One to one with Kevin Williams
AI coaching with Kevin Williams helps CEOs and senior leaders work through the decisions AI brings into their role: what to prioritize, how to evaluate a proposal, and how to lead the people who will make it work.
Work with a five-time CEO who brings operating experience and daily AI product-building practice into the same conversation. The work starts with your business context and the question in front of you.
Start with the SnapshotA five-minute assessment with AI practices matched to your working week.
This work is for CEOs and senior executives who need to lead through AI while still running the business. You may be weighing an investment, preparing a board discussion, or deciding how AI changes a team’s priorities. You do not need to arrive with the right answer.
The useful starting point is a real decision with consequences. A leader who needs help comparing two proposals has a different coaching agenda from one whose managers have access to AI tools but no shared expectations for using them.
Coaching connects the AI question to the wider leadership job: business direction, people, pricing, competitive position, and accountability. The technical details matter when they change the decision.
Start with the Snapshot assessment. It asks about your working practices and gives you practices to consider applying. If the fit looks right, Kevin follows up personally.
A useful initial conversation identifies the decision you are facing, the constraints you need to respect, and what progress would look like. The coaching scope can then be discussed around those needs. Session arrangements and expectations belong in that conversation rather than being assumed from a generic program.
Progress should become visible in your work: a clearer investment decision, a better question for a vendor, a more focused operating review, or an explicit choice to stop an unpromising experiment. Those are examples of possible coaching objectives, not promised outcomes.
Kevin has held five CEO roles and shipped four commercial products built on large language models. That combination brings practical context to conversations about what a system can do, what a team can maintain, and what the business should ask of either.
He is the founder of AscendAI and coaches leaders on the wider responsibilities of running a company. Read his background and hear from the leaders he works with.
For the firm’s executive advisory offer, visit AscendAI’s executive AI coaching page. This site focuses on Kevin’s personal coaching approach and the practical decisions explored in his guides.
Coaching develops your capacity to lead and decide. Training provides a shared set of skills; consulting supplies specialist analysis or implementation. You may need more than one, but each should have a clear purpose. Read the guide to preparing for a first coaching session to get more from a fit conversation.
You can start with the business question. Coaching can help you understand the technical assumptions well enough to challenge a proposal, identify what you need to learn, and involve the right specialist when the decision requires deeper expertise.
Kevin’s coaching is one to one. The work centers on your responsibilities and decisions. If your team needs a shared skills curriculum or an implementation project, that is a different need to define alongside the coaching.
Bring one decision you are trying to make, the options you are considering, and what feels unresolved. Describe the context without sharing confidential material until the appropriate handling arrangements are established.
Discuss your goals, the scope of the work, session cadence, and fees directly with Kevin. This site does not publish a standard price or fixed-duration package. The first step is establishing whether the coaching matches your needs.
Begin with a useful question
Leadership & strategy
Run a focused AI operating review with a practical agenda for CEOs: accepted work, recurring errors, ownership, decisions, and the next test to authorize.
4 min read
Read the guide: How to Run a Weekly AI Operating Review as CEOLeadership & strategy
Choose a first AI use case with a clear owner, usable inputs, reviewable output, and measurable value. A practical decision framework for executive leaders.
4 min read
Read the guide: How to Choose Your First Business AI Use CaseExecutive coaching
Prepare for a first executive AI coaching conversation with one real decision, your constraints, the options you see, and a clear definition of progress.
4 min read
Read the guide: How to Prepare for Your First AI Coaching Session