4 min read

Welcome to another edition of PEN Mondays! This week, we’re kicking it off with another series set on walking you straight to the Principals office.

So, you’ve decided you might want to leave behind the relative chaos of the classroom for the definitely-not-relative chaos of school administration.

First of all, congratulations!

Second of all, let’s talk about how to get there without losing your mind—or your sense of humor.

Our last Monday series focused on AI in education. If you want to check it out, you can catch up with those posts (and many others) on our website! Check it out here:

Part 1 - Part 2 - Part 3

Making the leap from teaching to leadership is less about becoming an entirely new person and more about evolving into a version of yourself that thrives in meetings, knows how to say “data-driven decision-making” with a straight face, and can survive an angry email or two. (Or a hundred.)

Here’s how to start preparing for the transition.

Skills You Already Have (and Those You’ll Need)

Let’s be real—teachers already have a lot of the skills administrators need. If you’ve ever negotiated with a room full of third graders about why glitter isn’t a food group, you’re well on your way to mastering conflict resolution.

If you’ve balanced grading, lesson planning, and accidentally volunteering to coach soccer, you’ve got time management down.

But there are a few new tricks you’ll need to add to your toolkit:

• Budgeting: You might think wrangling a classroom supply budget has prepared you, but school-wide budgeting is like comparing your personal finances to running a small country. Start learning the basics—there are workshops, online courses, and probably a math teacher down the hall who’d love to explain spreadsheets.

• Strategic Planning: As a teacher, you focus on your students. As an administrator, you’ll focus on everyone’s students. Start practicing thinking big-picture—how can the school improve? What initiatives could help?

• Communication: No, you won’t stop emailing, but now you’ll also be hosting staff meetings, talking to parents, and occasionally explaining to a student why climbing the flagpole isn’t a valid science project.

Growing into Leadership

You don’t have to wait for an official title to start acting like a leader. Schools are full of opportunities to stretch your leadership muscles while still rocking the teacher life.

• Take on a Role: Volunteer to chair a committee, lead a department, or organize a professional development session. It’s like leadership training with the added bonus of knowing how to use the copier in three different modes.

• Seek Feedback: Administrators live and die by constructive feedback. Start seeking it now—ask colleagues, supervisors, and even students how you can improve. It’ll help you grow, and it’ll prepare you for those moments when the feedback isn’t so kind.

• Invest in Professional Development: Find workshops or programs that focus on leadership in education. Not only will they teach you valuable skills, but you’ll also meet others who are considering—or have made—the jump into administration.

Finding a Mentor

No one becomes a great administrator in a vacuum (unless your vacuum is full of seasoned vice-principals). Reach out to administrators you admire and ask them about their journey.

Most will be flattered—and relieved that someone wants to talk about something other than bus schedules for once.

Ask questions like:

• Why are you in School Administration and not something else?

• What do you wish you had known before becoming an administrator?

• How do you handle tough decisions?

• What’s the hardest part of the job—and what’s the most rewarding?

Mentors can provide a wealth of insight, plus they’ll help you navigate the unwritten rules of administration. (Like always keeping a backup mug in your office because someone will steal yours.)

The Mindset Shift

Moving into administration means broadening your focus. As a teacher, your priority is your students; as an administrator, your priority is everyone’s students—and the teachers who serve them. This shift can feel daunting, but it’s also incredibly empowering.

You’ll need to learn how to balance compassion with decision-making. Not every choice will make you popular, but if your decisions are rooted in what’s best for the school community, you’ll sleep better at night. (Assuming you don’t have a meeting scheduled at 6 a.m.)

So, Is It Time?

If you’re thinking about making the leap, don’t rush into it. Dip your toes into leadership roles, gather experiences, and reflect on whether administration aligns with your long-term goals.

Not everyone is cut out for it, and that’s okay. Schools need great teachers just as much as they need great administrators.

But if you feel the pull to lead—to shape school culture, advocate for students and staff, and tackle challenges head-on—start preparing now. Because while administration isn’t easy, it’s a chance to make a difference on a whole new level.

And remember, no one expects you to have all the answers. Even administrators don’t have all the answers—they just have better coffee.

WHAT DO YOU THINK?

We would LOVE to hear from you!

Reply to this email, or send us a message on Instagram (link below)! We’re here to walk with you in these crazy times!

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