How to Apply Empathy to Your Uphill Battle for Change

We recently wrote The Fable of the Table to illustrate the differences between worried school leaders and innovative school leaders. The former presents a challenge for educators working to transform learning at their respective schools. We posed the question:

If these two parties cannot find a way to empathize with one another, doors may close — literally and figuratively — as their visions for student success fragment. With every splinter, efficiency wanes and the likelihood of any pursuit achieving its goal lessens.

How might we resolve the tensions between the two?

The Power of Empathy

This is where empathy and design thinking come in. Empathy extends to understanding a leader’s motivations and choices in the creation and maintenance of a healthy learning environment. Design thinking transforms that empathy into actionable solutions.

  • What is the motivation of the worried leader? To stay stable, even though it will likely cause concerns about preparation for the future and frustrations about staleness of practice.
  • What is the motivation of the innovating leader? To question, imagine, and create, even though it will likely cause uncertainty, instability, and a messy trail of fail-up experiences.

Of course, these two characterizations are incomplete. There’s an absence of nuance and a touch of bias. They are based on the past experiences, conversations, and observations of us as authors and they are deliberately broad. That is because authentic, problem solving empathy works best in the immediate, with the bare minimum of barriers and filters.

It begins with a simple, yet challenging goal: to develop an understanding of the other’s point of view. How might a conversation driven by empathy look?


  • “Tell me about a time when you felt like this school was firing on all cylinders in the service of a student.”
  • “Tell me about a time when you felt like nothing you were doing was helping.”
  • “Tell me about a time when you felt like you you felt like you nailed it.”


  • “Describe what a successful day looks like for you.”
  • “What is your biggest worry on the first day of school?”
  • “What excites you most about working here?”


  • “Imagine this school could do everything you want it to do for students.  What does that look like?”
  • “If you only had twenty dollars for a budget for the year, what would you spend it on?”
  • “What if every senior school had a job lined up after college?  Where might they work?”

Leveraging the power of story, belief, and imagination to fuel improvement is powerful work, but it requires listening above all else. Listening with the whole self — focusing on words, body language, tone, and intention underlying the responses — is the most sure path to effective communication.

And turning the understandings gained through empathy is the most sure path to a meaningful solution.

This post was co-authored by Allison Zmuda and Dan Ryder. Allison is the founder of the Learning Personalized community and a full-time education consultant working with educators to grow ideas on how to make learning for students challenging, possible and worthy of the attempt. Dan is a veteran English teacher who presents workshops on technology integration, improvisation and design thinking throughout the state and beyond. Find him at

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