Episode Details
Back to EpisodesPMP169: Leading into the Wind – Lessons from Dave Sandowich
Description
A few weeks ago, I had the privilege to spend a few hours sailing on the Chesapeake Bay with Dave Sandowich.

He commanded his 42-foot sailboat, Charis, with the skill of a man who has spent the past forty years on the water anytime when he wasn’t leading his school or his family. Dave, a 65-year old father of three and grandfather of eight, had relocated to Kent Island, Maryland seven years earlier, renovating a 120-year old farm house – a house with a very important accessory – access to a pier for a permanent home for Charis. Although he still consults younger principals, he spends his spare time with his boat or entertaining guests and family members who visit through the sailing season May through October.
With sleeves rolled up, he showed me how to handle the jib sheet, trim the main sail , navigate through changing depths and mark distant points for reference. His graying hair blowing in the wind, Dave’s deep voice rattled like a coach patiently giving orders. “Keep the wind at 30 degrees and head for the red buoy ahead.”
“Sailing is a lot like leadership,” he explains. “On a sailboat your destination may be directly from where the wind is coming from. A sailboat can’t sail directly into the wind but it can work its way up wind by sailing at angles off the wind and working its way up wind to the destination. It is more work and will take more time but you will get there if you stay the course, apply your sailing knowledge and get the feedback from your instruments and instincts and adjust along the way.”
Dave’s Bio

David Sandowich is a retired principal from Kent Island, Maryland. For 21 years, he was the principal of Haddon Heights High School in Haddon Heights, NJ. Although he still consults younger principals, he spends a lot of time focused on his favorite hobby – sailing. His experience as a teacher, coach, principal, father, mentor and as a sailing-enthusiast has given him a unique perspective on leadership.
During our time together, Dave was a great listener and a teacher. I’m honored to share the lessons and metaphors we discussed about sailing, and how they nay help you rethink the way you lead. In this conversation, we talk about the following:
- Physics in sailing and leadership
- First order changes, vs second order changes
- Backwards design
- Advice for new leaders and experienced leaders
- Book and leadership recommendations
I thought about Dave’s words a day later when I was attending the National Association of Secondary School Principals. Joann Bartoletti, NASSP’s Executive Director, was introducing State Principals of the Year in a ceremony recognizing principals from across the country. First of all, Bartoletti pointed out recent research from the Pew Research Center showing 84% of respondents trust principals over every other public servant-leadership role for caring about others and working ethically on behalf of their communities.
“If we want great sch