How to Tell When Someone Is Ready for an Administrative Role

Randy Dalton doesn’t have many regrets about his career path, but he does wish he hadn’t become a principal so quickly.

In Dalton’s defense, his administrative pivot was somewhat of an accident. After a few years at his first teaching gig, he volunteered to help tabulate student attendance. Dalton’s district superintendent found out about this valuable, if informal, step toward leadership, and asked Dalton to apply for a middle school vice principal position. He took a leap of faith and got the job—but when the middle school struggled to fill its lead principal vacancy, Dalton, then just 25, went straight from teaching to leading a whole school.

Almost two decades later, Dalton is still a principal. He oversees Molalla River Middle School, and in 2025, was named Oregon’s Principal of the Year by the National Association of Secondary School Principals (NASSP). But Dalton’s success may obscure the fact that it’s not easy to transition into administration without a thorough grasp of how to manage people and navigate the complexities of schoolwide systems. Absent steady support and guidance, new administrators run the risk of becoming overwhelmed by managing other staffers—a feeling that can turn into regret at taking the role. In fact, there’s evidence that “reluctant managers” are increasingly commonplace, including outside of education.

According to a 2025 survey cited by Harvard Business Review, “one in four managers would prefer not to be people managers, up from one in five just two years ago.” Not only that: Like Dalton, “many of these managers found themselves in the role without knowing much about it beforehand, with less than a third reporting exposure to simulations, mentorship, or opportunities to gauge whether they were suited to becoming a manager.”

How can school leaders recognize and nurture aspiring administrators? How can they prepare them for management and all it entails? I posed these questions to Dalton and Spencer Long, a Tennessee principal who also made an early-career transition from teaching to leadership.

Notice the Staffers Who Look for Opportunities to Lead

Dalton and Long told me they keep an eye out for problem-solvers, high performers, and teachers who are genuinely focused on learning more about what comes with administration. Dalton looks for someone who’s “ready for anything, someone who can be objective and calm in the face of crises, and has an unwillingness to quit,” he said. “You know when somebody has those things.”

Long was a science teacher when he began thinking about an administrative career. He developed a rapport with his colleagues and became an elected member of his school’s teacher leadership team, where he was exposed to school-level challenges for the first time. “I sat with one of the assistant principals to help build the master schedule for a couple of years while I was still a classroom teacher, which helped,” Long recalled. “I was also a lead teacher, where I was responsible for evaluating and providing feedback to other teachers. I navigated some challenging conversations before I entered the world of administration.”

Long was able to wrap his head around why certain decisions were made at the school level that didn’t benefit him directly as a science teacher. The work also fostered his curiosity about schoolwide systems, which is a quality he seeks out today. He gave an example: After a teacher has completed their credentials to become an assistant principal, what do they do next? He wants someone who’s proactive and asks for opportunities, such as attending a difficult conversation between leadership and parents.

Kallie Ash is an aspiring administrator who recently wrote a piece for Edutopia about how she’s preparing for future leadership openings. She identified four ongoing efforts, which were suggested to her by a trusted school leader mentor:

1. Work on authentic networking
2. Learn how the entire school functions
3. Offer to lead professional development
4. Join schoolwide committees

Through these efforts, Ash hopes to demonstrate her sincere interest in management and leadership. Surveys cited by HBR indicate that Ash’s interest is a great sign about how she’d treat an administrative job—highly engaged managers are “more than twice as likely” to stick around, because they genuinely enjoy their jobs.

Plant the Seed, Provide Ample Opportunities, and Listen Closely

Some administration-curious educators don’t actively pursue leadership opportunities. They have the right skillset, but might be hesitant to leave the classroom, or perhaps haven’t considered what a leadership track entails. “It’s hard to know your own potential, and not everybody is confident in their abilities,” Dalton said. “You need to point that out.”

Dalton regularly approaches club advisors and tells them they might want to try out additional leadership responsibilities. He finds that they’re often surprised to hear they have administrative potential. Long regularly initiates conversations about administration with teachers, too. He holds meetings with each teacher at the beginning and end of the school year, and asks about their three-, five-, and 10-year professional goals. Some volunteer their interest in administration, while others require a bit of nudging. For especially impressive teachers, Long will float the possibility that they could shift their career down the line, just to see how they react. 

In response, a few teachers have been definitive: They have no interest in the idea. That’s useful information for Long, who’s perfectly happy when a teacher indicates they’d prefer to stay in the classroom. Long wants his best teachers to keep teaching, especially if that’s what brings them personal and professional enrichment. But he’s also found that sometimes, initially hesitant educators become much less reluctant about a move to administration when they receive encouragement and guidance. 

“I have seen people go from, ‘There’s no way I could do this,’ to, ‘I’m eager to do this,’” Long said. The switchover is the result of patience on Long’s part—he’s not trying to rush a great teacher out of the classroom—as well as “intentional exposure to being a people manager at a school,” Long said. 

He and his team coordinate shadowing sessions and teacher-led faculty and professional development meetings, and allow teachers to handle some parent conferences (with administrative oversight). In doing so, “once-reluctant teachers can preview the pressures of being in a managerial role,” Long said. “They realize that there are systems and strategies that help us navigate challenges, and that those systems and strategies can be learned in the same way that teaching strategies can be learned in the classroom. It’s just a new skill set.”

Don’t Leave New Hires to Fend for Themselves

It doesn’t matter whether an educator enthusiastically moves into administration or requires coaxing and time—in their adjustment to the new role, they need guardrails and diligent feedback. Even the most promising of candidates can quickly burn out on the job unless they’re made to feel that they matter, and that they have adequate support to learn the ropes.

A recent NASSP article laid out a six-step process that bridges the gap for new administrators between orientation and onboarding. It runs for 12 weeks, which gives leaders time to really work with new hires and establish “manageable milestones,” writes former administrator Robyn R. Jackson. The steps are:

1. “Define their role in terms of your vision.” Lay out the schoolwide mission, and how the new hire fits into it.
2. “Create and review an onboarding document that defines success.” Be specific! Make sure the administrator is crystal clear about their responsibilities.
3. “Develop a 12-week plan for ownership.” For each responsibility, new hires should be assessing their progress from “not started” to “building competency,” then “preparing to take ownership,” followed by “partial ownership,” ending with “full ownership.”
4. “Establish a communication rhythm that supports ownership.” Be proactive and consistent—check in on how new hires are tracking their own progress.
5. “Conduct a 12-week review.” This is the moment for “self-reflection,” as well as “feedback and evidence,” and “future focus,” Jackson writes.
6. “Establish regular check-ins after ownership is established.”

The last point rings true for Dalton, who believes “the only way to onboard someone is to model behaviors—the planning, the problem-solving—and communicate on a consistent basis.” 

He brought up an administrator who’s been in the role for a few years; she and Dalton speak multiple times per day, running through scenarios. To Dalton, this is proof of a hard-working and thoughtful administrator, someone who wants to grow as a manager and leader. “When you can talk to somebody who’s experienced, and reflect on the bigger picture, you’ll come out with a better result,” he said.

Long similarly makes more space for new administrators, so he can personally aid in their adjustment period. He already has weekly administrative team meetings and monthly one-on-ones with administrators.

For his first-year assistant principal, Long aims for additional, daily interactions. Before the school year began, he reallocated a few areas of responsibility to experienced assistant principals, and moved other responsibilities to the new assistant principal—all of which are intended to build the person’s confidence without overwhelming them. 

“I’m not spending quite as much time with my experienced admins, so that I can spend more one-on-one time collaborating with my new admin,” Long said. “It’s a gradual release concept.”