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Dear Product Roadmap, I’m Breaking Up with You


The top product roadmap challenges according to product leaders, and what you can do to overcome them.

Have you ever felt the urge to pen a “Dear John” letter to your roadmap and/or your roadmap process? If you have, you are not alone. Over 75% of product managers report having responsibility for crafting the product roadmap (who are these 25% who don’t!?), so it is among the most common and important responsibilities of a product leader.

But it’s also among the most difficult and sometimes frustrating parts of the job. Respondents to the 2017 Product Management Insights survey ranked a clearer product roadmap/strategy behind only more resources and a salary increase as their biggest wish for the coming year. Even more impressive were responses to the following open-ended question on a recent Mind the Product survey:

What was the primary challenge for 49% of respondents? You guessed it, the product roadmap. More specifically, respondents reported challenges with setting roadmap priorities without real market feedback. Add the responses from enterprise software product managers, and this figure jumps up to 62%. That means that two thirds of enterprise product leaders are currently struggling with which projects, features, and functionality should come first and which should come later.

Common Roadmap Friction Points

A little over a week ago, we kicked off one of our quarterly Product Roadmapping workshops by asking attendees to write a Dear John letter to their roadmap process. The letters were heartfelt, detailed, and in some cases quite humorous. More importantly, almost everyone in the room could empathize with all of the challenges at one point or another in their role as a product leader. Listed below are the points of friction identified by workshop attendees along with tips on how to start working toward overcoming them.

Common roadmap friction points post-its

Our roadmap is not tied to our business strategy

The best roadmap is a strategic communication artifact that is focused on the big picture and conveys the path you’ll take to fulfill your product vision. It helps you avoid getting caught in a never-ending vortex of incrementalism and bug fixes and enforces a discipline of addressing clearly-defined problems for your customers by understanding your users’ needs. An effective roadmap helps teams balance short-term priorities with long-term strategic thinking.

The roadmap is typically one of the final steps in the strategic planning process, which means you should already have several assets to make it more closely tied to your business strategy, including:

  • A clearly defined problem and solution. You have to know what you’re doing and why that’s valuable before you start thinking about where you’re going.
  • An understanding of your users’ needs. You need to be able to empathize with your users so you can understand and anticipate their needs.
  • User Journeys for the current experience. Why the current experience? You need to fully visualize or map how they are currently solving their problem in order to understand how it will be improved or replaced by your offering.

These important pieces of the strategic puzzle should be organized into the following outline:

With these artifacts in place, you can more confidently and strongly tie your roadmap to your organization’s strategy and your product’s goals.

We don’t collect or include enough customer feedback

Yes, it’s a bit of a long acronym that doesn’t exactly roll off the tongue, but the oft-repeated Pragmatic Marketing mantra is apt. In short, you won’t find the answers to important questions about your product inside your office without “getting out” to talk to customers or users.

These days it’s easier to collect feedback, often without even actually leaving your office (though we realize that runs afoul of the acronym). Tools like SurveyMonkey and Google Forms make it easier for product teams to collect customer feedback on the cheap and in higher numbers. Tools like Crazy Egg can help you observe how and where users click and scroll through your website or application.

And of course, there’s the old fashioned and important customer conversation that never fails to reveal important information about how customers use and think about your products and solutions. Even the most well-constructed survey will miss important details that your customers may reveal as part of a live conversation. If you really want to go deep (and get it right), you should think of this as more than “just” interviewing your customers. You should think of it as Continuous Discovery, described so well by Nate Walkingshaw, CXO at Pluralsight.

Ultimately, you need to collect and combine both quantitative and qualitative feedback from your customers.

We have not defined a consistent roadmap management plan

When you’re looking at the finished work of a well-executed product everything seems perfect. Of course what you don’t see is all the hard work that went into creating this product. You don’t see the people and processes that go into making that amazing thing. Behind every great product is a great team doing work in a way that guarantees results. They are following a roadmap from the starting point to the end product.

Your product team should have a defined process for creating, using, and maintaining the roadmap, and each member of the team should be totally clear on that. Whether or not it’s working is another story. The management plan can be tweaked and improved along the way, but not having one (or having an ill-defined one) is much worse.

Your process will likely include some of the following people and elements: a product leader and/or manager, a product team (designers, engineers, QA, etc.), components, roadmap, tools, UI Kit, marketing team, a marketing website, and of course, customers. Remove any one of these elements and the outcome will be different.

We need more objective criteria for prioritization

Most product managers seek customer feedback to construct their roadmap and prioritize the work that’s to be done. But this doesn’t mean they don’t also struggle to collect even more or to keep the focus on customer feedback as a way to prioritize. In fact, half of product managers report having to deal with executive orders and sales teams as the source of product features and ideas. This leads us to a discussion of how not to prioritize your strategic goals and activities. Knowing what filters not to use is as important as knowing what filters you should use.

  • Your CEO’s gut reaction to a feature is not a good place to start. It’s not that your CEO isn’t smart or that they don’t have great insights, but all subjective opinions are frequently influenced by personal bias.
  • Requests from sales teams or support teams reacting to one or two customer requests need to be checked for consistency and relevancy across the broader customer base. Prioritizing a feature because one customer says they need it will set a precedent for this kind of interruption to the workflow.
  • We also recommend not relying too heavily on analyst opinions. These industry pundits are basing their suggestions on historical and aggregate sector data so beware of using them to forecast the future of your narrow market.

Prioritization is best done through the lens of the following criteria:

  1. Feasibility:  Feasibility is a technical consideration and will need the inputs of the technical team members. Product leaders are not looking for opinions here, rather just what is technically possible versus impossible or highly improbable.
  2. Desirability:  Desirability is the customer focused part of the analysis. This takes into consideration the needs of the end user, the interaction elements, affordances, and how these are to be marketed or sold.
  3. Viability:  The viability of the work being considered needs to be considered as a function of the overall business. This insight is provided by the product manager/s and relevant executives.

You can then map these criteria against the features under consideration to develop a matrix. Each feature or element is then scored from 1 to 5 in terms of its feasibility, desirability and viability. The final column, representing the total scores, represents the priority. Ultimately, the matrix aims to objectively focus on the most important theme and the order that they would be sequenced.

Our roadmap is a broken record

“Broken record roadmapping” refers to a situation where the same themes, features, fixes, and solutions keep cropping up on your roadmap time and time again – without ever bubbling up to the top and making their way into a release. These items never seem to make their way into the sprint or release despite their longstanding appearance on the roadmap. “The backlog we have is never retired.”

A key question for product teams to consider is, if these items keep getting de-prioritized and never make their way into a release, is it possible they are not (or are no longer) important to your users (internal or external)? Or perhaps enough time has passed that you need to at least revisit the original reason the item appeared in the first place. Did the request come from a single or very few stakeholders? Has the need changed? Has the product and/or use case changed such that you can de-clutter your roadmap and remove these items from consideration?

Our roadmap is too often used only as a sales tool

How often have you heard the following statement from members of your sales team?

Previously we said that requests from sales teams reacting to one or two customer requests need to be checked for consistency and relevancy across the broader customer base. While this is certainly true, sales teams are and should remain an important stakeholder in the product roadmapping process. They are, after all, often the ones closest to the customer, and in theory,  at least initially best understood the customer’s needs back when they were a prospect.

As you think about how to involve the sales organization in the roadmapping process, you need to consider how to collect product feedback, competitive market information, and customer needs from the lens of a sales rep. Customers will often open up to sales in a way that’s different from how they will provide similar information to the product team.

You also need to think about how you will communicate the roadmap to the sales organization and the format this information should take. Take care not to over-promise or present features and releases as firm dates. If given the chance to sell on “futures,” sales reps will take that ball and run with it, setting you up for potential customer satisfaction or expectation challenges in the long run. Or worse, create revenue recognition challenges for your Finance department.

Some roadmaps include specific features, but we recommend keeping these very high-level or confined to near-term periods. Alternatively you can leave them out completely and use the anticipated user experience outcome in it’s place. Here is our list of elements that should be included in all roadmaps:

  • Broad time frames
  • Themes by time frame
  • High-level product goals (as covered above)
  • Metrics for measuring each stage’s progress
  • Risks and considerations
  • Status of each stage
  • Sales and marketing effects

Customer facing roadmaps, assuming you need to share these with customers, will be different from internal roadmaps. There will be less information to share and a focus on themes over commitments to features. A customer-facing roadmap might look something like this:

Our roadmap leads to broken promises

This is, unfortunately, the common result of a broken roadmap process. But a well-defined roadmap and process should actually help you deliver on the product work by delivering:

  • Focus: An effective roadmap puts a lens around the work and focuses in on the core value. It also helps us understand what we are not going to give our attention to.
  • Alignment: The roadmap helps create alignment by getting an entire team working toward the same goals. Once the roadmap has been discussed, the team will have clarity on what their roles are and what their efforts will create.
  • Priority: Knowing what to do is half the story, knowing when to do those things is the other half. Prioritization is a core part of having a roadmap that works. Another way to look at it is to substitute the statement, “we won’t have time for that” for the clarification “that isn’t a priority for us to be successful.”
  • Visibility: Seeing the way the team works and what they will be doing makes everything easier. Visualizing potential pitfalls and opportunities can be done by mapping out the work in terms of priority and importance.
  • Coordination: Overlapping efforts or misaligned work that cancels out progress causes stress and waste. Getting the team working in a rhythm is going to be a big part of creating and maintaining momentum. Everybody should know their contribution and how it dovetails with the others on the team.
  • Vision: The best companies and products have a clear vision of where they are going. The most famous, and possibly one of the best, customer-centric visions was Disney’s original “Make People Happy.” Simple and easy to use as a lens for what needs to be done each day. A roadmap should paint a picture of what comes next to achieve a long-lasting relationship with your customers.

You can read up on more tips in Building a Product Roadmap and How to Prioritize Product Features and Improvements. Or send an email to our Chief Design Strategist C. Todd Lombardo to talk about your product roadmapping challenges.
Register for one of our Quarterly Roadmapping Workshops.

Author Heath Umbach

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