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I think my best hire is about to quit, but they haven't said anything. What do I do?

Asked by Operations Director, logistics · Director · 100-150 employees · 22 June 2026

Oblong's answer

Trust the signal, not the silence. People rarely announce disengagement — they show it through smaller effort, less initiative, or simply doing exactly what's asked and nothing more. Don't open with "are you leaving," which invites a denial either way. Open with genuine curiosity about how the role is actually going for them right now, and be prepared to hear something you don't want to. If there's a real issue, you likely still have a small window to address it — but only if you ask before they've already decided.

I'm worried about losing my best peopleRetention

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