Roadmap Season Is a Myth

In my early days as a Product Manager, building the roadmap for the next semester felt like quite a challenge. I had to prepare team goals and objectives, scope initiatives in detail, and make sure everything was ready to be picked up by the team.

It felt like I had to prepare everything in advance and have it all set in stone.

But what scared me the most was what the head of the department would say. Presenting the roadmap felt like a big reveal. I was worried that I would show him something he had no clue about until that very moment.

Of course, all of these were mistakes.💩

💡Roadmap season isn't really a season

It's something we, as Product people, should be doing all the time: constantly looking for new opportunities and exploring customer problems.

It took me a while to realize that.

The key is not to have a sealed roadmap, but rather a rich backlog of opportunities. A backlog of initiatives assessed in terms of their potential impact, ready to be picked up when they make sense.

And no, I'm not sharing anything revolutionary here. It's more of a mindset shift.

Things often change, and most of the time, these changes are outside our control. Business priorities shift, budget constraints arise, and unexpected opportunities emerge.

We shouldn't have all our eggs locked in one basket (aka the roadmap). Instead, we should be able to adjust and pick up other important opportunities when the circumstances call for it.

🐻The story of the Bear

I clearly remember a time when we were fully focused on scoping the next big thing at the company I was working for.

Let's call the product Bear.

The Bear was coming in Q2. It would take up all our resources. The Bear was coming...

Except... no Bear until the following year.

At first, I was hesitant to scope new things because the Bear — or, as we could also call it, the Beast — was coming.

That was a huge mistake.

The Bear involved multiple teams and, as we all know, too many cooks in the kitchen spoil the broth. As a result, my team had work to do during that period, but not necessarily the most impactful work.

And because I hadn't scoped any new initiatives, we ended up spending time on meta-analysis and showing some love to our tech debt — something I had consistently been putting off.

Don't get me wrong. Working on tech debt is important, and sometimes meta-analysis is exactly what you need. But the point is that we could have been working on something more impactful if I had been better prepared.

That was the turning point for me. I had to take that lesson on board and change my perspective on roadmap planning.

🙌My tips for better roadmap planning

Here are a few things I do differently now.

1. I constantly look for customer problems and scope new initiatives.

I keep exploring opportunities and scoping potential solutions. I might have to pause the scoping work to support BAU (business as usual), but I make sure it's something I'm conscious of, rather than something I forget about until the next roadmap cycle.

2. I keep a list of candidates ready for the next roadmap.

Every quarter, I have a list of initiatives that could be officially shared with top management. Not everything will make it into the roadmap, of course, but that's not the point. The goal is to have options ready when priorities change.

3. I mention potential alternatives during roadmap presentations.

When presenting the roadmap for the semester, I'm also mindful of mentioning one or two backlog items that could enter the roadmap if priorities shift or additional capacity becomes available.

This way, we're not starting from scratch when things change.

4. I always keep some buffer for experimentation.

As an AI Product Manager, I believe it's crucial to have an experimentation track within the team. We need room to try new things, learn, and explore ideas that could eventually make it into production.

And if an experiment doesn't lead to something that makes it to production? That's fine, too. It was an experiment after all.

5. I leave some room for the tech roadmap.

I also keep some capacity for tech roadmap items that the tech lead brings to the table. These are things the team needs to work on, even if they don't have a direct business impact in the short term.

Not everything we do needs to be tied to an immediate business outcome. Sometimes, we need to invest in the foundations that will help us move faster in the future.

6. I make it clear that the roadmap isn't set in stone.

One thing I like to emphasize during roadmap presentations is that we're not locking ourselves into a fixed plan. We're proposing initiatives based on what we know today, while staying flexible enough to switch gears if needed.

A roadmap should give us direction, not become a constraint.

7. I don't turn the roadmap into a Gantt chart.

The roadmap view I usually share doesn't look like a detailed Gantt chart. It's a much higher-level view, focused on initiatives and direction rather than pretending we know exactly when everything will happen.

The goal is to communicate where we're heading, not to create a false sense of certainty.

8. I refresh the roadmap more frequently.

One final note: in most of the organizations I've worked in, roadmap planning happened on a semester basis. However, I made sure to keep the roadmap updated and share it quarterly.

No surprises this way! Management had better visibility, and so did our stakeholders.

So, refresh your roadmap more frequently. Don't wait until someone asks you for an update. By that point, it's usually too late.

🎨How do I share the roadmap?

I like using Miro, with Jira epics integrated into it. I've also used Excel (not my favourite!) or simply a Jira view.

Whatever works best for your team and organization is fine. The tool isn't the most important thing; it's how you use it to communicate priorities, create alignment, and keep everyone informed.

Happy roadmapping!

Roadmap planning isn't about predicting the future perfectly or preparing a plan that nobody can challenge. It's about understanding opportunities, making informed decisions, and being ready to adapt when things change.

So, keep exploring, keep scoping, and don't let the next Bear stop you from looking for other opportunities.

You never know when it will actually arrive.

Hope you found my story interesting and learned something from my mistakes.

Happy roadmapping!