How a Strategy With All the Right Pieces Still Failed

Most strategies fail before they even begin.

Not because the market shifts. Not because execution breaks down. But because they were never real choices to begin with.

The deck looked great. The words were ambitious. The diagrams were clean.

But the choices? They were safe. Vague. Politely agreed to in a room and then quietly ignored.

If you’ve led a strategy, you know the difference between what’s on the slide and what actually shapes decisions, behavior, and results. You’ve sat through presentations where everyone nods enthusiastically, only to watch those same people quietly undermine every meaningful change the strategy requires.

Real strategy isn’t a document. It’s a set of visible, risky, committed choices.

And there are five realities—undeniable forces—you have to align with if you want that strategy to hold up in the real world. I’ve seen this play out in corporate and product strategy work for years: the organizations that win align with all five. The ones that struggle almost always drop one. Or two. Or all of them.

And when you drop one, the others start to fall apart.

The Multi-Million Dollar Strategy That Wasn’t

Several years ago, I worked with a national distribution company attempting what looked like a textbook strategic pivot. They were investing millions in customer experience capabilities - not just capital investments, but complete organizational restructuring, new technologies, and entirely new teams with talent recruited from across the globe.

On paper, it was brilliant. The market was demanding digital transformation. Their competitors were moving online. Customer expectations were evolving. The strategy made perfect sense.

What could go wrong?

Everything.

Within three years, the entire CX team was dismantled. Leadership was fired. Teams were scattered. Millions of dollars evaporated. My own reporting structure changed seven times in a single year - a telling indicator of the organizational chaos this “strategy” created.

But here’s the kicker: the strategy wasn’t wrong about the market. It wasn’t wrong about customer needs. It was wrong about reality.

They had dropped not one, but multiple realities. And once the first domino fell, the rest followed in rapid succession.

The Five Realities Every Strategy Must Face

Through working with dozens of organizations over the years, I’ve identified five fundamental realities that every strategy must align with to succeed:

1. Customer: If you can’t name them clearly, you can’t serve them meaningfully. But it goes deeper than demographics - different parts of your organization often serve completely different customer realities.

2. Capabilities: Strategy without unique capability is just ambition. But new capabilities don’t just appear - they often conflict directly with existing ones, creating internal wars that tear strategies apart.

3. Competition: If your strategy sounds good regardless of who else is playing, it’s not a strategy. It’s about difference, contrast, and betting differently about the future than your competitors.

4. Costs: Every choice has a cost, and strategy means owning it. The organizations that succeed make deliberate tradeoffs - they stop doing things to make room for what matters most.

5. Culture: Culture doesn’t support strategy - it delivers it. Or kills it. When strategy conflicts with culture, culture wins every time unless you plan for that conflict.

Drop One, Drop Them All

These five realities aren’t independent modules you can address separately. They’re interconnected like a spider web - when one strand breaks, the vibration affects everything else.

At the distribution company, the failure cascade looked like this:

They started with conflicting customer realities between their sales team and new CX team. This led them to build capabilities that directly opposed each other. When competitors proved their market assumptions wrong, they refused to adapt. They wouldn’t make the cost tradeoffs necessary to fund transformation properly. And when culture resisted change, leadership chose comfort over customer value.

One broken reality became five broken realities in rapid succession.

What’s Coming Next

Over the next four posts, we’ll dive deep into each of these realities using the distribution company’s story as our guide. You’ll see exactly how each reality was ignored or mismanaged, and more importantly, you’ll get practical frameworks for ensuring your strategy aligns with all five.

Part 2 explores Customer Reality - how the same organization can serve completely different customer definitions, and why that misalignment kills even the best strategies.

Part 3 dives into Capability Reality - why new strengths often fight with old ones, and how to manage capability evolution without destroying what you’ve built.

Part 4 tackles Competition and Costs together - how false beliefs about competitors combine with unwillingness to make tradeoffs to create strategic paralysis.

Part 5 concludes with Culture Reality - the ultimate test of whether your strategy will live or die in the real world.

Because here’s what I’ve learned after watching countless strategies succeed and fail:

Strategy isn’t about being clever. It’s about being coherent.

And coherence requires aligning with all five realities, not just the comfortable ones.

Photo by Yuvraj Singh Parmar on Unsplash

Mini-series