Walk me through a time you had to tell someone something you knew they didn't want to hear. How did you actually say it?
Why this works
Bad news tests the gap between knowing and telling: delay and cushioning both transfer cost onto the listener. Asking for the actual words gets past "I was honest but tactful" to what was really said, which is where the skill lives.
Follow-up probes
- How long between knowing and telling — and why?
- What did you say in the first two sentences?
- How did they take it, and what happened to the relationship?
What good looks like
News delivered promptly and plainly rather than buried in preamble, the receiver's reaction anticipated and given room, and something useful offered alongside — options, next steps — without softening the facts.
Red flags
The message was cushioned until it stopped being true, delivery pushed to email or another person to avoid the room, or the story is mostly about how hard it was for the teller.
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