Learning and Leading is a Team Sport

Being a Head of School can sometimes feel like a lonely and isolating job, and the one-on-one coaching approarch for Heads can feel similarly siloed . L+D has re-envisioned a new model that brings together individual coaching with a shared learning experience for Heads. Starting in the fall of 2025, we will offer a year-long experience for a cohort of 8-12 Heads from around the country, in non-competing markets, who will come together monthly online to connect and share their journeys with each other, as well as do individual coaching that supports their specific challenges and goals. Human connection is the simple greatest antidote to burning out, and never has it been more important for Heads of School.

Leadership+Design has created a new three-pillar approach to coaching Heads of School, with a fourth, in-person pillar, as an option.

  1. Individual Coaching: Similar to other coaching models, Heads in this cohort will meet with a L+D coach for a one on one meeting 1x/month for 75 minutes.

  2. Cohort Meeting: Once a month, the cohort of Heads from around the country will gather for a monthly discussion on the aspects of the job that are not tactical.

    • How do I show up?

    • Where am I feeling stuck?

    • What is the difference between how I am perceived and how I want to be perceived?

    • How can I feel more joy?

      These shared sessions will focus on the intangible challenge of being the sole employee of the board, the key person that faculty, parents and staff project on, and the person ultimately responsible for what happens at school. This responsibility can feel heavy, and it is easier when carried together in a cohort.

  3. An Asynchronous Space: Online space to connect with your cohort, ask questions, share resources, and keep the conversation going. As you get to know your cohort, this space will be yours for discussion and collaboration on your own schedule.

A New Model for Head of School Coaching

Optional In-Person Meeting

This year, coinciding with the NAIS Annual Conference in Seattle, WA, in February 2026, we will offer an optional in-person meeting for all members of the cohort. This meeting will be held near the NAIS conference site to make it easy to attend for Heads already attending NAIS, and we will gather to learn together and also laugh and connect. You do not need to attend this gathering to take part in this cohort.

What Clients Say About Coaching

“Through the coaching process, I felt like I had the space I needed to vent, get clear, and then focus on what really mattered.”

— Coaching Client

“I didn’t realize how alone I felt until I had a coach. It was nice to look forward to an unbiased person to work through my challenges with. I always looked forward to our time, and I learned a great deal about myself in the process.”

— Coaching Client