Level up your AI assistant

Have you ever tried something I suggested here, watched it fall flat, and quietly wondered if I’m working with a better version of the tool than you are?

I’m probably not. But I get the suspicion, because I’ve been on the other side of it. I was recently completely convinced the people around me had some advantage I didn’t.

Many companies use Copilot. And let me be honest about Copilot — it is, by a wide margin, the most cautious and locked-down of the major assistants. It comes wrapped in guardrails my industry genuinely needs, and those same guardrails are a big part of why it is so underwhelming out of the box. Nobody is going to call Copilot brilliant.

And yet mine has become genuinely useful to me. Not because the tool is impressive, but because I use it constantly. In the lanes I actually drive it, it has learned how I think and who I present to, and it does a passable impression of my writing voice, mostly because I have corrected it again and again. Then one afternoon I asked it to do one simple thing I had never used it for, and it fell apart completely.

Here is what I say often and still manage to forget — AI doesn’t work like traditional software. It learns. It gets good at whatever you actually use it for, and it stays clumsy at everything else. The best way to make it more useful is…to use it. I have said that a hundred times. It took a room full of better slides than mine to remind me what it meant.

Let me tell you about that afternoon.

We were at a team offsite, and they gave us a small group exercise —build one slide with Copilot to pitch a nonprofit. We had thirty minutes. The winning nonprofit walks away with three thousand dollars. Real money, going to a real cause. I was motivated.

I was also confident. I use Copilot every day. My prompting is good. And I am genuinely excellent at PowerPoint. The one thing I knew going in was that Copilot is really bad at making slides. No problem, I thought. I’ve got this.

We picked our nonprofit and that left us about fifteen minutes to actually build. Everyone put their heads down and started prompting.

My first slides were terrible. That didn’t surprise me. I knew they would be. So I did what I do. I refined. I tightened the prompt, added detail, tried again.

Here’s what surprised me. A few people on my team were getting decent slides. Clean layouts. Warm photos. Moms snuggling with babies — exactly the kind of image you would want for a pitch like this. I looked at mine, then looked at theirs, and I could not understand the gap.

So I kept refining. Better prompts. More specific asks. And my output did not get any better. Not a little. Not. At. All.

Eventually I landed on the only explanation that made sense to me. This team must have a different version of Copilot. A plugin. An add-on. Something I didn’t have. That had to be it.

The exercise ended. But it kept bugging me for days. What did they have that I didn’t? How could I get access to it?

A week of comparing configs with colleagues and the answer was Nothing. Same version, different results. And once I sat with that, I had to admit something uncomfortable. I know AI assistants don’t work like traditional software. I say it all the time. And I still walked into that room expecting it.

Copilot is not good at slides — my Copilot was worse than theirs because I hadn’t tried to make it better. It sounds like me because I have written with it daily. It knows my audiences because I think out loud with it before every big meeting. But slides? It had never even left the tutorial. I walked in expecting the leveled-up parts to carry the parts I had never touched, and that is not how levels work.

An AI assistant is like a character in a role playing game. You can buy a better sword. You can’t buy a higher level. I spent nearly two years leveling up the parts of Copilot I use every day and zero time on slides, then was shocked when the slide skill was at level one. You level up the skills you play.

Here are three simple ways to put more reps into yours.

1. Ask it to write your bio

This is the easiest place to begin, and you will actually use what comes out. Don’t open with “write my bio,” though. Cold, it will hand you something generic, and a bad first try is exactly how people decide AI is hype. So start one step back.

Ask it what it already knows about you, and what it would need to know to write a bio worth using. That answer is the whole lesson. Maybe it knows more than you expected. Maybe it knows almost nothing. Either way, you can now see exactly where the gaps are. Fill them in your own words, then ask for the bio. It remembers all of it, so you didn’t just get a bio. You taught it who you are, and it will be sharper at everything you ask next.

2. Get in the habit of giving feedback

This one pays off no matter how good you already are with these tools. The habit is simple. Tell it what you think. When something isn’t quite right, don’t quietly fix it yourself and move on. Say what’s off and let it try again. Most people get that far. Here’s the part they miss.

Give feedback even after you’re done.

When you land on a decision, or settle on the final wording, tell it. “I went with this version.” “We decided to hold the launch.” It feels pointless, since you already got what you needed. It isn’t. That closing note is the rep that makes your next conversation start ten steps ahead instead of from scratch.

3. Bring it something you actually care about

The best practice is on something you genuinely care about, with no pressure to produce anything. Not a throwaway topic, but not a deliverable you’re depending on either. A decision you’re weighing is perfect for this. Pick one you have right now. Whether to raise something with your boss. Which option to go with on a thing that’s been nagging you.

Then use the assistant to think it through, instead of asking it for the answer. Give it the situation, the choices, and what’s pulling you each way. Ask what you might be missing. Have it argue one side, then the other. You can’t really get this wrong, because the only thing you walk away with is a clearer head. That is what makes it easy to start, and it is also when these tools are at their very best.

So pick one and start. Write the bio. Give it feedback. Think a real decision through. None of it needs a tool you don’t already have. It just needs you in the game. Go play.