I manage ~6 people and recently had a direct report leave. We had regular 1:1s and the feedback was always that things were “going great!”
In the exit conversation, they shared they’d actually been struggling for a while but didn’t know how to raise it earlier. How often have others seen this? Do 1:1s surface issues early, or mostly what’s polite / what people feel ready to say?

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TBH they probably left for a better paycheck and did not want to say it —especially if you did not notice changes in their behavior, mood, and productivity as their manager

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I have found you need to foster the relationships in 1:1s so they feel comfortable sharing. For example I always start with how are things going in life outside of work. What’s some fun stuff you have going on. This way you don’t probe but you are interested in their life outside of work. Make sure that as a leader you let them know you have an open door policy. When they feel comfortable they will share more about how things are going on in work also.

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This is not a "software solutions" type of problem. This is an issue of personal relationships, company culture and trust.

The report likely didn't feel comfortable sharing that they are struggling. At firms that have up/out or cutthroat/competitive cultures, sharing that you are struggling could end your career or cause your manager to write you off and focus elsewhere. Maybe this is a firm culture issue you can't really fix, but your relationship building can help. If you don't build a relationship where the report can tell you that they're struggling and trust that you won't penalize them, you won't get early warning.

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Totally possible. What gave me pause is that they described the struggle as starting months earlier, well before they were interviewing elsewhere. I would imagine if it were just money, they would’ve said so in their exit convo.

That said, I’m less focused on the reason they ultimately left, and more on whether there are ways to surface earlier internal signals before things become crystallized / irreversible. Any tips or software solutions you’ve seen do this well? Would employees actually even trust something like this?

You said, OP, “they were struggling for a while” – struggling with what? Did they state it was work related? If they did, what was the issue?

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