Leadership Hiring: Evaluating Experience and Comfort With Change

One capability virtually all schools could deepen is organizational adaptability. As many schools are now in the midst of searching for new senior leadership team members, evaluating whether a candidate has experience and comfort with change is important. 

Here are some questions that may help you evaluate candidates on this front:

1. Tell me about a time when you needed to lead through significant ambiguity. What did uncertainty teach you about yourself as a leader?
2. Describe a situation where you had to help your community hold two seemingly contradictory truths. Walk us through your approach and what you learned.
3. Share an example of when data or feedback led you to significantly alter or abandon a plan you were invested in. What was your process for changing course?
4. How do you determine the right pace for change? Give us a specific example where you had to carefully calibrate the speed of implementation.
5. Tell me about a pilot program that failed. What did you learn, and how did that learning inform your next steps?
6. Describe a time when you had to build support for an unconventional idea. What resistance did you encounter, and how did you address it?
7. When have you been wrong about something important? How did you recognize it, and what did you do next
8. What's the most significant cognitive bias you've had to overcome as a leader? How does this awareness impact your decision-making now?
9. Tell me about a time when you had to maintain community trust while navigating a complex situation you couldn't fully explain.
10. How do you determine which stakeholder voices need to be included in a decision-making process? Give an example where this approach proved crucial.
11. Tell me about a change initiative where you realized midway that your initial approach wasn't working. How did you course-correct?
12. What's the most significant resistance you've encountered to a change you believed in? Walk us through how you responded.
13. Describe a time when you inherited a change process that was already underway. How did you evaluate its effectiveness and decide what to maintain or adjust?
14. How do you gauge when a school is experiencing change fatigue? Give a specific example of how you've addressed this.
15. Describe a situation where you recognized that a department or team's resistance to change actually highlighted important considerations you'd missed.