CTO Fraction

The Question You're Not Asking About Your Product Roadmap

We’ve all been there – sitting through another product roadmap presentation. The slide deck looks impressive, filled with timelines, feature lists, and optimistic delivery dates. Stakeholders nod along, mentally ticking off their priority items. It all seems so clear and well-planned. But in the midst of this familiar scene, there is an important question that often no one asks.

 

The Typical Product Roadmap

Most product roadmaps are slick presentations featuring Gantt charts that project into the future. They’re definitive, showing clear start and end dates for various product features. These visual representations make it easy to see what features are expected and when.

At first glance, these roadmaps look convincing. They present a clear timeline of feature completions, giving stakeholders a sense of certainty about the product’s future.

 

The Roadmap Creation Process

Generally, the Product team spearheads the roadmap creation. They identify priorities based on business needs and work towards a future time horizon. However, this process often has some critical flaws:

  1. Engineering is often minimally involved, if at all.
  2. Business stakeholders heavily influence the process.
  3. Product teams face pressure from business and customer demands.
  4. Time constraints often prevent thorough market and customer validation.
  5. There’s typically more work than time or resources available.
  6. Features get crammed into unrealistic time frames.

The conversation with Engineering often goes like this:

Product: “Can you deliver all these features in this timeframe?” 

Engineering: “We need detailed requirements for accurate estimation.” 

Product: “We have some requirements, but not all.” 

Engineering: “That’s not enough for a realistic estimate.” 

Product: “That’s all we have, and we’re presenting next week.” 

Engineering: “But that’s not enough time or information!” 

Product: “We know, just do your best.”

The result? A polished presentation that promises to meet business needs and customer demands, but may not reflect reality.

 

The Core Problem

When the roadmap is presented, the entire company sees a plan that appears to meet company goals. The problem is – no one questions the validity of the roadmap. Stakeholders only scan its content to make sure that all priorities are on it. Worse, separate stakeholders make sure that their priorities are on the roadmap. The main issue is this:

No one asks the question:

“How do we know we can accomplish all of this?”

In my experience nobody pauses to ask questions like:

  • Have we assessed our teams’ capacity?
  • What effort estimates have been done?
  • Was Engineering involved in creating this roadmap?
  • What do the implementers of the work think about this plan?
  • How confident are they in its realism?
  • If they had concerns would our culture allow them to safely express those?
  • What evidence supports the feasibility of this roadmap?

Consequences of an Unrealistic Product Roadmap

This approach leads to several problems:

  1. The roadmap becomes aspirational rather than realistic.
  2. Stakeholders assume it’s achievable and focus mainly on accuracy.
  3. Everyone believes in a promise that may not be grounded in reality.
  4. Sometimes brave individuals voice concerns about unknowns and risks, but while they are briefly acknowledged they are quickly forgotten.
  5. When deadlines are missed weeks or months later, initial concerns are overlooked, and everyone wants to know what went wrong and how we missed our goals.

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Creating a Realistic Product Roadmap

A pretty roadmap containing desired outcomes doesn’t guarantee feasibility. Here’s how to improve:

  1. Prioritize Realism: In my experience it has been really useful when the tech company strives to produce realistic roadmaps in the first place. This involves both product and engineering. Product sets the priorities and Engineering the timelines. The combination of the two creates a more realistic roadmap.

  2. Make It a Company-Wide Goal: As a senior leadership team, be interested in the validity of the roadmap and not just its accuracy. Unless your Product and Engineering teams are consistently delivering the majority of the work on the roadmap, do not take a roadmap for granted. Ask the right questions to hold Product and Engineering accountable for the plan they are presenting. Also make sure that both departments collaborated on creating this plan and that it was not one sided.


Software project planning and estimation is notoriously difficult. There will never be a perfect roadmap. However, if realistic is as important as accurate during the planning process, there will be fewer disappointments at the end.