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7 Questions on Leadership with Nathan Sheldon

Name: Nathan Sheldon

Title: Head of School

Organisation: Casady School

In the first post-college stage, I enjoyed a remarkable career in Accounting, tax, and finance. About twenty years ago, I took on the role of CFO at a small Independent School in OKC called Casady School.

Eleven years into my work and enjoying teaching a math class and coaching kids soccer, I found myself applying for the Head of School position during a leadership transition. More than nine years into this role, I can say I have been blessed to lead a remarkable faculty and staff team.

Together, we develop excellence, confidence, and integrity in PK-12th-grade kids through the development of skills and knowledge so that they can go on to live lives of balance, purpose, and joy. I never saw this path as something that would bring so much joy, and I am grateful for the team that gives me the honor to lead.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Nathan's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

When you trust in people, and they let you down intentionally. I have learned to "trust and verify."

2. How did you become a leader? Can you please briefly tell the story?

My career started with Deloitte & Touche, and I steadily rose in responsibilities. I grew in my responsibilities and progressed in leading departments and even whole groups.

However, fate put me in the Independent School world, and about nine years ago, I was asked to lead the School. It has been the reward of a lifetime; I work with nearly 250 incredibly talented teachers and staff, guiding and teaching a little more than 1,000 PK-12th grade day students.

3. How do you structure your work days from waking up to going to sleep?

I am an early riser, typically up around 4:30a to get to the office before too many people come in. This is the time to reflect and think about what is before us. Then often, my day goes into the evening as I like to go to students' various showcases, games, or performances.

If it is late, I will miss out on a run; otherwise, I try to go for a 30-minute run. And then spend some time with my wife, Staci, before retiring to bed by 9:30 or 10p.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

Trust and let go, then hold ourselves accountable. The other important lesson is that leadership is about vision, humility, and high-drive.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Walk the Walk by Alan Deutschman. I love how he says, Leadership is about creating change; and all too often, leaders fall into the trap of thinking it's about rulership, lemmingship, and stewardship. People watch what you do and not what you say, so effective leadership involves humility and vulnerability.

(Clarity note: The abov link clicks through to the book on Amazon. As an Amazon affiliate we receive a small commission if you purchase through this link).

6. If you could only give one piece of advice to a young leader, what would you say to them?

Don't be afraid to be vulnerable; you don't have to know everything! And hire the best, and allow them to be smarter than you, it will make leading fun.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

None comes to mind right now.

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