Name: Christopher Oldham

Title: Principal, Waller High School

Organisation: Waller Independent School District

Christopher Oldham is a dedicated educational leader and Principal of Waller High School in Waller ISD. He holds a BA from Sam Houston State University and an M.Ed. from Lamar University. His career spans roles as Assistant Principal, Principal, and Instructional Specialist for Career and Technical Education (CTE), with expertise in instructional leadership, school finance, and district operations.

A U.S. Army veteran, Christopher brings a service-driven mindset to education, emphasizing strong community relationships, student-centered leadership, and continuous professional growth. He is a Superintendent-certified leader and has served as a college professor. Passionate about mentorship and innovation, he works to ensure that students and teachers have the tools they need to succeed.

Outside of work, Christopher values family, lifelong learning, and community engagement. His leadership philosophy centers on building meaningful connections, fostering excellence, and preparing students for a bright future.

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

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

Cheers,

Jonno White

1. What have you found most challenging as an Educational Leader?

Balancing high expectations for student achievement with limited resources, diverse needs, and evolving challenges is one of the biggest hurdles in educational leadership. Having served as both a junior high principal and now a high school principal, I’ve seen these challenges shift—from building strong academic foundations to ensuring students are prepared for post-secondary success.

Navigating policy, staffing, instructional priorities, and community expectations while keeping students and teachers at the center of every decision is a constant challenge. Whether it’s advocating for stronger instructional practices or implementing policies like a cell phone ban, leadership requires strategic decision-making and a focus on continuous improvement. Despite the challenges, clear communication, strong relationships, and a student-first mindset help turn obstacles into opportunities for growth.

2. How did you become an Educational Leader? Can you please briefly tell the story?

My leadership journey began in the U.S. Army, where I learned discipline, adaptability, and teamwork. After transitioning to education, I taught science and health science technology before moving into administration. I’ve served as a junior high principal, high school principal, and district instructional specialist, each role reinforcing my belief that strong leadership drives student and teacher success. Now, as a high school principal, my focus is on building a culture of excellence and ensuring every decision supports student achievement.

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

For the past 23 years, I’ve woken up at 4:30 AM, not because I have to, but because leadership demands clarity, and the early hours provide space for reflection. Mornings set the tone—I use this time to process, prioritize, and prepare before the day takes on a life of its own.

Once the school day begins, leadership is about presence and adaptability. No two days are the same, but the constants remain: supporting teachers, engaging with students, making decisions that shape the school culture, and ensuring the focus stays on learning. Some moments require careful strategy, while others call for quick action. The key is staying grounded in the purpose of the work rather than being consumed by the urgency of the moment.

Evenings are for reflection, preparation, and balance—whether that means catching up on tasks, attending school events, or simply resetting for the next day. Leadership is never about clocking in and out; it’s about being fully present, making the most of each moment, and ensuring every decision moves the school forward.

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

One lesson that leadership never stops reinforcing is that clarity matters more than intent. No matter how well-thought-out a decision or initiative is, if it’s not communicated clearly and consistently, it can create confusion, resistance, or unintended consequences. As a principal, I’m constantly reminded that people don’t just need to hear what we’re doing—they need to understand why we’re doing it and how it benefits students.

Whether it’s a new policy, instructional shift, or a challenging conversation, leadership isn’t just about making decisions; it’s about ensuring they are understood, supported, and effectively implemented. The best leaders don’t just set direction—they build trust by ensuring their message is clear, their actions align with their words, and they take the time to bring people along in the process.

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?

One book that has profoundly influenced my leadership journey is Good to Great by Jim Collins. The concept that resonated most with me is the Stockdale Paradox—the idea that true leaders confront harsh realities while maintaining unwavering faith in eventual success. This lesson has been particularly relevant in school leadership, where challenges—whether staffing shortages, student discipline, or shifting expectations—are constant. As a principal, I’ve learned that ignoring problems only makes them worse, but facing them head-on with a commitment to long-term success transforms obstacles into progress.

Collins’ work reinforced my belief that great leadership isn’t about quick fixes—it’s about building the right team, focusing on what truly matters, and leading with both realism and resilience.

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?

One book that has profoundly influenced my leadership journey is Good to Great by Jim Collins. The concept that resonated most with me is the Stockdale Paradox—the idea that true leaders confront harsh realities while maintaining unwavering faith in eventual success. This lesson has been particularly relevant in school leadership, where challenges—whether staffing shortages, student discipline, or shifting expectations—are constant.

As a principal, I’ve learned that ignoring problems only makes them worse, but facing them head-on with a commitment to long-term success transforms obstacles into progress. Collins’ work reinforced my belief that great leadership isn’t about quick fixes—it’s about building the right team, focusing on what truly matters, and leading with both realism and resilience.

7. What is one meaningful story that comes to mind from your time as an Educational Leader, so far?

Three years ago, I stepped into my role as principal of a brand-new, large high school in Texas with a leadership team that was also new to their positions. The temptation to jump in and fix everything was strong, but I knew real leadership meant building capacity, not dependency.

Over the past three years, my team has faced many complex situations—from difficult student discipline cases to high-stakes instructional decisions. Instead of providing immediate answers, I’ve focused on guiding them through the process, helping them ask the right questions, apply policies effectively, and see the bigger picture.

That approach has transformed our leadership team. Today, they own their decisions, lead with confidence, and mentor others, proving that great leadership isn’t about solving every problem—it’s about empowering others to lead.