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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.

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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.

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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.

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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.

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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.

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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.

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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:

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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.

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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.

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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.

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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.

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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.

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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.

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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

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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.

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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

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📌: 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.

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Inspired to keep improving your career:

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.

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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.

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

Last month I spent a few weeks in London for my first visit to the Zero100 office. My family joined me over Thanksgiving and during that week I saw my sons in a new light. I was there for work and they were tourists, but I realized that one day they will be in my shoes.

As they raced up the stairs of a red double-decker bus and looked up at Christmas lights glowing over Regent Street, they seemed older and younger at the same time. Something about being far from home made their growth impossible to miss. Being there with them made me think about the world they’re growing up into and the kind of advice that will actually matter when they begin their own careers someday.

Below are five lessons I’m sharing with them this holiday season.

1. Be Curious

Like London, the world moves fast. This past year alone we saw massive jumps in satellite deployment, humanoid robotics, TikTok ecommerce, and agentic AI.

The pace of change will only accelerate in 2026. No one will be able to keep up with every advancement, but the people who stay curious and keep learning will always find their way. Curiosity is the only skill that compounds for a lifetime.

Satya Nadella said it best:

Many who know me say I am also defined by my curiosity and thirst for learning. I buy more books than I can finish. I sign up for more online courses than I can complete. I fundamentally believe that if you are not learning new things, you stop doing great and useful things. So family, curiosity and hunger for knowledge all define me.1

Curiosity keeps you relevant. More importantly, it keeps you alive to the world.

2. Be a Relationship Builder

One thing you notice in London is how many worlds fit into one city. I lost count of the number of languages I heard on the Tube, in cafes, and in conversations between friends walking by.

Technical skills matter, but career success is shaped by a long series of people who teach you something, help you grow, or open a door you didn’t know existed. Relationships, not resumes, are the real capital of work.

If you can be the person who builds relationships and connects people across cultures, companies, departments, and teams, you will rarely be without opportunity. Interesting work tends to find the people who make others feel seen.

As I’ve written before on networking: be helpful, genuinely care about people, and always go to the happy hour.

3. Be a Light

During my trip to London, I took a weekend train up to Lille, a bustling university city in northern France. As I crossed the countryside, snow began to fall.

Cities can feel cold and anonymous, especially when you don’t know the language, but small acts stand out: a woman who held the cafe door for me, the barista who brought me the Wi-Fi password in English after noticing my confusion, the gracious waitress who patiently took my order in broken French. Your character is most visible when the world around you is moving too fast to notice itself.

In work and in life, be the person who creates warmth. People remember light. They follow it. And in moments of uncertainty, they rely on it more than they’ll ever say.

4. Be Optimistic

There are real reasons to worry about the future: layoffs, the rise of AI, political and economic instability. But all of that faded the moment I saw my boys press their faces to the bus windows, pointing out every Christmas light display.

It reminded me that even in uncertain times, people still build beauty. They still imagine something better and bring it to life.

The world is changed by people who believe progress is possible. Not because they are naive, but because optimism makes action possible. There is wisdom in maturity, but we could all benefit from maintaining a childlike optimism that we have the power to care for one another and to use our careers to create good in the world.

5. Be Practical

Traveling with kids teaches you flexibility quickly. After a long day, we boarded the wrong train (twice) with very tired children who just wanted to get back to the flat. But as in life, you adapt.

Optimism does not mean naiveté. The company that asks you for two weeks’ notice can become the same company that lays you off by text2. We all want the world to be better, but we have to play the chessboard in front of us. Learn how the game works. Understand the incentives, the players, the terrain. Wish for better, but operate with clarity.

Walking through London with my sons and watching them explore, adapt, and light up with curiosity reminded me that the world they’re inheriting will be unpredictable, but not unkind. These five principles won’t guarantee them a perfect path, but they will help them navigate anything with integrity, courage, and joy. And in many ways, they’re the reason I started Career Field Guide in the first place.

Rooting for you,

Justin

If these ideas resonate, I hope you’ll join me in 2026 as I post weekly essays to build resilient, meaningful careers in a world that won’t stop changing. Career Field Guide is for anyone navigating the future of work with curiosity, courage, and hope.

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I was in a London hotel room after my first week at Zero100 when I turned on BBC and realized how narrow my news consumption had become. Almost everything I followed was centered on the United States.

I grew up working class in the Pacific Northwest. My worldview was shaped by what I could see directly in front of me: the warehouse floor, the factory line, the distribution center. Sitting in that hotel room, I understood something uncomfortable. The world I advise global executives about is far larger than my information diet suggested. My perspective needed to expand faster than it currently was.

That realization connected to something that has carried me across four industries and fifteen years of operations leadership. Learning speed determines career trajectory.

But here is the deeper truth. Learning fast and learning deep are not the same thing. You need both. Learning fast helps you navigate change. Learning deep builds expertise that lasts.

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This distinction shapes how I approach every new domain, every career pivot, and every client engagement. Here is the system I rely on.

1. Build a Deliberately Diverse Information Diet

Most professionals optimize for speed over diversity. They follow the same sources, consume the same narratives, and develop the same blind spots. Then they are surprised when market shifts catch them off guard.

The executives I advise face this at organizational scale. The professionals I mentor face it individually. The pattern is identical. Similar inputs create predictable thinking.

After that night in London, I rebuilt my information architecture around a simple idea. Choose sources that disagree with each other and cover different parts of the world.

Here is what I follow now:

• For markets and demographics: The Prof G Pod with Scott Galloway and Ed Elson. Broad, data driven, willing to challenge assumptions.

• For international perspective: BBC News. When I travel, I watch local news to understand what matters to people in that region, not just to the U.S. market.

• For technology and capital formation: The All In Podcast. Four investors with different worldviews debating the same topics. The disagreement is the point.

• For depth: I rotate between The Economist, Wall Street Journal, and New York Times. Each one provides a different lens on global context, business mechanics, and cultural dynamics.

• What I removed: Anything optimized for engagement over insight. That eliminated most social media and the majority of newsletters that simply repackage other people’s thinking.

Better inputs sharpen judgment. Global inputs extend your horizon.

But consumption alone does not create learning. You need a mechanism to synthesize.

To build this capability:

• Select three sources from different worldviews

• Choose two publications you will read consistently

• Add one international or regional source

• Schedule time to consume them

• Remove sources that make you feel informed without changing how you think

2. Create a Weekly Learning Loop

The fastest learners are not the ones who consume the most content. They are the ones who synthesize consistently.

I use the same learning loop across every industry shift and role transition. It works because it forces application, not just accumulation.

• Sense: Scan widely for early signals. I capture anything surprising, contradictory, or repeating across sources.

• Filter: Decide what might matter. My test is simple. Does this affect my industry. Does it surprise me. Does it repeat across unrelated sources.

• Connect: Link patterns across technology, behavior, and incentives. This is where insight emerges.

• Rerank: At week’s end, review what repeated and what shifted your understanding.

• Act: Apply one insight the following week. This step matters most. Learning without application is just expensive entertainment.

Here is what this looked like last month.

I captured twelve insights on AI implementation across enterprises. Two survived the filter. First, companies struggle more with change management than with technology. Second, successful implementations start with narrow use cases, not large transformation programs.

That pattern showed up in manufacturing, logistics, and financial services. Different industries, identical constraint.

I applied it immediately. A client asked about scaling their AI investment across planning functions. Instead of recommending a broad roadmap, I suggested they start with one planning process, prove value, and expand. That recommendation came directly from synthesizing multiple weak signals into one strong pattern.

Synthesis compounds into judgment. Judgment compounds into decisions others trust.

To build this capability:

• Capture ten insights weekly

• Highlight the two that pass your filter

• Link them to your work in one sentence

• Apply one insight within seven days

• Track what worked and what did not

Time investment: about ninety minutes weekly.

3. Learn by Immersion When It Matters

Fast learning helps you navigate breadth. Deep learning builds authority.

When I need to understand a domain that is unfamiliar, I use a principle from manufacturing. Go to the Gemba. In Japanese, ‘Gemba’ means the actual place. It is the idea that you cannot understand a system from conference rooms or slide decks. You have to go where the work happens.

As my boss loved to say, you cannot solve factory problems from a board room.

At UPS, I started in the warehouse. At Starbucks, I ran distribution operations and worked directly with store teams. At Microsoft Azure and Amazon AWS, I visited supplier facilities and manufacturing lines to understand infrastructure decisions. At Amazon’s Project Kuiper, I sat with RF engineers and studied how they designed component level tradeoffs and produced Computer Added Designs (CAD).

When I moved into renewable energy, I spent time on solar farms with field operators. Not to become an electrician, but to understand where theory meets reality.

Immersion collapses the gap between concept and constraint. It exposes how a system actually works. It builds credibility with practitioners who know immediately whether you are operating from theory or experience.

This applies far beyond operations. When I advise executives on AI strategy, I spend time with the teams implementing it. I look at their workflows, their data pipelines, and their change management constraints. That ground truth shapes everything I recommend.

My process:

• Build a first principles mental model

• Immerse deliberately by visiting the work

• Update the model in real time

• Reinforce with structured learning afterward

Recent example. In my first weeks at Zero100, I needed to understand how Chief Supply Chain Officers make technology investment decisions. Instead of reading analyst reports, I spoke directly with executive leaders across industries about their evaluation criteria, budget constraints, and organizational dynamics.

Those conversations revealed something reports often miss. Technology decisions are rarely about technology. They are about readiness, risk tolerance, and expectations from the Board. That insight now shapes my research.

To build this capability:

• Identify one domain to understand deeply in the next ninety days

• Go where the work happens

• Prepare five basic questions

• Document assumptions before and after immersion

• Return to more formal learning with your new context

Immersion does not scale, so reserve it for domains where credibility truly matters.

Why This Matters Now

I have worked across industries that could not be more different. Retail, cloud infrastructure, satellite manufacturing, renewable energy, and enterprise research. The companies, technologies, and business models all changed.

The skill that made every transition possible stayed the same: I learned faster than the role required.

Learning speed is not about knowing everything. It is about choosing better inputs, synthesizing faster, and applying insights sooner than others.

Careers compound when you do two things well. Learn fast enough to navigate change and learn deep enough to build expertise that outlasts it.

Learning fast made my transitions possible. Learning deep made them meaningful.

If you are navigating a career transition, evaluating a new industry, or building credibility in an unfamiliar domain, focus less on consuming more information and more on learning better.

Rooting for you,

Justin

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Early in my career, I made a mistake so embarrassing that everyone in the room noticed except me.

It was one of my first broader staff meetings at Microsoft, my first time inside a real big tech conference room. My background up to that point had been warehouses, factories, and night shifts. I knew how to run a floor. I did not know how to read rooms filled with senior leaders wearing Patagonia vests and discussing quarterly priorities.

So I did what anyone does when they do not know the rules: I guessed.

I showed up early, walked into a large conference room, and grabbed an open seat at the head of the table. It seemed logical. It was open, it had a good view of the screens, and no one was there yet. I did not realize that this was the seat people informally held for the executive who led our organization.

I had no idea. None.

A few minutes later, the executive walked in. He paused behind me. Then he stood next to me. Then he leaned in slightly. All subtle cues that I should move.

And I did not notice any of them.

I was not being bold or trying to make a statement. I was simply unaware. I did not understand how these rooms worked. I knew the rules of a warehouse floor. I did not know the unwritten rules of a corporate conference room.

After the meeting, one of our senior leaders pulled me aside. He did not embarrass me. He did not speak to me like I was in trouble. He simply said, quietly and directly:

“Just so you know, that seat is usually where our exec sits. When he stood near you he was giving you a chance to move. It is totally fine. You will get used to this.”

I will never forget how calm he was. He treated it as a learning moment, not a moment of judgment. His approach earned my trust for years.

The executive whose seat I took eventually became an important mentor. But in the moment I wanted to sink through the floor.

And I learned something I still carry with me.

That moment crystallized something I had felt but could not yet name: corporate environments run on invisible rules, and nobody explains them until you break one.

Presence, awareness, and perception are skills just as much as coding, understanding financial markets, or marketing. None of them are automatic, you learn them through real and—sometimes painful—experience. People early in their career are often not taught this, especially first generation professionals or anyone coming from hands on roles. You do not understand the social rules of corporate life until you trip over a few of them.

After that meeting, I started paying attention more intentionally. I noted where leaders sat and how they entered rooms. I noticed that our VP always arrived exactly two minutes after meetings started, not late enough to disrupt, but late enough that everyone was already seated. I realized that it wasn’t carelessness, it was deliberate.

I listened to how they handled small talk, how they behaved at happy hours, and how they presented themselves on work trips. I observed when they spoke and when they stayed quiet. What they wore and why. What seemed normal and what seemed unusual.

I was not trying to become someone else. I was trying to understand the environment well enough to figure out how I wanted to show up.

Here is a cheat code for your career: Watch how people who have earned respect navigate the culture. Not to become them, but to understand the rhythm of the environment so you can build your own style.

Here are a few lessons I wish someone had given me earlier:

1. You will screw up. Publicly.

It is unavoidable. Do not let it define you.

2. Say sorry once and then move on.

Over-apologizing creates more awkwardness than the original mistake.

3. Let people tease you about harmless mistakes.

When someone ribs you about sitting in the wrong seat or mispronouncing a colleague’s name, lean into it. Self-deprecating humor builds trust and belonging. But learn the difference between teasing that includes you and mockery that diminishes you. The first brings you closer to the team. The second pushes you out.

4. Before work trips or offsites, ask questions.

What is the dress code?

Is there anything I should know about ordering a drink?

Is there any guidance around expectations?

It is not naive. It is proactive. The people who have been there before want to help you. Let them.

5. Read your company’s policies.

Things like reimbursements, gifts, alcohol, and travel expectations are small details that can prevent big mistakes. Err on the side of conservative actions (not having another drink, not taking a gift, not reimbursing unnecessary items).

6. Presence is quiet and perception is subtle.

Learn to read cues. Who sits where. Who has influence. Who speaks last. Who people look toward for reactions.

These are the details that separate people who stay stuck from people who accelerate.

And the most important part. Give yourself grace.

That Microsoft meeting was uncomfortable and humbling. I wanted to disappear. But it made me better. It taught me to observe, pause, and understand the room before jumping in.

Your career will be full of moments like this. Do not avoid them. Do not overthink them. Learn from them.

They become stories you carry forward. And years later, you laugh about them with the people who helped you grow.

Rooting for you,

Justin

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Networking gets a bad rap. Too often it’s seen as transactional, just a way to get something from someone else. I’ve written before about how networking can open doors to job opportunities, but only if you’re doing it the right way.

Networking events are often performative theatre, with everyone pretending to feign interest in others (“Wow, you’re also on LinkedIn? That’s so interesting. Tell me more!”), when we all know that most networking events are the career equivalent of speed dating as everyone tries to connect with the most powerful people in the room in a desperate hope that the right “date” will offer them the job, opportunities, and income they’ve always dreamed about achieving. Yuck.

But alas, I joined the corporate herd and danced to the same music for years. I quickly came to realize that the issue with traditional networking is that it only works for people established in their careers who already have something meaningful to offer.

As a first-generation college student from a working-class family who had just barely exchanged his steel-toed boots for a pair of dress shoes, I knew that this type of mutual back-scratching networking was not going to work for me.

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As a newcomer to the corporate world, I was desperate for advice. I read books, listened to podcasts, and scoured YouTube for anyone who could help me learn to build my career. Enter: bombastic Gary Vaynerchuck with his infamous motivational advice to make the most of the chances you get, “You’re gonna die.”

GaryVee (as he is casually known) clicked for me. As a hard-working underdog who didn’t always fit in, I loved his irreverent, provocative, and helpful guidance for how to pursue a life well lived. I remember the first time I heard him talk about the 51/49 principle and how it freed me from the stodgy networking platitudes that only worked for people who were already in positions of power.

The premise is simple: give 51%, take 49%. That tiny edge toward generosity compounds into real trust over time.

Why Most People Approach Networking Backwards

You need a network, and the old advice still stands:

• “Build your network before you need it.”

• “Connect with people in your industry.”

• “Go where the successful people are or industries are growing.”

But the vast majority of people don’t know what to practically do when they’re trying to build their network. Whether it’s through LinkedIn, an industry meetup, or an official networking event, everyone is a “here I am” person, as opposed to a “there you are” person. Their focus is on them and what people can do for them, not what they can do to add value to others.

Networking has become a room full of people trying to extract value from strangers, and when everyone’s taking, nobody’s getting anything.

I’m not even saying people are doing this with a bad intent, but here’s the reality. If you don’t think you have anything to offer, then you will always default to taking from others (49/51) as opposed to offering value to others (51/49).

I’m a senior leader with a lot of executive experience at Fortune 500 companies, but here are a few unique ways that people with less experience have recently provided value to me:

• A graduate student with minimal professional experience shared with me her experience growing up and working in India, helping me to better understand another culture.

• A mid-level professional sent me an article about how AI is being leveraged in a unique business context

• An entry-level professional sent me an encouraging LinkedIn message sharing that one of my posts really encouraged her

Stop believing that you don’t have any value to add and start discovering what you can offer to others around you (regardless of their role or experience).

Ask a few questions:

• Where have I lived or travelled that would be interesting or helpful to people?

• What industry or context have I worked in that would be worth sharing?

• How can I genuinely encourage or compliment people?

Your “unremarkable” life or career is brilliant and exciting to people who have not had those experiences. You have a lot to offer other people. If you believe that then you will naturally start to offer more to people.

How Being Useful Got Me In at Microsoft

In grad school at University of Washington, I was stretched to the limit. I was working full-time at Starbucks corporate during the day, taking classes at night, and I had a family at home.

I could have put in minimum effort to graduate. But I recognized the program as more than academics: it was a chance to build relationships and practice the 51/49 principle.

Two of my classmates worked in Azure Operations at Microsoft. We weren’t friends, we were just three people who ended up in the same group projects. Throughout the program, I shared frameworks I’d used at Starbucks, went out for happy hours to build relationships, and asked about their work at Microsoft. I also shared my background (warehouses, factories, corporate ops) and how I went from working blue-collar roles to attending college and working in supply chain.

I wasn’t networking. I was just showing up, being useful, and becoming a friend.

Months later, through a referral of one of those classmates, I was able to get an interview at Microsoft. I was starting as a Supply Chain Manager in Azure Operations and those classmates became coworkers. When I graduated I did not leave with the highest GPA, I left with a better job.

That’s the entire game.

The Framework: 5 Ways to Be Useful (That Actually Work)

1. Pick 10-15 People You Actually Respect

Not “people who can help me.” People doing work you find genuinely interesting. They could be classmates, colleagues, people writing stuff on LinkedIn that makes you think, or former coworkers you haven’t talked to in a year.

The only rule: You actually care about what they’re doing.

If you’re faking interest to “network,” they’ll smell it and you’ll both waste your time.

2. Be Useful in Small, Specific Ways

You’re not trying to change their life. You’re trying to make their week 1% better.

Examples:

• “Saw your post about XYZ ops challenges. I just dealt with something similar. Here’s what worked: [2 specific things]. Happy to elaborate if useful.”

• “You mentioned you’re hiring. I know someone who’d be perfect for this. Want me to connect you?”

• “I read your article on agentic AI. Have you seen [this research]? Seems relevant to what you’re working on.”

Notice what you’re NOT doing:

• You’re not asking them to coffee.

• You’re not asking them to “pick their brain.”

• You’re not asking for anything.

• You’re just being useful.

Do this once every 4-6 weeks per person.

Not weekly (annoying). Not yearly (forgettable).

3. Make It Specific (Or Don’t Do It at All)

Generic messages get ignored.

• “Hey! We should catch up!” = Delete.

• “Saw your LinkedIn post about [specific thing]. I just went through [specific similar experience]. Happy to share what worked if you’re interested.” = Response.

Specificity proves you’re paying attention.

4. Help 3-4 Times Before You Ask Once

This is the 51/49 principle in practice.

• Month 1: Help them with something.

• Month 3: Help them with something else.

• Month 5: Make an introduction.

• Month 8: “I’m thinking about roles at your company. Got 15 minutes to tell me what it’s like there?”

By Month 8, they want to help you because you’ve already helped them. You’re not extracting value from a stranger. You’re asking someone who already knows you’re generous.

Big difference.

5. Build in Public (So People Come to You)

Here’s the secret that took me way too long to figure out:

The best networking happens when you’re not trying to network.

Post on LinkedIn 2-3x/week. Share what you’re learning. Comment thoughtfully on other people’s posts. Write about problems you’ve solved.

Do this consistently for 6 months and you’ll attract more valuable connections than 10 years of conferences. It works because you’re demonstrating your thinking in public. People who care about the same things will find you and they’ll already know you’re useful before they reach out.

I’ve received more opportunities from LinkedIn posts and this Substack than from any networking event I’ve ever attended.

The Pattern: How This Keeps Working

Microsoft → Amazon:

At Microsoft, I helped a coworker think through supply chain constraints, reviewed his presentation to leadership, and shared a vendor negotiation framework.

Never asked him for anything.

A year later, he left Microsoft for Amazon. Shortly after, he called: “We’re building a new supply chain org. I told my director about you. Apply.”

He didn’t just refer me. He told his new boss I was someone he wanted to work with.

Amazon → Clean Energy Industry:

A former exec from Microsoft joined a renewable energy developer. Years earlier, I’d helped him launch an initiative, shared operational insights, made useful introductions.

Never asked for anything.

Two years after we last worked together, he reached out: “We’re building a supply chain org at a PE-backed renewable energy developer. I want you to lead it.”

Pattern:

Help people. Don’t keep score. Let time pass.

When opportunities arise, they’ll think of you first, not because you “networked,” but because you were useful when you had nothing to gain.

What to Actually Do (Next Steps)

This Week:

Monday:

• List 10 people doing interesting work. Colleagues, former classmates, people on LinkedIn whose content makes you think.

Tuesday-Friday:

Be useful to 2 of them. Could be:

• Article they’d find valuable

• Introduction to someone who can help them

• Specific answer to a problem they’re working on

• Thoughtful comment on their LinkedIn post

Don’t ask for anything. Just help.

This Month:

• Post or comment on LinkedIn 2x/week. What you’re learning, problems you’re solving, observations from your work.

• Be useful to 8-10 people. Different people each week.

This Year:

• Help 100 people before you ask anyone for anything.

Not joking. Track it. Make it a goal.

100 useful interactions. Big or small. Doesn’t matter.

Be consistently useful to people doing work you respect.

Then watch what happens.

The Uncomfortable Truth

Here’s what nobody wants to hear:

Traditional networking works if you’re already successful, extroverted, and well-connected.

If you’re none of those things? It’s brutal.

I wasn’t successful when I started. I’m an introvert. I had zero connections in corporate America as a first-gen college student from a working-class family. Networking events were torture. Everyone seemed to know everyone, and I didn’t know anyone. I’d stand there with a drink, pretending to belong, collecting contact info from people who forgot me before I left the room.

Being useful first leveled the playing field.

I didn’t need to be charismatic. I didn’t need family connections. I didn’t need to be comfortable with small talk.

I just needed to be helpful to people doing work I respected, which anyone can do.

The Bottom Line

Be helpful, genuinely care about people, go to the happy hour.

Do this for a year and your “network” will be stronger than people who’ve spent a decade working rooms at conferences.

You’re building a network of people who remember you made their life easier when you had nothing to gain.

When opportunities come up, you’re the first person they think of.

Being useful is the best career strategy there is.

Rooting for you,
Justin

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