Is a Kick Off Retreat Right for You?

Wickenden Associates
September 6, 2019

One excellent tool for launching a new Head’s tenure is a late-summer retreat that brings the new Head together with the administration, the Board of Trustees, and perhaps senior faculty members for an open exchange of ideas about the school’s most pressing needs. The summer retreat serves several purposes:

  1. It strengthens relationships among the Board, faculty, and administration, and promotes greater understanding of the unique perspectives of each group among members of the other groups.
  2. It helps the new Head to become acquainted with key members of the school community and to gain a greater understanding of their interactions with one another in a relatively non-threatening setting.
  3. It provides the Head with valuable information about the range of perspectives within and across various constituent groups with respect to key issues facing the school.
  4. It helps all participants to begin the school year with a sense of inclusion, common purpose, and mutual understanding.

The event, which might be scheduled over a day and a half, should include ample opportunities for relaxed social interchanges as well as for structured conversations about the needs of the school. The Board President can kick off the event with a welcoming address identifying the purposes of the retreat and reiterating the Board’s excitement about the arrival of the new leader.

After the initial plenary session, the participants should be divided into small groups, each of which should include trustees, faculty members, and administrators. During most of the retreat, the new Head should function primarily as a listener and observer, moving among the breakout groups and contributing where appropriate without driving the discussions. Discussion topics will vary depending upon the school’s situation with respect to previous planning efforts. If a strategic plan or accreditation self-study has been completed recently, items for discussion can be drawn from the goals identified in those documents. If no up-to-date planning documents exist, the retreat agenda can be designed to elicit a list of goals the school should pursue in the years ahead.

The final item on the retreat agenda should be closing remarks from the new Head of School in which the Head summarizes what he or she has heard during the retreat, offers some personal observations about the issues discussed, and describes in broad terms how he or she intends to proceed in the months ahead.

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