E40 | From West Point to Workplace: How Ryan Hill is Rewriting the Rules of Leadership Development

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What do hand-to-hand combat, corporate coaching, and navigating uncertainty have in common?

Apparently, a lot, when you're chatting with Ryan Hill.

In this episode of Trailblazing for Success, we sat down with Ryan Hill—Army vet, former West Point instructor, business coach, leadership nerd, and all-around incredible human.

We laughed, we learned, and at one point, we briefly entertained the idea of a “Leadership Octagon.” (Spoiler: we’re not doing that. Unless it comes with sumo suits.)

From artillery and logistics in the U.S. Army to leadership development in the boardroom, he’s done it all - with grit, humor, and the kind of insight that makes you stop mid-sentence and scribble something down.

One of our favorite mic-drop moments? When Ryan reminded us that behavior change isn’t a weekend workshop. (Amen!) As he said, “People who quit smoking cold turkey? Success rate is 4 to 7%. Real change takes time.” And haven't we been screaming from the improv stage for YEARS?

Here’s the leadership gold we uncovered:

It’s not good data or bad data—it’s just data

.Ryan shared a formative experience early in his career with a... let’s just say challenging leader. His mentor reframed it for him: this is still a learning opportunity. You may not want to emulate them, but you will walk away knowing what NOT to do and that’s data, too.

Lead. Follow. Or get out of the way.

This gem from the military world still hits hard in business. As Ryan explained, knowing when to lead and when to support someone else’s lead is the secret sauce to high-functioning teams. (Also, can we get this stitched on a pillow?)

Uncertainty is not the enemy

Ryan spoke about a practice we LOVE: when facing ambiguity, pause and write down what is certain. Your values. Your relationships. Your love of Oreos (seriously - it's the perfect cookie). Whatever grounds you. Certainty gives you footing when the rest feels like a lava field.

Leadership development is an opportunity, not a reward.

This one hit us right in the feels. In the military, Ryan was trained to lead. In corporate? We promote someone and hope for the best. He’s on a mission to change that - so are we.

Oh, and we also learned that Ryan used to fight on a minor league MMA circuit (no big deal), and that Gail has a not-so-secret love of UFC. There were actual gasps. 👀

The Big Takeaway?

Ryan Hill is the real deal. He’s building a business that prioritizes behavior change over box-checking. He’s working with people who care more about long-term growth than quick fixes. And he’s reminding all of us that leadership is learned, earned, and constantly evolving.

Ryan, thank you for your service, your stories, and your octagon jokes. The world needs more coaches like you - ones who fight for real change (outside the cage, of course).

To connect with Ryan or learn more about his work, check out Ryan Hill Coaching (and maybe ask him how to throw a leadership punch... metaphorically).

Stay curious, stay bold, and remember: it’s not good data or bad data—it’s just data.

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Ryan Hill Coaching: With decades of leadership in military combat zones and fast-paced corporate transitions—where trust, extreme accountability, and disciplined decision-making were non-negotiable - we develop leaders who excel in both stability and crisis. Working with us, leaders build trust-filled, high-performance cultures by applying disciplined execution, proactive strategies for stability, and responsive approaches to disruption, equipping them to drive results in any environment.

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ExperienceYes is not just in the business of learning and development – we're in the business of team transformation. Imagine a world where we don't just fix teams; we supercharge them.

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