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The Role of The Head of School

Ask the Big Questions

If it is true that you can tell the quality of an institution’s thinking by the questions it is asking itself – that is, requiring its administrators to answer – then we propose that the key question for heads of schools is, "What are the most important questions you are currently asking your school to answer?"

Asking "important questions" is inextricably interwoven with strategic planning, its processes and outcomes.

Ask the Big Questions in the Right Way

In his book The Professional Decision Thinker, Ben Heirs cautions against simple questions advocating "rich" questions that truly reflect the complexity of a situation. Heirs maintains that "simple questions cannot generate rich thinking" in a decision-thinking process.

Here are three ways to test the richness of the questions before the institution:

Do not frame the question too tightly.

Example: How can we move from K8 to K12?

    Better: How can we move from K8 to K12 with full enrollment within the next five years?

    Even Better: How can we move from K8 to K12 with full enrollment within the next five years without:

  • Demoralizing our teachers? or
  • Offending or losing current families? or
  • Opening our market to new competitors? or
  • Destroying our long-term competitiveness? or
  • Weakening our reputation for quality? or
  • Using fund raising practices that would alarm our donors and accountants? or
  • Making ourselves open to attack from Board members?
Remove complexity from language when framing a question, but don’t remove complexity from the question itself. Do not gloss over important factors just because they are difficult to express concisely.

Resist the temptation to reduce the whole issue to a single financial point, i.e. "What’s the bottom line?" When an issue of any complexity is involved there will be many bottom lines. Consider the bottom lines of relationships, image and satisfaction. Each must weigh in when attempting to frame the right question.

16 Ways to Get and Keep Strategic Planning on the Right Track

Once a head of school begins thinking about strategic planning, there are

  1. Test for Board readiness for strategic planning Click for Assessment Tool (download only, 72K)
  2. Ascertain the state of the institution and the type of planning required. (Crisis, holistic, first plan?
  3. Determine the planning parameters (budget; timeline: 6 months, 9 months, a school year? Click for Plan Schedules; planning cycle Click for Planning Cycle Matrix
  4. Determine if outside facilitation is needed; if yes, select provider; if no, identify Core Strategic Planning Team
  5. Guide the overall process
  6. Understand and champion the principles of strategic planning
  7. Act as the vision-bearer
  8. Include planning team among the top school councils
  9. Endorse all research efforts
  10. Meet regularly with the planning team
  11. Avoid the trap question of "what is that you don’t like?" in favor of "What and how can we improve?"
  12. Participate in evaluation
  13. Be the school’s chief ambassador of the plan
  14. Identify and act on strategies to get the plan off the shelf and into action.
  15. Identify and act on strategies to communicate the plan to all constituencies
  16. Watch for gridlock and plan atrophy; unblock logjams and facilitate progress; be flexible.

Download this document (MSFT Word, 46K)