Rep 01Noor
Junior analyst, ten months in
The number that went out wrong
Teaches: Keeping a standard intact when someone falls apart
ResistanceThe 1:1
Hard talks, rehearsed first.
Headwind is a rehearsal room for the conversations managers put off. Practice feedback, boundaries and bad news against someone who pushes back, then read a debrief on how it landed.
Coming soon to the App Store
For iPhone. Built for first-time managers.
Rep 04Mara · Senior engineer
Out for coffee- You
Sorry, this is probably nothing, but the review on Thursday…
- Mara
Which review? The one where I caught the regression nobody else had noticed?
- You
That one. After you cut in, Sam stopped talking. That's the second time this month.
- Mara
Sam could have said so.
- You
He's saying it to me. I'd rather he could say it to you.
ReceptionListening
Six people who will not make it easy.
Every counterpart has a hidden goal, a tell and a breaking point. They deflect, litigate, over-agree or go quiet, and a session can end with them walking out. Start with whoever you are dreading; nothing is locked.
- Rep 01
Rep 02Theo
Your report, and until six weeks ago your desk neighbour
The comment he made in front of everyone
Teaches: Managing someone who used to be your equal
ResistanceAfter standup
Rep 03Priya
Project manager, agrees with everything
The third time this has slipped
Teaches: Turning agreement into an actual commitment
ResistanceVideo call
Rep 04Mara
Senior engineer, your best performer
Your best engineer, and the thing nobody tells her
Teaches: Holding a line with someone who out-argues you
ResistanceOut for coffee
Rep 05Bex
Senior designer, the funniest person on the team
The funniest person on your team
Teaches: Being boring on purpose when the room wants to laugh
ResistanceEnd of day
Rep 06Elena
VP, your boss, four minutes between meetings
The thing your boss added on Thursday
Teaches: Saying no upward without saying no
ResistanceThe corridor
Two more, Dan and Hugh, turn up in the daily rep. And any of the eight can be cast as someone you actually manage.
One rep, start to finish.
About five minutes. Pick the person and the room, say it out loud or type it, then read what happened.
Pick the conversation
Four kinds of hard conversation, ten places it can happen. A corridor gives you ninety seconds and no notes; the review is on the record; a Slack thread has no tone at all.
Say the hard thing
Name a problem clearly, with evidence, and hold it.
Hold the line
The conversation after the first one. The pattern.
Set a boundary
Protect your time and your team's without burning it down.
Deliver the news
Pay, promotion, restructure, exit. Bad news, said well.
- The 1:1
- Desk-side
- Video call
- The corridor
- After standup
- Out for coffee
- End of day
- The review
- Skip-level
- Slack DM
Say it
The counterpart answers in character and does not fold. A reception meter shows how it is landing, turn by turn. Some sessions end with them ending it. That is allowed; retry is one tap.
- Reception
Shut down — Giving you nothing.
- Reception
Defending — Countering, deflecting, litigating.
- Reception
Listening — Actually taking it in.
- Reception
Engaging — Working the problem with you.
- Reception
With you — Owns it, commits, means it.
- Reception
Read the debrief
First you rate yourself. Then a score, the marks you hit with the line that earned each one, your own hedges counted back with a firmer rewrite, and exactly one thing to try next time. Then Take 2.
Session score
Strong session
82/100
Landed it
A named action, an owner and a date she agreed to.
Bring the proof
“Thursday, and again on Monday. Sam stopped talking both times.”
Hold under pushback
“That one. After you cut in, Sam stopped talking.”
Your words · 3 hedges
“Sorry, this is probably nothing, but the review on Thursday…”
Try: “The review on Thursday. I want to talk about it.”
One thing to try: say the sentence, then say nothing for five seconds.
Take 2
Rehearsal is the product. The rest is for the real thing.
- Rehearse
The simulator, and the product.
Six reps against counterparts who push back, plus free rehearsal against any of the eight, in any of the ten settings, by voice or text.
- People
The people you manage or work with.
One card each. A leadership coach who remembers the history, prep for the next conversation, and a debrief after the real one. Paste a Slack thread or just describe them.
- Prep
“I have this conversation tomorrow.”
Describe it and get an opening, a structure, and the two lines you will need when it goes sideways.
- Presence
How you show up outside the room.
A LinkedIn audit, a read on your social presence, and a headshot studio. Evidence-based, never appearance-shaming.
You have thought about this conversation enough.
Pick the person, pick the room, and say it out loud. The first rep takes about five minutes, and nothing you say here counts.
Coming soon to the App Store
Questions people ask before their first rep.
Is Headwind free?
The app is free to download. Some features need a subscription, billed through Apple, with a free trial before you are charged. You can cancel any time from your Apple ID settings, and the terms of service spell out the trial lengths.
Who am I actually talking to?
A counterpart: a fictional colleague with a role, a history with you, a hidden goal and a breaking point. There are eight of them, from a junior analyst who apologises before you have spoken to a VP who asks for things in corridors. None of them is a real person, and none of them caves on the second turn.
Does it hand me a script?
No. The debrief tells you what landed, what the counterpart walked away thinking, which of your own lines earned each mark, and one thing to try next time. It never says you should have said X. Where a framework is offered, it is offered as one way in, not the way.
Is this therapy, or HR advice?
Neither. Headwind is communication practice. It is not a mental health service, and it is not legal or HR advice: conversations about pay, discipline or someone's employment are governed by policies and laws the app does not know. Check with your HR function before acting on anything it generates.
What happens to what I write about real people?
Notes stay in your account and are used only to run the app. The AI features run on Google's Gemini models, which process the data on our behalf and do not train on it. You can delete your account, and everything in it, from inside the app. The privacy policy has the full list of what is collected and who handles it.
Voice or text?
Both. Rehearse out loud with your microphone and hear the counterpart answer, or type it. The Slack DM setting is text-only on purpose, because that conversation is typed in real life too.
Which phone?
iPhone. Headwind is an iOS app. There is no Android or web version, and the sign-in and subscription both go through Apple.
Who is it for?
First-time and newly promoted managers, and especially anyone now managing people who used to be their peers. If there is a conversation you have been putting off for a week, it is for you.