The Interview Questions Every School Leader Needs to Ask

I remember early on in my career when I was interviewing at a prestigious school just outside of New York City. I thought the interview was going well. We had spent the last hour diving deep into pedagogy, discussing my core teaching philosophy, troubleshooting classroom management strategies, and exploring potential coaching opportunities.

As the conversation began to wind down, the head of the upper school leaned back and asked me two questions I did not expect: “How is your social life? What do you like to do outside of school?”

At first, the question caught me off guard, and I initially felt it was a bit inappropriate for a professional interview. I must have given him a look that betrayed my confusion because he quickly smiled and stepped in to explain his reasoning.

He told me that a great teacher needs genuine balance in their life. In his eyes, a school should never consume a teacher’s entire existence. He believed that educators who cultivate vibrant, fulfilling lives outside the classroom bring more energy, creativity, and resilience to their students. Ultimately, he wasn’t trying to pry into my personal business; he wanted to ensure he was building a faculty that prioritized long-term well-being and a healthy work-life balance.

As a young teacher, this profound realization deeply resonated with me. Over the years, it has served as a guiding principle throughout my professional journey, constantly reminding me to stay actively invested in my personal passions and life outside the classroom.

I must admit, maintaining this equilibrium is often much harder than it should be. Throughout my career, specific challenges—like prepping a brand-new course for the first time or navigating a school environment with toxic leadership—have repeatedly threatened to derail my boundaries. There were seasons when these intense pressures actively stole precious time from my family and my life outside the classroom.

However, experiencing those difficult chapters taught me a vital lesson: simply recognizing that your balance is off is the necessary first step to reclaiming your time and your sanity. Looking back, I am profoundly grateful for that interview conversation which took place almost forty years ago. It planted the seed for a lifetime of self-awareness.

Now, as an experienced educator, that very mindset has become an invaluable tool in how I mentor newer teachers. When I check in with my mentees, I intentionally ask about their lives outside of school. Their answers reveal a great deal about how they approach their day-to-day workload. If a teacher’s personal life is entirely consumed or severely restricted by the unending demands of the job, it serves as an immediate red flag. Without conscious boundaries, they will struggle to sustain their teaching career and quickly find themselves on a direct path to chronic burnout. Guiding them toward this realization isn’t just advice—it is an essential act of colleagueship. We should all do this for each other.

So, how is your social life? Does your family get enough of your time? If you are worried about your answers then please stop working so hard. Thanks for reading! kim