The Advantage • Issue 6 • June 09, 2025

The Advantage

⛓️‍💥 When Strategy Breaks

This week’s lead story is a little different — it’s something I wrote. 😅

It’s the first in a five-part series I’ll be sharing over the next month. Each piece will unpack one of the hard-won lessons I’ve learned about why strategies fail — even when everything looks perfect on paper. This series is deeply personal and honestly a bit vulnerable to share. But it reflects years of in-the-trenches experience, working through strategic challenges that didn’t go the way we hoped.

The first article sets the stage. It tells the story of a multi-million dollar strategy that had all the right ingredients — clear goals, market alignment, strong execution plans — and still collapsed. Not because the strategy was wrong, but because it ignored five essential realities that every strategy must face.

Those five realities — Customer, Capability, Competition, Cost, and Culture — are the core of what we’ll explore together in this series. Miss one, and everything else starts to unravel. I’ve seen this happen over and over again, and I’ve been in the room when it did.

If you’ve ever led or launched a strategy, I think you’ll recognize some of these patterns. My hope is that this series helps you spot them sooner — and avoid the same pitfalls I’ve seen (and lived through).

The rest of the links this week focus on change management — the often-overlooked sibling of strategy. You can’t execute a strategy well if you don’t know how to manage change. And too many organizations treat change as an afterthought. That’s where things tend to go sideways.

If this issue resonates, I’d be grateful if you shared it with a friend or colleague. The more we talk about the real challenges behind strategic failure, the better we get at avoiding them.

Chess breaking

How a Strategy With All the Right Pieces Still Failed ♟️

Discover the five strategic realities every leader must face. This piece unpacks a multi-million dollar initiative that looked great on paper—but collapsed when faced with the messiness of real-world execution. From hidden organizational dynamics to subtle cultural friction, it explores the blind spots that can break even the most carefully planned strategy. These lessons weren’t pulled from a textbook; they were learned the hard way. (Read More →)

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🧭 Leadership

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This newsletter, The Advantage, has really stretched me so far. We’re only six issues in, and already I’ve gotten thoughtful notes from readers who found something useful here. That means a lot — thank you. I work hard to make each issue worth your time, and I’m always looking for ways to improve. Got an idea, a question, or something you’re wrestling with? Hit reply — I’d love to hear from you.

Until next time,

⁓ Kedron

P.S. Currently juggling two reading extremes: Peter Drucker’s Management — 800+ pages of pure strategic goodness — and a stack of comic books. Strategy by day, superheroes by night. That’s balance, right?

Management, by Peter Drucker

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