Training · May 12, 2026 · 4 min read
What managers get wrong about coaching
Most coaching is a monologue about last month. Good coaching is a rep about next week.
The postmortem trap
The default coaching session is a review of things that already happened — a deal lost three weeks ago, a call from last quarter. Useful context, zero reps. The person leaves informed and unchanged.
Skills don't move on insight. They move on attempts. A coaching session that ends without the person actually saying the words out loud is a meeting, not practice.
Coach the moment, not the month
The highest-leverage question a manager can ask is: what conversation are you dreading this week? Then practice that exact conversation, twice, right there. Five minutes of rehearsal against the real upcoming moment beats an hour of retrospective analysis.
This is also where AI roleplay quietly changes the manager's job: the rehearsal partner doesn't need to be you anymore. You assign the scenario; the reps happen without your calendar.
The manager as editor
The best coaches we see act like editors, not lecturers. The person does the take; the coach names one thing to keep and one thing to change; another take happens immediately. Short loop, high frequency, visible progress. That rhythm is the whole method — and it finally scales when the takes don't all need an audience.
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