An Open Letter from a New Head to His Board Chair

With his retirement in 2012, David Dougherty completed 44 years of service in independent schools, including 21 years at the Episcopal High School (VA) and 19 as Headmaster of The Hill School (PA). As teacher, administrator, and trustee he has served boarding, day, single-sex, and co-educational schools. Here he addresses an early “conundrum” with TEG’s Executive Coaching Program: New Heads thought the idea was terrific, and Board Chairs the same, but neither was willing to raise the idea with the other. The new Head who was brimming with confidence was anxious about asking for help; the Board Chair who had just excitedly announced the completion of the school’s search did not want to suggest that the new Head might need support. What to do?! Here in e-mails back and forth, a new head and board chair tackle that problem:

Dear Charlie:

Heather and I are back home, still bursting with pride after our three days at Fair Lawn Academy, and can’t wait to get started on the many opportunities and challenges that we see at the school. We are grateful for your candor about some of the key issues there, and look forward to facing them with you.

Of course, as soon as I returned to my office here, I was greeted by four students (who are sad we’re leaving); my leadership team (who’ve reminded me of the long-range plan we must complete here); and several parents (who say they’ll lean on me until the last day of school). For sure, as eager as I am to tackle the tasks at Fair Lawn, I want to finish strong here. They’re counting on me. I’m told that Heads must be two places at once. It’s time for me to get some practice!

Make that three. Both Heather and I are tending to the mixed emotions of our kids, who are excited about a move, but anxious about making friends at a new school and leaving their pals here. They’re counting on me too. With your terrific family, you understand that better than anyone.

Meantime, I’ve heard from the Daily Courier there, who have scheduled an article about my appointment, and I hope to dovetail it with an interview with WHTR. I’m not accustomed to this kind of fanfare, especially all at once! And the advancement office at Fair Lawn is already eager to set up meetings with the head of the Clear Sky and the Upshur Foundations, who seem impatient to meet me. I realized pretty quickly how important they are to the School.

Anyway, I met this morning with my Head here, who was eager to learn about my weekend. He has been unbelievably supportive of me, and has offered me wonderful advice from the beginning of the search. He’s also offered me counsel whenever I want it next year – even if it’s just to hear a “primal scream” from me, as he puts it! – but he also offered me some advice, which I’d like to share with you.

He told me that when he accepted the headship here, the Board Chair asked him whether he’d like an “executive coach,” an idea he’d had success with in business. My Head thanked him but declined, yet told me that was a big mistake. He thought he could do it all, and he wanted to show it. He’s done great, but confesses that it was a slog at first, a lot of it avoidable, he said, if he’d had just one objective, experienced, and caring person to confide in. To him everyone – even his wife – had a “point of view” and couldn’t be really objective. My Head recommended firms that pair new Heads with a retired Head, experienced and successful, who can in a spirit of trust and confidentiality offer advice, support, wisdom, and (maybe most importantly) the willingness to listen. One of them even offers to read a Head’s speeches before he delivers it! I could use that!

In our talks over the weekend, I was most appreciative of your openness with me, and I want to respond in kind. I am very excited about my future at Fair Lawn, and I’m very confident. I believe I will serve the school well. I’ve been preparing for this opportunity all of my adult life. But I don’t walk on water, and I don’t know everything – heck I’ve never prepared a budget or raised a dollar in my life – but I believe I have the ability to do well. But when I “hit the ground running,” I think I’d like to have the ear of a man or woman who has been in my shoes, who knows what it’s like to experience the kinds of things I’ve mentioned above, and whom I can call on to help me think through the challenges of making Fair Lawn Academy the best independent school in the state.

There I’ve said it. I wasn’t sure I could! Maybe you were thinking the same thing. You’re a businessman and probably know all about executive coaches. Anyway, could we talk about it? I’ve heard a million times that the relationship of the Head and Board Chair is the most important one at a school. This seems like a good way for us to get started!



Dear Jared:

I have read your letter and I thank you for it. So you don’t walk on water! Heck, after writing our announcement about your appointment, I was beginning to wonder whether you were even human! I hope I haven’t scared you out of your wits! Let’s talk. I think your idea sounds great. And I admire your candor – and your self-assurance – in raising it with me. I’m enjoying my work with you already. Call me after you read this and we’ll talk seriously about an “executive coach.”


TEG’s “Executive Coaches” are certain about the need for the service we offer. We’re certain too that other educators recognize the need; we’ve heard that from heads, trustees, directors of independent school organizations (many of them think it’s a crying need). But at many schools, new Heads and their Board Chairs have trouble talking about it. It really is quite simple though, once the new Head confidently acknowledges that he’s not perfect (everyone already knew that!), and his Board Chair assures him that he wants to do everything he can to support him (everyone knew that!). That sounds like the beginning of a great relationship.