Career Coaching for Tech Professionals: Figure Out Your Next Move

A career coach for tech professionals is a thinking partner, not an advice machine. You already know the frameworks. What you need is someone to help you figure out what’s actually going on: what you want, what’s stopping you, and what the next concrete step is.

Most career coaching is generic advice delivered by someone who hasn’t been inside a tech org. If you’re a software engineer, product manager, or engineering leader who is genuinely stuck, that’s not useful.

This is coaching for people who are done with the vague stuff and ready to work through the specifics.

Who this is for

You’re a professional with real experience in tech, product, engineering, or a digital-adjacent field. You’re not early-career. You’ve built things, led things, or shipped things. And you’re at a point where the next move isn’t obvious.

The most common situations I work with:

Software engineers at the senior IC level who are trying to figure out whether management is actually what they want, or whether the drive toward leadership is just the only visible path forward at their company.

Product managers and technical PMs deciding whether to go deeper into the product path, pivot to something adjacent, or exit a tech role altogether.

Engineering managers who got the title and now aren’t sure they made the right call. Or who are good at the job but can see the ceiling from here.

Mid-career professionals in tech who are considering a career change out of the industry entirely, and are trying to figure out what’s realistic versus what’s wishful thinking.

Professionals post-layoff who have the breathing room to be intentional, but are finding that the clarity they expected hasn’t arrived.

Maybe you’ve outgrown your current role but can’t see what comes next. Maybe you’re considering a career change at 35, 40, or 45 and aren’t sure whether you’re thinking clearly about it. Maybe you have a direction in mind but don’t know how to get there without starting over.

The people I work with aren’t stuck because they lack ambition or skill. They’re stuck because career decisions are genuinely hard to think through clearly when you’re inside them. Eight of the most common reasons are here.

Is career coaching the right tool for you?

Career coaching is the right tool when the problem is a decision, a transition, or a situation where you need to think more clearly. It’s the wrong tool when the problem is skills (you need training), credentials (you need a certification or degree), or clinical mental health support (you need a therapist).

Most of the tech professionals I talk with are not in the wrong category. They have the skills. They have the experience. What they’re missing is a structured space to work through a decision that feels genuinely high-stakes, with someone who isn’t trying to steer them toward a predetermined answer.

If that’s where you are, coaching is probably useful. If you’re not sure, the free call will make it clear.

Why tech career decisions are harder than they look

The standard career advice doesn’t account for a few things that are specific to working in tech.

The comp structure raises the stakes. If you’re vested into significant RSUs or sitting on unvested equity, every career decision carries a financial dimension that makes it harder to think clearly about what you actually want. The money becomes a reason to stay even when the staying isn’t working.

The pace of change adds noise. Layoffs, AI displacement, org reorgs, and role consolidation mean that what looks like a stable path this year can look very different in 18 months. It’s hard to make a decision about the future when the landscape keeps shifting.

The IC versus management fork is a false binary. Most tech orgs present one visible growth path. That doesn’t mean it’s the only path, but it takes real thinking to see around it.

Tech culture doesn’t talk about career uncertainty openly. Everyone on LinkedIn looks confident. The people I work with are often relieved to be in a room (or a call) where the question “I don’t know what I’m doing next” is not treated as a failure.

None of this makes tech careers uniquely terrible. It makes career decisions in tech harder to think through clearly without a structured conversation.

What career coaching actually does

Coaching doesn’t give you a career plan. It gives you a clearer picture of what’s actually going on: what you want, what’s stopping you, and what the next concrete step is.

In practice that means asking better questions than you’re asking yourself, surfacing assumptions you’re treating as facts, and helping you move from “I’m not sure what to do” to “here is the decision I’m making and why.”

Here is what that looks like in practice. A software engineer comes in saying they want to move into product management. Within one session, it often becomes clear they don’t actually want to be a PM. What they want is to have more say over what gets built. That’s a different problem with a different solution: it might be a different team, a different company, a staff-level role with more influence, or a shift to a smaller org where technical leaders have more scope. The PM path was the first visible answer to the underlying question. Coaching is what gets to the actual question.

What a first session actually covers. The first session is diagnostic. We spend the time understanding what’s actually going on: what the decision or situation is, what you’ve already tried, what assumptions you’re making, and what’s actually in the way. You don’t need to have it organized before the call. Part of the value is that organizing it for someone else forces you to see it differently. By the end of a first session, most people have at least one assumption they were treating as a fact that they’re now questioning.

The ICF’s research on professional coaching consistently documents improved self-confidence and better decision-making outcomes in people who work with certified coaches. My observation from coaching conversations is more specific: the main value isn’t the insight itself, it’s the ability to act on a decision you’ve been avoiding. The insight is usually already there. What’s missing is the clarity to move.

The goal is not to feel better about being stuck. The goal is to not be stuck anymore.

About this coaching

I’m Kendall Guillemette. I’ve spent 25+ years working in and around digital and tech organizations: building web experiences for B2B companies, working alongside engineering and product teams, and watching the same career inflection points come up repeatedly for smart, capable people who couldn’t see their own situation clearly from inside it.

I’m not a recruiter. I’m not a resume coach. I’m not going to give you a template for your LinkedIn profile. What I do is focused: thinking through the decision or the situation you’re stuck on, until you can see it clearly enough to act.

The people I work with come from a range of tech environments: large companies like Google, Amazon, and Microsoft, pre-IPO startups, and mid-sized SaaS companies. The specific company matters less than the situation. What tends to be consistent is the profile: experienced, competent, not stuck because they’re not smart enough to figure it out, but stuck because they’re too close to it to see it clearly.

Career coaching is formally defined by the International Coaching Federation (ICF) as “partnering with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential.” That’s accurate but dry. More practically: I ask questions than you’re not asking yourself. That may because you don’t know the questions to ask, or there’s something stopping you from asking yourself those questions. I hold the context across sessions. I don’t have a stake in the outcome, which is the thing your manager, your spouse, your recruiter, and your LinkedIn network all have.

The ICF is the primary professional credentialing body for coaches globally. Certified coaches meet specific training hour requirements and adhere to a code of ethics that prohibits giving advice in disguise as coaching. That distinction matters when you’re evaluating who to work with.

I work with tech and digital professionals, primarily in the US. Sessions are by phone or video.

What to expect from coaching

The starting point is a free 15-minute conversation to understand what you’re working through and whether there’s a fit. If we move forward, sessions are 45-60 minutes.

Most people I work with don’t need a long engagement. The value usually comes from two to four focused sessions where we get specific about what’s actually going on, cut through the noise, and identify the next concrete move.

Between sessions: I don’t assign homework or send you worksheets. If you want to reflect or write things down, go ahead. The work happens in the conversation.

The goal at the end of any engagement is that you have a decision you can commit to, or a direction you can take action on. Not a vision board. Not a “clearer sense of purpose.” A next step.

How to choose a career coach for tech

Not every career coach understands the specific dynamics of working in tech. Here’s what to look for and what to avoid.

Look for someone who has been in or around tech organizations. Career coaching is generic. Career coaching for tech professionals is specific. Someone who has spent their career coaching marketing executives will give you different questions than someone who understands how engineering orgs actually work, what the IC/manager split means, and how RSUs and vesting affect the decision calculus.

Look for a coach, not a consultant. If someone leads with their own career story as the primary credential, you’re talking to someone who’s going to give you advice, not coaching. A coach’s job is to help you think through your situation, not to tell you what they would do. The difference matters.

Avoid coaches who want long commitments upfront. A three- or six-month “coaching program” with a large upfront fee should raise a question: who is that structure for? The best coaching relationships are as long as they need to be, and rarely need to be long. A coach who is confident in the value they provide doesn’t need to lock you in.

Test for fit on the first call. A serious career coach will offer a short introductory call before asking you to commit to anything. Use it. Notice whether they ask better questions than you’ve been asking yourself. That’s the job.

What you’ll find here

This section covers career transitions, career changes, and the work of getting unstuck, written for professionals who want direct thinking, not motivation.

• How to evaluate whether you’re stuck in a role or stuck in a career
• What career change actually looks like at different life stages, and what the data says vs. what people fear
• How to find a career coach who will actually help (and what to avoid)
• The difference between a career transition and a career pivot, and why it matters for how you plan

Common situations

You’ve hit a ceiling. You’re good at what you do, maybe very good, but the path forward in your current org isn’t there or isn’t something you want. You need to figure out what “forward” looks like when upward isn’t an option.

You’re considering a career change. The role worked for a long time. It doesn’t anymore. You’re looking at adjacent fields or completely different directions and trying to assess what’s realistic versus what’s wishful thinking.

You’re at a career crossroads. Two or three legitimate options, each with real tradeoffs. The decision feels high-stakes and you don’t trust yourself to think about it clearly when you’re under pressure to decide.

You want to work differently. Less corporate, more independent. More ownership, less execution. You can see the direction but not the path.

None of these situations are unusual. They’re hard to navigate not because they’re rare but because career decisions have high stakes, long time horizons, and limited feedback loops. It’s hard to learn from a decision you only get to make once.

Most people in tech wait longer than they should to get outside perspective on a career decision. By the time they reach out, they’ve often been sitting in the same mental loop for 6 to 18 months, cycling through the same considerations without getting any closer to clarity. That’s not a failure of intelligence or resolve. It’s what happens when you’re trying to think clearly about something you’re too close to.

Last updated: May 2026

How to get started

If you’re thinking about coaching, the first step is a conversation. Fifteen minutes to understand what you’re working through and whether there’s a fit.

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