his firm, the roles of product manager, UX designer, and developer are merging. One person with the right AI tools now does the work of all three. The specialist who mastered one of those roles has a problem. The person who understands all three has an opportunity.

What AI still cannot do is move between domains. It can’t understand the incentives of a finance team well enough to know which supply chain tradeoffs they’ll accept. It can’t translate what an engineering team is building into what a sales team can actually promise. It can’t sit in a room where operations, product, and customers are all pulling in different directions and find a path forward.

That’s cross-domain fluency. And the research backs it up.

David Epstein spent years studying the world’s top performers across sports, science, and business. His finding, published in Range is that in complex, unpredictable fields (which is every field now), generalists consistently outperform specialists. A study of nearly 400 MBA graduates found that those with broader cross-functional backgrounds received more job offers than their specialist peers and in some cases earned up to $48,000 more.

McKinsey’s research on the emerging agentic organization goes further. The most valuable human workers in an AI-first company, they found, are what they call “M-shaped supervisors” or people with broad fluency across multiple domains who can orchestrate AI agents and human teams simultaneously. The World Economic Forum estimates that nearly 40% of current skillsets will be overhauled or outdated by 2030.

The specialist isn’t disappearing, but the specialist who can only operate inside one domain is quickly losing value.

The two traps

Most people pick one of two losing strategies.

The first is specializing and staying there. Depth feels safe and allows many to get promoted early in their careers, but this is where many stop developing range. AI is now compressing the value of their single-domain skill, the same way it compressed the value of knowing more Excel than anyone else in the room. By the time the ceiling appears, it’s too late to start building fluency elsewhere.

The second is knowing a little about everything and being indispensable to no one. This is the person who can speak every team’s language well enough to seem valuable but isn’t the person anyone calls when something actually has to get done. This person is classic style over substance and may build some credibility early on but is revealed as lacking depth over time.

To be successful in an AI-first world, you need a better strategy. You should develop one primary domain with real depth, plus one adjacent domain with working fluency. Enough to understand how decisions get made on the other side of the table, and enough to be taken seriously when you’re sitting at it.

Which adjacency to pick

Your best adjacency is usually the domain that controls whether your work gets funded, approved, or acted on.

• Engineering: product or finance — the people who decide what gets built and whether it’s worth building.

• Data science: communication and storytelling, because insights that don’t move decisions don’t move organizations.

• Marketing: sales or operations, because promises need to be deliverable.

• Supply chain or Operations: finance, because every operational decision eventually becomes a business case, and the people who can build that case themselves are the ones who get resources.

• HR: technology, because the future of that function is building systems, not administering processes.

• Design: sales or market research, because design decisions backed by data analysis become strategic defensible investments.

You don’t need to become an expert. You need to know enough to ask smart questions, understand the answers, and translate between your world and theirs.

What about AI skills?

Regardless of your domain + adjacency pairing, everyone should be building AI fluency in parallel. Here’s a step-by-step guide to start building basic AI fluency in 30 days.

Three things to do this week

• Tonight: Name your adjacency. Write down one sentence: “My primary domain is [X]. The adjacent domain I need to develop fluency in is [Y].” If you’re not sure, ask yourself who says yes or no to what you’re trying to do. That’s your adjacency.

• This week: Have one real conversation. Find one person in that domain and ask for 30 minutes. The message: “I’m trying to understand how [their function] actually works in practice. Would you be willing to meet for 15 minutes (coffee or call) so that I can ask 3-5 questions?” When you’re there, ask them: “What’s a decision you make regularly that people outside your function almost never understand correctly?” Don’t sell yourself. Just use the time to learn and follow up with a thank you email or text.

• This month: Get in a cross-functional room. There is a project happening in your organization right now that spans your domain and your target adjacency. Volunteer for it. You don’t need to be the expert; you just need to be in the room. Fluency doesn’t develop by reading about it. It develops by having to use it under real conditions, when something is actually at stake.

The compounding effect

Over the last four weeks, we’ve discussed how AI fluency amplifies your performance, strong relationships build career optionality, and cross-domain fluency multiplies both.

In the years ahead, every company will have specialists and AI tools. The advantage will belong to the people who become the Rosetta Stone between them.

Subscribe now

Inspired to keep reading?

Week 3 of a four-part series on building career resilience.

• Week 1: You vs the Robot

• Week 2: “I’m Comfortable With AI” Is the New “I Know Excel”

• Week 3: Stop Waiting to Be Discovered

Subscribe now

The Job Application Process is Broken

AI didn’t just change how we write resumes, it changed the economics of hiring. For $20 a month, anyone can generate a clean, well-written, ATS-optimized resume and a tailored cover letter for every job they apply to. The marginal cost of sending one more application is effectively zero, so people don’t send five applications anymore. They send fifty or hundreds.

That may feel empowering for candidates, but it’s a supply shock from the hiring side. When everyone can bypass the qualification process and look qualified on paper, resumes stop being a signal and start being noise. Hiring teams respond the only way they can: they stop relying on the application process and start relying on their people to recommend candidates.

Last week, I argued that AI fluency is the skill that gets you in the room. Wall Street Journal shared this week that grads with AI skills are in high demand. That said, it is increasingly true that a human is what will actually get you in front of a hiring team.

This week, we’ll unpack how to build strong relationships that open doors for you throughout your career.

The Math Nobody Wants to Hear

If you graduate with 200 people who share your major, you don’t have 200 peers. You have 199 near-substitutes. Add in the impact of globalization and the power of AI tools, it’s become clear that most college degrees have become commodities to the point that many are debating whether a college degree is still worth it at all.

Generative AI has created a market where:

• The cost of applying to a job is near zero

• Everyone’s resume and cover letter looks essentially the same

• The volume of applicants per role has exploded

Imagine a hiring manager posts a role on Monday morning. By Tuesday, they have 1,000 applications. Nine hundred of the resumes are clean, well-written, and “tailored.” Two hundred are genuinely good. Fifty are great. Five come with a trusted internal referral or a note from someone they respect. Guess which people are going to get the first interviews.

As Scott Galloway illustrates above, most hiring decisions are effectively made before the job posting ever goes live. 70% already have an in with the hiring team and the job posting is often just the compliance layer on top of a decision that’s already forming.

If no one is willing to vouch for you, you’re competing for the leftover 30% of roles in the most crowded, AI-saturated, and commoditized part of the market. That’s not a winning strategy.

The Career Bicycle That Might Save You

I want to introduce you to my Career Bicycle Framework™. Think of your career like a bicycle that runs on two pedals: Performance, the work that earns you a paycheck, and Optionality, the relationships that earn you a future.

Most early-career professionals obsess over Pedal One. That makes sense because performance is concrete, shows up in reviews, and gets you promoted.

Pedal Two is what gives your career resilience. It’s what creates opportunities when your team gets cut, your company reorganizes, or your manager changes. It’s what turns a cold job search into a warm introduction. It’s also what leads to once-in-a-lifetime opportunities that you may not be fully qualified for yet.

Performance, by itself, is becoming more commoditized over time as people leverage LLMs throughout their workday. Trust, reputation, and human endorsement are becoming more valuable.

• Pedal One = Keeps You Employed

• Pedal Two = Keeps you Employable

The Two Traps Early-Career Professionals Fall Into

In the first decade of your career, I see the same two mistakes over and over.

Trap #1: Waiting

Let’s call her Mary.

Mary is great at her job. She’s competent, reliable, and consistently delivers strong work. She tells herself things like, “If I just keep performing, I’ll get noticed,” or “I’m not really into networking, I just want to do great work.”

Mary believes the system will eventually reward her and while sometimes it might, often it does not.

When a reorg hits, or a manager leaves, or her team gets cut, Mary discovers something uncomfortable: almost all of her career equity is locked inside her current org chart. Outside her team, very few people know her work and even less would go to bat for her.

She wasn’t wrong to focus on performance (Pedal One), but she was wrong to think it was enough to accelerate a great career.

Trap #2: Spraying

Now meet John.

John is charismatic and ambitious. He believes volume is the game. When he sees a role posted on LinkedIn, he immediately messages the hiring manager or recruiter with a short note and his resume. Sometimes he references the wrong role and it’s clear most of his messages are written by AI, but he thinks this is all part of network building.

In reality, John’s burning social capital before he ever builds any and annoying a lot of people in the process. People don’t remember strangers and they definitely don’t vouch for them.

Both Mary and John may occasionally get lucky, but neither is building a system that compounds over time.

How to Actually Build Strong Relationships

Start Early (and Make It Boring)

Most people only start “networking” when they’re laid off or desperate for a job. That’s exactly when it feels transactional, awkward, and self-serving. People can feel that energy from a mile away.

The best relationships are built when you don’t need anything. You need to treat Pedal Two activities as a normal, continuous part of your career.

Start close:

• Book regular 1:1s with coworkers (even if it’s 1x per quarter)

• Build relationships across functions

• Default to yes for coffee, lunch, and happy hour invites

Then widen the circle:

• Clean up your LinkedIn

• Engage thoughtfully online with people in your field

• Have one real conversation a month with someone outside your company

This positions you to build strong internal and external relationships, which are critical to building your career over the long term.

2. Put Yourself Where Opportunity Can Happen

When I was at Starbucks, I started in manufacturing but wanted to move into corporate roles. That meant finishing a 10-hour shift south of Seattle and then driving north to the corporate office just to have coffee with people doing the jobs I wanted one day.

This was inconvenient and exhausting, but it eventually worked. Those conversations led to a corporate role and multiple mentors, some of whom still shape my career today.

I also moved my entire family from Seattle, WA to Austin, TX for a career opportunity that provided outsized impact and scope, relative to my previous experience. Not every action needs to be as dramatic, but you do have to put yourself in places that provide opportunity.

You can start online, but the strongest ties are built over coffee, meals, projects, and shared context. Put yourself in rooms, cities, and conversations where the kind of work you want is actually happening.

Do Cool Stuff (in Public)

Visibility and action create a surface area for luck and opportunities. Build cool things, share what you’re learning, get curious with AI, and create products or tools that show how you build, not just what you’ve been assigned at work.

You don’t need to be impressive. It’s far more important to 1) get started on something and 2) build momentum as you iterate and make it a habit. You can start with any of the below:

• A simple newsletter

• A GitHub project

• A YouTube channel

• A short LinkedIn post explaining something you just learned

People are drawn to momentum. They remember people who are working on cool stuff, and, over time, this creates something far more powerful than a resume: a reputation and network that you can rely on for decades.

Time to Take Action

AI didn’t make relationships “nice to have,” it made them the moat for your career.

This week, do three things:

1. Book one conversation with someone you don’t need (yet).

2. Share one small piece of work in public.

3. Help one person with no immediate upside for you.

Next week, I’ll close this series by unpacking the final pillar of career resilience: how to develop cross-domain fluency. This will cover the ability to move between domains, translate between worlds, and stay valuable even as roles, tools, and org charts keep changing. Subscribe below to get the article in your inbox next Thursday!

Subscribe now

I write Career Field Guide to give young people the roadmap I never had. No paywall, no gatekeeping — just practical guidance from someone who’s been in the seat.

☕ If it’s been useful, buy me a coffee to keep it going!

Buy Me a Coffee

Inspired to keep reading?

Week 2 of a four-part series on building career resilience.

• Week 1: You vs the Robot

• Week 2: “I’m Comfortable With AI” Is the New “I Know Excel”

• Week 3: Stop Waiting to Be Discovered

• Week 4: Developing Cross-Domain Fluency

Subscribe now

What COOs Actually Want From the Next Generation

I spent 15 years as an operator before I started advising the people who run large organizations. Now I sit across from COOs and Chief Supply Chain Officers asking what they can’t find in the next generation of talent.

Three capabilities come up every time: AI fluency, relationship depth, and the ability to think across domains. This series is my attempt to translate what they’re asking for into a playbook you can actually use.

The Opportunity Nobody Is Capturing

Only 6% of organizations have turned AI into measurable business impact. Meanwhile, 42% abandoned most of their AI initiatives this year. The bottleneck was never the tool—it was the judgment of the people using it. That gap is where your career opportunity lives.

The Productivity Gap is Already Happening

In a PwC survey of nearly 50,000 workers,1 daily AI users were dramatically outpacing their peers: 92% reported productivity gains (versus 58% for infrequent users), 58% felt more job secure (versus 36%), and 52% saw salary increases (versus 32%). That 30 minutes a day compounds to roughly 130 hours a year—time power-users reinvest into higher-visibility work and the contributions that lead to faster promotions. The difference isn’t talent or technical background, i’s habit. And habit is learnable.

“Try ChatGPT!” is not a Strategy

Using AI to rewrite your resume or summarize an article is the equivalent of using Excel to make a grocery list. It works, but you’re nowhere near the real capability of the tool.

Learning science calls this the experience trap — confusing familiarity with mastery. You can use ChatGPT every day for a year and still be a novice if you’re always asking the same kinds of questions the same way. What changes the trajectory is structured experimentation with increasing stakes—and producing something you can show.

This 30-day challenge is designed so you can start tonight with ten minutes and zero background in AI.

The Career Bicycle in Action

If you've been following along, you know the Career Bicycle runs on two pedals: Performance (what you can do) and Optionality (who knows you can do it). Most people treat AI learning as a solo, private activity and get stuck in the one-pedal trap.

This challenge is designed to turn both simultaneously. Your learning becomes visible, which means it compounds beyond the skill itself.

The payoff is that in 4 weeks (or less) you can develop genuine AI skill and have multiple interview- or review-ready artifacts that you can add to your portfolio.

Week 1: Stress-Test the Tool

Goal: Understand where AI is strong, where it confidently falls apart, and build the verification muscle to tell the difference.

In 2024, 39% of AI-powered customer service bots were pulled back or reworked because they were confidently giving customers wrong information. Air Canada got forced by a tribunal to honor a discount after its AI chatbot invented a bereavement fare policy that didn’t exist.2 A lawyer submitted court filings citing legal cases that AI fabricated out of thin air—twice, in separate cases.3

Companies need people who can catch these mistakes before they become expensive. That skill—verification—is one of the most valuable and underrated things you can walk into an interview with.

The Exercise:

• Pick one AI tool (Claude, ChatGPT, or Gemini) and subscribe for the premium version (download on your phone for ease of access)

• Register for Claude 101 (free) or watch the video below to the building blocks of prompt basics and AI Fluency.

• Then, as the week progresses, deliberately try to break the model in your domain. Give the model questions you already know the answers to, feed it contradictory constraints, ask about edge cases, and grade its responses.

Start here - copy this prompt:

“I’m a [your field] professional. Explain [core concept in your domain] as if you were briefing a hiring manager. After your explanation, list the three most common mistakes people make when applying this concept in practice.”

Read the response, grade it, and then follow up:

“What might be wrong or incomplete about the explanation you just gave me? Where would an expert in this field push back?”

That second prompt is the one that builds real skill. You’re training yourself to interrogate AI output—the exact judgment that employers are paying a premium for.

Your artifact: A one-page “AI Blind Spots in [Your Field]” document. List three to five specific examples of where AI got it wrong and what the correct answer is. This becomes an interview talking point and you can post it on LinkedIn tonight after even one round of this exercise.

Week 2: Build a Repeatable Workflow

Goal: Move from one-off prompts to a repeatable human+AI process you can describe, repeat, and improve.

The gap between AI users and AI power-users are systems and processes for partnering with models. Interviewers increasingly ask candidates how they'd use AI in the role. Having a real workflow to describe is the difference between a generic answer and a memorable one.

The Exercise:

• Check out the Claude for Work course to get a sense for the difference between personal vs professional capabilities that LLMs offer.

• Pick one recurring deliverable from your work or coursework (a weekly report, competitive analysis, or project update).

Then run this four-step loop:

1. You define the problem and constraints (what question are we answering, for whom, with what limitations)

2. AI generates a first draft using a detailed prompt that includes context, audience, and format

3. You evaluate, correct, and refine—this is where your judgment lives

4. AI iterates based on your feedback, now it’s working with your expertise, not replacing it

Use this prompt to start:

“I need to create a [deliverable type] for [audience]. The goal is [specific objective]. Key constraints: [time, data available, scope]. Please draft a first version, and flag any assumptions you’re making so I can correct them.”

That last line—“flag any assumptions”—is critical. It forces the AI to surface where it’s guessing, which gives you clear targets for applying your judgment. Run this loop on the same type of deliverable at least three times this week, improving your prompt each time.

Your artifact: A before/after comparison. The AI's first output next to your final version, with annotations on what you changed and why. This demonstrates exactly the kind of judgment AI cannot replicate.

Week 3: Build Something Real

Goal: Produce a professional-quality deliverable that demonstrates AI-augmented thinking.

Anyone can write "comfortable with AI" on a resume. Very few can show a concrete example like AI-generated analysis with their judgment layered visibly on top.

The exercise: Using the workflow from Week 2, produce something relevant to the job or field you're targeting. If you've never built a deliverable like this before, ask AI to show you three examples of the format, then use the strongest as your template.

• Business or strategy: A competitive landscape analysis of a company you’d want to work for.

• Engineering or data: A technical comparison of approaches to a problem in your field.

• Marketing or communications: An audience analysis and content strategy for a real brand.

• Operations or supply chain: A process improvement proposal grounded in implementation realities.

The key: don’t hide the AI. Explicitly show where AI contributed and where your judgment improved the output. Include a brief "How I Built This" section: two paragraphs on your human+AI process. That transparency is itself a signal of sophistication.

Your artifact: A polished deliverable you can share on LinkedIn, bring to an interview, or add to a portfolio. When an interviewer asks, "How do you use AI?", you now have a 60-second answer backed by proof.

Week 4: Teach What You Learned

Goal: Convert your learning into relationships and visibility—Pedal Two.

Harvard researcher Amy Edmondson found that the activities most associated with genuine skill development are sharing information, talking about errors, and experimenting in the open. Teaching doesn't just help others; it rewires your own understanding. It's also how you close the loop on the Career Bicycle.

If you do Weeks 1–3 privately, you've only turned Pedal One. Week 4 is where the skill becomes leverage.

The exercise:

• Write one LinkedIn post about something specific you learned. Not “AI is amazing”—something concrete: “I spent a week testing AI on demand forecasting problems. Here’s the one type of question it consistently gets wrong and why that matters.”

• Share your portfolio piece with a brief explanation of your process.

• Have one conversation with someone in your network (a boss, professor, or coworker) about what you built. Ask what they think.

Your artifact: The post itself, the engagement it generates, and ideally a conversation that wouldn't have happened otherwise. That's how learning becomes leverage.

If you need help setting up your profile or engaging on LinkedIn, bookmark this article for later: “I Don’t Have Anything Valuable to Say on LinkedIn.”

Your Move

You don’t need permission to start. You don’t need a budget, a manager’s approval, or a technical background.

You need one AI tool, one hour a day, and the willingness to document what you learn.

Four weeks from now, you'll have something most candidates don't: proof that you know how to work with AI, not just use it. The interface skill is table stakes, but the judgment behind it: knowing what to ask, recognizing when the output is wrong, and contextualizing results against your domain expertise, is what this challenge actually builds.

You've read enough. The only question left is whether you'll do something with it. Open a tab, paste the prompt, and see what you find. Four weeks from now, you'll know exactly what you're capable of—and so will everyone watching!

Next week we will cover Capability 2 — Build Strong Relationships. We’ll unpack how to build a professional network that actually works, especially when you’re starting from zero. Subscribe below to get the article in your inbox next Thursday!

Subscribe now

Inspired to keep reading?

Week 1 of a four-part series on building career resilience.

• Week 1: You vs the Robot

• Week 2: “I’m Comfortable With AI” Is the New “I Know Excel”

• Week 3: Stop Waiting to Be Discovered

• Week 4: Developing Cross-Domain Fluency

Subscribe now

The Mood of the Market

When I asked students what worried them most about entering the job market right now, the answers were blunt and consistent:

• Too many applicants, not enough roles (43%)

• Lack of real-world experience (33%)

• Not knowing what companies actually want (19%)

• AI replacing the work I’m trained to do (5%)

At the same time, 78% reported using AI tools daily in coursework or job searching. That contrast matters as AI isn’t theoretical to this generation, it’s already embedded in how they work. The concern is not whether AI will affect employment, but how individuals should approach career planning in response.

The Core Shift: From Job Titles to Capabilities

The labor market feels unstable because it’s re-pricing work faster than people can adapt. AI compresses execution, which means value no longer comes from doing tasks but from:

1. Asking the right questions

2. Directing systems (human + machine)

3. Verifying and improving outcomes

This is why resumes feel less effective and referrals matter more. Companies aren’t hiring for static skills, but for people who can navigate ambiguity.

Subscribe now

3 Capabilities to Build Career Resiliency

I shared with the graduate students three capabilities that all of us need to build in order to have a resilient career in the age of AI.

Capability 1: Get AI Curious (Not AI Afraid)

AI anxiety often shows up as a single thought: AI will be able to do my job.

Although job roles include technical tasks such as typing speed and task volume that AI can replicate, the value of human work extends beyond the mechanical actions machines can imitate. As execution becomes commoditized, careers will be built on the ability to exercise judgment and handle ambiguity, including defining the right problem, selecting an appropriate approach, weighing tradeoffs, and taking responsibility for outcomes.

What “AI Curious” Actually Means

Being AI curious is not about becoming a machine learning engineer. It’s about learning how to:

• Experiment with 1–2 core models regularly

• Understand how models break, hallucinate, and fail

• Building workflows where AI drafts and you decide

In practice:

• Let AI write the first version

• You refine, contextualize, and validate

This mirrors how senior professionals already work with junior teammates. AI is becoming your newest (very fast) coworker.

Key insight from the room: STEM students already use AI daily, but mostly tactically. The gap is moving from usage to leverage.

Capability 2: Build Strong Relationships

One slide landed harder than any AI stat:

“70% of roles are filled through referrals and networks, not applications”-Scott Galloway

This isn’t new, but it’s more punishing now. When AI increases applicant volume, companies rely more heavily on trust signals and relationships become an easy filter.

The Career-as-a-Bicycle Framework

Think of your career as a bike.

• Pedal One: Performance Today

  • Do good work

  • Be reliable

  • Deliver results

    • Provides pay and promotions today

• Pedal Two: Options Tomorrow

  • Relationships

  • Visibility

  • Optionality

    • Provides network and opportunities tomorrow

If you only pedal performance, your career stalls when conditions change. Relationships are what allow you to keep momentum and maintain resiliency amidst disruptions and layoffs.

What Relationship-Building Looks Like (Practically)

Not networking events or transactional coffee chats.

Instead:

• Optimize your LinkedIn and engage weekly

• Share what you’re learning (projects, GitHub, reflections)

• Be a connector: introduce people without asking for anything

Students often say: “I don’t have anything valuable to share yet,” but I’ve previously written how easy it is to setup your LinkedIn, build you network, and start adding value.

Capability 3: Develop Cross-Domain Fluency

AI is improving at a breakneck pace, but it still struggles with asking the right question and verifying the results, a helpful framework from Erik Brynjolfsson at Stanford.

AI is getting increasingly excellent at the ‘Execute The Task’ part of the formula so the most resilient careers will be filled by people who can build strong judgement across multiple domains:

• A primary domain (engineering, biology, analytics, design)

• A secondary domain (business process, product, UX, operations)

This is how generalists beat specialists with AI.

Examples of High-Leverage Pairings

• Engineering + Product thinking

• Data science + storytelling

• Domain science + customer insight

• Technical depth + change management

You don’t need mastery in both. You need fluency.

How to Build It

1. Pick an adjacent domain (finance, supply chain, UX)

2. Talk to someone who works there—ask how decisions are made

3. Tackle a cross-functional project in class or at work

Cross-domain fluency makes you harder to replace because AI struggles with context-switching across incentives.

Career Fragility vs. Career Resilience

Careers become fragile when:

• Identity is tied to a single tool

• Skills are optimized for one workflow

• Value comes only from execution

Careers become resilient when:

• You can reassemble skills in new contexts

• You build social and informational leverage

• You treat AI as infrastructure, not competition

Your job is not to predict the future, but to stay adaptable inside it. This helps you to avoid the one-pedal trap of focusing on performance to the detriment of building a strong network that can support you amidst the inevitable job layoffs and disruptions that will occur in the coming years.

The Bottom Line

The students were right to be uneasy. The market is tighter. AI is moving fast.

But the path forward isn’t panic or perfection, it’s capability-building across three areas.

Follow along for the next three weeks as we unpack how to build these capabilities.

Subscribe now

Excited to keep reading? Below are popular posts from the archives:

Anthropic CEO Dario Amodei published an essay renewing his warning about the economic impacts of AI:

New technologies often bring labor market shocks, and in the past humans have always recovered from them, but I am concerned that this is because these previous shocks affected only a small fraction of the full possible range of human abilities, leaving room for humans to expand to new tasks. AI will have effects that are much broader and occur much faster, and therefore I worry it will be much more challenging to make things work out well.

None of us know the true impact of AI, but it’s critical to recognize that we are in another significant economic shift that may dwarf what occurred throughout the Industrial Revolution.

Amidst the noise, I want to help you think about the skills you should be focused on to be prepared in this age of AI.

Subscribe now

Bad Career Advice

Career advice has been remarkably consistent over the last decade: Learn to code, gain technical skills, and engage primarily in STEM disciplines. The advice was not wrong, but it is being exposed in the age of AI. According to OpenAI CEO Sam Altman, “AI can [now] perform the work of entry-level employees.”1 Meanwhile, Anthropic revealed that Claude writes 90% of its own company code.2

If AI can write code, analyze date, and generate reports then what exactly should you be learning to do in 2026?

What Harvard Discovered in 1980

Economist David Deming at Harvard has been tracking something fascinating: how the labor market values different combinations of skills over time. His research3 reveals a pattern that most career advice completely ignores.

Since 1980:

• Jobs requiring high math skills AND high social skills grew by 7.2 percentage points (with wages up 26%)

• Jobs requiring ONLY high math skills (but low social skills) actually shrank by 3.3 percentage points

• Jobs requiring only social skills stayed flat

The jobs that required strong technical skills without strong people skills have been declining for four decades.

It’s clear that winners in the economy have not been the most technical, but the ones who combined technical capability with human connection.

How AI Makes This Worse and Better

Erik Brynjolfsson at Stanford frames this beautifully. He argues that almost every valuable task breaks down into three phases:

1. Asking the right question (defining the problem)

2. Execution (carrying out the steps)

3. Evaluation (verifying results and refining)

"As execution becomes commoditized, the bottleneck—and the value—shifts to asking the right questions and evaluating results."

Brynjolfsson argues that AI is getting “astonishingly good” at Step 2 (Execution) so the critical skills to develop are asking the right questions and evaluating the results. Workers, he argues, are becoming “Chief Question Officers.”4

Your primary job is not doing the work, but having the judgement to know what to ask, why it matters, and whether the AI actually succeeded.

The Three Skills That Matter Now

Three capabilities consistently emerge as the skills that protect and accelerate careers in the AI economy.

1. AI Fluency (Not AI Expertise)

Jensen Huang, CEO of Nvidia, put it plainly at Davos5: “Learning to work with AI will soon be as fundamental as learning to manage people. Prompting, supervising, and evaluating AI systems will become core skills across industries.”

LinkedIn’s data confirms this. “AI Literacy” is the #1 skill on the rise, defined not as machine learning engineering, but as effectively using tools like ChatGPT and GitHub Copilot. The premium goes to people who can leverage AI as a force multiplier, not people who can explain how transformers work.

2. Domain Judgment

Domain judgment is the pattern recognition that tells you what “good” looks like and it’s one of the hardest for AI to replicate. It’s knowing which customer complaint signals a systemic problem versus a one-off issue or recognizing when a financial model’s assumptions don’t match reality. Broadly, it’s the instinct that something is off before you can articulate why.

The Economist recently highlighted the paradox facing entry-level workers: if AI handles the grunt work that used to teach judgment, how do you develop it? Their answer: the smartest companies are redesigning junior roles around higher-order tasks, such as client interaction, negotiation, and exposure to decision-making.6

The implication for your career: seek roles where you’re evaluated on outcomes, not tasks. Find mentors who can transfer tacit knowledge and build judgment through exposure, not just execution.

3. Human Connection

Scott Galloway shared a stat that should change how you think about job searching: “Google puts out a job opening, they get 200 CVs within eight minutes. They limit it down to the 20 most qualified. Seventy percent of the time, the person they pick is someone who has an internal advocate.”7

In a world where AI can help anyone look qualified on paper, relationships become the differentiator. The highest-value people in organizations are those that can bridge technical and business domains.

This is one of the reasons that you should always go to the happy hour, find opportunities to connect with your coworkers, and start building your network on LinkedIn.

The Career Bicycle Connection

If you’ve been following Career Field Guide, you know I think about careers as a bicycle where one pedal is focused on Performance (excelling at your current role) and the other on Optionality (building capabilities that transfer across jobs, companies, and industries).

The three skills I’ve outlined (AI fluency, domain judgment, and human connection) are critical ‘Pedal Two’ investments. They’re portable, compound over time, and protect you when industries shift or companies restructure.

Subscribe now

Building these skills isn’t just about surviving the AI transition, it’s about learning to position yourself for the opportunities that emerge on the other side.

My Challenge to You

This week, audit your skill development. Are you focused on learning tools that AI might master next year? Or are you building judgment that takes years to develop and relationships that can’t be automated?

If you’re early-career: Stop optimizing for tasks. Start optimizing for exposure. Seek roles that put you in rooms where decisions are made, even if you’re just observing. The judgment you absorb is worth more than the spreadsheets you build.

If you’re mid-career: Your domain expertise is more valuable than you think, but only if you can translate it. Learn enough about AI tools to spot where they can augment your judgment (start with generative AI) and become the person who bridges the technical and the strategic.

If you’re leading others: The companies that win will be the ones that redesign entry-level roles for judgment-building, not task-completion. As McKinsey’s Bob Sternfels said at CES: organizations are growing client-facing roles by 25% while cutting back-office roles by the same amount8. The question is which side of that equation your team is on.

The skill everyone’s getting wrong isn’t technical versus soft. It’s thinking you only need one. The future belongs to people who can do both and who build relationships with others who can vouch for that rare combination.

Justin

I taught my oldest son to ride his bike in a small park in Seattle. He pushed off hard, focused on one pedal, and kept tipping over—exhausted and frustrated.

From his perspective, he was doing everything right and still not moving.

A lot of careers look exactly like that.

“Every job will be changed.”

Jensen Huang sounded optimistic about AI recently at CSIS, but most Americans are not.1 Whether it’s the more than 1.1 million job cuts in 20252 or the drumbeat of AI-driven displacement, the result is the same: people are scared.

I argued that strong performance at work is no longer protection from layoffs and the response confirmed what many people already feel: fear, confusion, and no clear career strategy in the age of AI.

The most vulnerable workers in the AI transition are not low performers. They’re high performers with no external leverage.

Why High Performers Get Stuck

Over the past few years, tens of thousands of people woke up to an email or text message telling them their job was gone. The surprise wasn’t the scale of the layoffs, but who was laid off.

Those impacted learned two things:

1. Being great at your job is not the same thing as building a resilient career.

2. People who rebounded quickly had strong networks outside their company.

The One-Pedal Trap

Most successful careers follow the same pattern: years of becoming exceptional at the job, earning mastery, promotions, and praise inside the company. In reality, high performers are in a more precarious position than they realize:

• Their professional network rarely extends beyond current colleagues

• They lack relationships with people who could readily hire them elsewhere

• Their skills are tied to proprietary systems unique to their employer

When change hits—a reorg, a layoff, or new leadership—the very traits that drove their success become liabilities.

I call this the One-Pedal Trap. You rode so hard on performance that you forgot the other pedal existed.

The Two-Pedal Framework

After watching thousands of people struggle after layoffs, a clear pattern emerged: some people could maintain career momentum, while others could not. The difference wasn’t talent, but how they had been using the two pedals of their career.

A career works like a bicycle. One pedal drives performance today. The other builds strategic growth for tomorrow.

🚴Pedal One: Performance

The work you do every day

This is your current job: execution, reliability, results. It’s how you earn trust and build your reputation. You need to perform well, deliver outcomes, and build credibility with your manager and team. This is what gets you promoted, paid, and praised today.

🚴Pedal Two: Optionality

The work you do on your long-term direction

This is the strategic side of your career: skills, positioning, relationships, visibility, and clarity about what comes next. This is what protects you and creates opportunity tomorrow.

Optionality doesn’t only mean “post on LinkedIn.” It can mean one coffee a month with someone two titles ahead of you at a different company, or deliberately owning a cross-functional project that creates portable signal outside your current org.

Most people focus almost entirely on the first pedal. They work hard, deliver, and stay busy. They assume that strong performance today will automatically create opportunity tomorrow, but it rarely works that way.

The Pedal Ratio

Here’s what most people miss: you don’t need to push both pedals with equal force. You need to be intentional about your Pedal Ratio.

Early in a role, you earn the right to build externally by delivering internally first. No one wants to grab coffee with someone who hasn’t done anything yet. Performance buys credibility, and credibility is the currency that makes Pedal Two work. When you’re new or early in your career, you’re 80/20 (almost all performance), proving you belong.

The danger is never changing that ratio. The person who was 80/20 in year one and is still 80/20 in year eight has built a career entirely dependent on one company’s continued appreciation, which increases career risk.

When you’re established and maturing in your career, you shift to 60/40, then 50/50. The shift to 50/50 isn’t about checking out. It’s about building a career that compounds in two directions at once—one inside your company, one outside of it.

And if you’re sensing instability? That’s when you flip aggressively. When you sense instability—a reorg rumor, a leadership change, an industry shift—you might flip to 30/70, investing heavily in optionality while you still have a paycheck. A 30/70 ratio while you still have a paycheck, a title, and access is infinitely easier than trying to build a network from scratch with a LinkedIn headline that says, “Open to Work.”

The best time to shift your ratio is before it’s forced on you.

How I Learned This the Hard Way

At Starbucks, I only knew Pedal One existed.

I worked my way up from leading a plant team to running complex planning exercises at corporate. I was heads-down, executing, and proving I belonged, but my entire career lived inside the company.

After I joined Microsoft, I sat through a training session on building your network and one of the focuses was getting started on LinkedIn.

That night, I looked at the profiles of a few senior leaders and saw that they weren’t just accomplished internally. They were shaping industry conversations and building relationships with people they’d never worked with directly.

Their careers existed outside the company, not just inside it.

That’s when it clicked: a resilient career requires both pedals moving at once, performance today and optionality for what comes next.

Don’t Crash Your Bike

Both pedals have traps.

⚠️The Performance-Only Cyclist

Profile:

• High performer, reliable, exceeding expectations.

• Loved by managers.

• Network is almost entirely current colleagues.

• Few recent interviews and little external signal.

• Busy on Teams, quiet on texts.

Result: When layoffs hit, they’re forced to take the first offer and they don’t have options.

⚠️The Optionality-Only Cyclist

The opposite. They’re everywhere.

Profile:

• Constant LinkedIn activity

• Coffee chats booked weeks out

• Heavy focus on personal brand

• Mediocre execution

• Regularly passed over for promotion

Result: When they try to activate their network, they learn a hard truth: people refer performers, not self-promoters.

Which Pedal Are You Neglecting?

If you’re neglecting Performance:

• When did you last ship something your manager bragged about?

• Are you known for results, or just for being visible?

If you’re neglecting Optionality:

• If you were laid off, how many people outside your company would take your call?

• What skills are you building that would transfer to another company?

Most people don’t crash because they stop pedaling, they crash because they ignore imbalance.

The Uncomfortable Truth

Your job doesn’t love you back. Your company will make the decision that’s right for the company. That’s not evil, it’s just how organizations work. The goal is not to care less about your job. It’s to care enough about your future to stop betting it on a single employer.

The answer isn’t to stop performing. The answer is to stop only performing.

You don’t control the environment. You control your exposure to it.

Building a Resilient Career

Wherever you are in your career, this is the question to ask: Which pedal am I neglecting?

If you’re 25 and heads-down proving yourself, great. Keep pedaling on performance, earn trust, and build credibility, but spend at least 20% of your energy developing relationships and skills that exist outside your company’s walls.

If you’re 40 and realizing you have little optionality, it’s not too late. Start now: update your LinkedIn, reconnect with former colleagues, and develop a skill that isn’t tied to your current role.

The best time to build your network was ten years ago, but the second-best time is today.

Rooting for you,

Justin

Subscribe now

📌: Share this article with someone who’s grinding hard at work but might be neglecting their second pedal.

Inspired to keep reading:

I met with a mentee last week who shared the below:

I know I should build my presence on LinkedIn, but I don’t have anything valuable to say and don’t really have the time or know how to do it.

The Motivation Question: Why LinkedIn

Look—if you don’t feel motivated to do something, then you won’t do it. I know this is super deep stuff, but you should start with whether you actually want to build a presence on LinkedIn. If you don’t, then don’t do it. Figure out another way to network, such as industry meetups, connecting on TikTok/Insta with people, or posting on X.

Three reasons why I build my network (primarily) on LinkedIn:

• LinkedIn is built for career networking. People are (generally) not posting about personal life, politics, or their pets so it’s less cringe when you post your work wins, milestones, and career-related accomplishments because people expect (and celebrate) it.

• It’s a less awkward way to stay in touch with people. As of this article, I have 5.7K followers and 5.5K connections on LinkedIn. There is no way I would have asked for 10K+ people’s phone numbers or emails. LinkedIn allows me to keep in touch with people, ask for their advice, and share with I’m working on. I think of LinkedIn as my personal assistant who allows me to reach out or stay in touch at a moment’s notice.

• There is a correlation between your network and opportunities in your career. Opportunities ultimately come from people. Unless you went to an ivy league or got an internship at Goldman, building a network is the primary way that you will get opportunities in life and LinkedIn makes it easy to build those connections.

Still not sure? Start small and see what happens. Here’s how…

Step 1: Build the Network

1. Follow/Connect: Add people who are already in your network and those you meet or find interesting. Unless you want to be talking into the void, you have to start with connecting with people on LinkedIn. There are two ways to get connected to someone on LinkedIn: Connect and Follow.

Connect: If you click this, they receive a notification and have to Accept or Decline your connection request. TL/DR: connection requests max out at a certain point, so some people are touchier with who they connect with—don’t overthink it. If they are at your company, someone who knows you, or you’ve partnered with them then connect.

Follow: If you click this, they receive a notification that you followed them, but there is no approval process on their end. This allows you to see all of their posts and you can interact with it on the main feed. I recommend you follow a ton of people, including thought leaders, authors, business leaders, and anyone you find inspiring.

TL/DR: Connect: we know each other, let’s keep in touch. Follow: you don’t know me, but I think you’re cool and want to learn from you.

Step 2: Show Up in the Network

1. 5-10 Minutes per Week: Post thoughtful/non-AI-generated comments on others’ LinkedIn posts. Imagine that every single post on the main LinkedIn feed is someone talking directly to you (1:1 IRL) and then your comment is how you would respond. If you’re talking to someone at dinner, you’re not going to listen to them, think deeply about it, pull up ChatGPT, ask them to refine your response, and then reply. You’re just going to talk—do this for 5 minutes daily or a few minutes multiple times per week and you are on your journey to building your LinkedIn presence. When you comment, others see it, see that you are engaged in interesting discussions, and respect you a bit more.

2. 15 Minutes per Week: Post an interesting article related to career or industry on your own LinkedIn profile. This means that you’re actually reading interesting things related to your career, but this is a pretty easy one. Read an industry publication (Google: top news for XYZ industry or XYZ role), think about/form a thought, and then post it. It can be as simple as sharing the link, a brief thought, “Really inspired/interested/encouraged by this article last week,” or “This changed my mind about how I approach X/Y/Z.” Don’t overthink it—the cringe feeling creeping up your body is called climbing cringe mountain, but you have to get over it and just do it. Also, do this step in combination with step 1 for maximum impact.

It’s Really That Easy?

Yup—it’s really that easy. Keep Connecting or Following people that you meet at college, work, conferences, events, happy hours, and throughout work travel. Every person you add on LinkedIn is increasing the surface area of you getting lucky and finding an incredible career opportunity.

That’s It, seriously. Already doing this and want to go deeper?

Here are three ways to level up once you’ve built the habit:

1. Use the Featured section of your profile to post cool stuff you’re working on. If you’re at a big company and then post about something you’ve helped deliver, then add the link of the article to your Featured section (this helps recruiters and hiring managers know what you’ve done). Below is the section from my Linkedin.

   

2. Write an article highlighting your work, career-related things you’re thinking about, or where you see the world moving. LinkedIn has a built-in article and newsletter feature so you can create these without having to setup anything on Substack or your own site.

   

3. Comment on a LinkedIn news article. Click on any of the stories in the LinkedIn News section of your main feed, click Share in the top right of the article, and create your own post or comment on someone else’s thoughts. On the DL, LinkedIn’s own editorial people review the activity in this section of the site and may feature your work if it gains traction or is particularly thoughtful.

It’s a snowy day in Austin, TX so I’m going to wrap it up, but you can do this! Start small, build your network, and before you know you’ll have a valuable community of people that you can rely on throughout your working life.

Subscribe now

Inspired to keep improving your career:

25,000 Agents and Counting…

The CEO of McKinsey shared at CES that they now count 25,000 AI agents in their headcount1. These workers don’t sit in meetings, ask for promotions, or complain about the coffee, but they are doing a lot of the work previously reserved for entry-level employees.

The stakes are clear: Agents are eliminating the work that shaped the first years of a worker's experience—the same work that college career centers tell graduating students will be their foot in the door.

Subscribe now

2026: The Year Agentic Goes Mainstream

We have strong conviction that AI agents will change how we all work and live…there will be billions of these agents, across every company and in every imaginable field…many of these agents have yet to be built, but make no mistake, they’re coming, and coming fast.

We will need fewer people doing some of the jobs that are being done today, and more people doing other types of jobs. It’s hard to know exactly where this nets out over time, but in the next few years, we expect that this will reduce our total corporate workforce as we get efficiency gains from using AI extensively across the company.

Andy Jassy, CEO of Amazon2

This is corporate speak for “there will be blood.” Amazon is investing tens of billions of dollars into AI infrastructure because it believes that it will yield an outsized financial return, a significant portion of which will be their ability to reduce their headcount and manage agents vs humans.

The Work That’s Disappearing

The data confirms what hiring managers already know: young workers are being priced out of entry-level roles.

Since 2021, hiring of workers aged 22-25 has dropped 20% in software development and 13% in customer service - the two fields with the highest AI exposure. Meanwhile, hiring of workers 31+ has grown or held steady. This isn’t a recession pattern where everyone suffers equally. Unfortunately for younger workers, this trend is a structural displacement of the bottom rung of the career ladder.

Conversely, the most experienced workers are fine. They have context, relationships, and judgment that agents can’t replicate yet. But the work that creates that experience—the grunt work, the repetitive tasks, the “figure it out” projects that teach you how things work—that’s what agents are consuming first.

If you're under 30 and trying to break into these fields, the game has fundamentally changed. The internships and entry-level roles your professors and parents describe may no longer exist by the time you're ready to apply for them.

When Entry-Level Work Disappears, So Does the Learning

When I joined Microsoft’s Azure supply chain team, a significant portion of my early work was building Excel-based planning tools, compiling KPI dashboards, and creating decks with data analysis and recommendations for leadership. This work wasn’t glamorous, but it was essential to the business and to my development. The work taught me how our supply chain actually functioned, which metrics mattered and why, how different stakeholders interpreted the same data differently, and what “good” analysis looked like versus what just looked impressive.

Today, an AI agent could handle 60-70% of what I did in my first 18 months, including pulling data from multiple systems, generating variance analysis, creating visualizations, even drafting initial recommendations based on historical patterns, faster and more consistently than I ever could.

Here’s the problem: You can’t learn to direct work you’ve never done. The new supply chain analyst gets hired to ‘manage AI tools and provide strategic recommendations,’ but how do you know if the agent’s demand forecast is reasonable if you’ve never built one manually? You can’t develop judgment about what good looks like without first doing the work that creates that judgment.

Companies are hiring people to oversee AI doing entry-level work, which means we're creating a generation of "managers" who've never been managed, "strategists" who've never executed strategy, and "analysts" who've never analyzed anything from scratch—the exact experience that would teach them what good looks like.

What Actually Matters Now (And What to Do About It)

The initial labor reduction is reality and we’ll see continued reductions in entry-level roles in the next few years, particularly in functions where the work is repeatable, digital, and doesn’t require physical presence. New jobs will emerge simultaneously, as companies realize they need people who can bridge the gap between human judgment and AI capability.

If you're graduating into this market, you have every right to be frustrated. You're being asked to compete for disappearing jobs while building judgment through work that no longer exists. That frustration is valid, but it won't protect you. The people who survive this transition will be the ones who build business and technical skills, regardless of their role. Here are three no-regret actions to take:

1. Engage with AI as a tool, not as a threat or a mystery. This doesn’t mean becoming a machine learning engineer, but you must develop a comfort with experimentation. Learn to debug prompts, recognize when output is garbage, understand the constraints of what these systems can and cannot do. The supply chain analyst who spends weekends testing ChatGPT’s ability to generate demand scenarios learns more about both AI capabilities and demand planning than the one waiting for formal training.

2. Become bilingual in technical and business language. You need to understand enough about how systems work to spot opportunity and risk, to have credible conversations with the people building these tools, and to translate between what the business needs and what’s technically possible. This doesn’t require a computer science degree, but it does require curiosity about how things actually work and a willingness to sit in meetings where you don’t understand every term, and the patience to ask questions until you do.

3. Chase project exposure over job titles. The emerging roles: prompt engineer, AI training specialist, agent orchestration manager (or whatever we’re calling them next month). In that these roles didn’t exist two years ago, the people doing them now didn’t wait for a job description to appear on LinkedIn to enter into the field. Instead, they volunteered to help IT test the new planning agent, asked to shadow the team implementing the customer service automation, or made themselves useful to the groups building these solutions. The early adopters are riding the first edge of the wave because they learned the emerging technology even when it wasn’t their “job” because they understood that proximity to AI teaches you more in three months than waiting for assignments teaches you in three years.

Do you wish you’d learned to code back when the internet was simple HTML pages and Flash players? This is that moment—again. Right now, companies are figuring out AI integration in real time. They’re deploying agents without clear success metrics, running into failure modes they didn’t anticipate, and realizing—often too late—that no one actually knows how to manage the transition.

AI technology is moving faster than organizational understanding and that gap is the opportunity window. Relevant expertise is still operationally scarce and every industry needs people who can evaluate where agents work, where they break, and how to design workflows that blend human judgment with AI execution. That window won’t stay open forever, but it’s open now, and it rewards speed over credentials.

Subscribe now

Those 25,000 agents at McKinsey still need managing, training, debugging, and strategic direction. The people who learn how to do that well will be the ones who built the career ladders that replace the ones we lost.

P.S. If you're a college career counselor, MBA program director, or corporate L&D leader trying to prepare your people for this transition, I'd welcome a conversation. You can find me on LinkedIn or reach out at justin.gillebo@gmail.com

If you’re inspired to keep reading, here are popular posts:

Lebron James was drafted first overall in the 2003 NBA Draft at just 18 years old. On day one of his career, he was expected to raise the floor of a struggling franchise and help them win immediately. Fortunately for us, you and I are not Lebron James.

I thought I needed to be excellent at everything on day one. I remember the pressure I felt showing up to my desk at Starbucks in my first corporate role. The first-time imposter syndrome hits differently when you’re a first-generation college student whose family is more familiar with hard work than navigating a corporate campus.

Early in your career, it’s easy to believe that opportunity goes to the most exceptional person in the room: the fastest learner, the smartest voice, the one who nails everything on day one, but that’s wrong. Maybe this perspective is born out of the education system where students are expected to know the answers and are graded on their performance, but that model doesn’t carry over from school to work.

Managers do not expect interns or early-to-mid career professionals to be exceptional on day one. Even senior executives are given structured onboarding plans, so they don’t break things before they understand them.

In most roles, opportunity doesn’t flow to brilliance; it flows to reliability.

If you want more opportunities at work, do three things consistently:

1. Excellent at the basics

2. Enjoyable as a colleague

3. Someone your boss can depend on

Opportunity compounds around people who make work easier for others and get better without needing attention.

Subscribe now

A Day in the Life of Your Manager

If you want to succeed at work, one of your primary jobs is to make your manager’s life easier.

Most managers are not spending their days doing deep, focused work. They’re moving between back-to-back meetings, juggling competing priorities, and translating vague executive direction into something the team can actually execute. Their attention is fragmented which is why you want them to be encouraged and energized when they see your name on their calendar or pass you in the hall.

The people who get the best projects, most flexibility, and stronger sponsorship at work tend to share a set of unglamorous traits. Typically, it’s not because they’re the most talented but because they reduce uncertainty for the person accountable for the outcome. If you create great work inconsistently and unreliably, you become more of a headache than star.

Before reading further, take a moment to score yourself from 1–5 on each of the three traits from your manager's perspective:

1. Excellent at the basics

2. Enjoyable as a colleague

3. Someone your boss can depend on

Excellent at the Basics

Your work holds up without supervision

One of the strongest early-career people I ever managed struggled mightily with public speaking, but when something was assigned to them, it came back complete, on time, and at a high level of quality. I trusted them to deliver without creating more work for everyone else.

Practically, this means closing loops, hitting timelines, and catching small issues before they turn into bigger ones. When your name is on something, your manager shouldn’t feel the need to double-check or chase.

This kind of excellence is quiet and unglamorous, but it earns autonomy. People who are excellent at the basics get more freedom not because they ask for it, but because their work consistently holds up when no one is watching.

When this person later asked for extended remote work over the summer, I didn’t hesitate because I knew the work would be done the same way. Regardless of what HR policies may suggest, flexibility doesn’t come from a policy. It comes from trust.

Enjoyable as a Colleague

People want to work with you

When you’re being interviewed, hiring managers are quietly weighing three things: can this person do the job, will they help take us to the next level, and do I actually want to spend time with them on a work trip.

You spend 40–60 hours a week with your colleagues. Over time, managers don’t just assign work based on skill, they choose for who they want more of in their day.

Being enjoyable to work with doesn’t mean being funny or extroverted, but it does mean reducing emotional friction. Here’s what that looks like in practice:

• When feedback arrives, the enjoyable colleague says “Let me think about that and get back to you” instead of immediately defending their approach. They treat feedback as information, not an attack.

• When a meeting is spiraling, they’re the person who says “I can take that” rather than explaining why something isn’t their responsibility. They make the path forward clearer, not more complicated.

• When stress is high, they don’t amplify it. They stay steady when others are spinning, which makes them the person managers want in the room when things get hard. If they flag a problem, they also bring a solution.

One of the harder lessons I’ve learned over my career is that driving results isn’t the only goal. How you get the work done matters just as much, especially as responsibility grows because when work gets intense, people gravitate toward colleagues who make it feel lighter rather than heavier. Those are the people who get pulled into better projects, given the benefit of the doubt, and trusted when things get messy.

Someone Your Boss Can Depend On

Managers know what they’re getting.

I once managed someone who, on their best weeks, was high energy, fast, and knocked assignments out of the park. I also managed someone who was defensive, missed details, and needed constant reminders to get work across the finish line. Unfortunately, this wasn’t two different people. It was the same person, depending on the week.

From a manager’s perspective, that volatility is expensive. Even strong results lose value when they’re unpredictable, because it becomes harder to plan around you. Work quality is a piece of the puzzle, but it’s also emotional stability, attitude, and how you interact with coworkers or clients.

Everyone has an off day occasionally, but managers gravitate toward people who show up the same way because consistency makes everything else easier to manage. Early in your career, steady progress beats occasional brilliance. Consistency earns trust, larger responsibilities, and eventually the freedom to take bigger swings.

Managers can’t bet bigger on people they can’t plan around.

Next Steps

You don’t need to be like Lebron. Success can look like Tim Duncan—consistent on the fundamentals and quietly reliable. The people who get more opportunities aren't exceptional on day 1, they're reliable on day 100.

Getting more opportunity isn’t about trying to be exceptional at everything all at once. It’s about earning trust in the moments that matter: being excellent at the basics, enjoyable as a colleague, and someone your boss can depend on.

What’s one specific behavior you’ll change this week to close that gap?

To help you move from assessment to action, I’ve created a worksheet that walks you through:

1. Assessing your strengths and current patterns of reliability

2. Identifying specific behaviors to adjust

3. Applying those changes in a practical, immediate way

Set aside 15 minutes to work through it. The people who get more opportunities aren't always the smartest in the room, they're the ones their managers can count on when it matters.

Subscribe now

If you’re inspired to keep reading, here are popular posts: