What to Do When One of Your Best Teachers Leaves

There isn’t a perfect way for a principal to break the news to faculty about a departing educator—especially a star educator, the type who serves as the connective tissue of an entire grade or department. But there is a wrong way: getting ahead of the educator’s own announcement.

When I recently spoke to Deborah Dennie, principal of Leonardtown Middle School in Maryland, she described how she once faced this very predicament. One of her best teachers made the decision not to return but asked Dennie to wait to notify everyone else because they were dealing with a family issue, and they also didn’t want their imminent exit to impact colleagues or students before the school year wound down.

Dennie agreed to the teacher’s request. It was the least she could do, she told me. Behind the scenes, the teacher returned the favor—they had given her months of heads-up, and also made a great recommendation for a candidate who wanted to interview for their job.

Staff departures are an inevitability in any industry. Some are weightier than others. It stings when a beloved colleague—someone who is relied on as a mentor, a thought leader, and/or a work friend—steps back or decides to embrace a new opportunity. And it’s not always obvious how to properly celebrate someone before they go.

“You might have a star person who just decides they need a change and goes to another school, and that celebration would not be the same as for someone retiring after so many years, because for them it’s final,” Dennie said. And “some people just like to go off into the sunset without any pomp and fanfare.”

When leaders pick up on the right cues and show deference to a respected staffer, they demonstrate self-awareness and self-assuredness, sending a message that they’re paying attention to the departing staffer’s wishes and their importance, while simultaneously projecting a positive outlook about a replacement plan. “It may not sound like good news, but losing a veteran top performer can sometimes be a blessing in disguise,” writes Gallup editor Ryan Pendell. “It can provide teams with an opportunity to be creative, question old habits, and recommit to their mission.”

I talked with Dennie; Heather Bardwell, principal at Mountain Gap Middle School in Alabama; and Rob Reetz, principal at Mounds View High School in Minnesota, about how they navigate one-on-one conversations with key staffers who are eyeing the exits—and how they handle the aftermath with everyone else at their schools.

Keeping Your Best Educators Around as Long as Possible

When star educators are thinking of heading for the exits, it’s typically for one of two reasons: They’re considering taking a new job, or they’re approaching retirement.

In the former scenario, it’s worth gauging whether they have fully made up their mind. Sometimes, there’s not much to discuss; another school has offered a promotion or raise, or the educator needs to relocate for personal reasons. But sometimes it’s possible to identify and convey a compelling reason to stick around.

Bardwell gave an example: A great history teacher once called her up in midsummer to inform her that he’d found another job that would pay more money. As Bardwell listened to the details, though, she heard warning signs. He was going to have to add significantly more responsibilities to his plate: bus driving and coaching multiple sports on top of his academic duties.

“I said, ‘I know you want more money, but your quality of life is not going to be as good because you’re going to be working constantly,’” Bardwell recalled. The teacher reconsidered, and according to Bardwell, he believes he made the right choice by staying. But she’s also careful not to give that sort of advice every time. “Selfishly, I’d love to tell them they can never leave,” she said, but “as educators, we typically put ourselves last. Teachers have to do what’s right for them.”

Principals can build schoolwide trust by giving measured, discerning advice so that it’s clear they’ll fight to keep their best educators, while also acknowledging that some staff are going to outgrow their current roles. “I think it’s really important that teachers are working in spaces that make them happy,” Reetz said.

For legendary veteran teachers who are thinking about retirement, the equation is different. All three principals said there is often wiggle room on the subject of when longtime educators call it a career. These conversations are a wind-down negotiation: How much longer do you want to teach? Can you help prepare your potential replacements before you leave?

Dennie brought up a staff member who’d been at Leonardtown for 18 years. The staffer first told Dennie they were considering retirement a few years ago, and then made it official at the beginning of the 2025–26 school year. Dennie had ample warning to figure out next steps, and she’s been able to count down the days with an educator she really respects. “It wasn’t about talking her out of it—it was about supporting her along the way,” Dennie said.

Honoring Outgoing Educators

When beloved educators at Bardwell’s school formally announce that they’re going to retire, “some like to go quietly into the night and don’t want any fanfare,” while “others want roses at their feet,” she joked.

Deferring to these teachers is key: The staff want to see that their favorite colleagues are being appropriately honored before they go. Bardwell asks departing teachers when they plan on giving the news to other staffers—her only request is that they not wait too long. She’s happy to keep things quiet as she sources other candidates, but she needs to start a formal search at some point, which will make the departure public.

Dennie similarly defers to outgoing staffers when they request privacy. “When I have a conversation with the broader team, it’s because there’s no shadow of a doubt that the person is leaving,” she said. At that point, she’ll talk to assistant principals and department heads about the best path forward.

Maureen Hoch, an editor at Harvard Business Review, believes that when a leader discloses a departure to everyone else, they need to make sure the rest of the staff is confident that “yes, this is a change, but we’re going to see it through,” she said. “On the other hand, you don’t want to act like this is no big deal… [If] you don’t recognize and thank that person for all the ways that they’ve made a difference, that’s going to hit your team wrong.”

Dennie will modulate her celebrations depending on a staffer’s seniority—and crucially, whether they want the spotlight. “If the person sees it as a great thing, we make it a big thing,” she said, referring to how she addresses a departure at all-staff meetings. She’s also taken teachers out for dinner at the end of their tenures.

At Reetz’s school, departing teachers are usually recognized during the first week of May, Minnesota’s Teacher Appreciation Month. There’s an entire morning without students when teachers give presentations about their departing colleagues, unless those colleagues wish to opt out. “The longer they’ve been there, the more involved the presentation, and the more people speak to the impact that a teacher had on their colleagues’ careers and on students,” Reetz said. Reetz also asks retiring teachers if they’d like to give a speech during the graduation ceremony.

Filling Gaps and Projecting Confidence

Whenever a teacher makes it clear that they’re leaving, there are a few universal steps to follow. These are the same as the ones a CEO of a business might take when an employee quits: Rich Reinecke, co-managing partner of business consulting firm Fahrenheit Advisors, told Fast Company that leaders should spend time with a departing staffer going over all of their critical tasks and responsibilities. When one of Bardwell’s science teachers left, for example, she didn’t just have to find someone to fill their classes—she also wanted someone who could continue the STEM program that the outgoing teacher had created.

Every once in a while, either the administrative team or the outgoing teacher will identify a great replacement candidate. “Your really good teachers try to source it themselves,” Bardwell said. There are times when a single replacement can admirably pick up where their predecessor left off. This is easier when the newcomer can learn from the outgoing teacher, a luxury worth taking advantage of whenever possible. When Bardwell knew her longtime star English teacher was winding down her career, she assigned that teacher an understudy, clearing a period for the new teacher to observe the veteran so the new teacher could “learn from them and understand how they think,” she said. 

While a new staffer is getting caught up to speed—or in the event of a midyear departure—school leaders can also lean on the rest of their top teachers. Dennie said she has “called on other master teachers” to assist “with lesson plans, modeling how to teach the content, helping with classroom management, and so on.”

But there are inevitably occasions when it isn’t obvious who can step in for a well-respected teacher and when no amount of mentoring or preparation will suffice. Reetz cited one of his soon-to-be-departing business teachers, who’s “genuinely one of the most student-centered, hardworking teachers we have,” he said. Reetz considered a variety of replacement plans but ultimately decided to break up the departing teacher’s courses among multiple staffers. There “simply weren’t enough candidates who came close to what she brings,” he said.

The most important thing a principal can do in developing replacement plans, Reetz said, is to work on them before you need them. “I believe in the notion of trying to see around corners,” he said, meaning that he tries to figure out who can step into a particular role “even if it’s not imminent that someone’s going to leave.”