What Is AI Coaching for Executives? A Practical Guide for 2026

Here is a question worth sitting with: when was the last time you made a major AI decision for your organization and felt genuinely confident about it?

If you are like most executives I talk to, the honest answer is somewhere between "not sure" and "never." And that is not because you lack intelligence or ambition. It is because the AI landscape in 2026 is genuinely overwhelming. There are thousands of tools, new models shipping every month, and a constant stream of vendors promising that their platform will transform your business. Meanwhile, your board expects an AI strategy, your team is already using ChatGPT on their own, and you are stuck trying to separate the signal from an extraordinary amount of noise.

The solution is not another tool. It is not another course. It is having a thinking partner who understands both AI and business well enough to help you make decisions that stick.

That is what AI coaching for executives is. And in this guide, I will walk you through exactly what it looks like, who it is for, and how to know if it is the right move for you.

What AI Coaching for Executives Actually Is

Let me clear up the biggest misconception first. AI coaching for executives is not an AI tool that coaches you. It is a human coach, someone with deep experience in both AI and business strategy, who works with you one-on-one to help you think more clearly about how AI fits into your organization.

That distinction matters because the market is flooded with "AI coaching" products that are really just chatbots with a motivational tone. A January 2025 study from The Conference Board found that AI can replicate roughly 90% of what a career coach does in terms of information delivery and basic guidance. But that remaining 10%, the strategic, nuanced, context-dependent thinking, is exactly where executives need the most help. Chatbots cannot sit in on your leadership team meeting and notice that your VP of Operations is quietly resistant to the new workflow. A human coach can.

So how does executive AI coaching differ from the alternatives? An AI course teaches general concepts to a broad audience. You learn what is possible, but not what is right for your specific situation. AI consulting firms tend to come in, build a deliverable, and leave. They hand you a strategy deck, but you still need to execute it. And AI chatbot coaching platforms can answer questions, but they have no context about your team dynamics, your competitive position, or the political realities inside your organization.

AI coaching sits in a different category entirely. It is an ongoing relationship with someone who knows your business, challenges your thinking, and helps you build the muscle to make AI decisions confidently on your own. The goal is not to make you dependent on a coach forever. It is to get you to a place where you trust your own judgment about AI.

Why 2026 Is the Year Executives Cannot Afford to Wait

Look, AI has been "important" for a few years now. But 2026 is different for a specific reason: the consequences of inaction have become visible.

In its 2025 Predictions report, Forrester projected that 60% of Fortune 100 companies would appoint dedicated heads of AI governance by the end of 2026. That is not a trend. That is a structural shift. It means AI strategy is no longer a side project that lives in IT. It is a board-level priority with named accountability.

At the same time, research from Rand Corporation published in August 2024 found that roughly 80% of AI projects fail to deliver meaningful ROI. The most common reason is not bad technology. It is bad strategy: organizations that jump to tool selection before clarifying what problems they are actually solving and who needs to change their behavior to make it work.

This is the gap that AI coaching for executives fills. Your team does not need you to become a prompt engineer. They need you to be the person who can articulate why your organization is using AI, where it fits, and what "good" looks like. That is a leadership skill, not a technical one. And like any leadership skill, it develops faster with the right coach.

Here is the thing: your competitors are not waiting. According to McKinsey's May 2025 Global AI Survey, 78% of organizations reported using AI in at least one business function, up from 55% in early 2023. The window to lead, rather than follow, is closing.

What a Typical AI Coaching Engagement Looks Like

I want to make this concrete because "coaching" can feel vague. Here is how I work with executives, broken into phases.

Phase 1: Assessment (Week 1-2). We start by mapping your current state. What tools is your team already using? Where are the biggest bottlenecks? What decisions about AI have been sitting on your desk for weeks? I also want to understand your leadership context: your board's expectations, your team's readiness, and your own comfort level with AI. This is not a survey. It is a series of focused conversations.

Phase 2: High-Impact Use Case Identification (Week 2-3). Based on the assessment, I help you identify the two or three AI use cases that will create the most value for your organization in the next 90 days. Not the flashiest ones. The ones that solve real problems your team already has. We prioritize ruthlessly because trying to do ten things with AI at once is the fastest way to do none of them well.

Phase 3: Roadmap and Decision Framework (Week 3-4). We build a concrete 90-day roadmap. This includes which tools to use, who on your team owns what, what success looks like, and how you will communicate the plan internally. I also help you build a decision framework you can use long after our engagement ends, so the next time a vendor pitches you a shiny new AI platform, you have a clear rubric for evaluating it.

Phase 4: Ongoing Coaching (Biweekly or Monthly). This is where the real work happens. We meet regularly to review progress, troubleshoot roadblocks, and adjust the plan as conditions change. Between sessions, I am available for quick questions and gut checks. Think of it as having an AI-savvy advisor on speed dial.

Stop reading for a moment. Write down the three biggest decisions about AI sitting on your desk right now. If you can name them clearly, you are closer to progress than you think. If you cannot, that is exactly where a coaching engagement starts.

Who AI Coaching Is For (And Who It Is Not For)

AI coaching for executives works best for:

• CEOs and founders who know AI matters for their business but are not sure where to start or what to prioritize
• VPs and directors who have been asked to "figure out AI" for their department and need a strategic framework, not just tools
• Nonprofit leaders who want to use AI to amplify their mission without massive budgets (I wrote about this in my AI for nonprofits guide)
• Entrepreneurs and small business owners who want to stay competitive but cannot afford to hire an internal AI team

AI coaching is probably not the right fit if:

• You want someone to build AI systems for you. That is consulting or development work. (I offer that too through custom AI app builds, but it is a different engagement.)
• You just want to learn better prompts. That is a course or a tutorial, and there are plenty of good free ones. Coaching is about strategic thinking, not tactical tips.
• You are looking for a magic bullet. AI coaching requires your active participation. I bring the expertise. You bring the context about your business. Neither works without the other.

The leaders I have seen get the most value from coaching are the ones who treat it like what it is: a leadership development investment. They show up to sessions with questions, they do the thinking between sessions, and they are willing to make real decisions rather than just collecting information. If that sounds like you, coaching will probably be one of the highest-ROI investments you make this year.

How to Choose the Right AI Coach

Not all AI coaches are created equal. Here is what to look for. First, your coach should have actual experience building and using AI, not just talking about it. Ask them what they have built. Ask what tools they use daily. If they cannot give you specific answers, keep looking.

Second, look for someone who understands business strategy, not just technology. The best AI coaches translate between the two worlds. They can explain a complex AI concept in plain language and, more importantly, they can connect it to a business outcome you care about. As I explain in my guide on building a human-centered AI strategy, the best AI strategies start with people and business problems, not technology.

Third, find someone who will challenge you. A coach who agrees with everything you say is not a coach. They are an expensive yes-person. You want someone who will tell you when your AI idea is a distraction, when your timeline is unrealistic, or when you are avoiding a decision because it is uncomfortable.