difficult conversations
Prompts tagged with "difficult conversations"
Decide Whether to Resign a Client
Tests whether an account is genuinely unrecoverable or merely badly managed, and if it is unrecoverable, plans an exit that protects your reputatio...
Diagnose an Engagement That's Going Wrong
Separates the delivery problem from the relationship problem from the scoping problem, because they look identical from the inside and have complet...
Have the Price Reduction Conversation
Prepares the conversation with a seller whose listing isn't moving — built on showing and feedback data rather than on pressure, with the arithmeti...
Split Equity With a Co-Founder Without Wrecking It
Works through a founder equity split and vesting terms while the conversation is still easy, covering the scenarios that break partnerships later. ...
Recover an Account After You've Let Them Down
Builds the repair plan after a serious failure — what to say, what to commit to, and how to rebuild trust with evidence rather than apology. Use it...
Save an Account That Has Told You It's Leaving
Structures the cancellation conversation to find the real reason, make a credible offer, and exit well if the answer stays no. Use it the day a cus...
Manage a Former Peer
Handles the awkward transition from teammate to manager: what to say in the first conversation, which friendships have to change and how, and how t...
Handle Conflict Between Two People on Your Team
Works out what the conflict is actually about — often a structural ambiguity rather than a personality clash — then plans the separate and joint co...
Write a Performance Improvement Plan
Structures a PIP with specific gaps, measurable expectations, the support you'll provide, and a genuine chance of success — plus a hard check on wh...
Say No to a Customer Request Without Losing Them
Decline a refund, exception, or request where the answer is no — clearly and kindly, while keeping the relationship.
Prepare for a Difficult Conversation
Get ready for a hard 1:1 — your goal, calm phrasing for the key points, likely reactions, and how to respond.
Say No or Push Back Without Damaging the Relationship
Decline a request, meeting, or scope change — with a few phrasings from direct to diplomatic so you can match the relationship.
Guides on difficult conversations
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How to Use AI to Write Work Emails
The largest study of ChatGPT use found two-thirds of writing requests are edits, not drafts — so stop starting from a blank page. Tone di...
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