Roadmapping: First Principles Questions

This post is by Giff Constable from

This post roughly mirrors a talk I gave about a month ago to two product manager communities (Product School and Product Faculty). If you prefer watching video, a recording of one of the talks is here.

Roadmaps are an important and necessary part of the product manager job. They allow us to refine our own thoughts, set expectations inside (and often outside) of our companies, and build alignment. That said, there are also land mines to avoid.

When I joined Meetup as CPO, the newly-installed CEO had just completed a strategy document that laid out big, outsized goals. At the time, all things WeWork had outsized goals! The strategy doc was clear on vision and targets, but it didn’t include a path how to get there. That’s where a roadmap was needed, and it was my job, with the help of a great team, to create it.

During the creation of that roadmap, I’ll freely admit that I made a few avoidable mistakes that came from one root cause: I didn’t ask all the right questions. Even worse, these were questions that I *knew* I should ask but which I still neglected in the heat of moment.

I’ve come to believe that good product management is so context-specific, the most important thing for any PM is to make sure they ask the right questions. Put another way, while you can and should try out best-practices, a sophisticated PM doesn’t blindly copy other people’s answers.

In this post, I (Read more…)