There was an email sitting in my drafts for three days.
I knew what I needed to say. I’d known it since Monday. But every time I sat down to write it, something happened — I’d find something more urgent, make another cup of tea, tell myself I’d do it after the next meeting. By Wednesday evening it was still there, untouched, quietly making me feel worse about myself every time I opened Outlook.
The email was to a senior stakeholder who had a habit of finding fault. Not aggressively — that would have been easier to deal with. Just persistently, patiently, in a way that made you feel like every word you chose was being weighed. I’d worked with people like this for years. I knew how to handle it in a room. On paper, somehow, I went to pieces.
So on Wednesday night, tired of the whole thing, I opened Copilot and typed out the situation.
Not the email. The situation. What I was trying to say, why it was complicated, what I was worried about, what I needed the outcome to be.
Then I added: “Help me write a professional email that addresses this directly without being defensive, and keeps the relationship intact.”
What Came Back
It wasn’t perfect. It was a little more formal than I’d usually write, and one phrase in the middle was the kind of thing no human being has ever actually said out loud. But the structure was right. It addressed the issue head-on, didn’t over-explain, and closed with something that left the door open rather than slamming it.
I rewrote the middle section in my own voice, cut the phrase that sounded like a terms and conditions document, and kept the opening and close almost exactly as Copilot had written them.
I sent it Thursday morning. Got a perfectly civil reply by lunchtime.
I won’t pretend I didn’t feel slightly smug.
Why It Worked
The email I’d been trying to write for three days was paralysed by my own anxiety about it. Every word I chose felt loaded because I was writing from inside the situation — running every sentence through a filter of how it might land, what it might imply, whether it would make things worse.
Copilot doesn’t have that filter. It has no history with your stakeholder, no memory of the last difficult exchange, no skin in the game. It reads the brief you give it and produces the most functional version of what you’ve asked for.
What I gave it was actually good. The brief was clear. I knew what I wanted — I just couldn’t get there myself.
That’s the real thing AI is useful for. Not replacing your judgement. Giving you something to react to instead of a blank page.
The Prompt I Used
In case it’s useful, here it is exactly:
“I need to write an email to a senior stakeholder who tends to be critical. The situation is [describe the situation in 2–3 sentences]. I want to address the issue directly without being defensive, acknowledge their concern, and keep the relationship professional and intact. Please draft an email I can adapt.”
Fill in the situation, adjust the tone, and rewrite anything that doesn’t sound like you. The structural thinking it does for you — leading with the issue not the context, closing with a next step not a question — is the part worth borrowing.
One More Thing
The emails that sit in drafts are always the ones that matter most. They’re sitting there because you care about getting them right — which means you already have most of what you need. You just need something to push against.
That’s what this is for.
— Anna