Lessons Learned: A Retrospective on Four Decades of Christian School Leadership

Not counting the year when I tried to escape, I‘ve been a head of school for 43 years. 

Five schools, three states, with an average tenure of seven years–until I accepted the invitation to lead Little Rock Christian Academy. Once planted in Little Rock, I served for 16 years–the best sixteen years imaginable. I could have easily served longer, but wisely stuck to the succession plan in the best long-term interest of the school. (In a follow-up post, I’ll lay out ten guiding principles to drive a seamless, mission-centric, honorable head of school succession.)

Speaking of “in the best long-term interest of the school” . . . when all is said and done, I attribute my longevity in this career as head of school to keeping this goal in the forefront. 

The journey started in a cedar-shake schoolhouse on February 1, 1980, a cold, gray day on Cape Cod,  the first day of my life as head of school. I was standing in the school office amidst the board chair, the interim head, the school administrative assistant, the custodian, and a student. 

The student was on the phone, and when the bell rang, I tapped him on the shoulder and whispered, “Mark, it’s time to get to class.” Wide-eyed, he looked up. The next thing I saw was the phone flying across the room, smashing into pieces against the office wall. Before I could take my eyes off the explosion, the student was gone–out the door, running towards the highway. No one moved. No one spoke. Everyone stared at me. I could hear the silent words: “What’s the new guy going to do now?”

“Each situation deepened my roots in the idiosyncratic call of Christian schooling.”

The story ended well. At first, I wondered if it was a cruel test but quickly realized I had merely experienced a day in the life of a school head. By the grace of God, I also made my first deposit in the proverbial bank of trust.

Each situation deepened my roots in the idiosyncratic call of Christian schooling. To what do I attribute this vocational stickiness? I offer these climbing holds. 

Love people. 

My father changed careers four times. Why? People. On his deathbed, I asked my pharmacist father, “If you could do it all over, what would you have done differently?” For the first time, I heard him say, “Be an electrical engineer.” Schematics, yes. People, no.

Colleagues, before you sign another contract, ask yourself, “Do I love people?” How do you know? Start with this question: “Are you interested in other people?” 

Remember whom you work for. 

In independent schools, the head of school is the sole employee of the school board. The board holds the school’s mission in trust and is ultimately responsible to the school’s stakeholders that the mission is well executed. Accountability to the board for the overall well-being of the school is a given. Ideally, this relationship is a strategic partnership that requires alignment and a mutual submission to the heart of the mission. Are you okay with this leadership model?

Be present and visible. 

These are two different things. Ideally, the head is in the moment among the people as much as possible. In my mid-career years, it was heroic to work on a strategic plan or budget at the expense of a school assembly or game. Heroically wrong. I finally learned that an hour with the drama or debate team was worth many more hours of future vitality. 

Love your enemy. 

My mother advised me over and over to obey Paul’s command to offer our enemy food to eat and water to drink (Rom 12:20). This wisdom is corroborated by the Teacher in Proverbs 25:21: in so doing, “the Lord shall reward you.” 

Possess a growth mindset. 

The line between a growth mindset and a fixed mindset is the continental divide of education. Without a growth mindset, a school leader has no chance of survival. 

Build up others. 

An early mentor and professor of Christian education at Wheaton College and Wheaton Graduate School regarded Ephesians 4:11-13 to be the sine qua non of the Christian life and our work as Christian educators: 

And He gave some as . . . teachers, for the equipping of the saints for the work of service, to the building up of the body of Christ; until we all attain to . . . the measure of the stature which belongs to the fullness of Christ. 

Does the call to invest in and encourage others motivate you to endure the tedium, the tensions, or the disappointments of our work?

Be happy. 

Cicero counseled his students that if they were to be effective leaders, they needed to be winsome, affable, and happy “in the eyes and face.” I love that qualifier. When people meet you, what are your eyes and your face telling them? The answer will impact your future.

Communicate. 

While interviewing for my final headship, I asked the outgoing chair what was most important to the board. He said three things: communication, communication, communication. Four months later, a CEO board member of the school asked me to help his company in the area of communication. I took that request as a vote of confidence.

Say ”we” more than “I.” 

I’m breaking this rule in this post because it’s a personal reflection, but as we lead others, pronouns matter. I told a development officer once to stop saying “I” so much. He was not happy yet took my counsel. Today he is a head of school and still comments on that particular day, saying that those words of wisdom prepared him for headship.  

Listen to the culture canaries. 

Every school has a labyrinth of message chambers. In the process of creating culture (every head’s responsibility), keep an ear open to the myriad of signals that indicate shifts, cracks, and warps in the school’s precious culture. Take the feedback seriously before things choke, wither, or die. 

Salute the mission–every day. 

Governance, personnel, budget, curriculum, program–do all your decisions boost the mission? Are your decisions consistent with the mission? That alignment is what we mean when we say, “Act in the best long-term interest of the school.” 

Partner with your board chair.

A key to longevity is building a strategic partnership with your board chair. Learn to steer the canoe together before you take the rapids. 

“Some say valiant leaders know how to die valiantly. I say valiant leaders know how to live valiantly. “

Make sure you are on the board’s nominating committee.

Often referred to as the Committee on Trust, this committee defines the school’s future and, to a great extent, your future. Be there. In this role you can help avoid dangerous, loaded, and fatal board nominations as much as is within your power. 

Choose your battles wisely. 

When your side isn’t winning, look for alternative solutions. There is almost always a third way. Some heads stand their ground on a perceived principle of integrity. Too often, it’s more a matter of personal intransigence. Some say valiant leaders know how to die valiantly. I say valiant leaders know how to live valiantly. 

Team with an exceptional executive assistant. 

It took me way too long to learn this lesson. I underestimated my need for help. Teaming with a brilliant, dedicated, motivated, people-loving, alert, wise assistant is a game-changer. Find, keep, and reward your most important teammate.

Know when it’s time to leave.

Know when it’s time to pass the baton of leadership. It may be mid-career or at the apex of your call. The day is coming when it will be time to move forward. I always kept this page from Christianity Today tucked into my journal: “Is It Time To Leave?” This classic piece may help you answer that question. 

Give thanks. 

There is no greater privilege than shepherding the next generation of Christian school professionals, parents, and children. You are called. You are chosen. You are commissioned. Stay the course. Remember these words of Ray Noah: “The greatness of our lives is not in what we leave behind, but in what we send forward.” 

May it be so.