Can Copilot make your imposter syndrome worse? Oh yes. Yes it can. Here’s how I fell into that trap — and climbed back out.

Join me exploring Microsoft Copilot through each letter of the alphabet. This time, I is for Imposter Syndrome.

Confession time

When I was first given access to Copilot, I thought I was using it well. I was asking thoughtful, reflective questions. I was being intentional. I was practically glowing with self-improvement.

Took me a while to realise that I was actually sleepwalking back into old imposter syndrome habits… 

Ah imposter syndrome. If you know, you know, and if you don’t; lucky you!

It’s that little voice that whispers (or sometimes shouts!) that you don’t really know what you’re doing, that everyone around you is more capable than you, and that it’s only a matter of time before someone figures that out, or worse, calls you out.

In recent years I’ve done a lot to try and get this feeling under control, but Copilot opened the door again. 

How I built a Copilot echo chamber

Here’s the thing about Microsoft Copilot. It has access to your emails, your meeting transcripts, your Teams chats. It can build a pretty detailed picture of how you show up at work every single day.

Which, for someone with a well-practiced imposter syndrome habit, is basically handing them the keys to an anxiety machine.

My questions started innocently enough:

• How confident did I sound in the all-company meeting yesterday?
• How could I have done a better job in this meeting?
• How am I coming across in my emails?
• Summarise my week in the style of a comedy roast (this one is really funny though)

On the surface, these look like the questions of a reflective, growth-oriented professional. But look at the subtext. Every single one is asking: “I don’t think I’m doing a good job; help me prove it.”

I was essentially asking Copilot to confirm my worst suspicions about myself, on a loop, and then wondering why I felt rubbish.

The moment I noticed

The good news is that I am, these days, quite self-aware. I caught myself in the loop — and realised I needed to flip it.

I’d recently read a book called Will It Make the Boat Go Faster? about the GB rowing team’s journey to Olympic gold. One idea that stuck with me was the evidence wall. A physical collection of proof that you are capable. That you’ve done hard things. That you belong in the boat.

I didn’t have wall space. But I did have Copilot.

So instead of asking “How could I have come across more confidently in that meeting?”, I started asking “Show me examples of where I came across confidently in that meeting.”

Same meeting. Same data. Completely different energy.

Reaffirming that you already are confident does wonders for your confidence, funnily enough.

How to try this yourself

1. Notice it (yes, this is the hard part)

Imposter syndrome is sneaky because it disguises itself as self-improvement. A useful clue: if most of your Copilot questions are about what you did wrong or how you could be better, that’s worth a pause. You’re allowed to also ask what you’re doing right, too.

It would be great if you can add contextual information to Copilot so that it could remember to look out for this for you, without you being on high alert all the time. For now, amending your prompts is the best bet. 

2. Reframe the question — and ask Copilot to help

If you’re asking for feedback, first ask Copilot itself to help you reframe the question. I tried this with the built-in Prompt Coach agent (mentioned back in A is for Agents) and asked: “I want constructive feedback, but I’m also trying not to feed my imposter syndrome — can you help me phrase my questions better?”

It gave me a whole set of reframed prompts I could use and tweak depending on the feedback I was after:

Why not build a prompt library of ‘safe’ prompts so that you know you’ll not end up straying into Imposter Syndrome territory?

3. Build your evidence wall

Start a document, or even a Copilot chat you return to, where you collect your wins. Ask things like:

• What’s an example from the last month where I handled something well?
• Find me a moment from my recent meetings where I added real value.

Read it when the imposter voice gets loud. The evidence is already there. You’ve just not been looking at it.

TLDR

Copilot’s access to all your work can accidentally become a self-doubt machine if you let it. Ask for evidence of your strengths, not just your gaps — and use it to build an evidence wall, not a case against yourself.

Have you ever caught yourself asking Copilot questions that were really just imposter syndrome in disguise? I’d love to know I’m not the only one — drop a comment below!

Useful links:

• Will It Make the Boat Go Faster? by Ben Hunt-Davis & Harriet Beveridge
• Get started with Prompt Coach in Microsoft 365 Copilot