Superintendent Retention, Interview Questions, & Strategic Plans

QUESTIONS AND RESPONSES

• Question: How do I know if we should keep our superintendent or not?  -- Board Member in California

• TESBM: Most importantly: there are no supernatural superintendent candidates out there. So every time you go looking for a new superintendent, you're blindly reaching into a random bag of talent and have no idea what you will pull out. The chances that the one you pull has more flaws than the one you've got are quite high; the main difference is you don't know what they are yet. So by default, focus on two things:

  • Is our school system making reasonable progress toward accomplishing our Goals  while honoring our Guardrails? If the answer is yes and the superintendent has broken no laws, you probably shouldn't be searching for a superintendent. 

  • If student performance isn't improving relative to the Goals, the board needs to know whether or not the superintendent is willing to do the hard work necessary to improve. If so, an improvement plan might be more beneficial for your students than a transition plan.

• If the answer to both of these is "no," then you're probably in a superintendent search situation. If the answer to either of these is "yes," then you're probably better off working with what you have. Effective school boards focus on previously agreed upon student outcome data -- not last minute, cherry picked student performance issues, the organizational fire of the moment (there will always be one), or adult personality drama.

• Question: What type of questions should we ask during the superintendent interview?  -- Board Member in Washington

• TESBM: Here are three major mistakes school boards make when it comes to superintendent interview questions:

  • They let the search firm select them. This is problematic because then it's the search firm that's determining what the board wants to know about its potential superintendent, not the board itself.

  • They pick from a list the search firm gave them. Functionally, the same issue as above.

  • They don't design and practice their own questions. Yes, I realize doing your job takes more effort than letting a search firm do your job for you. Yes, I realize taking time to practice and get calibrated is more time than you wanted to spend. This is the most important hiring decision board members will make, however, so it warrants the additional time and attention.

• What to do instead? Four things:

  • First, reach consensus as a board on what specifically you need to know from the candidates in order to make a decision. Make a list of each specific thing the board needs to know. Ideally three to ten items; less is more.

  • Then reach consensus as a board on a single question that will help the board get an answer to each individual item on its list.

  • Then reach consensus as a board on what an example of an unacceptable answer would be, what a weak answer would be, what an acceptable answer would be, and what an exemplary answer would be.

  • Finally, roleplay a practice run so that the board can further calibrate the rubric and get comfortable with the interview process.

• One downside is that it's not appropriate to do any of these steps in public. Some state laws will allow this to happen in closed session while others won't -- in which case the board may need to delegate this process to a subgroup of the board and/or get external support.

• Question: As a school board member, what should I be looking for in a strategic plan? How do I know if it's useful or not?  -- Board Member in Illinois

• TESBM: We recommend that strategic plans have three things -- which few have -- and a bonus fourth that almost none have.

  1. Outcomes: Board-adopted Priorities

     • SMART Goals about student outcomes that represent the community's vision for what students should know and be able to do.

     • Guardrails that describe the community's highest priority non-negotiable values that must be honored while in pursuit of the Goals.

  2. Outputs: Superintendent-adopted Interim Metrics

     • SMART Interim Goals that are predictive of the Goals, influenceable by the superintendent, and measurable multiple times per year

     • SMART Interim Guardrails that are a reasonable interpretation of the Guardrails, influenceable by the superintendent, and measurable multiple times per year

  3. Inputs: Staff-adopted Initiatives

     • Goal-aligned Initiatives that are predictive of their respective Interim Goals and that describe what the staff will do in an effort to accomplish the Interim Goal.

     • Guardrail-aligned Initiatives that are predictive of their respective Interim Guardrail and that describe what the staff will do in an effort to honor the Interim Guardrail.

  4. Implementation Instruments: Staff-adopted Playbooks

     • For each Initiative, staff creates a one-page "Playbook" document that describes the Initiative, who the owner is, the FTEs for it, the budget for it, a project timeline, and any other information the staff needs to monitor implementation.

INTERESTING READS

• A coach's view of why school board focus matters.
• A group of researchers watched a lot of school board budget meetings. Here's what they saw.

BOARD MEETING ANALYSIS

A subscriber asked us to watch a board meeting in Illinois. Here are the highlights from the regular board meetings:

• Total Public Minutes: 156
  • Public Minutes Focused on Student Outcomes: 0 (0%)
  • Minutes Not Focused on Student Outcomes: Board discussion (about censure) - 67, Public comment (mostly about censure) - 70
  • Key Topics: budget, censure
•  What Coach Celebrates: 

  • Agenda management prioritized completing required business (budget adoption) within statutory timelines.

  • Clear explanation of Public Participation norms and consistent facilitation supported an orderly forum

• What Coach Recommends:

  • Reallocate at least 50% of open-session time every month to monitoring progress toward the board-adopted student outcome Goals; in this meeting, that value was 0%. Add a scheduled Goal monitoring item with a superintendent report and board Q&A aligned to interim measures.

  • When budget items are on the agenda, explicitly connect appropriations to the Goals/Guardrails in the presentation and in board questions (e.g., which strategies in the budget most predictably move Goal X’s interim measures this semester?). This nudges budget time from inputs to outcomes-aligned oversight.

  • Limit board discussion time spent on adult behavior issues in open session; where unavoidable, timebox such items and protect a dedicated block for Goal monitoring.

  • Publish and adhere to a monthly monitoring calendar (Goals and Guardrails) so that procedural and business items don’t crowd out student-outcomes monitoring.

UPCOMING OPPORTUNITIES

• Effective Guardrail Setting
  •  We are continuing the Policy Leadership series with a 30-minute webinar on how to adopt high quality Guardrail policies and what to look for in Interim Guardrails.

    • 11am central on Friday, November 14th, 2025

    • RSVP Here

• Did you miss last month's 30-minute webinar? Email Greg for a make-up session on any of our growing list of topics, including governance policy, delegation policy, effective budgeting, superintendent evaluation, professional services management, strategic planning, or consent agendas.

BONUS MATERIAL

For paid subscribers, here are links to additional resources (to gain access to the links below, please consider subscribing):

• Additional details about the analyzed meeting -- including a video link, time use evaluation, and more.

  • Board Meeting Video

  • Meeting Materials

  • Strategic Plan

  • Completed Time Use Evaluation

• A guidance document on effective goal monitoring calendar creation.

• A guidance document on effectively transitioning from one superintendent to the next.
• A guidance document on writing effective superintendent interview questions.
• A guidance document on effective strategic planning practices.
  
  • Example of a one-page Playbook

Thank you for reading The Effective School Board Member. You ask tough questions and twice per month we get nationally certified school board coaches to provide answers. We help school board members tell their stories and provide additional resources to help them be more effective.

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