I asked AI to coach me.

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The prompt I’ve been testing.

As someone who coaches for differentiation, helping people find the language that actually sets them apart, I’ve started leaning into outcome-driven questions instead of task-driven ones. So I ran a small experiment. I opened MS365 Copilot and typed this:

“Based on what you know about me, what did I grow, fix, or save this past quarter?”

Three words did all the work: grow, fix, save. Not “what did I attend.” Not “what did I complete.” What changed because I was there.

The answer that came back wasn’t a task list. It was closer to a case for why my work mattered, the kind of language that gets you promoted, funded, or remembered, instead of quietly forgotten in a stack of quarterly updates.

Why this works

Most reflection questions are backward-looking in a passive way: what did you do? This prompt is backward-looking in an active way: what shifted because of you? That distinction is everything. It forces a search for cause and effect instead of a search for evidence of effort.

It’s also why I started asking a deeper set of questions modeled after the ones I use in real coaching sessions, the kind designed to surface leadership, not just output:

• What trend did you recognize before others did?

• What future organizational need were you preparing for that wasn’t yet obvious?

• Which problem did you solve at the root cause versus treating symptoms?

• If your company stopped investing in this area entirely, what enterprise risk would reappear?

• What organizational asset exists today because you insisted it should exist?

• Of everything you listed, which outcome required the most leadership rather than expertise?

Try answering all six honestly. It’s harder than it looks and that’s exactly the point. The questions that are hard to answer are usually the ones worth answering.

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Where AI helps and where it stops

Here’s the part I want to be clear about: AI didn’t write my story. It found the raw material.

Copilot can scan your calendar, your emails, your documents, and hand you a decent first draft of what you accomplished. That’s genuinely useful, most of us are terrible at remembering our own wins in real time. But a first draft isn’t the same as a differentiated narrative. It doesn’t know which outcome required courage. It doesn’t know which fix was actually a fight you had to win internally before you could even start. It doesn’t know which “asset that exists today” almost didn’t happen because you were the only one pushing for it.

That’s the layer a coach adds. Not more data, better editing. Turning “I managed a cross-functional initiative” into the specific sentence that makes a hiring manager, a promotion committee, or your own boss sit up and pay attention.

Try it yourself

If you have access to MS365 Copilot (or any AI assistant with context on your work), open it right now and ask:

“Based on what you know about me, what did I grow, fix, or save this past quarter?”

Then sit with the six questions above. Write your honest answers, not the polished version, the true one.

You’ll probably notice a gap between what you did and what you can currently say.

That gap is exactly where coaching earns its keep.