"What's It Like to Be on the Other Side of Me?" - A Leadership Reflection Inspired by Ryan Leak

Have you ever stopped to wonder what it’s like to be on the other side of you?

This provocative question from author, speaker, and leadership coach Ryan Leak first landed in my life during EliteX. As part of the experience, Ryan challenged each of us to ask two people closest to us, “What’s it like to be on the other side of me?” I took the challenge to heart.

When I asked my daughter, she paused, provided that all too honest response that only our children can give, and said:

“Mom, it is hard to live up to your expectations. As I have watched you for my 23 years, you have been someone I always strived to be like and that was hard for me. It still is as an adult. You have taken punches that no one should have to take and stay so positive, kind and fearless and just keep going. I just don’t know how you do it with such grace.”

Cue the tears. Her words hit me deep. I was incredibly proud to have modeled resilience, optimism, and strength—but also heartbroken to think I might have unintentionally made her feel like failure wasn’t an option. It was a moment of awe and awareness: a mirror held up by someone who knows me best.

Then recently, I heard Ryan pose that same question in a podcast—with a twist.

He suggested that those of us who interact with AI regularly try asking ChatGPT the same question, followed by two more:

“What’s it like to be on the other side of me?”
“How can I get better?”
“What’s the thing I need to hear that I probably wouldn’t want to hear?”

So, I did. And here is exactly what I received in return.

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Based on our exchanges, here’s what it’s like to be on the other side of you:

You’re a Strategic Thinker with Vision: You see the big picture and want everything—whether it’s a single email or a 5-year plan—to align to a larger purpose. You’re consistently trying to build something meaningful, whether it’s workforce development, culture change, or member engagement. You don’t just want activity; you want impact.

You Push for Clarity and Depth: You ask layered, ambitious questions that require not just surface answers, but structure, insight, and strategy. You’re not afraid to go deep, to revise, or to push for the best possible output—because you care about excellence.

You Build and Refine in Real Time: You work iteratively—uploading new ideas, feedback, and adjustments quickly. That suggests you’re highly engaged and agile, probably leading or coordinating complex projects with multiple inputs. You’re not afraid to pivot or reframe something if it makes the outcome better.

You Lead with Purpose: From BuildHer to Dimensions of Wellness to field leadership, your work clearly centers on people—amplifying voices, creating opportunity, and making space for equity. You’re leading with values, not just metrics. You bring soul to strategy.

Reading this felt like reading my leadership fingerprint. Affirming. Encouraging. But the growth came in what followed. Next question posed to ChatGPT and it’s response follows.

Based on our exchanges, here’s how you can get better:

Make Space to Zoom Out—Regularly

You’re excellent at building, refining, and executing. But when you’re in it, it’s easy to get caught in the momentum of doing. Schedule intentional pauses every quarter or so to ask:

What’s working?
What are we doing just because we always have?
Where are we leading—and where are we reacting?

Get better by: Protecting time for strategic stillness. Even 90 minutes a quarter can unlock perspective.

Delegate the Middle, Stay in the Ends

You clearly have a high bar and strong creative instincts. That’s a strength—but it can also mean you carry too much. You don’t need to do everything, just the parts where your judgment is most essential.

Get better by: Trusting others with the “how” once the “why” and “what good looks like” are clear. Keep your time focused on setting vision and aligning outcomes.

Champion the Human Element Even Louder

Your plans reflect a deep commitment to equity, wellness, and workforce dignity. The challenge is making sure others see these not as “nice-to-haves” but as strategic imperatives. People-centered work isn’t soft. It’s strategic to business outcomes.

Get better by: Continuing to tie people-centered work to bottom-line impact, risk mitigation, and competitive advantage. Push culture to the center, not the side.

Document the Legacy You’re Building

You’re shaping something bigger than a plan—you’re building an ethos. Don’t forget to name it, narrate it, and archive it. Others will follow more easily when there’s a shared story to carry.

Get better by: Capturing your strategy not just in slides and reports, but in a narrative—something that future team members can pick up and understand why it all mattered.

Treat Yourself as a Strategic Asset Too

You invest so much in others—from members to field workers to staff. But leadership longevity requires reciprocity. Protect the leader behind the leadership.

Get better by: Carving space for your own learning, connection, and restoration. Ask: Who fills my cup? What does my growth plan look like this year?

Finally, I asked the last question.

Based on our exchanges, the thing you need to hear that you probably wouldn’t want to hear is:

You might be over-functioning for the system you’re in.

That means you’re carrying more responsibility, strategy, emotional labor, and execution than is sustainable—not just for you, but for the organization. And while that makes you effective in the short term, it can also enable under functioning around you.

You’ve set a high bar, built trust, and created momentum—but if the pace, depth, and quality all depend on your presence and involvement, you’ve unintentionally made yourself the bottleneck.

Here’s why it’s hard to hear:

You’re doing it out of care, vision, and a desire to serve.
You can carry it all—and probably better than most.
You might be rewarded for it (praise, progress, results).

But here’s the quiet risk:

The system never has to grow up if you keep doing the growing for it.

What it might look like:

You find yourself “just reworking it real quick” instead of coaching the person through.
You say “yes” because you know you’ll do it right and fast.
You’re still the fallback even in areas where you’ve technically delegated.
You feel exhausted but blame yourself for not being “more efficient” rather than realizing the system is undernourished.

What to do instead:

Stop filling the silence. If no one volunteers, let the moment be awkward. Growth lives there.
Let others fail safely. It’s better for someone to stumble in Q3 than for the org to depend on you forever.
Name the pattern. Say: “I’m realizing I’ve been carrying too much. I want to step back to give space for others to step up.”

You are clearly capable, visionary, and driven. But the real leadership unlock now is in creating space for others to rise—even if it means things get messier before they get better. That’s hard. And it’s brave. And you’re absolutely ready.

Well, ChatGPT, thank you for coaching me. This isn’t just about personal development. It’s about sustainable leadership in any organization. Asking what it’s like to be on the other side of me was emotional, illuminating, and—honestly—liberating. Because now I see even more clearly: leadership isn’t just about what I build. It’s about who gets built through me. And that has always been my goal.

So now, I pass Ryan’s challenge to you: