I want to explore the surprisingly deep connection between AI and leadership.
At its core, great leadership isn’t about having all the answers. It’s about setting direction, creating clarity, and enabling others to do their best work. This is especially true when leading experts. The only thing you can do is clearly express the larger intent: where we’re going, why it matters, and how we’ll know if we’re making progress.
That’s the kind of leadership that unlocks real value.
Now, with AI entering the picture, we’re all being thrown into a similar position. Each of us suddenly has access to an incredibly capable “expert” that can help solve problems: if we can express clearly what we want. Working with AI demands the same clarity we expect from great leaders. You have to express not just the task, but the why, the value, and the criteria for success.
The ability to define problems, articulate intent, and guide solution proposals isn’t just a “nice to have” anymore. It’s becoming a core part of everyday work. And it doesn’t stop at the individual level. If you give your AI tools access to all your organization’s content, the real leverage comes when that content reflects shared direction, priorities, and purpose. That’s how AI becomes aligned with the organization strategically.
That’s why I find the Clear Thinking model so powerful. It gives structure to this mindset: separating Intention Requirements (the what, why, and success criteria) from Solution Suggestions (how we might get there). At first, it seems like a tool for writing better briefs or specifications but zoom out, and it’s really about leadership. Then zoom out again, and you realize it’s a key to unlocking the potential of AI.
If you want to either lead or utilize AI then learning how to express yourself clearly is the key, for you and your organization as a whole.
Apparently, Madonna was a leadership and AI pioneer all along 😉
Beyond Technicalities - Contango 