Why ‘Use Your People’ Is a Key Lesson for Principals

Tracie Swilley was burnt out.

Early in her career as a principal, she was working too many hours, taking on too many tasks and responsibilities. She knew she had capable staffers, but she wanted to do everything exactly right, and that meant doing everything her way. She even had “mom guilt,” she says, from putting her kids to bed and then going back to work.

In a moment of exhaustion, she got an unexpected pep talk from a teacher who had been an instructor in the Junior Reserve Officers’ Training Corps. As Swilley remembers it, the teacher pulled her aside and gave her a spiel as if he were “leading troops in the field,” she jokes.

“You can’t do this work alone,” he said. “Why do you have all these people working here and you’re around all times of the day and night? Use your people.”

That talk was a boon. Swilley relented and allowed herself to delegate, and she never looked back. She was named the 2025 National Principal of the Year by the National Association of Secondary School Principals and recently transitioned from overseeing Fairfield Central High School in Winnsboro, South Carolina, to serving as an assistant superintendent in the same district.

Leadership skills like delegation aren’t inherent; they develop over time as leaders become more comfortable in their roles. In fact, learning to let go of a little control is a common experience for leaders. As Rebecca Knight wrote in Harvard Business Review, “Delegating may seem simple, but the real challenge is overcoming the emotional hurdles.… Distrust, control issues, perfectionism, and fear of failure can keep you tangled in the details or stuck doing everything on your own.”

I recently spoke with three school leaders—Spencer Long, principal of Halls High School in Knoxville, Tennessee, and Mark Andresen, principal of Mandan Public Schools in Mandan, North Dakota, as well as Swilley—about relinquishing responsibilities, trusting their colleagues, and living with the results, both good and bad, that come with delegating.

Learning to Let Go

All three leaders told me that one of their most significant undertakings was coming to terms with the fact that they couldn’t perform every single task that came across their desks. “I can tell you, I tried to do everything by myself,” Andresen said.

“Most school principals are naturally driven to do things and do them right,” Long commiserated. “And with that personality trait, it’s hard to delegate.”

Long’s hesitancy was also born out of a separate concern—he worried that staffers would view the tasks he was doling out as burdensome. He wasn’t assigning unimportant tasks, but without prior delegating experience, he didn’t know how his staff would perceive the work he wanted to assign them. He gradually gained an appreciation for delegation after realizing that “there’s a sense of empowerment when somebody receives an additional assignment, a leadership role, or responsibility over something,” he said. “It’s a compliment to their capabilities.”

Andresen’s epiphany about delegation came from two realizations. First, delegation isn’t a final, forever decision—he could make adjustments or even reassign responsibilities if someone turned out to be ill-prepared or a poor fit. And second, the alternative to delegation is micromanaging—and that’s much, much more harmful. “If you micromanage, you basically are never going to sleep, you’re always going to be on edge, you’re always going to be on the phone,” Andresen said.

After accepting the necessity of delegating, the next step is to build trust with staff. Without that “relationship component,” as Long put it, the best-laid delegation plans are worth very little. “You’ve got to learn what their habits and beliefs are,” Andresen said of his staff. “You’ve got to understand them before you can actually delegate to them.”

One way to understand your staff, according to Swilley, is to utilize strength-finder tests. She found the tests helpful in identifying where staffers might excel and also as a means of launching conversations to get to know teachers and administrators better.

“Sometimes I’d say, ‘Based on your strength finders, this will be a good opportunity.’ Sometimes it was, ‘You’ve done this before and did very well,’ or ‘You said you want to learn more about this area,’” she said of how she got staff buy-in when delegating tasks.

Be Strategic and Purposeful

There’s not a one-size-fits-all guide to delegating—just a need for a consistent, top-down plan of action.

Andresen runs a large high school with about 1,200 students, so it isn’t possible for him to maintain a tight-knit bond with each and every person on staff. His English department, for instance, has 11 teachers. He relies on a tiered structure coanchored by his leadership team, which includes a variety of department chairs.

To fill those roles, staffers bring Andresen a list of one or two candidates to represent each of the core subject areas, and he makes the final choice on who’s going to serve as department chairs. Those leaders tend to have more experience and years’ worth of rapport with Andresen, he said, but that’s not always the case. Sometimes, he’ll consider a newer teacher’s prior leadership background and educational history, and talk with them one-on-one about their vision.

After the leadership team is set, Andresen holds periodic meetings where he and the team discuss school needs, issues, and successes. The department heads then take those conversations back to the rest of the staff. They also make recommendations; for instance, Andresen said he might ask the math department head about which math teacher he should send to an upcoming conference.

Long feels strongly that any delegation discussions—especially assigning a department chair—should be done in a one-on-one setting, always in person. “You can only communicate that through a face-to-face conversation, in my opinion,” Long said. “It’s impossible to have that conversation in a meaningful way through a text message or an email.”

For his department chair meetings, Long brings up organizational goals and highlights why he thinks that teacher “would be a strong fit for this leadership role, and what contribution I feel like they could make to their department,” he said. In doing so, he believes “you’re empowering somebody’s self-confidence and their own view of their professional effectiveness, and also I think it’s an opportunity to build trust, where the staffer understands that the leader of the building trusts them with the responsibility over something of great value.”

Once a person accepts that responsibility, Long makes sure to let them know exactly what the role entails and why the duties matter. “Delegating is only effective if people understand the mission, purpose, goal, the why behind what we do,” Long said.

Take the Good with the Bad

Delegating doesn’t always go seamlessly. It often requires tweaks, revisions, and a reality check. Swilley came to embrace a grounded barometer for success: Even if a delegated task wasn’t accomplished her way, if it “still met the standard of excellence,” then she understood she “needed to be OK with it,” she said.

Long described a recent experience at his school, where an assistant principal was handling an involved endeavor that Long had delegated. It was mostly going well, but the assistant principal worried about coming across as too authoritative in an upcoming meeting with a group of teacher leaders, where tough feedback might be necessary. The assistant principal had a “peer dynamic” with the teacher leaders, Long said, and this meeting had the potential to upset a balance that was otherwise working for all parties. Long decided to step in—he attended the meeting and provided the feedback himself, which gave the assistant principal some cover. The feedback was useful: “Growth happened very rapidly” afterward, Long said, which he fully credited to the assistant principal for stepping right back into their delegated role and demonstrating leadership skills and adaptability.

“I would say that’s an example of, once you’ve delegated a task to somebody, you check in with them, you sit alongside them when they’re working on that task and monitor how things are going,” Long said. “And when things are not going as well, you collaborate with them and help them to come up with solutions to those problems.”

As Long sees it, there’s nothing wrong with some bumps in the road while he’s delegating. His personal philosophy, which he tells his strongest teachers all the time, “is to push them out of their comfort zone and into the next leadership role, because that expands their positive impact on students,” he said.

The Downside of Delegating—Which Is Really an Upside

Of course, there’s a downside to encouraging more delegating: Your best administrators and teachers might outgrow their roles and leave.

“That’s the paradox of good leadership, right? If you’re a good leader, then you’re helping your followers grow into leaders, and then when they have fully feathered out their wings, you’ve got to let them fly,” Long said.

Swilley knows that paradox well. Before she moved into leadership, she was a math teacher—a very good one, in fact. Administrators told her how much she excelled and cautioned her against opportunities to advance in her career. “I know what it feels like to be pigeonholed because someone wants you to remain in a role you’re good at,” Swilley said.

Once she reached the leadership ranks, Swilley was passionate about “growing other leaders and being able to pass the torch with confidence,” she said. It was far more important to her “not to make staff stagnant, but to empower them,” she said.

Swilley acknowledged that it’s not easy to lose your best people. But she learned to put a positive spin on it: “If I have the opportunity to empower another building leader, I’ve established another thought partner,” she said. “Since this person already knows me and will be in my position, we can support each other.”