As I noted in my last post, I spent the 2015-2016 in an administrative role at my previous school. Serving as the Assistant Dean of Students at a boarding school was an eye-opening experience on many levels. Now that I’ve left administration (at least for now) to return to the teaching ranks, I thought I should take some time to reflect on what I learned. Much of this is common sense, of course, but I want to have a reminder of my current thinking should I ever go back.

Whenever I’m asked about my experience last year, I always say that if I had to describe it in a single word, that word would be “humbling.” The feedback I received from my supervisors was almost uniformly positive, but I rarely felt like I was doing a good job. This is no doubt a function of perfectionist tendencies, but in many ways, my first year as an administrator felt an awful lot like my first year as a teacher. I was learning on the fly, juggling a lot of new challenges at once, and at times, barely keeping my head above water. More importantly, I learned just how complex the task of running a school really is. As one colleague said to me after I took the position but before I started, “Get ready for lots of grey.” I wasn’t sure what she meant, but I quickly learned. Rarely does a school leader face a decision that is black and white. Most of the “easy calls” are made by others, so by default, the issues that land on an administrator’s desk are challenging and complex. There is often no right answer, and odds are good that someone will be upset with whatever decision you make.

The other thing that caught me off guard (but probably shouldn’t have) was the public nature of the job. There is a steep learning curve, but unlike your first year as a teacher, almost every mistake you make is exposed to your colleagues. As a teacher, you can close your door and make mistakes with the knowledge that the only people who (usually) see them are students–and they tend to be more forgiving than adults! Whether it’s a presentation in a faculty meeting or a difficult disciplinary decision, as an administrator, it can feel like your every move is being scrutinized behind your back. To do the job well, it takes thick skin and maybe even a bit of practiced nonchalance. Sometimes confidence is a choice–fake it ’til you make it!

A few other takeaways:

  • Before beginning, seek clarity about institutional priorities and how success will be defined in the role. There is only so much time in the day, and if you spread yourself too thin, nothing will get done well. When push comes to shove–as it almost certainly will–where should your attention be focused?
  • Find a mentor who is not your supervisor (or your supervisor’s supervisor). Ideally this would be someone who has done your job, but more important than that is finding someone who you feel comfortable asking questions of when you feel “stuck” or leaning on for support when the pressures of the job weigh you down. If you’re moving into an administrative role from the teaching ranks, this can be tricky, because many of the people you previously would have sought out may now report to you, which can alter the dynamic.
  • Early on, focus on “making sure the trains run on time” (that is, crucial logistical/organizational tasks and day-to-day management). We as a society seem to suffer from a “cult of leadership” in which “leaders” are visionary and heroic (think Steve Jobs) and “managers” are boring and maybe even a little bit soul-sucking (think Bill Lumbergh). Nobody aspires to be a “manager,” but in a leadership transition, it’s easy for things to fall through the cracks. No matter how incredible your vision may be, if you can’t (or don’t) “manage” the mundane aspects of the job early on, you will lose credibility and your ability to lead will be seriously compromised.
  • While you focus on the day-to-day, do take proactive steps to build your “leadership capital” for the long term. Even if you have a vision that you hope to implement, it makes sense to learn the lay of the land, and it’s always possible that your vision can be improved upon by others. Do this in the following ways:
    • Build relationships. Just talk to people. Get to know them better on a personal level, without an agenda. You don’t have to become best friends, but getting to know each other is more likely to create trust and make it easier to work through differences of opinion later on. (And for God’s sake, when those differences of opinion occur, don’t try to resolve them over e-mail. Get to know people well enough early on that you can say, “Hey, let’s talk.”)
    • “Seek first to understand, then to be understood.” In his Seven Habits of Highly Effective People, Stephen Covey adapted this from the Prayer of St. Francis (“O divine Master, grant that I may not so much seek . . . To be understood as to understand”). No matter where you get it, it’s good advice: ask questions in the spirit of curiosity. Envision yourself as the Direktor Grundsatzfragen or “Director of Fundamental Questions” (see p. 2 of the linked PDF), at least within your sphere of influence.
    • Empower people. I read recently that an administrator’s job is to “say yes as often as possible.” This makes a lot of sense to me, especially in schools. People typically choose to teach (or coach, or …) because they are passionate. Encourage them to develop their ideas, and if they bring one to you, find a way to make it happen if at all possible. It’s become a kind of cliche to say that leaders don’t have a monopoly on the best ideas, but just because it’s a cliche doesn’t mean it isn’t true.
    • Focus on getting a few small “early wins” to build momentum and show people that you can lead. Keep in mind, however, that in keeping with the above, you shouldn’t try to do too much too fast or risk alienating people, so choose the areas you want to tackle carefully.
  • On an ongoing (i.e., daily) basis, be relentless about maintaining your connection to others–both students and faculty. This is important for any leader, but it becomes (I imagine) even more important the higher you climb. (That is to say, it’s probably easier to become “detached” as head of school than as department chair.) Do this in the following ways:
    • If need be, manage your schedule ruthlessly. This may seem like an odd follow-up to “foster a spirit of connection,” but it’s far too easy to get bogged down in e-mail and sit behind your desk all day. Carve out specific times for things like e-mail, phone calls, and daily tasks. Schedule reminders for things that used to be spontaneous, because it won’t be anymore (see below).  The inevitable crisis will throw you off some days, but self-discipline is a must.
    • Be visible. Yes, keeping the trains running on time requires a lot of “desk work,” but people won’t follow you if they can’t see you. E-mails are not an acceptable substitute.
    • Show appreciation for faculty. They work hard and need to know that you recognize that. A small gesture (a handwritten note or a shout-out in a faculty meeting–there’s a big difference, so know your target!) can go a long way. Again, e-mail will not suffice.
    • Even if it’s not spontaneous for you (i.e., you scheduled it on your calendar weeks or months ago), bring joy to people’s day in a way that encourages connection. Have donuts for faculty on a random Tuesday. Set up a hot chocolate station for students as they pass between classes. (In schools–especially high schools–joy and food often go hand-in-hand.)

In terms of the big picture, I learned that leadership can be a lonely business (as when making difficult or controversial decisions), but it can become even more lonely–perhaps dangerously so–if you are not careful and intentional about how and where you spend your time. In addition, effecting positive change in schools is a long game. As with the stock market, invest wisely and be patient, seeking steady growth rather than quick gains, which can be lost just as quickly.

And what about for me going forward? Well, I’ve learned that a formal leadership role can wait until I feel the NEED to lead. Looking back, I wanted to lead and was drawn to some of the challenges of the job in an intellectual sense, but I didn’t have the deep wellspring of passion and energy for the job that it required. Moreover, given the personal/family considerations that ultimately led me to Tampa, I probably wasn’t prepared to play the long game that leadership requires. Someday I might be, and I think this experience helped to clarify for me what kind of leader I would want to be. I’m certainly grateful for the opportunity to learn so much relatively early in my career, but in the meantime, I’m happy to be back in the classroom, and as I get settled in my new school, I’ll seek out smaller, informal leadership opportunities in order to keep building my capacity.