Stop Setting Up Product Roadmaps To Fail

Why Read

Stop debating whether you are doing product roadmaps “right”, or whether roadmaps are evil. Look instead at the job you are hiring your roadmap to achieve. And then ask if the roadmap is the best tool for the job.


  • 14 common product roadmap problems
  • A summary of almost all methodology debates on Twitter
  • Roadmap Needs and Being Awesome

A Litany Of Roadmap Ills

Roadmaps are frequently abused. To save you thirty minutes, I’ve organized these observed problems into the list below.

  1. Stick to the plan when the plan is no longer optimal
  2. Chase harmfully high utilization rates (the jigsaw illusion)
  3. Future sell, instead of relying on the current merits of product
  4. Prioritize new feature development (items which can be easily understood and sold) over equally promising enhancements to the existing product
  5. Converage prematurely on solutions
  6. Rely on estimates, despite the fallibility of those estimates
“Big Batch” Planning
  1. Obscure underlying assumptions, rationale, and vision. Even when described (e.g. a theme), it is still difficult to parse why the theme matters
  2. Institutionalize “big batch” yearly planning, which in turn decreases agility
  3. Encourage group think — satisficing — over focus. Initiatives lose their bite
  4. Fail to address the needs of all “users” (e.g. your roadmap is fine for communicating with executives, but fails to meet the needs of your front-line teams)
  5. Discourage experimentation and acting on new insights / data
  6. Create dependencies across the organization (decreases agility

Challengers vs. Defenders

OK. That’s a pretty hairy list. I’m not the first to challenge roadmaps. Luckily this stuff is out there in the google-verse by the boatload. You will also find debates that look something like this:

If Things Were Awesome

To be clear, I advocate for thinking in terms of initiatives, problems to solve, and missions. And that’s nothing new or groundbreaking. I use mind maps like this:

Needs & Being Awesome

Continuing on that thought …

  • If things were Awesome, what would things look like?


Roadmaps aren’t the problem, obviously. We pick our tools and methods. My goal with this post was to encourage you to challenge the “why”: why use roadmaps, why use roadmaps the way we typically use roadmaps, and what it might take to be awesome (such that this conversation is irrelevant).

Multiple hat-wearer. Prod dev nut. I love wrangling complex problems and answering the why with qual/quant data. @johncutlefish on Twitter.

Multiple hat-wearer. Prod dev nut. I love wrangling complex problems and answering the why with qual/quant data. @johncutlefish on Twitter.