Leading With Questions: A Playbook For School Leaders

Steven WeberBlog, Connect Better, Lead Better, Reflect Better


  • Leading school during this pandemic is not something we were trained for.
  • Making decisions and finding direction can be difficult.
  • Ask better questions and listen to the questions of others to help find solutions.
  • Include others’ voices in seeking answers.

Leading schools during the pandemic has been challenging and at times school leaders may have uttered the words, “There is no playbook.”  Graduate school, internships, and job shadowing did not provide school leaders with an opportunity to learn about social distancing, substitute teacher shortages, teacher fatigue, transitioning to virtual learning, or even how to pivot.  During this time, leaders have possibly learned more about leadership than they did in their grad school courses.

Nothing creates an opportunity for leadership to shine like uncertainty. 

Nothing creates a platform for leadership like ambiguity. 

And nothing calls out for great leadership like a crisis (Allen, 2020).

Ask Better Questions

A school leader who attempts to navigate change alone and make all of the decisions will soon discover that it is futile.  During times of uncertainty, leaders can learn to ask better questions.  “Probably the two greatest failures of leaders are indecisiveness in times of urgent need for action and dead certainty that they are right in times of complexity” (Fullan, 2008).  It is common for a principal or assistant principal to solve problems or to remain calm under pressure.  During the past two years, school leaders have encountered many situations for the first time and the complexity of the situation may not have allowed the leader to identify a quick fix or solution.  “We have moved from a complicated world to a complex one.  The two aren’t the same – and complexity isn’t just complication on steroids” (Hefferman, 2020).

While no playbook may exist, questions become the playbook. Listening to multiple perspectives can support school leaders more than a single narrative. Click To Tweet

Leading with questions can support the leader and the organization.  While no playbook may exist, questions become the playbook.  Listening to multiple perspectives can support school leaders more than a single narrative.  There are leaders throughout the organization, and they may have a better perspective than the principal or assistant principal.  Questions can lead to strategies and short-term wins.  Short-term wins may open the leader’s perspective to new questions.  Try these questions as you continue to navigate change and unprecedented times.

Leading With Questions: A Playbook

  1. Where are we going? (A Roadmap)
  2. How will we get there? (A Strategy)
  3. What is one thing we can do today to guarantee students receive a quality education? (Clarity) 
  4. Which changes can we make in order to adapt to the barriers we are facing? (Adaptability) 
  5. Are we focused on the things that we can control? (Ownership)
  6. What do students need today? (Outward Focus) 
  7. How can we support our staff? (Relationships)
  8. What have we learned during the past year that can support our efforts this week? (Reflection) 
  9. Are we still in the business of changing lives? (Purpose)
  10. What do teachers need in order to feel supported? (Supportive)
  11. What does a high-performing team do when there is a substitute teacher shortage? (Flexibility and Problem Solving) 
  12. What are we learning about collaboration and supporting our colleagues? (Outward Focus) 
  13. How can we communicate with families during virtual learning? (Communication) 
  14. Which students need additional academic or behavioral support? (Care and Intervention)
  15. In the midst of uncertainty, what can our school team do to remain positive and supportive of our colleagues? (Purpose and Collective Commitments) 
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Listen and Hear Multiple Perspectives

As school leaders, we need to invite people to have a seat at the table.  More importantly, we need to listen and hear multiple perspectives.  The playbook may have changed, but the teachers, counselors, coaches, secretaries, custodians, and staff can provide valuable feedback and recommendations.  Listening to school staff has always been critically important.  “In [a] crisis, sometimes we must call for air support.  So, get on the radio and ask for help.  Your team needs you to be situationally aware, make some tough decisions and keep moving forward” (Gleeson, 2020).


Allen, T. (2020). This is the most important question leaders ask during a crisis. Forbes. https://www.forbes.com/sites/terinaallen/2020/05/06/this-is-the-most-important-question-leaders-ask-during-a-crisis/?sh=516ca9c677b1 

Fullan, M. (2008). The six secrets of change: What the best leaders do to help their organizations survive and thrive. Jossey-Bass.

Gleeson, B. 9 ways  crisis makes you a better leader. Forbes. https://www.forbes.com/sites/brentgleeson/2020/03/31/9-ways-crisis-makes-you-a-better-leader/?sh=2f2c14b643e2 

Hefferman, M. (2020). Uncharted: How to navigate the future. Avid Reader Press.

About Steven Weber

Dr. Steven Weber is the Associate Superintendent for Teaching and Learning with Fayetteville Public Schools (AR). His areas of research include curriculum design, formative assessment, professional learning, and school leadership.