Questions for Summer. (CtbG Y4:E17)

~ Angelo DelliSanti

With my last CtbG message before breaking for the summer, I wanted to provide a powerful reminder:

Great years are built before they begin.

While summer allows us to rest and recharge from the pace of the school year, it’s also an outstanding opportunity to prepare for the year ahead. As many of my previous posts have highlighted, choosing greatness requires “showing up” before we have to. In that way, summer isn’t an intermission, but a season of intentional planning and preparation.

I won’t pretend to know all the ways you need to prepare for the year ahead. You and your team are the only ones who know the answer to that. Instead, I’ll simply offer some questions that, I hope, will help position you for success next year.

Five Questions for You

  1. What kind of leader was I this year? Am I proud of it?
  2. What consistently brought out the best and the worst in me this year?
  3. What do I need to let go of so I can lead with greater focus next year?
  4. How do I want my team to experience me differently?
  5. What will I intentionally do this summer to restore my mind, body, and relationships?

Five Questions for Your Organization

  1. What did we do exceptionally well this year that deserves continued celebration? How can we draft off this success going into next year?
  2. Where did we fall short? What truth do we need the courage to confront in order to rise to our best?
  3. What components of our culture are helping us thrive? Which of them might be draining our team?
  4. Did our staff and students experience the climate we hoped to create, or was it merely the one we unintentionally allowed?
  5. If we could only improve one thing next year that would make everything else better, what would it be?

Remember, great years don’t often happen by accident. They’re the result of intentional, aspirational, disciplined, and systematic preparation.

This summer, that’s the work.

#ChooseToBeGreat

Angelo

PS – Send me the answers to any five of these questions by the end of the week and you will be entered into a drawing for Jim Collins’ new book: What to Make of a Life: Cliffs, Fog, Fire and the Self-Knowledge Imperative.

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Published by Angelo DelliSanti

“Education? You don’t want to do that with your life. You’ve got other plans.” That’s what Angelo DelliSanti’s high school counselor told him his senior year. And she was right—at first. Angelo had spent three years preparing to become a U.S. Navy officer. But an internship with a math teacher during his senior year changed everything. Helping struggling students master algebra sparked a passion for education that would shape his career. Over the next 15 years, Angelo served as a teacher, assistant principal, and principal, returning to his alma mater to teach World History and later advancing to leadership roles. As a principal, Angelo implemented the Capturing Kids’ Hearts process, leading to remarkable academic gains, increased scholarships, record-breaking graduation rates, and improved school culture. These achievements earned him recognition as the Rowan-Salisbury Schools Principal of the Year in 2018. In 2022, Angelo joined Capturing Kids’ Hearts as a Leadership Solutions Strategist where he is dedicated to working together with school leaders to create remarkable schools. He holds a Bachelor’s in History and Secondary Education from UNC Charlotte, where he was a North Carolina Teaching Fellow. He also completed a Master’s in School Administration and completed all the required coursework for a Doctorate in Educational Leadership from his alma mater, earning the Outstanding Student Philip Morris Educational Fellowship in 2017. Angelo lives in North Carolina with his wife, Kasey, whom he married in 2008. Together, they enjoy escapes to the mountains and beaches. Angelo’s passions include golf, non-fiction books, cooking, and sharing meals filled with laughter and connection around the table.

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