Why Your Smart Team Can’t Roadmap
Tell me if this story sounds familiar? You hire the best engineers, most charismatic sales leaders and most brilliant product managers and yet, every quarter, the same frustration arises. Dates begin to slip. Your leadership team pivots from talking about how to grow the company to firefighting mode. The strategy you worked so hard to create, and document with a roadmap is obsolete within weeks.
This recurring pattern is not because your team lacks business sense and intelligence. They are smart – you hired them. It is because you are using a tactical mindset to solve a complex problem.
The Tactical Trap
Research from the Product Board shows that nearly 50% of senior leaders admit their roadmaps fail to align with long-term business strategy or reflect how the business serves the customer. That is a shocking statistic, but consistent with my experience. Why? Because organizations, big and small, try to standardize strategic planning using a tactical mindset that is inherent to centralized planning processes.
This tactical mindset drives executive teams to think about the future as discrete chunks of work neatly arranged into boxes on a spreadsheet (or a slide deck). As a result, strategic planning becomes a check-the-box compliance activity with little or no critical thinking. Instead of using their roadmap as a guide to inform monthly and quarterly resource allocation discussions, the roadmap becomes obsolete as soon as the firefighting takes over.
Strategic Planning is a Complex Problem
Spreadsheets and slide decks are great for supporting tactical thinking. But these tools fall down when applied to a roadmap. In order to force your roadmap into a spreadsheet or three to four slides with a 16:9 aspect ratio, a massive amount of information and context has to be edited away. This forced simplification hides the very complexity you must solve to win.
A complex problem is any new or unusual challenge where you cannot know the solution up front. Complex problems do not follow predictable patterns. Complex problems possess two characteristics that render a tactical mindset obsolete:
- Multiple perspectives are required to resolve. No single person (spreadsheet or slide deck) can see the entire problem. To understand a complex problem, everyone must contribute their point-of-view to create a shared understanding.
- The problem changes over time. Your business does not exist in a vacuum. As you develop and refine your solution, competitors react and customer needs change. This means your strategic reality is fluid, and a static roadmap is a guarantee that you will ship a solution for a problem that no longer exists.
Stop Typing, Start Talking
The best product teams embrace this complexity. They recognize that building a roadmap is not a data entry task; it is a negotiated agreement between Sales, Marketing, Engineering, Support and Finance. This requires getting every leader into one room to reconcile their conflicting priorities before any development work begins.
Next, they lean into low-tech tools, like markers and sticky notes on a wall. With such a diverse group of perspectives and experiences, these are the tools that offer the fluidity necessary for creative problem-solving. Digital tools just create friction and get in the way of dialogue.
IME, physical tools allow just enough chaos to enter the process to pressure test your business assumptions. This chaos is not created for its own sake. It is the only way to move beyond “check-the-box” behavior and uncover the commercial logic needed to win.
