I didn’t walk into the Fundable & Findable book club expecting much. Don’t get me wrong… after following Kevin for some time and eventually buying his book, I knew the discussion would be rich; but I still assumed it would be one of those large, impersonal webinars where your camera stays off, your mic stays muted, and your presence barely registers.

So imagine my surprise when I hear my name — Kevin himself, warm as ever, mentioning I was the first to arrive and asking where I was joining from. Turns out I’m the first Trini to participate in the book club. And get this… one of the editors of his book is from Trinidad too. I had to laugh. Trinidadians show up everywhere.

What I entered into wasn’t a webinar at all. It was a circle… a real one. Cameras on, voices unmuted, people thinking out loud together. And right at the center was Kevin — calm, thoughtful, unpretentious — guiding us through the beautifully messy world of strategic planning. The kind of host who makes you exhale. The kind of facilitator who creates a space where people actually speak from where they are, not from where they think they should be.

The conversation moved the way good conversations do… slowly at first, then suddenly opening into deeper layers. What became clear, very quickly, is that strategic planning is far less about documents and far more about discipline. Less about “the plan” and more about the lived rhythm of a team. Less about the grand vision and more about the quiet, unglamorous mechanics of who does what, when, and how.

I found myself listening not just to what people were saying, but to what their comments revealed — about culture, capacity, complexity, fear, ambition. Strategy isn’t neat. It isn’t linear. And it certainly isn’t the pristine, glossy thing so many organizations try to make it. It’s far more human than that… more iterative… more experimental… more honest.

The smallness of the group made everything feel intimate. Real. There’s something about being seen — actually seen — in a space like that, where your contribution isn’t swallowed by the noise of hundreds, but actually carried forward by the room. And somewhere in that dynamic, I realized I wasn’t just attending a book club… I was witnessing the difference between strategic planning as theory and strategic planning as lived experience.

And that’s where the real learning began.

What struck me first was how familiar the dysfunction sounded. So many organizations create strategic plans that are really monuments… big, impressive, immovable, and utterly unused. Plans that were clearly built for presentation, not practice. They read like grand visions and sweeping philosophies, but when it comes to guiding real decisions — they’re hollow. They don’t breathe. They don’t speak.

Kevin reframed everything in a way that made sense to me.

If the theory of change is why, what, and where…
then the strategic plan is who, when, and how.

And suddenly the whole thing shifted from “document” to “discipline.” Something you live, not something you file away.

Someone shared that her globally scattered team has this habit of checking in about the weather every morning. It sounds small, almost trivial. But as she spoke, I realized… that’s rhythm. That’s culture. That’s an anchor in a distributed world. The little rituals that say “we see each other,” even when connection would otherwise be fractured. And it dawned on me – those invisible things are the real strategy. Not the frameworks. Not the slides. But the way a team moves together… the way it breathes.

There was another theme that threaded itself quietly through the conversation — experimentation. Hypothesis. Testing. Truthfully naming the parts of our work we’re still figuring out. I loved that. I loved the honesty of it. Because there’s something deeply liberating about acknowledging that most of us are building while walking. That we’re adjusting as we go because the world is shifting beneath our feet. That a pilot isn’t a lack of certainty… it’s the presence of courage.

You could feel the relief in the room when someone said, almost laughing, “We don’t have this fully formed yet. Should we even put it on our website?” And the collective answer was… not yet. Let it breathe internally first. Let it take shape. Let it earn its place in the outward story before you declare it as gospel.

And then…storytelling. The moment the conversation turned to it, everything softened. Someone shared that their partner organization told them: “Our job is to win hearts.” Such a simple sentence… but it landed like a truth I already knew. Strategy is structure, yes, but story is the gateway. Story makes work feel human. Story makes ideas stick. Story creates devotion long before metrics ever catch up.

What I loved most was the reminder that storytelling isn’t decoration. It’s the translation layer between your invisible work and the outside world. It’s the thing that helps people care enough to look deeper. And that winning hearts isn’t manipulation — it’s alignment. It’s resonance. It’s truth communicated well.

As the conversation closed, what stayed with me wasn’t the frameworks or the templates or the tools. It was something subtler… a kind of grounded permission.

• Permission to simplify.
• Permission to experiment.
• Permission to document what’s real rather than what sounds impressive.
• Permission to build a plan that breathes.

And underneath all of that… permission to let strategy be alive.

I left thinking about my own work — how often I remind clients to clarify before they amplify. How alignment is never imposed; it’s revealed through rhythm, decision, behavior, story. How a strategic plan is only as strong as the team that embodies it. And how every organization, no matter how seasoned, is still testing something.

Today made me remember why I love this work. Strategy, at its best, isn’t a document. It’s a way of being.

Strategic Reflection Prompt

Where in your work are you pretending something is “certain” when it’s really a hypothesis… and what would open up if you treated it like a pilot instead?

About Giselle

I’m Giselle Hudson — writer, possibility thinker, musician, Organization & People Development Sensemaker™, and MCODE Legacy Coach. I help leaders and soul-driven professionals decode the deeper patterns shaping their business, work, identities, and results especially when it look like a performance issue but it’s really misalignment in disguise.

If something in your life or business feels off and you can’t quite name it, message me. Sometimes one conversation is all it takes to see what’s really going on.