How to have difficult conversations at work
The 20 conversations people put off — each with an opening line, the three pushbacks you'll hear, and the point where you stop. Every one has a counterpart in Rehearsal to practise it with.
Ask
- How to ask a client for a deadline extensionThe new date in the first minute, what you knew when, and what's still protected: how to tell a client a launch is moving before he hears it sideways.
- How to ask for a promotionA case shaped like the level, not a highlights reel: the opening claim, three proof points, the objection pre-answered, and when to stop pushing a sponsor.
- How to ask for a raiseAn opening line that names a number, the three soft ways a manager says 'not now', and the point where you stop — a prep card for asking for a raise.
- How to ask for headcountOne role, one start month, the risk in his terms: an opening line for the headcount ask, the three offers that aren't a hire, and where you stop.
Give feedback
- How to give feedback on a presentation that missed the roomHow to answer 'be honest, how did it land?' when the exec review lost the CFO by slide four — one miss named plainly, the pushbacks, and one change next time.
- How to give negative feedback to someone on your teamHow to raise a performance concern with someone who's never had one — the hard sentence early, the pushbacks you'll get, and what to leave the room with.
- How to talk to a star employee who has quietly checked outHow to name a star engineer's withdrawal when nothing's failing — the observation, the 'which expectation did I miss?' reply, and the offer that wins her back.
- How to talk to someone who is always lateHow to raise lateness with someone whose work is good — the pattern and its cost in one breath, the 'it's ten minutes' reply, and the question that opens it up.
- How to tell someone their project is cancelledHow to deliver a final cancellation to the person who ran it — the decision in the first minute, the 'did you fight?' test, and what to protect by Monday.
- How to tell your fastest engineer their code reviews are too rushedHow to split Daniel's shipping speed from his rubber-stamp reviews — the evidence to bring, the 'so you want me slower?' pushback, and the ask to leave with.
Say no
- How to decline another working groupA decline that refuses the seat and not the cause, the three passes a chief of staff makes, and the one alternative she can still count — a prep card.
- How to say no to scope creep mid-sprintNo to this sprint, stated whole, then the cost of yes and a real date: how to hold the line when a senior colleague arrives with a signed deal and a 'tiny' ask.
- How to say no to weekend workA one-sentence boundary with a start date, the exception path, and the three ways a friendly director shrinks it: how to close weekends without a fight.
- How to say no when another team wants to borrow your engineerA no that covers the person and the pattern, the three ways a friendly peer re-asks, and the offer that keeps your roadmap intact — a prep card.
- How to set a limit with your managerA one-sentence limit, the trade-off that makes it real, the three warm ways a manager re-asks, and the growth conversation you get back — a prep card.
- How to tell someone they're not getting the promotionThe decision in one sentence, the three ways a strong candidate argues back, and the written path that gives her a reason to stay — a prep card.
Repair
- How to deal with a teammate who fights every code review commentHe answers every review comment with an essay or silence, and reviewers now avoid him. How to name the pattern, hold the line, and get him reviewers back.
- How to rebuild trust after you dropped the ballYou delivered the board cut late and wrong, and he covered for you. How to raise it yourself, own the cause, and bring a mechanism instead of an apology.
- How to repair a work relationship after a disagreementYour line got a laugh at her expense and she's been closed for six weeks. How to name the moment, apologise for the right thing, and propose one rebuild step.
- What to do when a colleague takes credit for your workShe presented your analysis as hers. How to name what happened without the word 'stole', ask for a correction that lands, and keep working with her.
Have the conversation before you have it for real.
Six minutes out loud with someone who pushes back the way they will, then a debrief with the line you should have said.
How Rehearsal works →