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When I was middle school director at Flint Hill School in Oakton, Va, the Head of School approached me. He informed me that the lower school director had quit in the middle of the year and asked if I would run both divisions for the next five months. 

Being known as someone who would take on almost any challenge, I said, “yes,” without hesitation. It was a great decision. Having spent my teaching and administrative career in the middle school, it was great to learn more deeply about the lower school. It helped me be a stronger candidate when I applied for Head of School jobs at PS--8 schools. 

Once I became a Head of School, I kept saying “yes” to whatever came my way, whether it was helping with a sticky student discipline issue or stepping in to teach an advanced math course. Saying “yes” to so much was exhausting. I spent the first few years of my headship tired and overstretched. 

Maybe most importantly, I began to realize that by saying “yes” to everything, I was inadvertently saying “no” to doing some of the most important elements of my new job. I did not have the time to think strategically, craft and effectively communicate about culture, and grow the school. 

I understand the inherent irony: to climb the ladder, you need to be known as someone who will say “yes” to any challenge and when you get to a high enough perch, you have to learn to say “no” to all but the most important priorities. Being a leader means determining the most important priorities and being laser focused on accomplishing those. It means saying “no” quite a bit. 


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