A founder I work with sent me a list last month. Five AI coaches she was considering. Two were former management consultants. Two were people who had written a book about ChatGPT. One was a former CIO. She asked me which one she should pick. I told her she was asking the wrong question.
The right question is what she wanted to be different about her week three months after the engagement ended. Once we had that, the names on the list reordered themselves.
This is a short guide to that reordering. Built for senior leaders who have decided to stop circling AI and want to put real reps in with the right coach, on the right material, at the right time.
The mismatch buyers run into
Most AI coaching offers are calibrated to a generic audience. The buyer is described as "leaders" or "professionals" or "executives," with no further specificity. The session covers "the fundamentals of AI" plus a tour of three or four popular tools. The pricing is set against a generic training market.
Senior buyers sit outside that audience. A CFO closing a quarter and a CMO running a pipeline launch ask different things of a model. A CEO doing a board read and a General Counsel reviewing a contract queue need different vocabulary. A founder-CEO at a fifteen-person company and a division president at a multi-line business need different engagements. The work they are trying to apply AI to has a specific shape, and a generic session will not survive contact with it.
The first thing to look for in a coach is whether they have built their offer around a specific seat. If they cannot tell you in one sentence who the session is for, the session is for nobody in particular.
Five questions that surface real expertise
These are the questions to ask in the intake call. They take five minutes. They cut through the polish on most decks.
1. What does a session calibrated to my function look like?
A real coach will name the artifacts you will sit with: the board pack, the close, the diligence queue, the campaign brief. A weaker coach will describe a generic curriculum and then say "we tailor it to your needs."
2. Which clients in my situation have you worked with, and what changed for them?
Real engagements produce specific operational changes. A coach who can tell you that a CFO at a $200M services company rebuilt how the team writes variance commentary, or that a founder-CEO at a forty-person company now runs board prep in half the time, has done the work. A coach who waves at "many clients across many industries" has not.
3. What is the work I will leave with?
The honest answer is artifacts: written summaries, custom templates, a small set of workflows the team can run after you leave. If the answer is a recording and a slide deck, the engagement is a presentation rather than a working session.
4. How does this differ from sending my team to a workshop or a course?
A 1:1 session is calibrated to your seat in a way that group formats cannot match. A coach who pretends the offers are equivalent does not understand the difference. There is room for both formats in a company's AI plan. A coach who is honest about which is which is more trustworthy than one who insists their format is the only one. We unpack this distinction in AI coaching vs AI training.
5. What happens after the session?
Real engagements have a tail: a follow-up window, a check-in, written takeaways the buyer can act on without further help. A session that ends when the call ends is a brittle product.
Credentials that actually matter
The certification market for AI has expanded faster than the field. Two-day "Certified AI Practitioner" courses now exist. Most of them are marketing rather than expertise. A few signals worth weighing:
Hands-on experience with the systems, not commentary about them. Coaches who use AI in their own working week speak about it differently. They know which model handles long documents better, which one understands ambiguity better, which one is currently better for code or for writing. That fluency is hard to fake in a working session.
Background that sits outside the AI hype cycle. Someone whose career was already substantial before 2023 has more to draw on. Strategy consulting, finance, operations, product, an academic discipline. The judgment that matters in an executive session is mostly business judgment, applied through AI rather than to it.
A point of view, in writing. A coach who has thought publicly about the field, in essays or working notes, is easier to evaluate than one whose entire footprint is a polished landing page. Read what they have written. The voice and the judgment come through.
Red flags
Vague case studies. "We helped a Fortune 500 leader transform their decision-making" is not a case study. It is a sentence.
Vendor lock-in. Coaches who only teach one platform, or who are quietly affiliated with one, will calibrate their advice to that platform. The right approach uses whichever tool earns its keep, and changes the tool as the field changes.
Certificate-shopping. Coaches who lead with "Certified AI Practitioner" or "AI Strategist Certification" credentials are positioning for a market of credential-buyers. Senior practitioners signal differently.
Promises of universal applicability. "Works for any function, any industry, any role" usually means built for none of them.
Pricing that does not match the seat. A senior executive's time is the constraint. A $200 group webinar and a $5,000 working session can both be the right answer in the right circumstance. A coach who cannot explain why their price matches the buyer they are aiming at has not thought it through.
What a real engagement looks like
For a senior leader, a serious 1:1 engagement runs in three movements.
The first is an intake. Real homework on your role, your function, your week. The coach reads what you sent before the meeting and arrives with questions, not a script. Sixty minutes is typical.
The second is a working session. Ninety minutes is a reasonable size for a single intensive. The screen is open. The material on screen is yours. The fundamentals get covered in the order you will use them, in the order they will earn their keep.
The third is the tail. A written summary of what got built. Custom templates the team can keep. A follow-up window where you can come back with questions while you put it to use.
That is the shape of a working engagement. If a coach is selling a one-off recorded webinar at a working-session price, the math is wrong. For a longer description of what executive AI coaching actually is, see what is executive AI coaching.
Where to start
The honest version of this work, for most senior leaders, starts with three questions for the coach you are considering:
Who is your session built for, in one sentence?
What artifact will be on screen during the working session?
What will be true about my week three months from now that is not true today?
If the answers are sharp, you have probably found a coach worth talking to. If the answers are general, keep looking.
Our own session for senior functional leaders is described at executive AI coaching. A good coach installs AI into the way you already work, and leaves behind the judgment to keep going without them.