Reflections in the Rearview Mirror of a Departing Board Chair

Summer 2010

By Joseph Di Prisco

This is my seventh year as board chair of Redwood Day School (California). This is also my ninth year on the board, and it will be (my decision) my last. I am told seven years is a long time to be board chair. No board chair at Redwood Day School had ever gone more than three. Maybe I am a slow learner, but it’s taken me seven years to figure out a few things that might be worth sharing. 

Once, a good friend asked me, “What’s it like being board chair?”

“I learn something every day,” I said.

He grimaced. “That bad, huh?”

By the way, I almost referred to these reflections as those of an “outgoing” board chair. I am not especially sociable, however, which may explain why everyone (including me) was stunned when I was first elected. Somebody else had prepped for a couple of years while serving as vice chair. Then he pulled out for personal reasons. He would have been a great board chair. In fact, he is still a friend and a first-year board chair today at another school. The truth is that I left the nominating committee meeting for a minute (hot day, 17 glasses of iced tea — get the picture?). When I returned, the committee was staring at me like a pack of hounds and I was a very large pork chop — which, I assure you, I do not normally resemble. I was going to say the rest is history, but it might be more like an obscure branch of anthropology. 

Nonetheless, here I am — and before I leave for good, I’d like to respond to some Frequently Unasked Questions. 

I have a panic attack when I think about public speaking. Will I have to speak in public as board chair?
Of course not. That’s what the advancement director and the head of school are there for. So cross that worry off your list right now.

Well, I am being a little bit subtle here, and by “subtle” I mean inaccurate, and by “inaccurate” I mean I am lying. As my head of school once said to me, “Have you ever been anywhere when you didn’t speak?” While a bit rude, he was right. So, yes, you will speak a lot. If you are good at it, you will get better. If you are uncomfortable about it, you will also get better. It is something worth getting better at. (Call me and I will give you some foolproof tips. Seriously.)

The board has the fiduciary duty for the school. I am not a numbers person. How can I be board chair?
What? You don’t have an MBA? You can buy one online, you know. But OK, I was an English major, so you can take my financial advice straight to the bank. Personally, I was privileged to have a fabulous ex-financier for the finance committee chair and a top-notch Finance Committee. And we had lots of MBAs on the board (real ones, too, from the B-schools everybody wants to attend). They do speak a different language. They say “strat plan” when they mean “strategic plan.” They say “outlier” and “one-off.” Apparently, they understand each other. Big picture: If the typical excellently educated board member cannot understand the finances, then get the Finance Committee to speak English. 

I have just been nominated to be board chair. I’m fearful, it may not be good timing. Should I accept?
No, don’t do it. You don’t have the time. Heck, who has the time these days? You legitimately worry about how your new public role would affect the way the community will treat your family, and how teachers will respond to your children. This is an unassailable and logical position, so avoid the whole thing.

Of course, maybe you are not the logical type, like me. I myself was the first non-parent ever to sit on the Redwood Day School’s board. When my son was growing up, I had never heard of the school. He went to a public K–8 school before following me to University High School in San Francisco, where I taught for a significant amount of time. If it weren’t for financial aid, in fact, he would have never attended University High School. These are experiences that I think helped me as board chair, though it’s hard to say exactly how. Besides, if you love schools the way I do, there’s nothing like the presence of kids and teachers working together on a mission to improve, if not the world, real lives.

Beyond that, I was not typical independent school stock, if there is such a thing these days, and it seems less and less like it with each passing year. That is, neither of my parents, and none of my four siblings, graduated from high school, much less attended an independent school. I was the designated School Boy. I may have received my Ph.D. from Berkeley, but the enormous social separator for me from my family was graduation from high school. So I taught for 20 years, middle school through university. I was also, at a Catholic high school, an associate head of school. I was not on the fast track, in other words, to board leadership. But then my personal circumstances changed. (Ah, who can forget “irrational exuberance” made famous by Alan Greenspan in 1996?) I decided to become a famous writer. I failed. Instead I became an obscure writer, publishing novels, a book of poems, and co-writing a couple of books about child development and parenting.

In any case, suddenly, it was 2000 and I had become a new person, I suppose. Now I was a prospect for board membership and, well, donations. My kind of life and professional experience put me in a position to appreciate and support the great work of an independent school: generous financial aid resources to accommodate underserved kids, facilities that sparkle, professionals who are passionate about their vocation, families dedicated to the school beyond the interests of their own children. I’ve seen how this works. For instance, my son, who wouldn’t have been able to attend University High School without financial aid, one day would come to serve as chair of the Finance Committee of its board of trustees. 

I have heard that the board chair should have gravitas. What is gravitas and where can I get some?
Good question. We could all use a little more gravitas, and not just at holiday parties. Before I define gravitas, though, let me say something I should have mentioned earlier. Gravitas is the reason you never start off your public remarks with a joke. The sole exception being — it’s a really funny joke. What was the question again?

What happens when there is a crisis?
Crisis. As everybody knows, the Chinese word for crisis has two characters. One signifying danger, the other opportunity. Danger + opportunity. Now, if I were going to make up a word for crisis, based upon my own experience in this area, it would also have two characters. And one would be Ben and the other Jerry’s. OK, sometimes one would be Cabernet and the other Sauvignon.

First off, there are real crises and the other sort. Schools are full of both. It takes experience to tell the difference. For instance, you may have a newish board member who picks up on the unhappy mood of a faculty member who has had a bad day with the clay experiment she was sure would work like a charm. It is very bracing for a newish board member to discover that the mood swings of a teacher are as sure and various as the diurnal path of the sun. Teachers have a tough job. Some days are long ones. But stand around the faculty room of any school in the country and there will always be a little bit of misery. Ah, I remember well my first year of teaching. It rained 366 days that year (yes, leap year)…. Newish board members tend to romanticize schools the neighbors’ children attend, where everything seems so rosy, and where all the children are brilliantly blissful.

Now, sometimes there are real problems, like lawsuits, budgetary or financial challenges, tragic events in the lives of staff or students, problems with the school’s neighbors, personnel turmoil. These things happen. The board needs to exercise leadership. Don’t worry about shaping the message, or about how anything looks to the outside world. I mean, worry about it, but realize that it is more important to do the right thing for the human beings in your community and for the long-term health of the school. Think that way, and you will be fine — eventually, though not necessarily right away.

Will I ever be allowed to be myself, or will I always have to be careful as board chair?
OK, I know what you are worried about. Yes, you will from time to time get irritated. There is always some board member who is on the verge of going all rogue-ian on you. Or you find that your fund-raising goals on the board are not likely to be met because [fill in the blank]. Or somebody doesn’t show up for a crucial meeting and then wants to be personally updated at length at his convenience. I recall somebody I counseled off the board who, at our annual dinner, sat in front of the podium and, while I spoke, signaled I was Number One in her book — with the wrong finger.

I get it, I do. This is your opportunity to do some spiritual work. Count to 10. Do tai chi. Count to 20. Whatever you do, however, don’t be a finger-wagger. Never never never never never never never wag a finger. People hate it, and what’s worse, you feel like a self-righteous idiot. And what is even worse is it doesn’t work! Get the right people on the bus. Which brings up the next question.

What should I look for in a prospective board member?
You are getting the hang of this board chair thing, good. Yes, the most crucial legacy a board can leave the school is the next board. New blood, new thinking, new energy, new leadership is crucial. As for me, I look for brilliant, team-oriented billionaires. This search will not take up much of your time, for this is a very short list, and Warren Buffett has never taken my call. I know conventional wisdom says you should look for financial capacity. Certainly, that’s not insignificant. After all, no money, no mission. But you also want economic diversity. I think that grounds you in real-world thinking and planning.

Otherwise, the convention is to factor in skill sets. They say you need lawyers, CEOs, HR professionals, money people, politicians, entrepreneurs, academics, etc. There’s usefulness to that thinking. (Some gratuitous counsel: you really can have too many lawyers, unless you are being indicted for, say, racketeering. Lawyers, who are articulate and protective, have the capacity to grind progress to an utter halt. Qualification: If you pair Mr. Cowboy Litigator with Ms. Risk Averse 2000, then you might get somewhere when they balance each other out.) Once you meet your basic requirements for professional competence, however, you should look for people of passion, people who want to learn, people who enjoy collaborating with others. A poet is good to have around, or a surrealist painter, or a rock star. People you could imagine inviting to your house for dinner.

Here’s something else you can get hung up on: the size of the board. You might worry about unwieldy proceedings. Maybe it’s my teaching background, but I like a big room, with lots of personalities and ideas (maybe even some of mine). True, at one stop in my teaching career, I was teaching 40 kids in a class. To me, 30 good and bright and diverse people on the board are a lot easier to work with than 10 prune-faced mirthless micromanagers.

Look. It’s a volunteer position, and life is short. Why would anybody with an ounce of sense spend a minute with a bunch of sourpuss finger-wagging snobs? If we had more time I could tell what’s wrong with conventional term limits, too. Don’t get me started. Oh, let’s dismiss the people when they become effective? This is a plan? And you will make a few bad choices. Somebody you thought was textbook perfect morphed into instant migraine material. This relates to why, evolutionarily speaking, speed-dating came into existence. Maybe your nominating committee can look into this recruitment tool.

So I guess it’s the head of school and board chair united against the world?
More like united for, though it can be hard to know sometimes. You owe it to your head to be honest, which is also what he or she owes to you. Gratuitous advice to heads: careful trying to manage the board chair. Like border collies, they don’t like it. Gratuitous advice to board chairs: don’t be a border collie. Conflict, remember, can be healthy. Avoidance of conflict, however, is always unhealthy, and public conflict is catastrophe. The more I think about it, there’s a whole book implied in this question, and it could be a good one. (Psssssst. One last thing about you and the head, and it is the open secret. Cultivating a strong relationship is the heart of your job.)

What’s the hardest thing about the job?
The beginning. Also the end. It’s hard to get started (so much to take in), but it’s even harder to let go. My first year as board chair, the head of school quit suddenly. Now that was dramatic. I didn’t know “phone ringing off the hook” was anything but an expression. But just as there is no perfect time to begin your tenure, there’s no perfect time to leave. On balance, better to leave a year too early than a year too late. At least that is the advice I am taking for myself.

What was the best thing about being chair?
Being a part of something beautiful we should never take for granted: the education of children. And while all that’s true, and I mean it 100 percent, there is something else, too. The other best thing is the friendships you will form with your colleagues. The people who will work alongside you. The people who will move you with their dedication and vision and competence. If you are lucky like me, some of your best friends will even be strat-planning MBAs. One last thing, and it’s important. Never send an email to the board addressed “Dear All.” Who talks like that? These are your colleagues.

Do you have any regrets?
No, I don’t. Yes, I do. Honestly, we had big plans for school expansion not so long ago and, after 10 years of effort, we had a clear path to success. In six months, we raised in cash and pledges about 10 times more than we had raised in the entire history of the school. And then… Did you happen to hear about the financial instability in the markets in 2008? Millions we expected from our friends and supporters simply disappeared. We like to teach kids how to learn from failure, don’t we? We tell them this is how we grow, through disappointment. Time to listen to ourselves. These are hard lessons, and now, at Redwood Day School, we’re re-loading. We moved the chains a long way downfield. We mixed our metaphors. Still, I have high hopes for the future of the school. I wish I could have been here to see them through. But it’s up to others now. That’s part of the genius of the self-sustaining nonprofit independent school board. It doesn’t take genius to make it happen, either. Which, to anticipate your next question, is a good thing:

Do I need to be a genius to be a good board chair?
Obviously not. And I can prove it: I — even I — was a pretty good board chair. I have the board evaluations to support that contention, too. And oh yes, make sure you get the board to evaluate itself and you every year. And listen hard to the criticisms. They are all valid, even when they are dead wrong and completely ill-informed and a little bit unkind and your feelings are hurt.

I know when sports figures retire they say they want to spend more time with their family. I, too, have two little grandsons now and time is precious. I also have a birthday next year with a zero in the number, and I have new books to write. So of course I would like to spend more time with my… money. But really, it was worth it, including every long board meeting. Well, I better stop before I begin to get sentimental and lose whatever credibility remains.

As the wise guy poet who couldn’t capitalize, e. e. cummings, once said: “Always the beautiful answer who asks a more beautiful question.” Enough with these questions of mine. Now it’s up to you to come up with your own more beautiful questions.

Joseph Di Prisco

Joseph Di Prisco, as it should be clear by now, was board chair at Redwood Day School (California) for seven years.