School & District Management Opinion

Why I Told an Excellent Teacher It Was Time to Leave Teaching

A good leader can have honest conversations—even when it feels hard
By Matthew Ebert — January 16, 2024 4 min read
Illustration of two silhouettes in a school hallway having a conversation about the future.
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Speaking the truth when others aren’t ready to hear it can feel impossible. Engaging in difficult conversations can make your heart race and your mouth dry. However, if you’re going to build and curate a healthy organization, there will be times when leaders must tell the truth, despite it being the last thing they want to do.

Leadership means being honest. Leadership means recognizing what people need even if it goes against the organization’s immediate need.

Sometimes, it means telling an excellent teacher that it’s time to leave.

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In this biweekly column, principals and other authorities on school leadership—including researchers, education professors, district administrators, and assistant principals—offer timely and timeless advice for their peers.

Which brings me back nine years—to Michael.

Michael was in his eighth year of teaching, and I had just become the principal of his school. He was smart, held high expectations, was an excellent teacher, worked incredibly hard, and had voted for me to get the job.

He was also done teaching but didn’t know it yet.

I saw it. Others did, too.

Michael arrived early and left late. Every moment was urgent. Michael struggled in team meetings when folks didn’t agree with his positions. He once told the school secretary that he didn’t like being interrupted for questions about attendance during class because “you wouldn’t interrupt a firefighter.” Michael felt like he was fighting fires every day.

We should all want someone with Michael’s passion teaching our kids. He expected the best out of himself and others at all times. Michael’s passion was a gift.

That’s where Michael existed. All heart, all the time. His reality was one where the challenges of our community were personal.

But without healthy limits, passion can destroy a person. Passion, especially in the daily struggle for educational equity, requires pacing.

Michael and I established a relationship during our weekly one-on-one check-ins. We would talk about all manner of topics ranging from life to love to dogs and to teaching. We built trust and a mutual respect. We laughed. We commiserated. Michael knew that I cared about him, and I knew that he trusted me.

Then, in the middle of the year, I told Michael that I thought he was done teaching—he just didn’t know it yet.

Just like that. In no uncertain terms. It wasn’t easy. I was scared about the conversation and the implications. I was worried that my words would shatter the world that he had crafted for himself. I was nervous that it would create a rift in our community and would negatively impact our team.

But I knew it had to be done. For Michael, for the team, and for the kids.

I told him what I saw. His passion had overtaken his perspective and made him unable to see or sustain the big picture. He couldn’t continue existing like this, and, if he did, it would eventually hurt our kids, our adults, and him. He wasn’t healthy and he wasn’t happy. He deserved to be both.

Michael was surprised by my remark. When we talked it through, he understood my perspective, even if he didn’t agree. We continued our wonderful relationship (which we still maintain). He completed the year with our school. Giving his all, every day.

At the end of the year, a close friend offered Michael a teaching position at another school. Michael was conflicted about leaving. I encouraged him to go.

He took the job.

The next year, he left that school.

Then, he went to one more.

Then, he left teaching.

He was done. He knew it.

When Michael began his career, someone should have been honest and said, “The fire will still be there tomorrow.” You have to take care of yourself first. You have to prioritize your own needs, and we’re going to show you how.

Leaders should have told Michael to slow down. To pace himself. To breathe. To pick his head up, look around, and understand that there is more to this life than his classroom. They should have told Michael that his best would look different each day because he was a living, breathing person. No one expected him or needed him to be perfect. They just needed him to be whole.

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Photo illustration of principal giving students a high five.
F. Sheehan/Education Week via Canva / Getty

That’s what a culture of care will do—allow you to have the difficult conversations and still move forward together. When people know that you truly care about them, it’s amazing how honest you can be.

I tried to do that for Michael, but I was too late. When I met him, he was already done. The most human thing I could do for him was to tell him the truth—even if he wasn’t ready to hear it. That was kindness. That was caring.

I spoke to Michael recently. He’s happier than ever. He’s pursuing a variety of interests and has cultivated a full life outside of work. He’s whole now.

I asked Michael what he would tell his past self. “It’s tough not to slip into cliche: ‘It’s a marathon, not a sprint.’ ‘You can’t be good for students if you aren’t good for yourself,’” Michael shared. “Maybe it would have been most effective to frame it in the context of modeling for students. As much as I would have wanted for them to have a healthy school/life balance, I certainly didn’t provide a strong blueprint for them. Unfortunately, I’m honestly not sure past-Michael would be able to hear the advice, but that doesn’t make it any less true.”

The key to long-term success for organizations is developing and curating a culture of care. It means creating a foundation of trust through honest conversations. It takes leaders who are willing to understand that organizations are best served by healthy, growing individuals. It means creating space for those individuals to evolve in ways that may even have them leave your school.

And it means telling the truth, to people you care about, even when it’s hard.

A version of this article appeared in the February 07, 2024 edition of Education Week as Why I Told an Excellent Teacher It Was Time to Leave


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