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Elo comments on The Problem (TM) - Analyse a conversation - Less Wrong
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At the time I considered the value of digging into this and decided against it. I suspect there was more to the story, but figured the details would come out if they were relevant. Given that it was the one example of hurting people, I don't think it was an ongoing problem. To shake up that specific event wouldn't have led to all the other possible problems.
(more to come later)
Scott wrote how "tell me more" is a very effective tool in his arsenal. It can be useful to go deep.
You did nothing to check whether that was the only example.
"What do you think is the biggest problem here?" is a different question than "What do you think I could have successfully started to address in one conversation?"