The Complexity Trap
Strategy execution fails in predictable ways. Over the next six weeks, I'll explore six traps nested inside the larger Strategy Trap. These are patterns that consistently derail even well-designed strategies, and what to do about each one.
Part 2 of 6
The strategy session went well. Really well. The leadership team spent two days working through the market, the priorities, and the tradeoffs. By the end, everyone in the room was aligned. The logic was sound, the language had been fine-tuned, and you walked out feeling like you'd built something great.
Then you rolled it out. And six weeks later, most of your organization still can't tell you what the strategy actually means for their work.
This is the Complexity Trap, and the villain is the assumption. Specifically, the assumption that because those in the room understood it, the organization would, too.
But the leadership team developed that understanding through extensive debates. They absorbed the context and internalized the shorthand. So when someone says "drive customer-centric innovation across our core verticals," they know exactly what it means. But that same phrase hits someone two levels down with no shared context, no backstory, and a to-do list already full of urgent work, and it means almost nothing. Or worse, it means something different to everyone who hears it.
Researchers call this the curse of knowledge. Once you understand something deeply, it becomes nearly impossible to remember what it felt like not to understand it. This is how the strategy makes complete sense at the top of the organization and loses meaning beyond that group of executives.
What It Looks Like in Practice
People nod in meetings but don't change their behavior. Everyone seems aligned when leadership is in the room, but then they go back to their desks and keep doing what they were doing before. The strategy didn't connect to anything specific enough to change how they spend their days.
The same terms mean different things to different teams. "Customer focus" means one thing to sales, something else to product, and something else entirely to operations. Nobody's necessarily wrong. It’s just that the language wasn’t specific enough to create a shared understanding.
Priorities feel everywhere and nowhere. There are six strategic pillars, four key initiatives, and three transformation themes, and nobody can tell you which one matters most when they have to make a tradeoff in their day-to-day.
People ask for clarification constantly. When your team is regularly coming back to ask what the strategy means for their specific work, that's a signal the strategy was delivered at a level of abstraction that didn't translate into action.
A few questions worth considering
Can people at the front lines of your organization accurately explain the strategy in a sentence or two in their own words, not the deck's words?
When you ask different teams how the strategy connects to their day-to-day work, do you get consistent answers?
If someone had to make a tradeoff between two competing priorities tomorrow, would the strategy give them enough guidance to make the right call?
When you last communicated the strategy, did you test whether people understood it, or did you just assume they did?
What to do about it
The antidote is clarity. Clarity requires understanding, not just communication. A strategy that lives only at the vision level isn't executable. It needs to be walked down the Ladder of Abstraction until it connects to the actual decisions people make every day. What does this mean for your team specifically? What does it mean for how they spend their time? What does it mean for the tradeoffs they make?
That work of translation—from vision to strategy to concrete action—is where so many organizations fall short. It’s hard. It requires leaders to get specific in ways that may feel tedious. But it's also what makes a strategy executable rather than performative.
If you want to go deeper on how to do this well—including tools for building common language, connecting strategy to daily decisions, and testing whether clarity has actually landed—I cover it in detail in The Strategy Trap.
