Run a difficult one-on-one conversation from prep to follow-up
A hard conversation that's under-prepared tends to either soften into nothing or land harder than intended.
- Outcome
- A conversation with a clear, specific message prepared in advance, delivered directly but without unnecessary harshness, and followed up in writing so it doesn't quietly get forgotten or reinterpreted.
- Time
- 45-60 minutes of prep, plus the conversation and a short follow-up
This workflow is part of PromptKit Pro
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Difficult one-on-one conversations — hard feedback, addressing a conflict, a sensitive ask — often go one of two bad ways when under-prepared: they get softened into vagueness that doesn't actually land, or the difficulty leaks out as unintended harshness. This playbook prepares the specific message in advance, delivers it directly without excess softening or harshness, and follows up in writing so the conversation's outcome doesn't depend on memory alone.
When not to use this
For a routine check-in with nothing genuinely difficult to say, this much preparation is unnecessary — this is for a conversation you're specifically dreading or unsure how to approach.
Did this work?
The other person understood the specific message clearly, and there's a written record of what was agreed, so it can't quietly be forgotten or remembered differently later.
Tested on claude-opus-5. Evidence status is draft; it moves to battle-tested only on recorded runs, never by hand.