The AI-Powered Board of Advisors that Eliminates Poor Decisions and Weak Strategy (For Good)

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The AI-Powered "Board of Advisors" That Eliminates Poor Strategic Decisions (For Good)

Last week I was on a coaching call with a principal I'll call Mike (name changed to protect his privacy).

Mike had just finished one of the most exhausting school years of his career. His staff meeting ended with him personally ordering lunch for 30 people because he couldn't delegate it to anyone. His reading specialist was frustrated that he wasn't more of a "data expert." His math coach needed help facilitating meetings. And on top of it all, his home life is chaotic at the moment.

"I feel like I'm all over the place," Mike said. "I don't know if I'm focusing on the right big rocks."

That's when I showed him something that changed everything.

I shared my screen and opened up ChatGPT. But this wasn't just any ChatGPT session — this was my AI-powered Board of Advisors.

"I've created a board to help me make strategic decisions," I explained. "Steve Jobs. Christopher Lochhead. Eddie Yoon."

Mike's eyes widened. "Wait, what?"

I walked him through how it works: Obviously not the real guys, but I've studied their thinking so deeply I can channel their perspectives on any decision I face.

Jobs reminds me to simplify, obsess over the user experience, and make things people beg for.

Lochhead brings the fire of category design. Teaching me to name, claim, and dominate new spaces instead of competing in old ones.

Yoon keeps me anchored in demand. Reminding me that legendary businesses don't just find customers, they serve superconsumers who become evangelists.

I demonstrated by asking my board a real business question about a summer product launch. Within seconds, I had three distinct perspectives from each board member, plus a unified strategic recommendation.

Mike was quiet for a moment. Then he said the words that made me realize I had to share this system:

"That would be really helpful."

What this means for you …

Mike's response revealed something every school principal knows but rarely talks about: You're expected to have all the answers, but you're given no one to think with.

• 75% of principals report feeling professionally isolated

• Less than 25% have access to meaningful mentorship

• Most "leadership development" is compliance theater disguised as professional growth

Meanwhile, successful CEOs, founders, and executives have boards, advisors, mentors, and coaches. They don't make major decisions alone.

Why should you?

The AI-powered Board of Advisors isn't just a clever productivity hack.

It's a strategic thinking system that helps isolated principals move from reactive management to visionary leadership.

Whether you choose real mentors, fellow educators, or thought leaders like mine, this approach gives you what every principal desperately needs: wise counsel when the stakes are high.

Mike left that call with a plan to delegate the lunch ordering, clarity on his role with data (spoiler: he doesn't need to be a spreadsheet expert), and most importantly, a framework for making better decisions without carrying the weight of leadership alone.

Here's what Mike helped me realize: The most dangerous principal isn't incompetent. They're isolated.

That ends today.

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