What questions should you ask in a stay interview?

What makes a stay interview question work?

The dead questions have an obvious safe answer. “Are you happy here?” Yes, obviously. “Is everything okay?” Fine, thanks. People aren’t lying when they say that. They are answering the easy question you asked instead of the hard one you meant.

Wording matters. “Are you thinking about leaving?” invites a defensive “no, of course not.” “What would make you think about leaving?” treats the answer as information. If you are new to the format, start with what a stay interview is and how it differs from an exit interview.

Seven stay interview questions and what to listen for

Ask them roughly in this order, but not like a checklist: ask one, follow the thread, and move on when it has run its course. Four questions explored deeply beat seven at the surface.

1. “What’s the best part of a good week for you right now? When does the work feel worth it?” Start with the good to build safety. Listen for what you must protect.
2. “When did you last feel like what you do here mattered, like it made a difference only you could’ve made?” Listen for how far back they have to reach. A story from eight months ago and nothing since is a leak they never had to complain about.
3. “What’s the most frustrating part of your week?” Asked right after the best part, frustration feels normal to say. This is where the leaks sit.
4. “A lot’s shifted in how the work gets done lately. Is there anything you used to do here that you actually miss?” Especially useful after a tool absorbed someone’s signature work. Listen for a loss they haven’t said out loud, and don’t reassure yet.
5. “What would make you start thinking about leaving? Doesn’t have to be likely. I want to know what’s on the list.” The center of the conversation. Let the silence work, and make your first response “okay, tell me more,” never a rebuttal.
6. “If you could change one thing about your role or how things run, what would you pick first?” Surfaces the want that, left alone, becomes the reason. Sometimes it’s small, like a draining meeting, and fixing it buys goodwill cheap.
7. “Anything I should’ve asked and didn’t?” Asked at the close, after you have said what you’ll do next. It hands them the last word.

Which follow-up prompts get past the first answer?

The opening question gets you a sentence; the follow-up gets you the truth. When someone says “I guess I’ve been feeling a bit stuck,” don’t start solving “stuck.” Keep pulling gently until you reach something concrete enough to act on.

• “Tell me more about that.”
• “Stuck how? Walk me through a day where you felt it.”
• “What does that look like for you, day to day?”
• “Say more about that.” Then a few seconds of silence, which often does more than any clever question.

How do you adapt the questions for a guarded, burned-out, or remote employee?

• The guarded person who says everything’s fine: make it smaller. “If you got to wave a wand and change one small annoying thing about a normal week, what’s the first that comes to mind?” If still nothing, leave the door open: “If something does come up, tell me early, while I can still do something about it.”
• The burned-out person: drop the future questions and ask about now. “Where’s the load coming from, and what’s the one thing that, if it lifted, would help most right now?”
• Over video or phone: name the gap and slow down. “I know this is easier in a room, so bear with me if I leave some pauses.” Keep your camera on and watch for a flat tone or a too-quick “it’s fine.”

What do you say when the answer is money?

Take it seriously. When Pew Research Center surveyed U.S. workers who quit a job in 2021, low pay (63%) and no opportunities for advancement (63%) were the most common reasons, followed by feeling disrespected at work (57%). If your read is that the person is underpaid, build a short case for your boss: how the role has changed, what the market pays for that work, and what replacing them would cost. Gallup puts replacement at “one-half to two times the employee’s annual salary”.

In the conversation itself, don’t defend the number and don’t promise one. Get specifics and commit to a process you control:

What if the answer is something you can’t give?

Two responses fail. The over-promise (“leave it with me”) buys a few months and spends your credibility when the maybe never arrives. The shrug (“the budget is what it is”) confirms they were right to start looking.

Before you respond, break the want into its pieces. “The work feels smaller” might hold three things: missing the standing they had with clients, wanting a specific task back, and a fear of being next on a list. Sort each into can move, partly, or can’t, and be strict. Then name the limit plainly and put specific, dated effort behind what sits next to it. If you need time, give it a shape: what you’ll find out, from whom, and by which day. Then come back on that day, even with bad news.

To spot who needs these questions soonest, see the signs a good employee is about to quit.

Which questions and phrases should you avoid?

• “So, you’re not planning to leave, right?” Turns the conversation into a loyalty test.
• “I’m sure that’s just temporary.” Dismisses what they risked telling you.
• “Well, here’s what you could do differently…” Flips it into feedback. Save coaching for another day.
• “We can’t really change any of that.” Said flat and early, it ends the conversation. Save constraints for the close and pair them with what you can do.