Why Roadmaps Fail

Dean Povey
17 min readMar 20, 2021

And how to make them succeed

Photo by Jennifer-Ann Coffin-Grey on Unsplash

If you work in a product team, chances are you have had something like the following experience. Your leadership regularly hands down the itemized list of features they want you to build over the next year or quarter. These features range from customer wants and sales commitments, to things that the leadership and other stakeholders think the product needs to do. They ask you to estimate and prioritize each of the features and put them on the product roadmap. Your product managers go away and do some research and write detailed specs for each of the features. Product design comes up with beautiful designs and mockups for how the features will look. The product delivery team then tries to break it down into estimates, maybe using story points, maybe using t-shirt sizes to try and work out the relative effort. The engineers are then asked to put a deadline on how long it will take. When they hand over the estimates, they are accused of padding the schedule — it can’t possibly take that long. So with some compromise and fiddling with numbers, the product roadmap is finalized. It lists each of the features, maybe with screen mockups and the timelines in which you plan to deliver them. sales gets excited and starts talking to prospects about the new features coming, and product marketing puts it in a pretty graphic and puts it on your website.

Two sprints in on your first feature and you find there is a whole bunch of stuff that you hadn’t anticipated. The UI that the product designer came up with is too complex to implement — but they won’t budge on simplifying it, citing “usability”. The feature relies on some APIs that are taking the engineers longer to build than you anticipate, and you have completely neglected to account for the impact on performance and the cost of new services you need to spin up. Some of the capabilities the product manager wants to add don’t make sense or require more thought, and some of your resources got pulled onto another project. The engineers want to cut scope, but the product manager doesn’t want to give up on features that they spent a long time writing specs for. Sales says you can’t cut this particular capability, because it’s now part of a customer commitment. Everyone pushes the team to work harder. The deadline looms, you compromise on some design and some of the capabilities, and cut corners to get it…

Dean Povey

Software Engineer, Architect and sometimes drummer.