The signs are all there. They're unavailable on certain mornings with no explanation. Their LinkedIn was freshly updated last week—new headline, skills reordered, a summary that didn't exist a month ago. They're dressing better for video calls with people who aren't on your calendar. They've stopped raising their hand for stretch assignments. You know what's happening, and so do they.
The conventional advice is to have the retention conversation. Pull them aside, tell them you've noticed, ask if everything's okay, maybe dangle a vague promise of future opportunity. That playbook almost never works—and often accelerates what you were trying to prevent. According to Gallup's 2023 analysis of voluntary exits, 52% of departing employees said their manager or organization could have done something to keep them. But only 51% of those had any conversation with their manager about job satisfaction in the three months before they left. The failure isn't caring. It's timing. By the time someone is actively interviewing, a retention conversation lands as confirmation that they should leave—because it signals you've noticed the drift but don't have anything concrete to offer.
So here's what to do instead.
First, before you do anything, do the business risk assessment. What does this person's departure actually cost you? Do you have someone who could step up? Could you backfill in a reasonable timeframe? Is their knowledge documented or is it entirely in their head? The answer shapes everything. If the risk is low, you have room to let the situation play out while staying engaged. If the risk is high—key client relationships, tribal knowledge, a function that would go dark—you need to start building succession depth right now, regardless of whether they leave. The irony is that the work of protecting yourself from their departure is also the work of making them slightly less essential, which quietly reduces your anxiety and theirs.
Second, don't ask if they're looking. Have the ongoing conversation instead. "Are you thinking of leaving?" gets you a denial almost every time—it's too direct and too loaded. What actually works is making their job satisfaction a standing agenda item, not a crisis intervention. "What would make this role more compelling to you in the next six months?" is a question they can answer honestly without feeling interrogated. If they're interviewing, their answer still tells you something real. If they're not, you've just done retention work without triggering defensiveness.
Third, remove the cost of honesty. The worst outcome in this scenario isn't the person leaving—it's the person leaving after months of partial effort, knowledge hoarding, and dropped balls, because they felt they had to hide what was coming. If your team members believe they can tell you they're thinking about a change without professional consequences, you get more lead time, better transition planning, and—occasionally—a problem you can actually fix. Some people explore the market to confirm they're valued where they are. Give them a reason to reach that conclusion before they have an offer in hand.
This advice doesn't apply when performance has already degraded visibly. If the interviewing is coming with missed deadlines and disengaged behavior, you have a performance management situation that needs to be addressed directly—the "they might be leaving" context is relevant, but it doesn't change the accountability conversation. Also, sometimes the reason they're looking is something you genuinely cannot fix: a promotion that doesn't exist on your org chart, a salary that's outside your band, a career path your company doesn't offer. In those cases, the right move is helping them land well and managing the knowledge transfer—not extending the timeline with half-promises.
The most effective retention strategy happens six months before someone starts interviewing. Once they're already looking, your job is risk management, not rescue.
