A meaty conversation can change two things: the discovery of useful insights in this context, and the net trust in the relationship.

There's a 2x2.

High Insight / Grows Trust: A wonderful conversation.

High Insight / Destroys Trust: A pyrrhic victory. Maybe it could be justified if the insight was so instrumentally important, but probably the wrong call.

Low Insight / Grows Trust: Didn't help in the short term, but might set the pair up to tackle meaty problems later.

Low Insight / Destroys Trust: A conversation that shouldn't have been had in the first place.

A surprising number of conversations are that last bucket.

Not all insights you uncover are relevant.

For example, maybe the insight helped the leader have more confidence in the solution… but it was already the plan of record the team was executing on anyway.

It's very easy to burn through trust.

If both sides think the other side doesn't know what they're talking about, the more turns of the conversation, the more trust that is eroded.

Perhaps they're engaging on different dimensions: each conversant thinking the other person is ignoring what they're saying, while simultaneously completely missing what the other side is saying.

If you find yourself in a conversation like this, get it to end as quickly as possible.

The longer it goes on, the more damage it does.

Just because a conversation was challenging does not mean it was worth having or created net value.