If you’ve ever struggled to create a roadmap that actually drives meaningful progress, you’re not alone. At Strobbo, I faced the same challenge. I spent a long time searching for the right format, experimenting with different approaches. My journey took me from a cumbersome version that looked more like a project Gantt chart to another where we focused on several strategic goals and the work we planned to tackle. But none of these approaches ever felt quite right.

Estimating large, future roadmap items can feel like trying to predict the weather next month—there’s just so much uncertainty. The bigger the item, the harder it is to figure out how much effort it will take. And when the item itself is still pretty fuzzy—maybe the scope isn’t fully defined—estimating becomes even trickier. What’s more, estimates usually come from the development team, which can make the conversation feel one-sided and, let’s be honest, sometimes uncomfortable.

Welcome back to my series on actionable experiments you can try as a Product Owner to boost your dev team’s productivity, alignment, and innovation. Each post offers practical strategies to rethink how your team handles their workload and priorities.