Your Roadmap Is a Lie (And That’s Okay)

The Myth of the Perfect Roadmap

Imagine this: You’re in your teams product meeting, and your boss walks in holding a glossy, color-coded paper or presentation - roadmap. With absolute excitement, they declare, “If we follow this plan, we’ll hit $10 million in revenue by year-end.”

Six months later?

• Half the planned features never see the light of day.
• The biggest revenue driver wasn’t even on that original color-coded paper or presentation - roadmap.
• And that timeline? Laughably outdated or never even followed.

The issue isn’t the roadmap itself. It’s the false sense of certainty it often creates and this happens a lot of times to startups and product teams.

Roadmaps Aren’t Promises—They’re Hypotheses

A roadmap should be a dynamic strategy document that evolves as your team learns—not a rigid contract.

Most roadmaps fail because they prioritise what will be built instead of why it should be built.

• Bad Roadmaps: Feature-heavy, deadline-centric, and rigid.
• Good Roadmaps: Focused on customer problems, outcomes, and flexibility.

If everything in your roadmap goes exactly as planned, you weren’t ambitious enough. — Gibson Biddle, Former VP of Product at Netflix

Why Most Roadmaps Fail

1. They Assume Predictability in an Unpredictable World

Markets change. Customers evolve. Internal priorities shift. Static roadmaps ignore these realities.

Static roadmaps often assume that the environment in which they were created will remain the same. But in a dynamic world, even the best-laid plans can quickly become obsolete. This is especially true in fast-growing markets like Africa, where regulatory landscapes and consumer behaviours evolve rapidly.

2. They Focus on Features Instead of Outcomes

A feature-centric roadmap without clear outcomes is a fast track to irrelevance.

Let's look at Boomplay here: Boomplay (Africa’s leading music streaming service) aimed for “30% growth in organic user acquisition,” allowing flexibility to experiment with multiple growth tactics instead of locking into one feature in their initial roadmap.

Focusing on outcomes encourages teams to explore different ways to achieve their goals. It promotes creativity, experimentation, and adaptation, all essential for staying competitive in a dynamic market.

3. They Set Rigid Deadlines Without Learning Loops

Strict deadlines often lead to shipping half-baked features. Great teams prioritise learning milestones over arbitrary timelines.

Another brand to learn from here is: A Ghanaian agritech startup tested an AI-powered crop disease detector via WhatsApp before full development. This iterative learning will saved months of potential rework.

Learning loops help teams gather insights, validate assumptions, and refine their approach before fully committing to a solution. This reduces risk and increases the likelihood of success.

How to Build a Roadmap That Works

1. Make It Outcome-Driven

• Replace “Build referral program” with “Increase organic signups by 25%”
• Replace “Launch mobile app” with “Grow daily active users by 40%”
• Outcome-focused roadmaps drive flexible, impactful execution.

Outcome-driven roadmaps align teams around common goals, rather than specific features or deadlines. This creates a shared sense of purpose and enables teams to adapt their approach based on what they learn along the way and your strategy can now carry the key breakdown on how to achieve those set outcomes, allowing you to iterate quickly.

2. Leave Room for Discovery

• Plan 80%, leave 20% open for strategic pivots.
• Test small before big—early insights prevent major missteps.

Leaving room for discovery encourages teams to experiment, learn, and iterate. It allows them to explore new ideas, validate assumptions, and refine their approach before fully committing to a solution this helps further in resource optimisation and allocation.

3. Communicate Changes Transparently

• Explain why changes occur, not just what changed.
• Reinforce that pivoting is driven by learning, not failure.

Transparency builds trust with stakeholders and ensures that everyone is on the same page. It helps manage expectations and reduces resistance to change because resistance could be a major blocker most times.

Frameworks for Building Better Roadmaps

• JTBD (Jobs-to-be-Done): Focus on the customer’s needs and desired outcomes.
• RICE (Reach, Impact, Confidence, Effort): Prioritise features based on their potential impact and feasibility.
• Kano Model: Categorise features based on their impact on customer satisfaction.

Using these frameworks can help your startup or team make data-driven decisions, prioritise effectively, and build roadmaps that deliver real value as they aligned well with dynamic and customer-centric roadmaps.

Actionable Takeaways and Insights to Note

• Align on Outcomes: Make sure everyone understands the goals and why they matter, this is very key as it marks the beginning of a great start.
• Embrace Flexibility: Be prepared to adapt based on new information and changing circumstances, take learnings along the way and be open minded.
• Prioritise Learning: Build in opportunities to test, learn, and iterate by focusing on the problem not the outlook.
• Communicate Transparently: Keep stakeholders informed and engaged throughout the process.

Adapt Fast or Fall Behind

Change is the only constant in product management. If your roadmap isn’t evolving, your product might be stalling.

So when asked, “Are we sticking to the roadmap?”

The right answer is: “We’re sticking to our goals, but adapting our path.”

??? How does your team handle roadmap changes? Reply and let’s discuss!

If this resonated with you, share it with someone navigating the roadmap chaos. Stay ahead in product—subscribe to Product Slice with JT for weekly slice of insights.