Conversations & Questions

A collection of conversation prompters to assist in mentoring, trust-building and continuous improvement.

Five dysfunctions

Peter Lencioni’s simple but powerful insights about the “Five Dysfunctions of a Team” provide a great starting place to ponder, discuss and sharpen your effort. Great for individual and team learning. Use Lencioni’s list as a work center. Jot down your thoughts in response to such questions as “How might we build strength in each of these areas of potential dysfunction?” or “How might we avoid this dysfunction?” or “How might we be known for the opposite of this dysfunction?”

  • Absence of trust
  • Fear of conflict
  • Lack of commitment
  • Avoidance of accountability
  • Inattention to results

Heart-of-the-matter, continuous-improvement questions

Good for developing, sustaining, measuring, and stepping up any team effort:

  • Why are we in this role, this business? Who are we?
  • How are we performing our role?
  • Where are we now, how is it going?
  • Where do we want to be/go?
  • How will we get there?
  • How will we know when we’ve arrived?

Good to great

Jim Collins’s Good to Great® is rich with learning possibilities. A special edition (simpler, focused) for non-profit leadership is available. His concept of focused heart-of-the-matter work is developed using three essential questions. As you work at honing your team’s purpose and focus, take some time to consider:

  • What is our team most passionate about?
  • What fuels our team's engine (e.g., people, finances, information, etc.)?
  • What is this team best at providing?


“The future ain’t what it used to be.” – Yogi Berra

  • What was school like when you were in elementary school?
  • What has changed in our leadership environment over the past 10 years?
  • How must we change to align to new mandates and challenges?
  • What habits of excellence are essential for the new era of educational leadership?
  • How do we prove our worth in this era of accountability?


“No other principle of effectiveness is violated as constantly today as the basic principle of concentration. . . . Our motto seems to be: ‘Let’s do a little bit of everything.’” – Peter Drucker

  • What if we did a lot with a little? What would we be about?
  • What is wildly important, absolutely critical to achieving our goals?
  • What “lesser things” keep consuming precious team time?
  • What do we want our legacy to be?
  • What do we want to be remembering with healthy pride 40 years from now?

Appreciative inquiry questions

  • What about _____'s achievements/accomplishments are you most proud?
  • What do you value most about _____?
  • What do you love about _____?
  • What are the sustaining strengths of _____?
  • Describe a personal HIGHlight of your _____ experience. What happened? Who was involved? What difference/impact was made? What core values were being expressed?
  • How does _____ inspire you?
  • What is/are _____ wildly important reason(s) for existing?
  • Ten years from now, _____ has changed/evolved but still holds the position of the premier organization for board of education advocacy and development. What has contributed to this great position? What leading-the-way decisions were made along the way? How does the organization look, feel and get things done?
  • Two years from now, members of the _____ are toasting cutting-edge breakout/breakthrough accomplishments. What’s being celebrated?
  • What are your greatest hopes for _____?
  • Five years from now, _____ is featured on the cover of Excellence Magazine for its excellence as a leading-the-way system/culture/network/organization. What does the headline say? What powerful characteristics/insights about ______ are described in the article? What does _____ look like? How do members assess the system?
  • If one crucial new aspect of _____ were to be developed over the next five years, what would it be?
  • What do you hope _____ achieves during the next five years? What will success look like? Why would that be important to you?
  • If _____ is to provide its very best during the next five years, what and how would be leading?
  • What trends/issues are driving _____’s need to change/improve/transform?
  • What significant trends, shifts, pressures, competition do you foresee impacting _____’s future?
  • What questions will launch us into deeper or next-level thinking about a new era?
  • What are the motivators or crucial reasons for improving/enhancing/transforming _____? Who needs this change the most?
  • What are the most promising practices for advancing _____, and why would we want to engage?
  • What/who are the most promising partners for advancing _____, and why would we/they be interested?
  • What will be the indicators of success/achievement/progress?
  • How will _____ sustain the change? Who will execute? How will the change be monitored and celebrated? What systems or financial/structural supports need to be in place?
  • What’s the first step? The second?
  • What steps does _____ need to take to effectively govern this next _____ era?
  • How will _____ constantly contribute to this advancement?
  • How will _____ lead the way in the new era?

"Interview" questions

Here's a smorgasbord of questions, all geared to help focus almost any conversation among board members, candidates or community leaders about the serious business of governing well.

  • Why are you or were you interested in becoming part of this governance team?
  • What does it take for a governance team to be highly effective?
  • What team behaviors are crucial for highly effective work?
  • What are your best hopes for this governing team?
  • What relationships/connections do you have with the school district?
  • What has your experience been like as an area volunteer?
  • What experience, assets or skills do you have that would benefit the governing team?
  • What personal strengths would you bring the governing team?
  • How would others describe your personal leadership style?
  • What experience do you have with team leadership of any kind?
  • How many board meetings have you attended in the last year and what were your observations?
  • What type of commitment will you bring to this governing team?
  • Which board policies are strong? Which need some review and work?
  • What are the most important responsibilities of the board?
  • How does a governing team best maximize its time?
  • What commitments to effectiveness would you bring to the governing team?
  • What insights do you have about real or perceived conflicts of interest that are a normal part of the governing challenge in small communities?
  • What is your vision for the future of the school district’s learning efforts?
  • What are the primary issues facing the future of the school district?
  • What top priorities should consume most of the board’s time this year?
  • In your first year on the team, what would you do to learn about great governing for the sake of the kids?
  • What are your opinions about...
    • The financial challenges built into the Colorado constitution?
    • The core focus of boards on student success?
    • State/federal mandates?
    • State/federal assessments?
    • The growing need for school districts to share resources and opportunities with neighboring districts?
    • Time/resources/financial pressures on teachers/principals?
    • The world our current kindergartners will inhabit at age 25?

For a conversation about building and improving board effectiveness, contact Randy Black or Brittany Crossman at 800-530-8430, 303-832-1000.