The Power of Curating Your Ideal Peer Group—Beyond Time, Space, and Reality

In a recent episode of the Arete Coach Podcast, guest host Larry Cassidy asked me a question that has stayed with me long after our conversation ended: If you could build your ideal peer group—past or present, real or fictional—who would you seat at the table, and why?

At first, it seemed like an interesting thought experiment. But the more I reflected, the more I realized: Who we surround ourselves with—whether in person, through books, or in our imagination—fundamentally shapes us.

As leaders, we often think about who is in our immediate circle, but we rarely take the time to ask: Who do I seek out for inspiration? Who is so far ahead that they serve as my North Star?

This question is particularly powerful because it isn’t constrained by time or reality. Your ideal peer group isn’t limited to colleagues, mentors, or industry figures you know today. It can be composed of thinkers from history, leaders from biographies, or even aspirational figures whose wisdom you weave into your own thinking.

With AI, you can gain direct access to great thinkers—their wisdom, ideas, frameworks, and even their personalities—echoing back to you words that sting, words that lift, and ideas that soar. You don’t need a personal invitation—you need the curiosity to seek them out.

This is the freedom—and responsibility—of choosing who influences you.

Choosing Peers with Intention

Most of us don’t think of peer groups as something we get to design. We inherit them—through work, industry circles, or existing relationships.

But what if you could handpick your ideal group? Not just for socializing, but to push your thinking, challenge your assumptions, and elevate your leadership?

What if your peer group included:

A philosopher to challenge your reasoning?
A pragmatic leader to ground ideas in action?
A moral compass to keep ethics at the forefront?
A visionary to expand your understanding of what’s possible?
A contrarian to force you to defend your ideas more rigorously?

Your ideal peer group might include mentors and colleagues. But it could also be drawn from history, literature, science, business, or even fiction—people whose wisdom shapes your thinking, even if you never meet them.

Who’s at My Table?

In answering this question for myself, I sought not just intelligence, but a diversity of thought, values, and expertise. Here’s who I chose:

Socrates – The Questioner A relentless inquirer of truth, Socrates wouldn’t allow assumptions to go unchallenged. His presence would ensure that every belief is interrogated, every strategy is questioned, and every response leads to deeper reflection.
George Washington – The Leader of Character A leader who understood duty, perseverance, and the weight of legacy. He possessed both the strength and the humility to recognize that stepping away from power voluntarily would set an irresistible example for generations—defining what true service looks like in the highest office. Adding Washington would ground discussions in the reality of leadership under immense pressure.
Jim Collins – The Researcher of Excellence Through Good to Great and beyond, Collins has studied what makes organizations endure. His disciplined approach to leadership and empirical thinking would keep the group focused on what actually works—not just theory, but proven application.
Fred Chaney – The Wisdom Keeper Former TEC (Vistage) CEO and an outstanding Vistage Chair, Chaney has processed over 10,000 business challenges. His ability to recognize patterns, distill lessons, and offer perspective from real-world leadership is invaluable.
Pat Hyndman – The Sage of Practicality A legend in the Vistage Chairing world, as an executive coach Pat had a way of making complex ideas simple. His ability to blend deep wisdom with actionable insight would ensure that the group never became lost in abstraction.
Norma Rosenberg – The Editor of Life Norma’s philosophy of “editing out of your life what doesn’t bring joy and editing in what does” has shaped how I think about purpose. A former high impact Banker, and now Vistage Chair, she would masterfully lead the group through questioning, ensuring that we never lost sight of what truly matters.
Mother Teresa – The Moral Compass It is easy to become consumed with strategy, power, and progress. Mother Teresa would remind us that leadership is, at its core, about service, humanity, and lifting others. She would ensure that even the boldest ambitions remained anchored in ethical purpose.
Dr. Samuel Johnson – The Master of Language and Thought A writer, philosopher, and the creator of one of the first English dictionaries, Johnson understood the power of words. His presence would sharpen how we communicate ideas, ensuring that clarity and precision shaped every discussion. I find Dr. Johnson’s focus on semantics and the delivery of ideas inspiring, as I seek to provide language and prompts designed to demystify AI—helping business leaders access greater clarity and power through their word choice and AI interactions.

Who’s at Your Table?

Surrounding yourself with the right peers isn’t just a thought exercise—it’s a strategic advantage. Great leaders don’t grow in isolation; they sharpen their thinking through challenging conversations, diverse perspectives, and trusted advisors.

That’s why Vistage peer executive groups have been invaluable for leaders seeking wisdom, accountability, and breakthrough insights. By engaging with experienced peers who’ve faced similar challenges, you gain perspective, clarity, and better decision-making in an ever-changing world.

And now, with AI, we have the ability to extend this idea even further.

Imagine that, in addition to your human peer group, you could create a custom AI-powered advisory board, trained on the insights of history’s greatest minds.

What if you could consult Washington on leadership, Socrates on inquiry, or Collins on business strategy—on demand?

The answer is: you can!

We are now at the intersection of history, wisdom, and AI, where the greatest minds of all time are not just ideas in books—but interactive, evolving resources for today’s leaders.

Now, I Turn the Question to You

If you could assemble your ultimate peer group—real or fictional, past or present—who would you invite, and why?

Would you select mentors who have shaped your career? Would you invite historical figures who built the foundations of modern thought? Would you seat contrarians who would challenge your blind spots?

The beauty of this exercise is that it’s not just a question—it’s a choice. You can start building that peer group today.

Read a biography of someone who inspires you.
Engage in deeper conversations with people who challenge your thinking.
Seek out the ideas, frameworks, and principles that elevate your perspective.

Expanding the Idea: Bringing Your Ideal Board to Life with AI

The beauty of this exercise is that it’s not just hypothetical anymore.

\With AI, you could take this concept even further—building a Custom GPT trained on the knowledge, philosophies, and decision-making styles of your ideal board.

Imagine an AI-driven peer group—where Socrates challenges your reasoning, Jim Collins evaluates your business strategy, and George Washington offers leadership guidance in moments of high-stakes decision-making.

Instead of just wondering What would they say?—you could engage with an AI model that reflects their thinking, using it as a sounding board, challenger, and guide in your leadership journey.

We are now at the point where history, wisdom, and AI intersect, giving us access to the most remarkable minds of all time—not just in books, but in interactive form.