Why we all need a coach and a large-language model
After nearly two decades of serving as a superintendent, I’ve learned that experience alone does not ensure wisdom. Reflection does. And reflection, when structured well, is amplified by two things: a great coach and the right questions.
If I could offer one piece of advice to my younger self (or to any emerging leader) it would be this: Always have a coach. Not just during hard seasons. Not just during transitions. Always.
Coaching is not about having someone else tell you what to do. It is about creating space for pause, insight and growth amid the busyness of leadership.
A good coach helps you name what you’re feeling before it becomes action. They help you locate meaning in patterns you might otherwise overlook. And the best ones don’t give you answers, they help you find the right questions.
Over the years, my coaching conversations have been invaluable. But here’s the surprising part: it’s not just the hour I spend in conversation that matters. It’s what I do before and after.
The “how” of making coaching matter
I take notes. After each session, I jot down phrases, symbols, questions and themes that resonate. I return to those notes often. I circle what I don’t yet understand. I star what I want to remember.
But by the end of the year, those pages (scattered with shorthand and fragments) represent something much bigger: a cognitive map of my leadership growth.
As this year drew to a close, I used a large language model—in this case ChatGPT—to help me reflect more deeply. I uploaded images of my notes and asked the model to synthesize what it saw.
What emerged was not just a summary, but a story: of evolving frameworks, internal tension, strategic clarity and areas still in development.
The AI surfaced themes I’d overlooked and made connections I hadn’t yet named. It didn’t replace my coach, it extended the work we’d done together.
If you already have a coach and take notes throughout the year, here’s a suggested activity: Use an AI to help you process the year’s worth of learning. Upload your notes, even if they’re messy.
Ask the large-language model to:
- Identify themes that appear repeatedly
- Surface tensions between leadership style and execution
- Distill insights that might support strategic planning
- Assess your evolution in areas like decision-making, communication, delegation and personal mindset
- Offer suggestions for future coaching conversations based on the year’s patterns
Doing this doesn’t just help you reflect more deeply, it accelerates the connection between individual growth and system-level leadership.
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Here’s the prompt I wish I’d written at the start of this reflection. It would have yielded an even better response and saved hours of refinement:
“I’m a veteran superintendent reflecting on a year’s worth of executive coaching sessions.
I’ve uploaded images of my handwritten notes from those sessions. Please analyze the notes and generate a comprehensive synthesis with the following elements:
- A high-level synopsis of the coaching journey
- Key leadership themes (with examples from the notes)
- Evidence of strength areas and developmental growth
- Patterns of leadership mindset or behavior that appear across the year
- Suggested questions or focus areas for future coaching
- Connections between my personal leadership development and broader organizational health
Assume this is for a reflective, end-of-year leadership retreat. Write with nuance and depth.”
That prompt gives the AI the task and the context, which is key to getting an answer that supports deeper leadership insight.
Final Thought: Maximize the tools you have
A coach will help you see yourself. A large-language model will help you see your patterns. But neither can do the work alone.
So my closing advice is simple: Have a coach. Use the coach. And let the tools we now have (AI among them) push your coaching further. In doing so, you’ll deepen your own growth while strengthening your system’s ability to learn, adapt and thrive.
