KENNY CHIEN / COACHING / EXECUTIVE COACHING
Executive Coaching
Private sessions for leaders making AI bets — strategy, vendor truth-telling, and what to build versus buy.
Executive coaching is a private, one-on-one engagement for leaders who have to make AI decisions they cannot delegate. We work on the calls you actually face: which bets to make, which vendors to believe, what to build versus buy, and how to talk about AI to a board without hype or fear.
This is not a briefing service, and I will not read you the news. Sessions are working sessions: we take a live decision from your desk — a budget line, a vendor contract, a reorg, a build-versus-buy call — and pressure-test it until it holds or breaks. Between sessions you get direct access for the questions that cannot wait for the calendar.
“Your vendors are not lying to you. They are paid to be optimistic. You need one advisor who is not.”
Who this is for
CEOs, CTOs, CAIOs, and business-unit leaders who own an AI mandate
Executives facing a build-versus-buy decision with real money attached
Leaders who need to evaluate vendor claims without a technical translator
Founders and operators repositioning their company for the agentic era
Format and structure
Recurring 1:1 sessions
Sixty to ninety minutes, typically every one or two weeks, remote by default. In person when the decision warrants a room.
Direct access
Async access for the time-sensitive questions — a vendor claim to sanity-check, a slide to challenge, a contract clause that smells off.
Your real decisions
We work on live artifacts: strategy memos, vendor proposals, architecture diagrams, hiring plans. No hypotheticals, no case studies.
What you walk away with
A clear, defensible AI thesis you can state in one paragraph
A build-versus-buy framework calibrated to your organization, not the industry average
Sharper instincts for separating vendor claims from vendor evidence
Board- and team-ready language for what you are doing and why
Common questions
Who is executive coaching for?
Leaders with an AI mandate and real decisions on their desk: CEOs, CTOs, CAIOs, and business-unit owners. It is judgment work, not a technical tutorial — developers who want hands-on skills belong in the Vibe Coding Bootcamp instead.
How is coaching different from consulting?
Consulting ships a system; coaching sharpens the leader. If you need an application launched or an architecture designed, that is a consulting engagement. Coaching is for the judgment no engagement can outsource.
Is executive coaching confidential?
Yes. Sessions cover live strategy, vendors, and personnel, and nothing is shared, referenced, or reused elsewhere. An NDA is standard practice, not an objection.
How do I request a slot?
Email kenny.chien@gmail.com with one paragraph: your role, the decision in front of you, and the timeline. I take a small number of executive clients at a time and will say plainly if there is no open slot. If your whole team needs the shift, start with a team workshop instead.
Request a slot
Send one paragraph on your role and the decision in front of you. I will reply with an honest read — including whether you need a coach at all.