6 Essential Lessons From a First-Year School Dean

It’s hard to find support, so here are some places to start.

first-year school leader

This year I took a job that moved me from the classroom into school administration as a dean at Manual High School in Denver, Colorado. There are so many articles and resources for first-year teachers. But as a first-year admin, I found myself floundering. Then, the months go by, and as we hit the last few days of the year, I’ve got a few tips to share with newbie admins like me.

1. Administrators have a different relationship with students than teachers do—and that’s important.

As a dean of students, I am in charge of discipline, culture, and classroom expectations. Though my goal is to focus more on developing school culture than on managing behavior, there remains a natural distrust about my position. I had to first prove I cared so that I could make room for deeper conversations with students. Once I did, I was able to find the root-cause of problems for many of our students because I was working closely with them and their families. I am surprised to find that I feel more connected to students, their families, and their community than I did as a teacher.

2. Sometimes, your relationships with your colleagues are going to get awkward.

As a teacher, there were many times when I was the one who was questioning the intentions of our administration. As a school leader, I am much more aware of all the moving parts, the reasons behind decisions, and the impact decisions have on students. I now promote decisions made instead of pushing back, which occasionally puts me at odds with former colleagues. Now that I am on the front end of decision making, it is my job to support those moves but also to explain them as best as I can to all the players

3. I need a mentor. You need a mentor. We all do.

First-year school leader isolation made it clear to me that it is essential to have mentors. Finding a mentor felt like coming up for air after having been underwater too long. Through my professional mentors I learned what I was going through as a first-year school leader was not unique—they were same challenges and pitfalls that they had all previously experienced or were currently experiencing even years into the work.

4. You’re going to make mistakes.

As a teacher, I had always rehearsed and planned every lesson. As a first-year school leader, I was prone to mistakes. There were times when I unintentionally negatively impacted kids. And other times when I impacted the school as a whole or put teachers in difficult situations. It wasn’t a matter of if I would make a mistake, but rather how I would handle my next step so as to not make the same mistake twice. To be effective as a school leader, I now know I will make mistakes. I can choose to become overwhelmed by mistakes or use them as a foundation to be more effective.

5. School leaders might have a tough time identifying the right next step.


As a first-year school leader, I often felt like I was sitting in front of a state of the art mixing-studio soundboard. I used to be able to control each of the dials for my own classroom, but now I had multiple people and actions in play. The song didn’t sound as smooth. Each time I made a decision, the next one was easier. Asking questions, reflecting on decisions made, and anticipating unintended consequences has become part of my daily rhythm as a leader.

6. Having a job in administration and showing leadership are two very different things

You can’t just count on your job title to speak for you. Leadership is about action. Once I stepped into the role, I found a new level of freedom, latitude, and influence that I learned to love. I chose to make a different students on a deeper level sometimes by taking actions I had watched my own mentors take before and sometimes by implementing ideas I had only wished for before.

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