Six months. That’s how long we took a break from our product roadmap. At first, it seemed harmless—a brief pause while other priorities took precedence. But as time passed, it became clear that our roadmap no longer reflected where we were as a company or where we wanted to go.
During that time, the world around us was changing faster than we anticipated. Customer needs shifted, new technologies emerged, and our internal dynamics evolved. We had to face the uncomfortable reality: our once-ideal roadmap was now obsolete. But here’s the twist: instead of seeing this as a setback, we saw it as an opportunity to rebuild something better.
When we returned to our roadmap, we knew we had to rethink our approach. It wasn’t just about filling in the missing pieces—it was about making our product roadmap a dynamic, learning-driven tool that aligned with our business environment, organisational strategy, and customer needs.
So, in this article, I’m going to walk you through the journey of rebuilding our roadmap after six months off. I’ll share the mistakes we made, the lessons we learned, and how we adapted our strategy to become more agile, flexible, and responsive to market demands. And, by the end, I hope you’ll have a better understanding of how you can apply these insights to your own product development and planning process.
When we first started rebuilding our product roadmap, we were torn between two opposing ideas:
Fixed Plan with Deadlines: A traditional, rigid roadmap with set deadlines and deliverables.
Agility and Flexibility: A dynamic roadmap that evolves as we learn and respond to changes.
We quickly realized that agile project management was essential, but it didn’t mean abandoning all structure. Instead, we adopted a hybrid approach:
Strategic Themes Over Deadlines: Focused on larger goals like improving user experience and expanding market reach.
Iterative Feedback: Allowed our roadmap to evolve based on customer feedback, rather than sticking rigidly to a fixed plan.
For example, we planned to launch a feature by Q3, but after gathering customer feedback, we realised their needs had shifted. By prioritising themes over dates, we could quickly adjust our roadmap to focus on what truly mattered to our users.
From Features to Outcomes: We moved away from focusing on features to solving customer problems.
Agility Over Rigidity: In today’s fast-paced world, agility and adaptability became essential for our product strategy.
By adopting this agile approach, we ensured our roadmap wasn’t just a timeline—it was a strategic guide that aligned with both our business goals and evolving customer needs.
No journey is without its bumps. We made our fair share of mistakes, but we used each one as an opportunity to learn.
Not Listening to Customer Feedback: Early on, we prioritised features based on assumptions, only to discover our customers wanted something completely different.
Focusing Too Much on the Roadmap, Not Enough on Execution: We spent too much time perfecting the roadmap and not enough time shipping.
Theme-Driven Approach: We shifted from a feature-driven roadmap to one focused on core customer needs, like improving retention and simplifying user experience.
Tech Stack Optimisation: We realised our internal systems were lagging behind. Once we invested in optimising our tech stack, we sped up feature delivery and reduced bottlenecks.
Start Shipping, Stop Rebuilding: We embraced agile development—delivering early, gathering feedback, and iterating quickly. Waiting for perfection only delayed progress.
Rebuilding the roadmap wasn’t just about adding features. It was about rethinking our entire approach to product development.
Align the Roadmap with Organisational Strategy: We ensured that every decision contributed to our larger mission and goals.
Focus on Strategic Themes: Instead of listing features, we grouped initiatives around key themes such as customer trust and product scalability.
Prioritise Business Goals: Each initiative was tied to long-term objectives, ensuring alignment with the company’s overall product vision.
Building Customer Trust: Enhancing onboarding, improving customer support, and personalising user experiences.
Expanding Market Reach: Adding new features that address untapped customer needs or explore new geographical markets.
By focusing on strategic themes, we could align our development process with our business strategy, ensuring we were always working toward the larger goals.
In our journey, we encountered several common pitfalls that many product teams face when developing and managing a product roadmap. Let’s talk about the five biggest traps that can derail your roadmap—and how you can avoid them.
One of the biggest mistakes we made early on was focusing too much on adding features. While features are important, they’re not the end-all, be-all. A feature-driven roadmap misses the bigger picture. Instead, we learned to focus on outcomes—the problems we were solving for our customers.
Sticking to deadlines no matter what may seem like the right approach, but it can cause stress, burnout, and poor decision-making. A rigid timeline doesn’t allow for the flexibility that’s necessary in agile project management. Instead, we started using milestones that could be adjusted as we learned more.
When we were focused on executing our roadmap, we weren’t paying enough attention to feedback. This led to misaligned features and missed opportunities. We realized that constant feedback loops were essential. Regular customer surveys, user testing, and stakeholder meetings helped us stay on track.
A roadmap that’s too detailed can overwhelm your team and stifle creativity. Instead, we kept the roadmap high-level—focusing on themes and strategic goals. This allowed us to be more flexible while still staying aligned with our product vision.
A roadmap is a strategic tool—it’s not just a list of tasks. When we started treating the roadmap as a to-do list, we lost sight of the bigger picture. We refocused on ensuring that each item on the roadmap was a strategic initiative that contributed to a larger objective.
By avoiding these traps, we were able to create a roadmap that was more aligned with our product strategy and responsive to customer needs.
In the past, our product roadmaps followed the Waterfall methodology—a linear approach where every task was mapped out, deadlines were set, and every feature had a predetermined release date. In theory, it was predictable and structured. But here’s the problem:
Waterfall Roadmaps: Everything was planned months in advance.
Fixed Deadlines: The roadmap locked in dates that didn’t allow for much flexibility.
Feature-Based Planning: Roadmaps focused on detailed features rather than solving customer problems.
While this worked for industries with stable markets, it wasn’t sustainable in the fast-paced world of tech. By the time we shipped features, customer needs and market conditions had already shifted, making our carefully planned roadmap outdated.
The Problem with Waterfall:
Missed Opportunities: Features that were relevant when planned became irrelevant by the time they were released.
Customer Disconnect: By focusing on internal goals, we failed to align with the evolving needs of our users.
We realised something critical: predicting everything upfront is not the best way forward.
When we shifted to the Internet Era, we adopted agile project management. The focus was no longer on creating a perfect plan but on being able to respond to changes in real-time. The new approach was flexible, adaptive, and continuously evolving.
Agile Methodologies: Shorter development cycles and frequent feedback loops.
Customer-Centric Focus: Roadmaps became focused on solving customer problems, not just adding features.
Real-Time Adjustments: The roadmap now adapts to new customer feedback and market changes.
The Benefits of Agile Project Management:
Faster Response Times: We could react to market shifts and customer feedback quickly.
Better Alignment: We aligned our product roadmap with our business strategy, ensuring every decision contributed to long-term goals.
Iterative Development: Instead of waiting for the perfect roadmap, we used short cycles to continuously refine our approach.
In the Internet Era, we stopped thinking of the roadmap as a static plan. Instead, it became a tool for learning. The key shift here was understanding that roadmaps are not about predicting every outcome—they are about learning and adjusting.
By focusing on strategic themes—like customer retention, market expansion, or improving product scalability—we ensured that our roadmap remained focused on delivering long-term value.
Lessons from the Shift:
Agility is Key: We focused on delivering value early and learning from each iteration.
Continuous Feedback: We incorporated ongoing customer feedback into every sprint, making our roadmap evolve as we gathered insights.
Adaptability: The roadmap needed to be a living document that reflected real-time changes, not a fixed plan.
When it came to organising our product roadmap, we learned that simplicity and clarity are critical. Instead of a long list of features, we adopted a framework that aligned our initiatives with business goals, customer needs, and market realities.
Clarity and Focus: Themes helped us see the big picture and avoid getting lost in details.
Better Resource Allocation: We could focus on the most important initiatives, ensuring optimal use of resources.
Alignment with Organizational Strategy: Every task and feature had a clear connection to company-wide goals.
By organising our roadmap around themes, we made it easier to prioritize work, focus on outcomes, and adjust quickly. This not only increased our productivity but also ensured that we were always working toward our product vision.
Rebuilding our product roadmap after six months was a pivotal moment in our journey. We learned that a product roadmap should never be a fixed plan—it's a strategic tool that needs to be adaptable, flexible, and aligned with both organisational strategy and business goals.
Here are the key takeaways from our journey:
Adopt Flexibility: In the Internet Era, your roadmap should evolve as you learn more about your customers, market conditions, and business priorities.
Focus on Themes, Not Features: By organising your roadmap around high-level themes, you stay focused on solving customer problems rather than just adding features.
Prioritise Based on Value: Use frameworks like the MoSCoW Method to prioritise initiatives that align with long-term business goals.
Iterate Continuously: Embrace shorter cycles to release products faster, gather feedback, and adjust the roadmap accordingly.
Don’t let an outdated roadmap hold you back. Make sure your internal roadmap is dynamic, responsive, and ready to guide your team toward success in the ever-changing business environment.
Is it still stuck in the old ways of planning? If it’s too rigid or outdated, it’s time for a change. Start organising around themes, prioritise for impact, and create a living document that evolves with the needs of your business and customers.
Rebuild your roadmap today, and align your product strategy with the ever-changing landscape of today’s market.