Why Even The Best Strategies Die Before They Reach a Single Customer
Strategic logic alone will never get your company to execute or customers to buy
Years ago, our division lead asked me to coach their managers in strategy.
Tired of our group’s nonstop firefighting, they wanted me to help the other leaders think more strategically to achieve division goals.
We stripped down to essentials, focusing on each leader’s “Where to Play” and “How to Win” choices, and how they rolled up to overarching goals. Progress was immediate. One leader turned their group around entirely. Another uncovered a hidden strength and made it even stronger.
We would walk through each leader’s matched WTP/HTW set, focusing on the raw strategic logic. Yet despite our initial success, something still felt off about how we were rolling out the strategies.
Eventually, another major initiative derailed our strategic focus, and the group rapidly slid back into task-level firefighting.
Beyond the logic, I was clearly still a missing piece to strategy.
The strategic logic survived. Don’t be surprised if no one follows it.
You do the hard work, designing multiple matched WTP/HTW sets and testing your “What Would Have to Be True?” conditions. You abandon the sets with insurmountable barriers. The lone matched set that survives has strong, defensible logic, and your team can actually deliver against it.
But none of that matters outside the team that designed it. Because while people like “winning,” no one outside your core team cares that “strategy” made it happen.
There’s no chance in hell that any strategy alone will inspire anyone to stay on track through the long, uncertain effort of execution.
People don’t speak the language of strategy. That’s your job.
So how can you bridge the gap between raw strategic choices and rallying people around a common purpose?
Moving the focus outward
Anytime you present strategic logic, the human brain is pre-wired to hunt for any weak link.
It’s helpful behavior in a “What Would Have to Be True? (“WWHTBT”) testing session. But fatal when you need a room full of people to commit and move in the same direction.
This is where stories can convey the essence of strategy but connect one level deeper.
A well-designed customer story runs what Chip and Dan Heath call a “mental flight simulator.” By engaging empathy, stories stop people from picking apart the logic and begin feeling the experience for themselves. And once someone has mentally experienced a customer’s challenge, the strategic choice that resolves it is no longer an abstraction they can argue with.
And now becomes a clear path toward resolving a problem they’ve felt for themselves.
One customer. One story. Many ways to make it real.
Three audiences inside your company will need to feel that story before any customer ever benefits from your strategy: Executive sponsors, management, and frontline teams.
But each group won’t need its own story. They’ll only need to be moved by the same customer’s story, and come up with the answers to two key questions: What does this story mean for me in my role? And what do I have to do differently to make it real?
If this is starting to sound a lot like the storytelling side of marketing, kudos. You’ve been paying attention.
Breaking down the wall between strategy and marketing
AirBnB’s Brian Chesky collapsed the product manager and product marketing manager roles, a breakthrough move he shared on Lenny’s Podcast.
Chesky’s insight was that designing the strategy, rallying people around it, and generating customer demand for it were all part of the same activity. But Chesky was simply following in the footsteps of P&G, which had merged its strategy and marketing departments way back in the 80’s. Apple, AtScale, OmniOn Power, and Pendo have all followed suit. It’s now everyone’s job to figure out both why we should build something and why anyone should care.
User-based narratives are part of that convergence, as strategy and story form two sides of the same customer-centric focus.

Your move from strategy to story
With this convergence, everyone’s job is now to be both strategist and storyteller.
No customer will ever benefit from your strategy unless you first wrap it in a customer-centric story and get it to travel through your organization. The paid section walks you through three frameworks to do just that.
You’ll learn how to create a compelling narrative and interpret it for each of your three main internal audiences. And you’ll also pick the right Money Story for that strategy and learn to defend it.
After completing the exercises and using the prompts, you’ll match your tested strategy to a story, a rollout plan, and a Money Story you can bring into your next planning cycle.
Join us!



