Admitting There’s a Problem Is the First Step

Alison Cumming, Wickenden Associates
September 10, 2019

Trustees today face a challenging set of financial, social, educational, and political issues. While navigating the tricky waters of Board-Head relationships, fulfilling their roles as financial stewards of the institution, and attempting to divine the future in an era of high stakes for independent schools, trustees need and deserve a governance model that respects their time and talents. Heads of School, in turn, need and deserve Boards that are organized for success, oriented to the future, and respectful of the Head’s central leadership role.

Every Board of Trustees is a work in progress. Developing a Board that is organized around key strategic challenges, that meshes well with the Head’s leadership style, and that effectively uses the talents of all of its members requires a willingness to identify problem areas and to consider new ways of accomplishing the work of governance.

For Boards interested in exploring potential problem areas, we suggest that the process begin with a wide-ranging conversation—perhaps during a Board-Head retreat in as relaxed a setting as possible—in which trustees discuss some or all of the following questions:

The Board’s contribution to the school: In what ways does our Board add value to the institution? What have been our major recent accomplishments? How would the school be different if the Board did not exist? Are we producing a good return on the school’s investment in the Board? Are we adequately focused on the mission of the school and the school’s success in accomplishing the mission? In what ways do we support the Head of School?

The rewards of trusteeship: How many of us find our Board service a fulfilling experience? Do past trustees typically maintain a connection with the school? Can each of us cite ways in which the school has been enriched by our presence on the Board? Are we using each trustee’s talents effectively? Do all of us have individual goals this year that are compatible with the Board’s goals as a whole?

The Board’s composition: Do we have a clash of governance values among our trustees? Does our membership include big-picture thinkers as well as specialists? Are we overly tolerant of destructive trustees? Do we have a pool of talented potential trustees from which to choose when vacancies occur? Do we have too many parents on our Board? Do we maintain a healthy balance of experienced trustees and “new blood?” Have some of us been around too long?

Board processes: Does the way in which our Board is structured cause us to think too much about process and not enough about results? Does the organizational structure of our committees help us to focus on critical “do or die” issues, or are we too often seduced into lower-level operational issues? Do we routinely demand and receive the governance information we need to make informed decisions about key issues? Do we truly exist as a Board or are we just a collection of committees? Are our Board meetings productive or perfunctory? Have we clearly identified our strategic priorities and goals for this year? If so, are we organized for success in focusing on those priorities and achieving those goals? Do we take time to celebrate our successes?

An open conversation around some or all of these questions can help trustees identify areas in which the Board is falling short of its potential—the essential first step in designing governance solutions.

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