How to Keep Your Best People: Two Critical Interview Strategies Every School Leader Should Use

By Dr. Tom Miller | Leaders Building Leaders

From 2020 to 2023, schools around the world were hit hard by what became known as The Great Resignation. Talented educators and staff left the profession in droves, and principals everywhere were left scrambling to fill the gaps—not just in staff, but in morale, trust, and momentum.

While some turnover is inevitable, what’s avoidable is being the cause of it.

As a school leader, I’ve been fortunate to lead teams where staff retention hasn’t been a major issue. But I also know that avoiding retention problems isn’t about luck—it’s about intentional leadership.

If you want to keep your best people and build a culture that attracts high performers, here are two strategies I use regularly—and recommend to every school and organizational leader I coach.

✅ Strategy #1: Stay Interviews

"If you don't prepare on the front end, you’ll spend even more time repairing on the back end."

A stay interview is a proactive, one-on-one conversation with a current team member—especially your high performers.

It’s designed to uncover the truth behind your culture before they decide to leave. In other words, it’s your chance to listen, learn, and lead… while there’s still time to make changes.

Here are a few powerful questions to guide the conversation:

• Do you have a clear picture of your future here?

• How do you usually hear about school-wide decisions? Is that communication working for you?

• What kinds of behaviors are rewarded—and what behaviors go unaddressed?

• How would you describe the current climate and culture here?

• What topics do we avoid that really need open discussion?

• What might I be missing that you see from your perspective?

• If you were in charge, what would you change immediately?

Bonus question: What are your expectations of me as a leader? What’s one thing I could do better or more often?

These conversations are not about fixing every problem immediately. They’re about building trust, surfacing blind spots, and making sure your best team members feel seen, heard, and valued.

✅ Strategy #2: Exit Interviews (Done Right)

If someone’s leaving your school or organization, don’t just send them off with a handshake and a thank-you. Conducting an unbiased, independent exit interview is one of the most overlooked leadership strategies—and one of the most valuable.

Why?

Because departing employees will often share feedback they were too afraid (or too discouraged) to share while they were still employed.

Here are some sample questions to include:

• What do you hope to find in your next role that you didn’t experience here?

• What challenges did you face that were never addressed?

• Are there unspoken cultural dynamics we should be more aware of?

• What conversations did we avoid as a leadership team that need to be had?

These interviews help you identify patterns that may be pushing great people away—and give you real data to lead better.

Culture Starts with Conversations

Whether someone’s staying or leaving, the key to keeping your culture healthy is simple: talk to your people—honestly and consistently.

You don’t need flashy perks or grand gestures.
You need systems of trust.
You need conversations that matter.

That’s where true leadership begins.

🎁 Want to Put This Into Practice?

I’ve created a free downloadable guide with sample Stay and Exit Interview questions you can start using this week.

👉 [Download Here]

And if you’re ready to go deeper…

If you're tired of difficult conversations, emotional exhaustion, and “problem people” taking up your time and energy—

Join me for our newest leadership study:
📘 How to Work with Complicated People
🎯 Based on Ryan Leak’s breakthrough book
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👉 Register here

You’ll learn how to turn your biggest people problems into your biggest leadership breakthroughs.

To leading well,
Dr. Tom