Anatomy of an actionable roadmap

Your strategic roadmap should be:

📉 Timelined:

Stakeholders want to know when they can expect something. Teams need to know what they should be working on today. Prioritization is good enough for short-term planning, but long-term plans need a timeline.

📉 Outcome-based:

Features don’t belong on the roadmap. It’s hard to keep promises about delivering specific features. Roadmap items should be timeboxed problems or outcomes. “Improved calender experience”, “Increased scalability of importer”, “Reduce churn”…

📉 Unified:

All work of all teams should be represented on a single roadmap. Having multiple strategic roadmaps for multiple teams is asking for trouble.

📉 Centralized:

Everyone should know where to find the up-to-date roadmap. Avoid sending it as documents or slideshows as this will cause multiple versions to circulate. There should be a URL to the roadmap and everyone in the organization should know it by heart.

📉 Hierarchical:

It should be possible to drill down all the way from the strategic roadmap to individual tasks. That way, we can measure actual progress against the roadmap and how much of our time we put into non-roadmap work.

📉 Focused:

Each team should work on one roadmap item at a time. Serialize, don’t parallelize. Multitasking is evil.

📉 Versioned:

We expect the roadmap to change. Make sure these changes can be referenced in the future. We want to be able to answer future questions about why the roadmap changed.

All of this takes quite some work.

It’s never just a Powerpoint slide.