Your Secret Weapon Against Surprise Resignations: How to Keep Great Employees

No One Wants to Be Blindsided 

You know the moment. A great employee schedules a “quick chat”—and five minutes later, they’re handing in their notice. You’re shocked. You thought they were happy. You thought things were fine. 

The truth? Most people don’t leave out of the blue. They leave quietly, months before they ever say it out loud. 

But there’s a simple way to change that. Not a new policy. Not a survey. Just a conversation. Flip the Script 

Exit interviews are too late. By the time an employee is walking out the door, your chance to keep them is already gone. Despite this knowledge, most businesses still wait until the resignation letter hits the desk before asking the important questions: “Why are you leaving?”, “What could we have done differently?” 

But smart, people-first businesses are flipping the script. Not with some corporate program, but with something simple and powerful. 

Enter the stay interview: a crucial tool that boosts retention, improves morale, and prevents burnout before it becomes a resignation letter. 

What Is a Stay Interview, Exactly? 

Let’s be clear: you don’t need to schedule a formal meeting labeled “Stay Interview” on anyone’s calendar. That feels stiff, forced, even a little scary. 

What we’re talking about is this: having regular, honest, human conversations with your team while they’re still engaged, not just when they’re on their way out. It’s about checking in before they check out. 

You might call it a one-on-one. A pulse check. Coffee and catch-up. Whatever works for your style and culture. The point isn’t the name. It’s the intention. 

Unlike a performance review, these conversations aren’t about the work—they’re about the why: why your team stays. What they value, what might cause them to leave, and how the company can better support them.

It’s proactive. It’s personal. And when done right, it shows your team that you’re invested in their success, not just their output. 

Why It Matters (Especially for Small Teams) 

When your business is small, every resignation hits harder. You don’t have ten people who can pick up the slack and replacing a great team member takes time, energy, and trust. 

“Stay-styled” conversations help: 

● Spot disengagement early and act on the feedback, fast 

● Show employees they matter beyond their job description 

● Create a workplace that grows with your people—not without them 

● Employees today value purpose, flexibility, and growth. Stay interviews reveal how well you're delivering on that. 

Retention is cheaper than recruitment. Always. 

What to Ask During a Stay Interview 

Here are some simple but powerful questions (plus alternatives) to get the conversation started: 

1. What do you look forward to each day at work? 

○ What part of your work lately do you enjoy the most? 

2. What do you wish you could do more of? 

○ Is there a skill you’d love to develop or use more here? 

3. What’s one thing that would make your job better? 

○ Is there anything slowing you down or frustrating you right now? 

4. Has anything ever made you feel disconnected from your work or the team? ○ Have you ever thought about leaving? What made you feel that way? 

5. What can I do to support your growth here? 

○ How can I support your success here? 

No need for a suit or cold formalities. Just open the door for a real conversation, with real impact. But make sure to be present and take the feedback seriously. 

Tips to Make It Work 

● Don’t Overthink It. Just make it a habit. 

● Skip the formal invite. Keep it relaxed and genuine. 

● Separate it from reviews so it feels distinct and safe.

● Take notes and act. If someone tells you what’s not working and nothing changes, mistrust develops. 

● Be ready for honesty. Stay interviews only work if you’re willing to hear (and fix) the tough stuff. 

● Repeat regularly. Once a year isn’t enough. Quarterly is ideal for small teams. ● Follow up. Circle back later and say, “You mentioned ___ a while back, how’s that going?” 

Don’t Wait Until They’re Gone: Start The Conversation Now 

The best time to find out what your team needs isn’t during their two weeks’ notice. It’s now, while they’re still here, still invested, still willing to share. 

A 30-minute conversation can reveal more than a year’s worth of anonymous surveys. And for a small business, those insights could mean the difference between turnover and team stability. 

In small teams, people don’t stick around because of a big brand name. They stay because they feel seen, supported, and valued. So ask the questions—even if you never call it a “stay interview.” We like to think of it more as a metaphor, anyway. 

You might be surprised by what you learn. More importantly, you’ll gain the clarity to help keep your best people right where they are. 

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Need help coaching managers to lead with retention in mind? 

Download our Manager Conversation Guide—a practical, down-to-earth resource for small business leaders. 

It’s packed with: 

● Actionable questions 

● Simple, repeatable strategies 

● Real-world tips to build trust and engagement to keep great employees longer 

Bonus: Don’t forget to download the Quick Reference one-pager version—a handy companion to keep key takeaways at your fingertips. 

Download both free resources now