Why Nobody Is Happy With Your Roadmap

This essay was originally written in 2020 for product managers who usually fear that the neither the sales team, nor the engineering team really understands the roadmap.

Feature prioritization and updating roadmaps are two common bugbears for product managers – experienced and new alike! I talk to a lot of product managers and they always exclaim that the sales team does not understand the roadmap or that engineering is complaining that they don’t know what to build.

Product managers often hide behind Agile or Kanban methodologies and send the list of features they plan on building in the next few cycles to sales. “Our backlog is our roadmap,” you hear. It’s not. It’s a detailed list, not a plan. No wonder sales can’t use it to close deals — they can’t tell their prospects what’s actually coming down the pike in terms of features.

On the flip side, sending a deck that articulates your plan for dominating an industry vertical while outflanking competition is not going to help your scrum masters decide what to put in the next sprint. They need a list of features they can break down into tasks.

Everyone is frustrated with your roadmap because they don’t get what they need. Calling a list of features your roadmap is myopic. Talking purely about your vision without a strategy or a plan is just grandstanding.

Your roadmap needs to include a master plan of markets and the strategy, a tactical plan with a list of features that address specific use cases for customers in your market, and a “super-detailed” plan that includes features, stability, and quality.

The Master Plan

This is the strategic section of your roadmap. The most important part of the master plan is articulating the objectives. Don’t mistake this for organizational vision statements. We are not talking about ending world hunger but rather a plan that will help your organization reach its stated goals.

Are you trying to grow into a particular segment or market? Are you going to maintain revenues from a specific product line while investing in other, breakthrough technologies? Are you going to outflank a competitor by finding an overlooked but deep niche? It helps to have organizational, or at least business-group-level goals agreed to by all parties (investors, board, senior management, etc.).

A key source of friction is that the product roadmap is not aligned with go-to-market (GTM) and sales compensation. If marketing is continuing to find B2C customers through Facebook advertising and your master plan calls for selling yearly subscriptions of corporate travel booking assistance, then you are going to have a problem.

Any discussion of GTM will involve a discussion about customer segmentation. Which kind of customers are you targeting? For B2C businesses, geographic and demographic information is often helpful. For B2B firms, organizational size, industry, and verticals are a good starting point. Are you building and targeting stay-at-home dads in large cities or European firms in the industrial sector?

A clear understanding of the target market helps drive both your GTM plan as well as your product design.

Setting up the master plan, getting alignment, and communicating it clearly, is the bedrock of your roadmap.

Send this part of your roadmap when your investors or board ask for your roadmap. Be judicious in sharing this with anyone outside the company. There are occasions when it makes sense to share this with industry analysts like Gartner or Forrester (often under NDA).

Tactical roadmap

Eighty percent of all product managers spend time thinking about what features to build. They worry about prioritization and read a lot of Medium articles on how to rank potential features. There are a lot of frameworks for feature prioritization, but they are all wrong. Why? Because they are not aligned with your master plan. You can’t decide what is must-have, could-have, or should-have if the objectives and strategy are not decided.

Your tactical roadmap should include what you are going to build, in what order, and in what approximate time frames. Feature prioritization now becomes a bit easier. If your strategy is customer retention, you will prioritize stability, customer experience, and breadth of features while protecting from flank from upstart newcomers. If you are hoping to widen that deep and narrow niche as an up-and-coming vendor, you’ll double down and provide deep features for select use cases.

The tactical roadmap section needs to show a timeline of when capabilities will be delivered to the market. You’ll want to include complexity, risk, and time estimates from engineering into this part of the plan.

This is the part your customers need to see. They’ll learn that the use cases they care about most are going to be solved by your product. This is also the part that engineering and UX teams should see and sign off on.

Feature and task backlog

Building new features all the time without any regard for internal housekeeping is like eating candy for lunch, breakfast, and dinner! It might taste good (does it?), but be ready for the sugar crash. Paying down technical debt, rearchitecting for scaling, etc. is like flossing. It is not fun, but that inevitable toothache is even less fun.

Any good plan will include a healthy mix of new features, quality-of-life improvements, tech debt, stability improvements, and bug fixes. But your customers, investors, and board don’t need to see the sausage-making. Your product owners, scrum masters, and the engineers working on your products do need this level of detail.

A good litmus test of whether your strategy and tactical roadmaps are set correctly is whether your product owners and scrum masters need any help in grooming the backlog. Given sufficient clarity, they will be able to do this part themselves.

Tailoring your roadmap

The reason why no one is happy with the roadmap you’ve been providing is that you have been sharing the wrong parts with the wrong audiences. The product roadmap has three parts that need to both tell a story and provide a detailed operating plan. It’s easy to see what anyone wants to see when the roadmap is laid out this way.

This article was first published by me in ProductCraft on June 8, 2020.