My Storytelling Journey

And Why Even Great Mentors Can't Do It All

I need to confess something.

For years, I thought I was a decent storyteller. Stories just seemed to "fall out of my brain" when I needed them. I'd pull from past experiences, share an anecdote, and watch people nod along. It felt natural. It felt good enough.

I was wrong. And here's the kicker: I had one of the best mentors in the business sitting right next to me the entire time.

The Reactive Storyteller

My approach to storytelling was entirely reactive. When I needed to make a point, inspire change, or address a team challenge, I'd just start talking and hope something meaningful would emerge. Sometimes it worked. Often it didn't.

Early in my leadership career, I was like a kid in a candy store with stories. I had so many insights to share, so many lessons learned, so many cultural shifts I wanted to drive. And I tried to jam them all into people's brains at once.

I over-storied my teams.

There were so many things I saw, so many things I wanted to communicate. I felt this urgency: "I've got to get all this out there. I've got to make all of this happen." So I'd pack meeting after meeting with multiple stories, each with its own lesson, its own call to action.

The result? Minimal impact. Confused teams. Eye rolls when I started yet another anecdote.

I was asking people to change in twenty different ways at once. That wasn't fair, given everything else they were trying to wrestle with in their daily work.

The Creative Disaster

When the shotgun approach failed, I swung to the other extreme. I thought I was being artistically brilliant, crafting these abstract narratives where people had to interpret the meaning.

Wrong again.

I had team members guessing what I was trying to say. Some people got it, others didn't. It felt like I was making a French art film when what my team needed was clear, direct communication.

I had to look myself in the eye and admit: "Stop making it harder on your team. They're doing their best. Don't make them guess what you're trying to say."

The Mentor I Wasn't Really Learning From

Throughout this entire journey of trial and error, Bob Galen was right there beside me.

Bob is a master storyteller. He has frameworks, techniques, and systematic approaches that I watched him use effectively for over fifteen years. He coached me through failures, gave me feedback, and modeled excellent storytelling constantly.

And I still made these mistakes.

Why? Because I wasn't being intentional enough to truly learn from what he was showing me. I was reactive, flying by the seat of my pants, thinking my natural ability was enough. I observed his success but didn't dig into the methodology behind it.

I had access to all the wisdom I needed, but having access isn't the same as being intentional about learning and applying it.

The Patience Breakthrough

My first real breakthrough came when I finally listened to something Bob had been modeling for years: patience.

Instead of trying to communicate everything at once, I forced myself to identify the ONE thing that mattered most. What was the most impactful change that, if we made it, would make us a step-change better as an organization?

This was harder than it sounds. It required real work to decide what that one thing was. Then it required even more work to figure out how to land that one story effectively.

But the results were transformative. Once I allowed the team to focus on one thing—really focus and internalize it—we took off as an organization.

The Clarity Evolution

My second breakthrough was abandoning artistic abstraction for crystal clear communication. The evolution I made was simple but powerful: Tell them what you're trying to say, then put a story around it. Or tell the story, then explicitly connect the dots. But never, ever make people guess.

This wasn't just about story structure—it was about respecting my team's time and cognitive load. They had real work to do. My job was to make their path forward clearer, not more confusing.

The Coaching Revelation

When Bob and I recently recorded a podcast episode about storytelling, something profound happened. He walked me through his systematic approach—his "field stone method," his emphasis on starting with the mic drop moment, his framework for testing and refining stories—and I realized I'd been watching him do this for years without truly understanding the structure beneath it.

Here's what Bob had been demonstrating that I should have been learning more intentionally:

Separate story-finding from storytelling. Don't just wing it in the moment. Collect your experiences—your "field stones"—and build a library you can draw from.

Start with the mic drop. Know exactly what point you're trying to land, then work backward to figure out how to set it up.

Test and refine. Your first telling of a story is just the beginning. Pay attention to how it lands and iterate.

One thread, one story. Resist the urge to pack multiple lessons into a single narrative.

The conversation was a revelation: even with the best mentor in the world, you're never done learning. And sometimes what you need isn't just a mentor who models excellence—you need someone who forces you to be intentional about your own development.

The Moment You Know It Worked

The ultimate measure of storytelling success? When you hear your story being told by someone else.

I still get that heart-exploding-with-joy feeling when I walk past a team and hear someone reference a concept we've talked about. That's when you know the story has truly landed—when it's become part of the organizational vocabulary without you having to keep repeating it.

But don't expect this to happen the first time you tell a story. It takes multiple iterations, consistent delivery, and patience. When it finally happens, celebrate briefly, then move on to your next story. There's always more work to do.

Why You Can't Go It Alone (Even When You Think You Have Help)

Here's what I want every leader reading this to understand: having access to good examples isn't the same as having structured development. Watching someone excel isn't the same as learning their methodology.

Bob was always there, always willing to help, always demonstrating the right way to do things. But I wasn't asking the right questions. I wasn't being systematic about learning from his approach. I was too comfortable thinking I had it figured out.

You need someone who will push you to be more intentional, who will ask you hard questions about your approach, who will help you see the patterns you're missing.

A Personal Offer:

If you're a leader struggling with storytelling, communication, or any of the challenges we write about in this newsletter, let's talk. I've learned these lessons the hard way—both the value of having great mentors and the necessity of being intentional about learning from them.

I work with leaders and organizations to accelerate their growth through fractional CTO services, agile coaching, and strategic leadership development. Sometimes what you need is someone who will help you be more systematic about developing the skills you know you need.

Reach out at kazi.io. Let's have a conversation about where you're stuck and how we can get you unstuck—intentionally.

The Never-Ending Journey

The truth about storytelling—and leadership in general—is that it's a craft you never stop refining. Even with excellent mentors, even with years of experience, there's always another level of intentionality you can bring to your development.

The goal isn't perfection; it's continuous, deliberate improvement. And the impact you can have when you get really good at connecting with people through stories? It's transformational.

Your team is waiting to be inspired, guided, and motivated by the stories only you can tell. The question is: are you ready to be intentional about learning how to tell them well?

Josh Anderson
Editor-In-Chief
The Leadership Lighthouse

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From the Studio

This newsletter emerged from one of my favorite Meta Cast episodes we've recorded in a while—one where Bob literally coached me through my storytelling blind spots in real time. What started as a discussion about storytelling techniques turned into Bob providing live coaching on frameworks I'd been watching him use for fifteen years but had never systematically learned.

We dove deep into Bob's "field stone method" for collecting story nuggets, the importance of starting with your "mic drop" moment and working backward, and why testing your stories with different audiences is crucial for refining your impact. Bob also shared some advanced techniques like the hero's journey framework and how to adapt the same story for different organizational levels.

If you want to hear the full coaching session—including Bob's systematic approach to building a story repository and why every leader needs AI-specific stories ready right now—check out our latest episode. Plus, you'll get to hear Bob's sound effects skills that he unleashed halfway through the recording.

Listen wherever you get your podcasts or watch on YouTube.

Warning: Bob gets passionate about storytelling frameworks, and it's contagious.