Dear Head of School:

Congratulations! You have won a highly coveted position and now have an opportunity to make a lasting difference in the lives of students and teachers. You are no doubt poised to make your mark on your new school, and you should be commended for your hard work and talent that have led you to this point in your career.

In all probability you are facing enrollment challenges. If you attended the NAIS Institute for New Heads, you may have commiserated with fellow rookies about soft admissions and increasing financial aid. You were asked by Monique DeVane if you were feeling stressed (concerning enrollment), and like most of your fellow new heads, you raised your hand (Chubb blog, July 2015).

But right now, in early October, you continue to enjoy the honeymoon. Teachers, parents, and students are friendly and welcoming; the trustees are supportive; you are soaking up the positive energy that comes with new beginnings. You are following the sage advice of experienced heads who told you not to make major moves in your first year. They cautioned you to listen and learn, to understand the school culture, and to develop relationships. So far, so good!

But the enrollment challenge lingers in the back of your mind. The admission season will begin in earnest in a few months. Trustees, some of whom want quick results, will expect a plan. You may have some program ideas from your former school. You may even have thoughts about how to address the problem of your school being “the best kept secret in town.” Perhaps more advertising? Speaking engagements at Rotary? You’re feeling better.

I hate to burst your bubble, but I must. The problem is that these remedies pale in the face of the magnitude of your challenge. Instead of cookie cutter solutions, you should try another path. Become a leader!

I want you to channel your “inner leader,” and during the course of the year, let it emerge because leadership is the only way you will turn around your school. What I am about to communicate to you may sound obscure and downright ridiculous, but believe me when I tell you that leadership – not a slick five bullet PowerPoint plan – is how you will be successful. Here’s where to start.

First, spend some time thinking about what you truly believe about education. What are you passionate about? This passion is often born from experience and direct observation, from success and failure. It is not merely an educational philosophy; it is an educational philosophy infused with emotion, and therein lies its power. Now, don’t think I can’t hear you saying, “I need a plan to present to the trustees, and this guy is telling me to navel gaze?” Yes, that is exactly what I am telling you to do. Leadership is about changing the way people think and behave in order to attain different and desired results. Your beliefs, communicated authentically, have far more power to inspire stakeholders than some silly plan without passion. Planning can be a part of leadership, but it is not leadership. If you are unconvinced, check out the TED Talk given by Simon Sinek.

Second, assess the quality of the education the school is delivering. How good is your school? Really? There may be a very good reason that parents do not enroll their children in your school; they just don’t think it’s worth it. Take advantage of your newcomer status and under the guise of learning about the school, assess how good the teaching is, how good the program is, and how much the school culture induces student growth. Post-2008, small classes with mediocre teachers are just not going to get the job done. Marketing is about finding drivers and barriers to behavior. What elements of your program can be leveraged to drive prospective parents to the school, and what elements are barriers. Schools are incredibly insular in their thinking. They actually believe much of the mythology that their historical narratives spew out. Use your newcomer status to penetrate past that mythology. You do not need to destroy it; you just need to make sure it does not obscure the truth.

Third, stop being a problem solver and become a visionary. Problem solving is a great skill-set, but it does not constitute leadership. I know what you’re thinking – what is a vision? Or better yet, what is the right vision for my school? Well, here’s what it should not be. It should not be the strategic goals of your former school. It should not be salient qualities of the rich, successful school down the street. It should not be the tired and unimaginative dribble that comes from so many schools who are jumping on the bandwagon of STEM, STEAM, Global Education, Centers for Excellent Teaching, and so on. Nope. If you want to solve your enrollment crisis, you are going to have to research and then think hard about your educational beliefs, the mission of the school, what the school really is, and how the school is perceived in the marketplace. Remember, this is post-2008. You are not only charged with adding value to the school by helping it do a better job of living its mission; you are also charged with helping the school win in the marketplace. Your job is to pull together your research and thinking in order to create a compelling “winning aspiration.” Only when you have completed this third step are you ready to devise a plan.

Finally, in order to realize a vision, you have to have the courage to execute. You have to work with others to devise a plan, attract talented people who can execute the plan, allocate resources in order to maximize the chances of the plan being successful, and create systems and modify culture so that the school can build on its initial success.

So, eschew the obvious answers; set aside your default of becoming the problem-solver-in-chief. The challenge you face requires you to be a leader. It requires you to be intentional in knowing yourself and learning about your new school and its place in the market. It requires you to be objective. It requires you to create a vision from a deep understanding of the school’s mission, the quality of its services and its brand. It requires you to change the way stakeholders think and behave in order to attain different and desired results. And finally, it requires you to have the courage to execute. The success of the school will be the result of your transformation from a problem solver to a leader.

You can learn to be a leader on the job, but you must give up the habits of mind and behavior that proved so successful in your previous job. Are you ready to take this leap of faith?

Much of what is in this letter may not make sense to you. That’s OK. But you need to trust me when I say that successfully facing the enrollment challenge at your school will require you to pay attention to the four steps outlined above. You do not need to fully understand each one. For now, you can “paint by the numbers.” That’s what I did in my first headship. But please don’t think that a plan based on superficial research and shallow thinking, a plan that is based on shaky assumptions is any kind of substitute for real leadership.

One last point. I know you are smart; otherwise you would not have landed this job. But resist the temptation to prove that you are the smartest person in the room. That is not leadership! Your school will only thrive if you cultivate and utilize the individual and collective intelligence that surrounds you. If you are not satisfied with that level of intelligence, then you will have to make some tough decisions. Know that an inspiring vision and a great plan will not get you to the winner’s circle if you do not have great talent.

I wish you the best.


Thomas P. Olverson