Take one difficult conversation you have to hold. Before it starts, check whether its purpose is honest, its evidence observable — and whether your opening could become the next move in an escalation.
Name the conversation
Not “difficult conversations”. One conversation, with one person or party, that you have to hold soon.
Four checkpoints
Each checkpoint comes from an Executive Insight Brief. Answer for this conversation, not for difficult conversations in general. “Don’t know” is an answer — often the most useful one.
The plan
Many hard conversations fail before they start: the purpose is blurred, the setting is wrong, progress is undefined. Check the plan while it can still change.
Your map
This map prepares one conversation. It cannot guarantee how the conversation goes or that it will improve anything — feedback can also make performance worse. It does not replace HR, legal, investigative, safety or due-process procedures. And a conflict that looks mutual may hide one-sided pressure: this map does not split responsibility between the parties. Every checkpoint rests on a published brief; none of them supplies a cutoff.
Next step
You now know, for this conversation, where the preparation is thin — and which part of it could turn the conversation into the next round of the problem.
The harder part is the conversation itself: saying what is decided and what is open, holding the evidence without prosecuting, and leaving with a next step both sides can observe. That is the conversation worth having first.
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Short answers first, then the briefs that read them, then essays and pages.