Question 1

How is this different from executive coaching?

Accepted Answer

Most exec coaching is reflective work. You talk through challenges, surface patterns, build self-awareness. I do that too, but the bulk of what we do is live decision work. We take the actual call you're carrying and structure it. Trade-offs, framing, second-order effects. You leave with the decision sharper, not just yourself.

Question 2

Why not just do this internally?

Accepted Answer

You can. The trade-off: internal coaches and HR see the same problems through the same lens. I sit outside the org chart, and I've sat in your seat. For the highest-stakes calls, that's the difference. Internal works for the calls everyone makes. Outside works for the calls only you carry.

Question 3

When does this become AI strategy vs leadership coaching?

Accepted Answer

Leadership coaching is about how you make decisions and align teams. AI strategy is about which AI bets to place. They overlap a lot in 2026. I work both lanes. If the work tilts heavily toward strategy and roadmap, you might want the 10-day AI Strategy Intensive instead.

Question 4

What kind of leaders does this NOT work for?

Accepted Answer

Leaders who want a cheerleader. Leaders who don't want their thinking challenged. Leaders below Senior IC level. You should be carrying real decisions, not learning the basics. And anyone hoping coaching will solve a structural problem coaching can't fix: wrong role, wrong company, wrong board.

Question 5

What does a typical engagement look like?

Accepted Answer

1:1 decision partner: biweekly 60-minute calls, 90-min kickoff, 6-month minimum, light async between sessions, optional 360. SLT coaching: 3 to 6 months, mix of group sessions and 1:1s, scoped on a discovery call. Fractional AI Partner: monthly retainer with regular check-ins and hands-on work alongside your team.

Question 6

What does your AI background actually change in practice?

Accepted Answer

I've shipped AI features and run AI teams. So when we get to the AI question (and we always do now), I can structure it with you instead of around you. We talk about what to build, what to kill, what your CTO actually means when they say what they say. Most coaches can only listen on AI. I can challenge.

Five questions. Find your archetype.