Most roadmaps are timelines. Rows and boxes and dates. They’re useful, but they rarely tell the real story of why we’re building anything, or what our work means for the person on the other end of the screen.
Customer stories, on the other hand, create instant clarity. They show us the stakes. They reveal the make-or-break moments. And they help teams align on the problem long before we talk about solutions. Ali Maaxa calls this the core dilemma — the moment where a customer’s adrenaline spikes because something matters. When we understand that moment deeply, the roadmap becomes less about features, and more about resolution.
What if we took a step back from our timelines and asked a different question:
What single customer story would explain our roadmap better than our roadmap?
Not a persona. Not a workflow diagram. But a customer story about a moment when something shifts in their world and they have a need. You can usually find the story by tracing backward from urgency: an alert, a deadline, a mistake, a handoff, a moment of pain. Look for the core dilemma or the moment that carries emotional weight for the user. Is it confusion? Risk? Embarrassment? Desire? Compulsion?
Once you spot that moment, the rest of the story becomes easier to see: the environment they were in, the people involved, the tools around them, the friction they’ve learned to tolerate. Are there workarounds they are using? Do some tools help or get in the way? And then to project into the future, what does the user hope will happen if things go right? What’s at stake if it doesn’t?
These elements form the real narrative spine of your product, and if you follow it honestly, you’ll often find your roadmap sitting right inside it. Some roadmap items resolve the tension beautifully. Others don’t belong at all. And sometimes you realize you’re missing the one thing that would change the entire experience.
When a team aligns on a story, the roadmap stops being a list and becomes a sort of promise: we understand this user moment, and we’re building toward a better one. Stories give teams meaning. And meaning invites better decisions.
STAND-UP EXERCISE
In your next team meeting or retrospective, ask everyone to individually jot down:
What is one customer story that explains why this roadmap exists?
Encourage simplicity. Look for the core dilemma.
Then, share your stories. Instead of debating accuracy, listen for:
patterns
emotional moments
stakes
recurring characters
recurring friction
Then see if you can coalesce around a story or two, and piece those into your roadmap.
If this story were our north star, what on the roadmap feels essential?
What feels optional?
What feels missing?
Continue to come back to your customer story during roadmap reviews and share-outs, and find and refine new ones over time.