Using AI to Learn Leadership - MAC128

Last week on the podcast ( https://managingacareer.com/127), we explored a career moment almost everyone encounters if they stay in the game long enough. Early on, progress comes from taking responsibility, delivering reliably, proving you can be trusted with more. Then one day the measurement changes. The path forward is no longer about what you can personally carry across the finish line; it becomes about what you can help others achieve. Responsibility built the foundation; influence becomes the multiplier.

That change can feel uncomfortable… even threatening. The people you now need to guide used to sit beside you. They may still feel like your inner circle. Pushing for results risks feeling controlling. Delegating risks disappointment. Letting go of the work that made you successful can feel like giving up the very identity that got you here. So the question becomes practical and emotional at the same time; how do you earn confidence as someone who produces outcomes through others rather than through your own hands?

Today we are going to explore a surprisingly safe training ground. A place where you can experiment with direction, clarity, feedback, and expectation setting without damaging relationships or reputations. We are going to talk about using AI as a practice field for leadership.

Why I Created This Podcast

I know this transition intimately because I wrestled with it myself -- and ultimately, it's the reason I created this podcast.

For a long stretch of my career, I was the person people counted on when something difficult landed. I could untangle the mess, close the gap, rescue the timeline. I prided myself on being generous with my time and quick with solutions. If there was a scoreboard, my name felt near the top.

And yet… I stopped moving.

I asked what I needed to do to advance. I expected something concrete; a certification, a bigger project, longer hours, sharper technical depth. Instead I received advice that felt vague and frustrating. I was told "Be more strategic". At the time, my thinking was "What does that even mean?"

What I eventually realized, much later than I wish I had, was that the standard had changed while I was still playing the old game. I kept proving I could personally execute, personally fix, personally deliver. But the next level required evidence that I could create results through other people. I was clinging to the work because I could do it faster and better. Handing it off felt inefficient. It felt risky. It felt like lowering the bar.

Letting go turned out to be the skill.

Here’s the part that should excite you. The practice environment available now is radically different from the one I had when I was learning this lesson. You have access to something that allows you to rehearse direction, delegation, coaching, and accountability whenever you want.

You have AI.

Leadership as a Practice Field

So let’s bring this down to earth.

If leadership is the requirement, then we need repetitions. Not philosophy… not inspiration… reps. The same way execution excellence came from doing the work again and again, influence grows from practicing how we set direction, clarify expectations, evaluate tradeoffs, and guide performance.

The challenge is that most workplaces are not designed as classrooms. Every attempt happens in public. Every mistake has witnesses. Every unclear instruction can slow a project or strain a relationship. That pressure makes experimentation feel dangerous, which is why so many capable people retreat back into doing the work themselves.

What if you had a place to practice where none of that risk existed?

Before we jump into the exercises, we should get specific about the capabilities that separate strong individual contributors from trusted...