It was 7:45 in the morning in Seattle on January 8. I had finished up my time at Included Health at the end of 2025, and we were up north to spend some family time over New Year’s, as our older son had moved to the area. I was sitting at the dining room table in the morning dark of our Airbnb.
I remember getting up, going out onto a patio, and taking a quick snapshot of the pink and blue sky over Elliott Bay, thinking about what would come next for me in 2026.
Since that morning I’ve had close to 200 conversations with senior product leaders, in a period of massive change in how we work.
TLDR: Underneath every question is self-doubt.
As I shifted to exec coaching and consulting, I distilled notebook writing, voice memos, and my vibe assessment across chats and live coffees so far this year. One side note: Tartine wins for top in-person coffee location. I recommend the morning bun and a cappuccino.
Here are five ideas plus two mega themes I’m hearing about often and loudly.
“What do I actually want next?” This one spans levels of seniority. The meta pattern: it’s rare for people to take time to step back and examine whether the path they’re on is what they really want. But people are doing this — I’ve heard different flavors of this all year from:
Should I work full-time or go solo?Should I move away from a difficult environment?
Am I selling myself short in my current role?
How do I get into a better environment to work on AI?
Should I switch careers away from tech entirely into my true passion?
If this one’s yours, start here: Make Time to Ask the Pause Question: Why the best fix isn’t always a tactic.The “below your level” conversation. The common theme is people examining ROI on their effort. Two different situations come up: people in a role who feel stuck and want to operate higher, or people who chose smaller on purpose — to learn, to get into a better company, or to reduce the craziness. The first group wants to assess and work on what’s holding them back. The second group wants to sanity-check the plan or work through regret.
“What is my unique differentiation?” How am I different from other leaders and what should I focus on to better bring that to life? Sometimes this one feels more like imposter syndrome. Other times it’s closer to “what do I actually want next?” (See #1.) An underlying theme in this one is the concern about AI commodifying aspects of past roles. In this context, unique product POV and judgment become even more of a separator. But in conversations, leaders want some help fleshing out how this comes to life for them or what they should work on next.
Executive communication, but with underlying drivers. This can start as wanting to be more crisp when communicating at increasing levels of company altitude. But the underlying driver is usually confidence or perfectionism, both affecting communication in the moment. So, over-explaining, freezing under pressure, challenges with probing or pushing others or just discomfort about senior-level communications all come up here. This is a rich area with a lot of tactical solutions that can help, but the core issues usually come back.
If this one’s yours, start here: Answer First: A Simple Framework for Executive Communication: The lesson I learned the hard way in a room full of leaders.Saying the important true thing out loud. Related to communication (#4) but different. This is about being true vs. being crisp. Sharp, clear perspectives held in mind, but someone finding it difficult stating them in rooms. Three versions I’ve seen:
Deference by default.
Forms of people-pleasing.
Asking permission where none is needed.
This is deeper than just “speak up more,” which is an oversimplification. The downstream cost is tough too: a POV missing from a big decision, overwork based on lack of boundaries, etc. It’s also at times hard to connect the downstream cost to this cause at first.If you want to go deeper on people-pleasing, start here: People-Pleasing May Be Holding You Back: How to spot this pattern, push through discomfort, and unlock better work—for yourself and your team.
Mega theme A: Self-doubt/imposter thinking. This one threads through many of the above. Sometimes it pre-dates the career altogether. Performance can mask it or help it subside for periods of time, but then it resurfaces. These conversations are often about figuring out what the right question is and then running small experiments to build confidence. This type of self-questioning can show up at first as questions that are more tactical and skill-oriented — “How do I get better at X?” Even when you keep deeper causes in mind, tactical tips are frequently where early experimentation starts.
Mega theme B: The org is the emerging AI problem. This also weaves through the above themes as teams work through the sea change of AI happening in real time. Two pieces here:
How to help teams move past AI demo and experimentation (at times performative only) into rewiring how a company works. This is moving past which model or tool to use in a flurry of options that constantly shift. The harder question is: What is our governance and workflow model?
Then there are broader people issues: Org shape changes, career paths, and where differentiated value emerges in a revised chain of work as executional costs drop.
This mega theme is the organizational version of #1 (What do we want next?) especially in contexts outside of AI-native-from-scratch companies. What’s really hard is evolving an existing company. The core issues are always human systems and people problems.
I’m curious what themes you’re seeing most. Try this: pick which one feels most relevant to you and ask yourself what you think the driver of that feeling is.
Hi, I’m Jeff. I spent 25 years building product at LinkedIn, Facebook, Headspace, and Included Health. Now I coach senior product leaders through the moments where the old playbook stops working: a bigger scope, a new company, communicating at the exec level, or figuring out what’s next. I work with a small number of 1:1 clients in six-month engagements, and every one started with a single conversation. If that’s you, or someone on your team — reply to this email. I read and answer every one.
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