7 Questions on Educational Leadership with Amy Skirvin

Name: Amy Skirvin
Title: Principal
Organisation: Waldport Middle High School
I have been a building principal of small schools for 12 years and currently serve as a board member for our state association. In 2021, I was honored as the Oregon Middle School Principal of the Year.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Educational Leadership!
I hope Amy's answers will encourage you in your leadership journey. Enjoy!
Cheers,
Jonno White
1. What have you found most challenging as an Educational Leader?
I believe one of the most challenging aspects of education is navigating the impact of politics. Too often, adult agendas and decisions can interfere with student learning and diminish the importance of student voice.
2. How did you become an Educational Leader? Can you please briefly tell the story?
I started my career as a PE teacher and later took on the role of advising the student council. Both my superintendent and principal saw potential in me as a leader and encouraged me to pursue my administrative license, suggesting I could become the middle school principal. Initially, I resisted, but after a year of their persistence, I decided to enroll and complete my administrative license. While I never became the middle school principal in that district, earning my license opened the door to my administrative career, which I began immediately after completing the program.
3. How do you structure your work days from waking up to going to sleep?
My calendar is the foundation of my daily structure. I rely on it to schedule meetings and sometimes even to organize my to-do lists. I also create separate to-do lists because, if it’s not in my email or written down, it likely won’t get done. Once the school day begins, flexibility is key. I’m constantly multitasking and staying prepared to respond to anything that arises at a moment’s notice.
4. What's a recent lesson you've learned for the first time or been reminded of as an Educational Leader?
A recent lesson I’ve been reminded of as an educational leader is the importance of self-care. A few years ago, when someone asked me about my self-care routine, my only response was, “What’s self-care?” Since then, I’ve been working on finding a healthier work-life balance and learning to appreciate the little things. After years of operating in a constant state of high stress, I’m now trying to train myself to embrace calm and be okay with it. It’s a challenging process, but one that I know is necessary for my well-being.
5. What's one book that has had a profound impact on your journey as an Educational Leader so far? Can you please briefly tell the story of how that book impacted you?
Todd Whitaker’s books, What Great Teachers Do Differently and What Great Principals Do Differently, have had a profound impact on my journey as an educational leader. During my first year as an administrator, I not only read his books but also invested in his DVDs and workbooks. His insights have always stayed with me. They’ve inspired me to think creatively, prioritize building meaningful relationships with both students and staff, and treat each individual uniquely. My goal is to inspire others to be their best, guided by the principles I learned from Whitaker’s work.
6. If you could only give one piece of advice to a young educator who aspires to be an Educational Leader, what would you say to them?
Educational leadership is a lifestyle—it’s not a role you can simply turn on and off. However, finding balance is crucial. Once you feel confident in your work, start delegating and building leadership capacity within your team. Early on, I believed my role was to take things off teachers’ plates, but I’ve since learned that shared leadership is the most effective kind of leadership. Empowering others not only lightens your load but also strengthens your school community.
7. What is one meaningful story that comes to mind from your time as an Educational Leader, so far?
One of the most meaningful stories from my time as an educational leader is about a student who taught me the importance of perseverance and belonging. Last year, this student had a 30% attendance rate, missed over 100 days of school, failed all his classes, and would only show up every 10th day to avoid being dropped. We had tried everything to engage him, but nothing seemed to work. In August, my husband came home from football practice and mentioned this student. I told him not to bother—it felt hopeless. But the vice principal encouraged the student to join the football team, and everything changed. The team embraced him, and he found a sense of belonging. Now, just a semester later, he has a 100% attendance rate, is passing all his classes with Cs or better, played football, is currently playing basketball, and plans to join the baseball team. He attends every school event and comes to school with a smile every day. The staff calls it a miracle, but it was really about finding the barrier and helping him remove it. This experience reminded me to never give up on a student. Every kid wants to belong—it’s our job to help them find their place.
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