Work
Every so often, someone pipes up: “Are we sure this is still the right thing to build?” And, as if on cue, everyone else looks at their shoes. Why? Because reviewing the roadmap means facing the horror of the all-hands workshop.
You know, the one: a marathon session where you could be forgiven for considering a fake power cut. So, the roadmap stays as it quietly gathers dust while the market and our customers move on without us.
Facing the feedback.
Eventually, reality bites. Maybe it's a customer who asks why we don't support a feature that's suddenly table stakes. Or maybe it's sales, waving a list of lost deals. Either way, we're forced to confront the uncomfortable truth: our assumptions are out of date.
So, we bite the bullet and schedule a quarterly review. It's not a big, soul-crushing workshop but a focused session with the right people, including product, engineering, sales, support, and the odd stakeholder who's wandered in for the biscuits.
We pull up the roadmap, dust off the cobwebs, and start asking awkward questions:
- What did we actually deliver this quarter?
- Did it solve the problems we thought it would?
- What did we learn from customers, analytics, and the market?
- Which assumptions have aged like milk?
We use tools like The Product Tree exercise, where everyone gets to stick their feature requests and learnings on a big, metaphorical tree. It’s a bit like group therapy but with more post-its and fewer tears (usually). The beauty of this approach is it gets everyone involved, surfaces hidden trade-offs, and makes it obvious when we’re veering off course.
We also run product critiques structured feedback loops where the team and stakeholders pick apart what’s working and what isn’t. These aren’t just gripe sessions; they’re a chance to catch issues early, iterate quickly, and avoid the “build it and they will come (they didn’t)” trap.
And crucially, we look at real data: customer feedback, usage analytics, support tickets, and yes, even the odd grumpy tweet. This isn’t about defending the roadmap; it’s about stress-testing it against reality.
What we learned (& never Do again).
Here’s the thing: reviewing the roadmap quarterly isn’t just a box-ticking exercise. It’s a relief. The team gets to air their doubts, challenge sacred cows, and occasionally admit that a feature nobody uses should probably be put out to pasture. Stakeholders see that their feedback actually shapes what we build, not just what we say we’ll build in PowerPoint.
Some discoveries are brutal (“Turns out nobody wants to integrate with fax machines anymore”), but some are surprisingly energizing (“Our MVP feature is being used in ways we never imagined. Should we double down on that?”). The roadmap becomes a living thing again, not a relic.
What worked:
- Short, focused reviews: No more day-long workshops. We keep it tight, relevant, and action-oriented.
- Transparent feedback loops: Everyone sees what’s being considered, what’s being cut, and why.
- Flexible timeframes: We stop pretending we can predict the future to the day. We use broader windows, allowing for course corrections as we learn
- Different views for different folks: The sales team sees how features map to deals; execs see how it ties to OKRs; engineers see what’s coming down the line
What didn’t work:
- Ignoring the roadmap between reviews: If you only look at it once a quarter, you’re already behind. We set up lightweight check-ins to keep it alive.
- Trying to please everyone: Not every piece of feedback makes the cut, and that’s okay. The roadmap is a product, not a democracy.
How it changed us:
- The team’s less anxious about raising concerns. There’s less “just build it” and more “let’s check if this still makes sense.”
- Stakeholders feel heard, not just managed.
- We’re quicker to spot when the market shifts or a competitor leapfrogs us.
And yes, we still grumble about meetings. But there’s something oddly satisfying about seeing a roadmap that actually reflects what we’ve learned, warts, pivots, and all. It’s not perfect, but it’s real. And that’s a lot better than pretending last year’s plan will magically work in a world that’s moved on.
Final thoughts.
If you’re tempted to let your roadmap grow stale because you dread the alignment meetings, remember that nothing ages faster than an unchecked assumption. Quarterly reviews and honest feedback loops aren’t just processes. They’re a lifeline. They keep your product, your team, and your sanity intact in a world that refuses to sit still.
