AI training teaches concepts to groups. AI coaching shows you how AI applies to your specific situation. One is a curriculum. The other is a mirror.
Both have a role. Picking the wrong one costs you months.
When Training Works
Training is useful for broad awareness across an organization. It builds shared vocabulary, ensures everyone has touched the tools, and creates a baseline of understanding that makes future conversations about AI more productive.
If you need to upskill a team of 10 or more, training is the efficient choice. A workshop on prompt engineering fundamentals, a half-day session on AI tools relevant to your industry, a structured curriculum that takes people from zero to functional. These programs work well for what they're designed to do.
The limitation is built into the format. A webinar on "AI for business leaders" covers what's possible in general. It cannot cover what's possible for you, specifically, because the instructor doesn't know your workflows, your data, your role, or your constraints. That generality is a feature for teams. For senior leaders, it's the gap that matters most.
When Coaching Works
Coaching is calibrated to one person's context. The value is in the specificity.
A senior leader needs to see AI solving their actual problems, in their actual workflows, with their actual data. A training course assumes you can map the concepts to your work on your own. A coaching session does that mapping with you, live, in real time.
The reason this matters for senior people comes back to the Articulation Gap: you cannot ask for what you don't know is possible. Training gives you concepts and hopes you'll make the connections. Coaching makes the connections explicit.
The 22-Minute Pattern
People come in thinking they need training. They want to "learn about AI tools" or "understand what's out there." Reasonable goals. But within the first 22 minutes, something else happens.
A specific pain point emerges. Something training would never surface because it requires conversation, follow-up questions, and someone who can recognize the AI opportunity hiding inside a workflow description.
A CCO said she had "no repetitive tasks." Then described a competitive analysis framework she runs three times a month, each cycle taking days. She couldn't see the pattern because her expertise made it invisible.
A CEO wanted to "learn about AI tools." What he actually needed was a specific platform replacement for an enterprise reporting system costing him over $30,000 per year. That discovery happened in conversation, not in a curriculum.
A VP of marketing asked for an "overview of AI in marketing." By minute 25, we were building a system that automated her weekly competitive intelligence process. She didn't need an overview. She needed someone to point at the three-hour task she'd been doing every Tuesday and say, "That can take fifteen minutes."
Choosing
Choose training when you need to upskill a team. Choose coaching when you're a senior leader who needs personal capability and clarity about what AI means for your specific role.
Most executives need coaching first, then training for their teams. The reason is practical: a leader who understands AI from personal experience makes better decisions about what kind of training their organization needs. They can evaluate programs, set realistic expectations, and distinguish between useful training and expensive theater.
If you want to understand what a coaching session involves, start there. If you're ready to see how AI applies to your work specifically, book a session.