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

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

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

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

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

The Three Questions

01: Why this Industry

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

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

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

02: Why this Company

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

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

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

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

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

Subscribe now

03: Why this Role

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

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

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

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

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

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

Using AI to Prep for Interviews

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

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

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

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

The Bar Just Got Higher

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

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

Leave a comment

Know Someone Interviewing or Looking for a Role?

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

Share

Inspired to Keep Reading?

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

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

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

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

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

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

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

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

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

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

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

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

The Side Door: The Humble Path That Actually Works

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

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

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

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

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

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

The Back Door: The Role That Finds You

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

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

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

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

The Question You Should Be Asking Before You Need a Job

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

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

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

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

Why Most Careers Run on One Pedal

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

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

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

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

Subscribe now

Inspired to keep reading?

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

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

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

The Market in Splitting in Two

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

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

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

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

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

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

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

What the people doing the hiring decisions are actually saying

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

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

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

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

The Full-Stack Worker

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

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

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

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

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

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

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

The Window is Open

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

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

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

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

Subscribe now

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

• Week 1: You vs the Robot

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

• Week 3: Stop Waiting to Be Discovered

Subscribe now

The Job Application Process is Broken

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

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

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

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

The Math Nobody Wants to Hear

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

Generative AI has created a market where:

• The cost of applying to a job is near zero

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

• The volume of applicants per role has exploded

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

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

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

The Career Bicycle That Might Save You

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

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

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

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

• Pedal One = Keeps You Employed

• Pedal Two = Keeps you Employable

The Two Traps Early-Career Professionals Fall Into

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

Trap #1: Waiting

Let’s call her Mary.

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

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

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

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

Trap #2: Spraying

Now meet John.

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

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

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

How to Actually Build Strong Relationships

Start Early (and Make It Boring)

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

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

Start close:

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

• Build relationships across functions

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

Then widen the circle:

• Clean up your LinkedIn

• Engage thoughtfully online with people in your field

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

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

2. Put Yourself Where Opportunity Can Happen

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

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

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

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

Do Cool Stuff (in Public)

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

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

• A simple newsletter

• A GitHub project

• A YouTube channel

• A short LinkedIn post explaining something you just learned

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

Time to Take Action

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

This week, do three things:

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

2. Share one small piece of work in public.

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

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

Subscribe now

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

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

Buy Me a Coffee

Inspired to keep reading?

Every role you accept optimizes for something and costs you something. I didn’t understand this at the time, but I can trace my own blind spot back to the moment I finally earned a role at Amazon.

Live to Work or Work to Live

I remember how proud I was to get my Amazon employee badge. I had just joined a world-class team and I eagerly shared the update on LinkedIn. Finally becoming an Amazonian felt like validation of all the work I had put in and proof that I was winning the career game.

Then an older mentor left a comment:

“Congrats, Justin! Just don’t forget to work to live too!”

The advice felt trite and ill-fitting for a moment when I was celebrating a big win. My only focus was how to keep climbing the ladder and I dismissed the message as something people say who’ve already won.

It took me years to realize that “work to live” wasn’t a dismissal of ambition—it was a warning about unchosen tradeoffs. Careers aren’t just shaped by companies, roles, and pay, but by what we quietly give up to get them.

Subscribe now

The Question You Should Be Asking

Every season of your life imposes constraints on what you can and should optimize for in your career. Most people, however, spend their time fixating on roles and companies while ignoring the more consequential tradeoff decisions underneath them. The real question you should ask is: What am I optimizing for in my career and what am I giving up as a result?

In practice, most people chase the shiny object or borrow their parent, spouse, or company’s vision for their career without considering what they want to make a priority.

I’ve summarized four career priorities below, including when it likely makes sense for you to pursue it and what tradeoffs it will require. If you want to dive deeper, there is a worksheet linked at the bottom of this post that will allow you to reflect and start making your priority intentional to start the new year.

4 Career Priorities

You can touch all four over a lifetime, but you can only optimize for one at a time.

Before you think about your next role, it’s worth naming which of these priorities you’re actually optimizing for right now.

1) Opportunity

Optimizing for a promotion, visibility or network growth.

When It Makes Sense: You’re early in your career or deliberately focused on expanding your reputation, network, or skills to take advantage of a unique opportunity. It may be that you want to work at a great company on the rise or choose a role that will catapult you to a new level of excellence. Molly Graham calls this a J-curve career move.

The Tradeoff: At Microsoft, I saw many people optimizing for opportunity. The issue is that these people build credibility inside their company, but weak networks outside of it. As your reputation increases, you become increasingly dependent on your manager, organization, and salary so pursuing a passion project or taking a parallel role (even if it better fits your skills or interests) is increasingly prohibitive. These opportunities are often highly demanding, so you have to be willing to pay the price of sacrificing personal time and flexibility for the opportunity.

2) Income

Chasing higher compensation or asymmetric upside.

When It Makes Sense: You’re intentionally building financial runway or at a place in life where sacrificing time for increasing financial reserves makes sense. It also may be the case that you’re required to pursue a higher income due to cost of living or personal obligations (paying off student loan debt, caring for an aged family member).

The Tradeoff: At Amazon, I watched (and experienced) how easily stress and long hours became normalized. Once equity starts vesting and lifestyle adjusts, it’s tough to choose a different role or take a step back when it means economic loss. Also, leadership is generally aware of how much everyone is paid, and higher pay often comes with higher expectations of being “always on” and available. Golden handcuffs can lead to a high personal cost to health, family, and loved ones. As Jon Bellion sung, “I know a lot of CEOs with billions and resentful kids, yikes.”

3) Flexibility

Choosing a job or company with options around hours, location, and remote work.

When It Makes Sense: You’re in a season when optimizing around family, health, or experiences is most important. If you have young kids and are in a two-income household, this priority can offer a lot of benefit for one or both partners. Alternatively, if you want to take 1-2 years and travel or experience the world, then a high flexibility role can provide a lot of value.

The Tradeoff: You’re willing to be the first to be laid off, the last to be promoted, and are in a place where flexibility is prized over higher earning or career development. Bluntly, this priority is riskier for people who are not yet mid-to-senior in their career and would limit this priority to 1-2 years for younger generations who want to grow their career over a long-time horizon. For the vast majority of people, early momentum still requires time, proximity, and sustained effort.

4) Stability

Reducing volatility, protecting against downside, and choosing a steady company/role.

When It Makes Sense: You’re deliberately prioritizing stability over growth to support caregiving, education, recovery, or a planned transition. It may also make sense if you are not looking to build your career but prefer a safe job where you can work 9-5, leave for the day, and not carry work home with you.

The Tradeoff: If you’re reading Career Field Guide, I’m going to assume that a small minority of you are going to prioritize this area. That said, stability trades optionality for predictability. In seasons of personal tumult or high obligations (death in the family, pursuing graduate school, or partner with a high-risk job), it can help to not have to think often about work-related stress. Also, if you’re nearing retirement, a stable job can keep you engaged while minimizing career-building expectations. That said, for early and mid-career professionals, stability can stagnate the development of new skills and make it tougher to take advantage of future opportunities.

What Are You Prioritizing and Does it Make Sense?

Clarity in your career comes when you name what you’re optimizing for and accept what that choice costs.

The goal isn’t to choose the "universally-correct” priority (there isn’t one) or to assume that the same priority must apply for an entire lifetime. The goal is to choose the right one for this season, on purpose, rather than inheriting it by default.

Put a meeting on your calendar right now for when you can take 30 minutes to work through this short worksheet and think through the season you’re in, what you’re actually optimizing for, and what you’re knowingly giving up as a result. While there’s no right answer, the goal is that you’re making these decisions on purpose. This type of work and alignment sets the foundation for a meaningful and rewarding career.

Subscribe now

Related posts if you want to keep reading:

Smart professionals love to believe they’re playing the game at a higher level. However, after a decade of leading teams and interviewing hundreds of candidates at Amazon, Microsoft, and beyond, I’ve noticed something uncomfortable:

It’s often the smartest people who hold onto the dumbest career habits.

It’s not because they lack ambition, it’s because these habits feel safe, familiar, or even logical. The problem? These habits quietly kill momentum and leave doors closed.

Here are five career habits that still trip up ambitious professionals and what you should do instead.

Habit 1: Updating Your Resume Instead of Building Leverage

Why it’s a trap: It’s career busywork. Tweaking your resume experience and finessing the formatting is like rearranging deck chairs on the Titanic; it might look nice but it won’t accomplish anything. You can polish bullet points all day, but resumes don’t open doors: people do.

What to do instead: Build visibility within your industry. Publish, present, or meaningfully interact with others’ content so that you stay top-of-mind with people who can unlock opportunities.

Habit 2: Treating Your Professional Network Like a Fire Alarm

Why it’s a trap: If you only message former coworkers when you’re looking for a job, people stop answering your calls. That’s not networking, it’s an SOS. Don’t wait to connect until you need something.

What to do instead: Stay visible year-round. One thoughtful comment on LinkedIn or text to an industry contact each week will do more for your career than blasting 50 applications. Stay present with your connections and industry to keep in touch with those who may be able to connect you to the next role.

Habit 3: Hiding Behind “More Skills”

Why it’s a trap: It feels safer to keep sharpening pencils than to actually write. Courses and certifications can become sophisticated procrastination.

“Don’t follow your passion. Follow your talent.” — Scott Galloway

What to do instead: Apply your skills in higher-stakes contexts. Build your skills in stretch projects where you can gain both experience and results. Experience beats endless credential-collecting.

Habit 4: Waiting for Clarity Before Acting

Why it’s a trap: Smart people overthink. They want perfect data before moving. You’re busy sharpening the axe while someone else is already chopping down the tree. By the time your plan is flawless, the opportunity’s gone.

What to do instead: Make small bets. Start the conversation, make the pitch, take the project—even before you feel truly ready. Momentum creates clarity, not the other way around.

Habit 5: Believing Talent Outweighs Preparation

Why it’s a trap: Natural sharpness feels like a gift that will carry you to the top until you’re up against someone who practiced harder. Raw talent without prep is just wasted potential.

What to do instead: Script your stories. Anticipate the questions. Rehearse until your delivery is sharp but natural.

Closing

You don’t need to reinvent your career to unlock more opportunity, you just need to cut the habits holding you back.

Stop polishing your resume. Stop hoarding skills. Stop waiting for perfect clarity. Professionals who break these habits position themselves for roles others never even hear about.

Your career isn’t capped by your potential. It’s capped by your habits.

Rooting For You,

Justin

Want to see the systems top candidates use to land roles at Amazon, Microsoft, and Meta? That’s what I share every week in Career Field Guide.

Subscribe now

If you want to continue reading, here are some popular posts:

As a hiring manager with experience at Amazon and Microsoft, I know firsthand how the best jobs are actually filled.

It’s not through job portals or blasting out resumes. The strongest candidates almost never came in through a cold application, they arrived via networks, referrals, or quiet recommendations long before a role was posted.

By the time most jobs hit LinkedIn, someone’s name is already penciled in. That’s why mass applying is one of the weakest ways to land your next role.

Here are the three steps top candidates quietly use to get hired before a job is ever posted.

1. Get Laser Focused

Before you send another resume, get crystal clear on the next role you actually want.

Ask yourself:

• Location: Where do you want to live and work?

• Work style: Remote, hybrid, or fully in-office?

• Compensation: What salary or equity makes this move worthwhile?

• Company size: Do you thrive in a startup, mid-sized firm, or large corporation?

Once you have that vision:

• Research requirements: Browse company career sites and study job descriptions for your target role.

• Assess your fit: Aim to meet roughly 70% of the qualifications for mid-level roles and closer to 90% for senior positions.

Finally, right-size your expectations:

• If you meet 95% or more, you might be underselling yourself—target a bigger challenge.

• If you meet less than 60%, it’s probably too far a stretch for now.

This clarity is what separates strategic career moves from reactive job hunting.

2. Work Your Network Early

When you have the privilege of time, remember: hiring decisions are made by people, not algorithms.

When I was running hiring panels, it was rare for someone to show up cold and win a role. The people who succeeded had someone on the inside saying, “You need to meet this candidate.”

Think of it like dating: nobody shows up to a first date, hands over a resume, and asks for a wedding date. Don’t be that person in your job search.

How to Build Warm Connections

• Start warm: Talk to friends, family, or past coworkers at companies you’re curious about.

• Tap alumni: People from your school or past employers are usually happy to help, especially if you’re polite and specific.

• Join the club: Industry communities, niche Slack channels, and professional associations surface roles before they hit job boards.

• Show up online: Posting one thoughtful comment or post on LinkedIn a week beats sending 50 blind applications.

Subscribe now

If You’re Short on Time

When you can’t afford months of networking, at least avoid sending your resume in the first message.

Instead of attaching your resume right away, send a short, human note to a hiring manager or insider:

“Hi [Name], I’m interested in [Role] because of [specific reason]. I’d love to understand what challenges the team is solving right now and where someone like me could help.”

It’s like asking for coffee before proposing marriage, it works better every time.

3. Close the Deal (Only After the First Two)

Once you’ve clarified your target and built real relationships, then you apply.

At this point, you’re not a random resume in a stack. You’re the candidate someone is already hoping will apply.

The posting is just a formality.

Why This Works

• Referrals float to the top: Hiring managers open referred candidates first.

• You bypass the algorithm: Applicant tracking systems (ATS) can’t screen out someone the VP already knows by name.

• You’re not competing blind: By talking to insiders, you’ve already learned what the hiring team actually cares about (most candidates never know this).

What to Do Differently

• Use the job portal as the last click, not the first.

• Send your resume knowing the hiring manager has already heard about you.

• When they read your cover note, it’s more “I know this person” than “Who is this applicant?”

Put it Into Action

When you finally click Apply, it shouldn’t feel like a gamble. It should feel like a confirmation: someone inside already knows your name, the ATS can’t filter you out, and the hiring manager has already decided you’re a fit.

Stop starting with applications. Define your target, build real relationships, and then—only then—send your resume. The best careers are built through conversations, not job portals.

In upcoming posts, I’ll show you exactly how to start those conversations, get referred, and land interviews before a job is ever posted.

Subscribe now

Rooting For You,

Justin

If you want to continue reading, here are some popular posts:

You’ve sent out 43 resumes. Maybe more. No calls. No responses. No idea what’s wrong.

Here’s the truth: your resume isn’t broken. The system is.

Gen Z is the most educated generation in history — and the most underemployed:

Everyone starts with their resume. But after reviewing thousands, I can tell you — the good ones all blur together.

The Resume is Dead

As Zoe Williams put it bluntly in The Guardian:

Forget polishing your CV – you’re better off working on your connections. That’s the depressing reality when every vacancy attracts thousands of applications, all written by AI.

She’s not wrong. With every job posting drawing thousands of AI-generated applications, even a great resume is just more noise.

You don’t need better formatting. You need more leverage.

Subscribe now

High-Value Activities to get a Job in 2025

1. Get Out of Your House

You need to get out of your house and get to know people because people (not resumes) help you get jobs. As a 1st generation college student, I know the challenges of building a network from scratch, but the highest value activity for someone looking for a job is getting to know people, sharing what you want to do, and building relationships.

Practically, start with who you already know and where you can get easy introductions. Make a list of your family, friends, and acquaintances. Then make a list of places you attended school, alumni/business networks, and any professional industries that could provide warm introductions to companies/places you want to work.

99% of you will not follow this advice because it’s easier to pretend you’re doing something high value (like refining the action verbs on your resume for the 1000th time) as opposed to actually doing something high value (making connections and meeting people).

Yes. Digital life is frictionless, but that ease is costing you opportunities.

You need to build a network of people that want to support you and are willing to vouch for you when the next job opens.

2. Use ChatGPT to Outwork 100 Applicants

If you’re reading this, I bet you spent $20 on something frivolous this month (me too).

You need to go to ChatGPT, sign up for a $20 monthly Plus plan, and use it for all of your job-seeking activities as a little assistant.

Here are some high value prompts you can give your new AI assistant:

• Refine my resume for these roles (and give it links to the roles you’re interested in)

• Create a list of 20 companies that I should target based on my education, background, experience, and goals. Give me specific titles of roles, current open roles on their Careers site, and build a tracker so that I can track my progress over time

• Write a creative and effective message that I can send to this person who works at X company. Here is the link to their LinkedIn profile. Craft it in a way that is tailored to their seniority and role at the company

• I’m frustrated and feel stuck. What are three things I can do to reset and make progress in my job search?

At some point in the future, access to this technology will be extremely expensive but, for now, it’s $20 per month.

You don’t need to master AI, just start using it. This $20 tool can 10x your job search if you let it.

3. Stay in the Game (Even When It Feels Rigged)

Look, the job market is broken. Applicant tracking systems ghost 95% of people without a glance. Your well-meaning parents say to “just follow up” or—even worse—you just need to try harder.

You’re not crazy. You’re just playing a game with invisible rules.

Don't be most people. Endurance is your edge.

The people who land jobs in this market aren’t always the smartest or most qualified — they’re the ones who have a plan and are still persisting when others stop trying.

The market doesn’t reward perfect resumes. It rewards persistence and people who make connections.

So build your system. Run your play. And keep showing up after others quit.

I’m rooting for you.

-Justin

Found this helpful? Share it with one person who’s stuck in their career search.

Want more strategies like this? Subscribe here:

Subscribe now

If you want to continue reading, here are some popular posts:

I still remember how stressed I was preparing for my interview at Amazon. I’d spent hours researching the company, dissecting the job description, and practicing my responses, but I couldn’t shake the nerves. Looking back, that preparation made all the difference—not just for the interview but for my confidence walking into the room.

As a hiring manager who has interviewed countless candidates at Amazon, Microsoft, and beyond, I’ve seen what separates strong candidates from the rest. Too often, people fail to do the basics: researching the company, understanding the role, or prepare to share their career story.

Last night I conducted mock interviews with graduate students from the University of Washington and it reminded me how transformative good preparation can be. No matter what level you’re interviewing for, the strategies here will help you walk into your next interview with confidence and clarity.

Interview Prep: Start to Finish

1. Know the Company

I can’t tell you how many candidates I’ve interviewed who couldn’t tell me the first thing about the company or the team they were hoping to join. If you aren’t willing to do a little research before the interview, how can I trust that you’ll put in the effort once you’re on the job?

Here’s how to stand out:

• Start with the Basics: Visit the company’s website to review their mission, vision, and recent news. Most companies have a dedicated press release or news section where you can learn about their latest projects, achievements, or priorities. Use this information to craft thoughtful answers to questions like, “Why do you want to work here?” or “What interested you about our company?” Think of it like dating: no one wants to hear, “I’m interested because you’re available.” Instead, show that you’ve taken the time to understand who they are and why you’re a great match. Figure out what the company is doing that you find interesting and lean into that.

• Understand the Team: Particularly at larger companies, take time to research the specific team. Review the job description you applied to and it will say the team in the title or the details. For example, the Amazon job description below is for a team on Prime Video.

  

  If I were interviewing for this role then I would do a combination of searching for “Prime Video Amazon business news” articles on Google, Yahoo News, and Amazon’s internal site.

• Understand the Industry: Read up on the company’s competitors, recent trends, or challenges in their space. Showing you know the broader context makes you look informed and invested.

Pro Tip: During the interview, weave your research into your answers. For example, “I saw in your recent press release that you’re expanding into new markets. I’d love to bring my experience in ___ to support that initiative.”

2. Understand the Role

Hiring managers want to see that you’ve thoughtfully considered not just why you want to work at their company, but why this specific role is the right fit for you. This is where many candidates struggle—they aren’t able to clearly articulate why they’re interested in the role beyond general statements.

How to Prepare:

• Understand the Why: Reflect on why you’re drawn to this role. Is it to advance your career, take on a new challenge, or because this type of work genuinely excites you? Be ready to explain how this role aligns with your personal and professional goals.

• Connect the Dots: Identify the overlap between the role’s responsibilities and your skills or passions. For example, if you love project management, talk about how the role lets you build on that strength.

• Understand the Role’s Purpose: Go deeper than the job description. Consider why the company is hiring for this position. Is it to scale a growing team? Bring structure to an existing one? Launch a new initiative? Understanding this context will help you position yourself as the ideal candidate.

• Prepare Specific Examples: Use the job description to identify key responsibilities and skills, then craft examples from your experience that directly address those needs.

Pro Tip: When answering “Why this role?” don’t just talk about the company or team—focus on what excites you about this role specifically. For example: “I’m passionate about managing a team and I see this role as an opportunity to build on that experience while helping your team achieve [specific goal].

3. Prepare STAR-Based Responses

One thing I’ve consistently noticed as a hiring manager is that candidates who don’t use the STAR method often struggle to provide clear, focused answers. They ramble, include irrelevant details, or fail to articulate the “R”—the results of their actions—which is the most important part for demonstrating impact.

Behavioral questions like “Tell me about a time…” are designed to assess how you handle real-world challenges. At large companies like Amazon, the STAR method is the gold standard for answering these questions because it ensures clarity and structure.

How to Prepare:

• Craft 5–7 STAR Stories: Identify examples from your experience that showcase skills like leadership, problem-solving, teamwork, and adaptability. Write them out in the STAR format to ensure they’re structured and impactful.

• Practice Common Behavioral Questions: Prepare for questions such as:

  • “Tell me about a time you overcame a significant challenge.”

  • “Describe a situation where you resolved a team conflict.”

  • “Can you share an example of how you managed competing priorities?”

• Keep It Concise: Aim for 2–3 minute responses. Stick to relevant details and avoid unnecessary tangents.

Pro Tip: Don’t skip the “R”—the results. Hiring managers want to know the measurable impact of your actions. For instance, instead of saying, “I handled the project well,” say, “I delivered the project two weeks ahead of schedule, increasing team productivity by 15%.”

4. Prepare for Common Interview Questions

While every interview is unique, there are common questions you should anticipate and prepare for. Having thoughtful, concise answers ready will not only boost your confidence but also help you make the most of your time with the interviewer.

• General Questions:

  • Walk me through your resume and experience.

  • Tell me about yourself.

  • Why do you want to work at this company?

  • Why do you want this role?

• Behavioral Questions:

  • Tell me about a time you solved a complex problem.

  • Describe a time you dealt with a difficult coworker.

  • How do you handle competing priorities?

Pro Tips:

1. Use the STAR Method: Even for “general” questions, the STAR framework can add depth and structure to your answers. For instance:

   1. Tell me about yourself: Highlight a key accomplishment (“S”), your role or skills that made it possible (“T” and “A”), and how it aligns with the role you’re interviewing for (“R”).

   2. Why do you want this role?: Share a specific moment or project that connects to the role’s responsibilities, using STAR to make your answer memorable.

2. Keep It Concise: Aim for answers that are 1.5–2 minutes long. Be substantive but avoid going too deep into details. If the interviewer wants more information, they’ll ask follow-up questions.

3. Prioritize Quality Over Quantity: Don’t spend 10 minutes answering one question—it wastes valuable time that could be used to highlight other strengths. Concise, impactful answers allow you to cover more ground.

5. Prepare Insightful Questions

• Why It Matters: Shows you’re engaged, curious, and serious about the opportunity.

• Sample Questions to Ask:

  • What does success look like in this role?

  • How do you measure performance in the first 90 days?

  • What do you enjoy about your company?

  • Can you tell me about the team I’d be working with?

• Pro Tip: Avoid questions that can easily be answered by a Google search.

Subscribe now

6. Mock Interviews and Practice

• Why It Matters: Confidence comes with repetition.

• How to Practice:

  • Conduct mock interviews with friends, colleagues, or career coaches.

  • Record yourself to analyze body language and tone.

  • Attend mock interview sessions (e.g., with career centers or mentors).

• Pro Tip: Treat mock interviews as seriously as the real thing.

7. Logistics and Final Prep

Preparing for the logistical aspects of your interview is just as important as preparing your answers. A little effort here can go a long way in making a polished and professional impression.

Checklist for Success

1. Research Your Interviewers:

   • If you’re provided with the names of your interviewers, look them up on LinkedIn ahead of time. Understanding their background can help you prepare thoughtful, personalized questions, such as:

     • “I saw on LinkedIn that you’ve been with the company for six years. How have you seen the company grow during that time?”

   • Be Strategic: Avoid viewing their profiles on the same day as your interview, as LinkedIn notifies users when someone views their profile. This could give the impression that you’re cramming last-minute rather than being thoroughly prepared.

2. Prepare for the Format:

   • In-Person:

     • Bring multiple copies of your resume in a professional leather portfolio (like this one on Amazon).

     • Know the building location, parking details, and check-in instructions. Reach out to the recruiter if you haven’t received this information at least one week before the interview. It’s their job to provide this support, and clarifying these details in advance will help you avoid any last-minute stress.

   • Virtual:

     • Test your tech setup in advance to ensure your camera, microphone, and internet are working smoothly.

     • Use wired headphones if possible to avoid audio delays from Bluetooth devices.

     • Choose a distraction-free, well-lit environment with a neutral background.

3. Plan Your Outfit:

   • Research what’s appropriate for the company’s culture. Look at the company’s Instagram, LinkedIn, or website for photos of employees at work or events. This will help you decide whether to dress formally or go for a smart-casual look.

   • Pro Tip: When in doubt, it’s better to be slightly overdressed than underdressed.

4. Confirm the Details:

   • Double-check the interview time, location, or meeting link.

   • If anything is unclear, don’t hesitate to ask the recruiter for clarification. Recruiters are there to support you, and it’s far better to confirm details than risk a mix-up.

5. Ask for Help if Needed:

   • If you’re unsure about anything—whether it’s logistics, dress code, or interview structure—reach out to the recruiting manager. There are no “dumb” questions, and it’s unlikely to negatively affect the outcome of your interview.

6. Arrive Early:

   • Aim to arrive 15 minutes early, whether it’s virtual or in-person. This shows professionalism and gives you a moment to collect yourself before the interview begins.

• Pro Tip: Preparation extends beyond just answers. Being organized, punctual, and polished in your approach creates a strong first impression and reinforces your professionalism. These small details can set the tone for a successful interview.

8. Follow Up After the Interview

Why It Matters: Following up shows professionalism, keeps you top of mind, and reinforces your enthusiasm for the role. It’s a simple step that can leave a lasting positive impression.

How to Follow Up:

1. Send a Thank-You Email:

   • Within 24 hours of the interview, send a personalized thank-you email to each of your interviewers.

   • If you don’t have their contact information, reach out to your recruiter. They can either provide the emails or, if the company keeps emails confidential, pass your message along to the interview team.

   • In your email, mention something specific from the conversation to show you were engaged and listening. For example:

     • “I appreciated our discussion about the company’s expansion plans and how this role supports that growth.”

   • Reiterate your interest in the role and thank them for their time.

2. Send a LinkedIn Connection Request:

   • After your thank-you email, visit their LinkedIn profiles and send a polite connection request with a short message:

     • “Thank you for your time today. I appreciated the opportunity to interview and look forward to hearing from the team!”

   • This step reinforces your interest and ensures you remain connected professionally, even if you don’t get the role.

Pro Tip: Keep your tone professional but warm in both your email and LinkedIn message. Thoughtful follow-up not only shows respect but also demonstrates your attention to detail—qualities every hiring manager values.

A Word of Encouragement

Preparing for an interview can feel daunting, but with the right approach, you’ll set yourself apart from the competition. Here’s what to remember:

• Research the company and role thoroughly: Understand their goals, challenges, and what they’re looking for in a candidate.

• Use the STAR method: Structure your answers to showcase your experience clearly, concisely, and compellingly.

• Practice, practice, practice: Confidence comes with preparation, so rehearse your answers, refine your delivery, and anticipate common questions.

Interviews are opportunities to demonstrate not just your skills but also your dedication, professionalism, and fit for the role. By taking the time to prepare, you’ll walk into your next interview with confidence and clarity.

If you found this guide helpful, share it with friends, classmates, or colleagues who are preparing for interviews. Sometimes, a little preparation is all it takes to turn nerves into success!

Looking for personalized interview or career support?

Partner with me for 1:1 coaching to create a personalized action plan that will help you prepare with confidence. Whether you need help refining your STAR stories, crafting a winning resume, or developing a long-term career strategy, I offer confidential guidance and accountability. With experience as a hiring manager at Fortune 500 companies like Amazon and Microsoft, I know what it takes to stand out—and I can help you land the role you’re aiming for.

Book a 1:1 Coaching Session