Executive Coaching in the Time of Transition

The Education Group Executive Coaching Program is designed to meet the challenges and complexities encountered by school leaders. It is targeted toward new school heads that face a very difficult job. Not only must a school head be the educational leader of the school, but he must be its business leader, a counselor, a visionary, its moral leader, a fundraiser, evaluator, and guardian of the school’s mission. He also has the responsibility of creating strong, credible relationships with, and selling the vision of the school, to widely divergent constituencies.


New heads must learn much of their job “on the ground, running.” And even with the most far-sighted plan, they will likely need counsel and support in what is both an exhilarating and lonely job. This is the kind of support the TEG program can offer to the head and the school:


  1.  An executive coaching program can be a valuable asset to the head of school and to the trustees that appointed him. Every head could benefit from an independent, objective, supportive agent who will help him develop stronger relations with all of the different constituencies of the school.

  2. What is a coach? In the TEG program the coach (a) supports the “person” of the head; (b) facilitates his thinking, drawing him out with questions; (c) serves as a “sounding board”; (d) is a cheerleader; (e) is a trusted confidante; (f) is available 24/7 “on call”; (g) is a “friend” with no “performance objectives” except the health, well-being, and success of the head – in fact he is the only person with whom the head interacts who is not self-interested. With that kind of support, the new head can optimize his skills and talents to lead the school.

  3. The Executive Coach must possess the following skills and attributes: (a) He must be an experienced and highly successful former head who has met the challenges of the job well over a long period of time. (b) He must be a good listener; ask good questions; be able to give time of himself; inspire trust from everyone at a school, not only the head himself; be highly empathetic; and have no “agenda” for the school except for the success of the head.

  4. What does an Executive Coach not do? Ideally, the executive coach does not “tell” or “direct” the head to do anything, let alone say, “The board has asked me to . . . .”  Instead, he would ask questions, for example “What are you thinking of doing?” “Why are you doing that?” “What problems do you foresee what that?” “Why don’t you talk with you board chair about that?” – drawing the head out and helping him clarify his thoughts. He would take the time to help the head fully construct a plan to meet the expectations of the board and the school community.

  5. If a school contracts for an Executive Coach after the new head’s term has begun, it is likely that the new head has encountered resistance or criticism at the school, or has made mistakes and miscalculations. Of course, the Executive Coach would support him in addressing those problems. However, the Executive Coach will not assume “intervention” responsibilities, but will employ the strategy of the “coach” to help the head address those issues and establish himself as the leader of the school. He and the board should then see that the head himself has responded appropriately to concerns that have been raised. TEG distinguishes between “intervention,” in which the executive coach is told a number of problems with the new head and asked to fix them, and “coaching,” by which the coach offers independent counsel and support to the head, supporting him as he addresses the problems himself; establishes himself as the leader of the school; and builds important relations within the school community.

  6. Shortly after the new head’s appointment, the Executive Coach can guide him through an “entry plan,” to include items like those listed in Item #8 in the “Principles of Transition” and to anticipate the key events or “flash points” during the school year for which he should be well prepared. The Executive Coach will tailor his efforts according to the strengths, weaknesses, experience, and inexperience of the new head.

  7. The Executive Coach can help a new head and his board chair to clarify expectations as they develop their important relationship. This is especially important when both the head and the board chair are new in their positions, as is sometimes the case.

  8. The Executive Coach can be a helpful guide to both the new head and the board of trustees in matters related to independent school and non-profit governance.

  9. The Executive Coach can help the head to “test-drive” his thoughts or plans before he takes them to his board chair, senior administrators, or other key school people. 

  10. If early in his tenure a new head considers changes – his own or those the board wishes him to make –

  11. an Executive Coach could be helpful. Some heads are called to be “revolutionary,” others “evolutionary,” and an Executive Coach can help a new head think through the impact of both.

  12. More likely, the new head will be assigned by the board certain tasks or asked to conduct studies in his first year, and the Executive Coach would support him in that endeavor.

  13. The Executive Coach can advise him about how to evaluate major personnel decisions early in his tenure.

  14. An Executive Coach can offer to serve as a proofreader for the head, who will spend a lot of time writing speeches, alumni magazine articles, and letters to the school community.

  15. The head and Executive Coach should determine early how and when they will correspond, agreeing on what is a “reasonable” amount of regular correspondence. The Executive Coach would respond to any unusual interruptions in correspondence.

  16. The Executive Coach must facilitate, not intervene, in the relationship between the head and the board: a head can’t communicate well with his Executive Coach and then ignore the board. However, the Executive Coach can be helpful in advising a new head in effective communications with the board and in resolution of potential problems.

  17.  Most heads rely on a professional crisis management professional in dealing with true crises or emergencies, but an Executive Coach can assist him at the beginning of his tenure in preparing a comprehensive “crisis management plan,” tailored specifically to the needs, personnel, and logistics of his school. Also, in a crisis he can be a helpful sounding board to the head dealing with an emergency.

  18. The head is expected to raise money, and the Executive Coach can be helpful to a new head in this enterprise, helping him assess how the school’s advancement leaders are organizing and preparing him for his development responsibilities.

  19. The role of the spouse/partner should be defined during the search process. If not, the Executive Coach can help the head and board chair clarify expectations for the spouse/partner. Short of becoming a marriage counselor, the Executive Coach (or indeed his own spouse, a former “Spouse of the Headmaster”) can serve as a sounding board for the head on issues related to the pivotal and yet often ill-defined role of the head’s spouse/partner.

  20. Though the Executive Coach is responsible to the board of trustees, he will communicate on a regular basis only with the new head and the board chair. With his goal to help the head meet the school’s expectations himself and to strengthen the critical relationship of the head and chair, the Executive Coach will empower him to provide appropriate feedback and reports to the board.

  21. Periodically during the year, and two weeks after the conclusion of his work with the head, the Executive Coach will submit a written report to the chair of the board of trustees and to the head himself, providing candid and proper feedback to them about the issues that they have addressed during the year and the manner in which they were resolved.