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Every leadership team is wrestling with the same questions right now. How will AI impact our organization, and what type of workforce will we need in the future?
These aren’t easy questions to answer. Only 19% of companies are effective at pl…
It’s Friday afternoon—and your favorite team member’s last day before they move on to a new organization. You wanted to work through their final handoffs, but they’re in HR’s office. And in that meeting, for the first time in three years, someone asks them: “What made you decide to leave, and what could we have done differently?”
They answer, in full detail. They joined because the company’s careers page promised “development opportunities,” but they got turned down for every leadership program they asked to attend. They were told more than once that a promotion was coming. It never came. And they never got the chance to really push on either one, because their one-on-ones happened so rarely that there were 28 other things they needed to cover first.
An exit interview is often the most candid conversation someone has at work. But it happens when it’s too late to do anything about it—and usually not with the person who could have done something.
Gallup research backs this up. Of people who voluntarily left a job, 42% said their manager or organization could have done something to keep them. And 45% said that in their last three months, neither their manager nor any other leader took the initiative to talk with them about their job satisfaction, performance, or future.
That’s why some people, often in HR, recommend a “stay interview”: the same questions, but asked while the person still works there.
I love the idea. But I don’t love the name, and I’d bet your team won’t either.
It doesn’t need to be an interview—or HR’s job
“Stay interview” sounds like a corporate program. HR can run those, and some do it really well.
But most employees don’t want to feel like part of a program. They’re used to talking with their manager. A meeting with HR feels more formal—especially when someone is taking notes, which HR usually needs to do so the right people can act on what they hear.
When you have the conversation yourself instead, it’s more direct. You assign the work. You have the most visibility into what someone’s day actually looks like, and the most control over it.
A conversation also goes both ways. You learn what motivates each person on your team: what they care about, what they like doing, and what they want next. And they learn that you care about more than just their work; you care about their career and about them as a person.
The second part matters more than most leaders realize. A boss who takes the time to listen can feel like water in the desert. And people care more about their work when they can tell someone cares about them doing it.
Before you ask, tell everyone
These conversations work best one-on-one. But don’t start by walking up to one person.
Picture it from their side. Their boss suddenly asks why they’re still here and what their plans are. They’re probably not thinking, “How thoughtful!” Instead, it’s “Why are we having this conversation? Am I on some list?”
Because when people don’t have context, they assume the worst—especially when it’s about them.
So tell your team first, “Over the next few weeks, I’m going to meet with each of you one-on-one to learn more about what you’re interested in. I want to make sure I’m not just leading the team in getting work done, but supporting each of you as individuals. And I wanted to make sure you know in advance that I’m doing this with everyone, so no one’s wondering if it’s just them.”
The “everyone” is important, because it’s easy to assume you already know where some people stand: the tenured employee you’re sure will never leave, or the new hire who’s barely finished orientation. Talk with them anyway. Skipping someone can make them feel like the odd one out—and if you do talk with them, you’ll likely learn something you didn’t expect.
Ask questions they’ll actually answer
Notice the script above doesn’t say “stay interview,” because it doesn’t need a formal title. And if you want people to open up, your questions shouldn’t sound like corporate-speak either. Instead, try:
- What to protect: “What part of your job would you be most upset to lose?”
- What’s wearing on them: “What part do you dread or keep putting off?”
- What you’re missing: “What are you good at that we’re not using?”
- What’s next: “What do you want to be doing a year from now, and how could I help you get there?”
- What matters most: “If a recruiter reached out tomorrow, what would make you set up a call?”
The last one feels risky. But you’re not asking whether—or where—they’re looking. You’re asking what matters to them, and showing them you don’t take them for granted.
Then, listen more than you talk. If something stings, don’t rush to defend or explain it. Use the Pause-Consider-Act framework: Pause before reacting, consider what they’re trusting you with, and act once you’ve had time to think.
If someone admits they’ve thought about leaving? That’s exactly the information you asked for. Nothing teaches a team member to stop telling you the truth faster than punishing them for being honest.
Don’t promise. Do follow up
The fastest way to ruin a stay conversation is to do nothing with it. The second fastest is to promise something you can’t deliver. As a former employment lawyer, I’ll emphasize this: Don’t promise a promotion or a raise you don’t control.
You don’t have to solve everything in one conversation. Sort what you hear into three piles:
- What you can change: The project they want to work on. The feedback they’re seeking. The meeting that feels like it could be an email. Commit to working on one of these within the next week.
- What you can push for: Pay, title, head count. If there’s a freeze on any, say so—then make the case, so it’s ready when budgets open back up. In the meantime, push for what isn’t frozen, from development opportunities to visibility in front of senior leaders. Tell them what you’re raising, with whom, and when you’ll get back to them.
- What you can’t change: Say so. “I can’t change that right now, and I’d rather tell you than leave you wondering.” People appreciate a certain “no” more than a half-hearted “maybe.”
Then, close the loop with each person, even when the update is “still working on it.”
Make it a habit, not an event
What makes someone stay today isn’t necessarily what will keep them next year. Work one of these questions into a one-on-one at least quarterly, so you’re not relying on outdated answers.
Exit interviews aren’t going away, and they shouldn’t. People will still leave, sometimes for reasons that have nothing to do with you. But what gets said in HR’s office on a Friday afternoon shouldn’t be news to you.
Pick a day this week and tell your team what you’re doing. Then ask your best questions to the people who are still there to answer them.
Your teenager gets into a fight with her best friend. She’s hurt, upset, and doesn’t know what to do. Maybe in the past she would have spent the day replaying the argument, venting to another friend about the drama, practicing an apology in the bathroom mirror, or laboring over what to text.
These days, she can skip all that and ask AI what to say. It probably sounds better than anything she would’ve written herself. And that is the problem.
Parents have spent years worrying about what technology exposes children to, how it impacts attention spans, and makes it easier to cheat on homework. But AI has created another issue: What happens when our kids can outsource the experiences that teach them how to become adults?
It’s not just that AI can write a good essay on To Kill a Mockingbird. It’s also eliminating the frustration of staring at a blank page, organizing an argument, and ultimately figuring out what you want and need to say.
The same goes for relationships (friendships and romantic) and everyday decisions. Why try to figure out what to say to your friend when you can have AI tell you? Why figure out what the other person is trying to tell you when AI can make the hard decision you’ve been avoiding? There is no need to labor over tough choices when the algorithm can shoot out a well-reasoned list of pros and cons.
The uncomfortable middle
Technology has essentially allowed young people to skip the uncomfortable middle, the period of muddling their way through to an answer. And growth is what happens during those uncomfortable and awkward moments. We learn confidence by failing. Kids need to know they can survive getting it wrong.
Developmental psychologists often talk about the importance of “mastery experiences”: situations in which people build confidence through their own experiences.
Remember all the times you learned from your failures? Maybe it was that friend who lied to you. Or when you apologized to someone and it went spectacularly wrong. And what about all those school projects you didn’t understand at the outset and had to work harder to grasp. Or that decision you thought was a great idea when you were 16 but terrible at 17.
Those painful moments teach something a computer program cannot. They show you how to recognize your instincts and to believe in your ability to figure things out. Relying on AI robs a child of these lessons. And this isn’t just hyperbolic bluster.
A Pew Research Center survey conducted in late 2025 found that 54% of American teens ages 13 to 17 use AI chatbots for schoolwork and 12% use it to talk about their feelings and get advice.
A fine line
That said, there is an upside to all this technology. AI can help a student struggling with algebra (especially when his parents are clueless), allow a shy teen to practice a difficult conversation, or provide tutoring for a family that lacks the resources to hire someone. But there is a fine line between using AI to help you think and letting AI think for you. We need to teach our children the difference. And if I’m being perfectly honest, this can help adults too.
What to do
Ask yourself what you think happened before asking AI to decode a friend’s behavior. Take 15 minutes to come up with your own argument before asking it to generate an essay outline. Use AI to challenge your thoughts and help you see other perspectives, not as a first pass.
As parents, we can help guide our kids as well. We’ve become great at clearing hurdles out of our children’s path. Sending teachers emails when our child doesn’t receive the grade we think they deserve. Jumping in to solve their conflicts with friends and ensuring they never let anything fall through the cracks or fail. But our kids need to learn how to fix things for themselves.
One day, your child will have to make decisions that they can’t ask a bot about. Maybe it’ll be whether to trust someone, walk away from a bad relationship, stand up to someone, or stand by beliefs when no one agrees with them. They may have access to more information than any other generation in history, but information and judgment are not the same thing.
I want my kids to know how to ask good questions. But I also want them to trust themselves enough to answer a few on their own.
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