The Slack message sat in the box for 45 minutes. A client had moved the goalposts for the third time, and everything I typed sounded either passive-aggressive or like a doormat.
So I did what I do now with anything emotionally loaded: I said it out loud first.
Here's my system. I open a blank note, hit my Wispr Flow hotkey, and rant — honestly, uncensored — for 60 seconds. The frustration, the boundary I actually want to set, all of it. Nobody sees this version.
Then I look at what I actually meant underneath the annoyance. It's almost always reasonable: "I need the deadline moved" or "this is out of scope." The anger was just packaging.
Then I dictate version two, calmly, out loud: "Hey, I want to flag that this is the third scope change this month. Happy to do it, but we'll need to adjust the timeline. Does Thursday work for a quick call?"
Wispr Flow cleans up the filler, fixes the grammar, keeps my tone firm but warm. I paste it and hit send before I can overthink it.
Total time: 4 minutes. Old method: 45 minutes of typing, deleting, and asking a friend "does this sound rude?"
Typing a difficult message puts you in your head — you rehearse the other person's reaction and soften everything into mush. Or you go the other way and sound sharp.
Talking puts you in your body. You hear yourself. The moment you say "that's a bit harsh" out loud, you know to rephrase. Your ear catches what your eyes miss.
I use this for client pushback, giving feedback to collaborators, declining things I don't want to do, even personal stuff — the "hey, I can't make it this weekend" texts I used to agonise over.
Phone dictation garbles exactly the sentences that matter most — the nuanced ones. Wispr Flow's accuracy is on another level, and it works in every app: Slack, Gmail, WhatsApp, wherever the awkward message lives.
The voice-editing is the killer feature here. I say "make it softer" or "more direct" and it rewrites the draft on the spot. It's like having a calm friend who redrafts with you in seconds.
Hard conversations cost me hours of dread every week. Now they cost 4 minutes of talking to myself in the kitchen.
If difficult messages pile up in your drafts (or worse, in your head), try saying them first.
I dictate with Wispr Flow every day — try it with my link and give the rant-then-refine method a go: https://ref.wisprflow.ai/hector-wheatley
Say the messy version. Send the calm one.