11 Observations From Coaching Tech Leaders Through Job Searches, Transitions, and Promotions
Eleven patterns I have seen repeatedly while coaching senior engineers, product leaders, directors, and VPs. I wish someone had told me number 9 when I was on the hiring side.
Eleven observations after coaching leaders in tech through job searches, career transitions, and promotions. I wish someone had told me number 9 when I was on the hiring side.
1. Your resume gets you in the room
How you talk about your work in the first 10 minutes decides if you stay.
2. The leaders who land fastest are not applying to more roles
They’re having better conversations with fewer people.
3. Most senior professionals have never practiced telling their own story out loud
They assume the experience speaks for itself. It does not.
4. Networking is not about finding someone who can hire you
It’s about reconnecting with past colleagues, making new connections, and pushing past the discomfort of putting yourself out there. You never know where the right opportunity actually comes from. (See two networking strategies for the exact templates I give my coaching clients.)
5. The gap between two equally qualified candidates almost always comes down to how they frame trade-offs, decisions, and outcomes
Not what they built. Why they built it — and what they chose not to build.
6. AI is not optional anymore
The leaders who land are actively upskilling to show they are ahead of the curve, and they’re using AI strategically in their search to stand out without sacrificing quality.
7. Managing up is a skill, not politics
The leaders who are getting stuck in their current roles are almost always the ones who have never learned how to make their value visible to the people making decisions above them.
8. Imposter syndrome does not go away at the director or VP level
It gets louder. And the leaders who deal with it honestly are the ones who move through it faster.
9. Most people dramatically undervalue how they show up in interviews
They treat it like a career recap instead of a leadership conversation. Those are two very different things.
10. The best career moves I have seen are not always upward
Sometimes the strongest move is a lateral step into a role where you actually run something real — instead of managing six layers of process.
11. Every leader I have worked with who stalled for 6 or more months had the same thing in common
They waited too long to ask for help. Not because they could not afford it. Because they thought they should be able to figure it out on their own.
P.S. If you’re a senior engineering or product leader and your search has been slower than you expected, contact me or book a discovery call, or read more about my career and interview coaching. The market is moving faster than most of us expected, and it is not slowing down for anyone. The leaders I work with always say the same thing: they wish they had started sooner.
