Years ago, I had a team member who sent every single piece of writing with typos.
Emails. Slack messages. Documents. Client-facing decks. Never anything spectacular- no mid-sentence horrors, nothing that would trip up the reader- but always a couple. A missing full stop. "There" instead of "their". A stray letter at the end of a word she'd retyped twice.
I gave her the same feedback so many times I could feel my own voice getting bored. "Just a heads up, a few typos in this one." "Worth another read before this goes out." "Small note- the second paragraph."
Nothing changed.
She was smart. She was diligent about the things she cared about. She was absolutely not the sort of person who ignored feedback. And yet- week after week- out went the emails, and in came the typos.
Reader, I was blue in the face.
What eventually cracked it wasn't more feedback. It wasn't a stern conversation. It wasn't a bullet in her development plan.
It was the realisation, sitting at my desk one afternoon, that I had told her what the problem was, over and over- but I had never once told her why it mattered.
I was telling her about typos. I needed to be telling her about the impact.
So I sat her down, and I said, plainly:
"I want to explain why I keep raising this, because I don't think I ever have properly. When you send an email with typos, the person on the other end doesn't think 'oh, she was rushing.' They think you don't care about their time. Some of them think you're lazy. Some of them start wondering whether the whole piece of work has been done to the same level. And when it's a client or a senior stakeholder, that impression sticks. I'm not raising this because I like being right- I'm raising it because I don't want other people quietly filing you into a box you don't deserve to be in."
The typos stopped within a fortnight.
Five things I learned from that, that I now use every time feedback isn't landing: