David Pereira Product Leader with 15+ years of experience. Partner at Value Rebels and interim CPO at omoqo. Almost every product team is trapped somehow; untrapping them is what drives me.

How to build a strategic roadmap: Examples and antipatterns

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How To Build A Strategic Roadmap: Examples And Antipatterns

A strategic roadmap can be a blessing or a curse. I’ve been on both sides of that coin.

Whenever I consider a new position or start coaching a company, the strategic roadmap is one of the first things I look into.

The strategic roadmap tells a lot about:

  • How agile is the company is
  • How empowered teams are
  • How aligned leadership and teams are
  • How risk-averse the organization is

As you can imagine, a poorly crafted strategic roadmap will trap your team and lead to mediocrity.

Let me walk you through what a strategic roadmap is and what it isn’t, common antipatterns, and how to build one that helps you create value for your customers and business.

Table of contents

What is a strategic roadmap?

I need to confess something: I dislike the term roadmap. Simply because it’s misleading.

When I think of a roadmap, I imagine that I know where I want to be and see a clear path to get there. For example, if you want to drive from Munich to Berlin, you might find different ways of getting there, but the path is predictable and repeatable. I guess you know where I’m going.

With digital products, you may know where you want to land, yet getting there is always an unknown journey. But that’s beside the point…

A strategic roadmap is a set of milestones you want to reach. Put simply, it’s a document describing changes you want to make and why they matter.

As the product manager, it’s your job to empower your teams to figure out how to make those changes. Hopefully, your roadmap is aligned with your product strategy and vision.

Unfortunately, life is rarely as simple as theory. Before we dive into examples to see what a strategic roadmap looks like in practice, I want to explore what roadmaps aren’t.

What is not a strategic roadmap?

We are risk-averse animals. We’re not at peace with the unknown.

That means setting milestones isn’t enough for us. We’ve got to create a plan, and that’s where the nightmare starts.

A strategic roadmap should not include any of the following:

  • Defined outputs — A set of features set in stone to deliver
  • Plans — A scary Gantt chart defining what happens when
  • Top-down decisions — Management decides what to deliver and teams execute without knowing what to achieve

It might sound silly, but it’s true: we simply don’t know what we don’t know.

Setting a plan will trap the team because they will fall into execution mode. Creativity will disappear and they will have little chance to stand out.

If you want a team of achievers, give them a goal and empower them to reach it.

Steve Jobs said it best: “You don’t hire smart people to tell them what to do. You hire them so that they tell you what to do.”

Common antipatterns to avoid

Let’s talk about some traps and antipatterns. We touched on some already, but I’ll give you more hints on weird things you will eventually face.

Product strategy vs. vision vs. roadmap

The first trap is creating a strategic roadmap without a product strategy. That’s simply nonsense.

A strategic roadmap doesn’t replace a product strategy. I will do my best to help you understand the connections between crucial product documents:

  • Product vision — Your product vision points where you want to be. For example, SpaceX’s product vision is to eventually populate Mars
  • Product strategy — Defines who you serve, how you differentiate, and what value you create. There are gazillions of frameworks for product strategy; you can keep it sweet and simple using Lean Canvas or a classic business model canvas
  • Product roadmap — The product roadmap sets milestones that will enable the organization to get closer to its vision. As such, the strategic roadmap is tightly aligned with the product strategy

If any of the above pieces is missing, you can expect a lot of confusion and misunderstandings with your team.

Micromanagement vs. customer centricity

The second trap has to do with how the strategic roadmap is born.

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Often, top management struggles to renounce old behaviors of command and control. When that happens, they probably define everything on their own, throw the roadmap over the fence, and demand commitment from the team. Sorry, that won’t work.

To get the team committed, you must contact them onboard. It’s simple: involve them while crafting the roadmap and listen to them. Remember, they are closer to the customers than you are.

Milestones vs. outputs

The third trap is the fear of the unknown. A strategic roadmap shouldn’t contain a list of outputs to create but a list of milestones to reach.

How to develop a strategic roadmap

Now it’s time to craft a meaningful strategic roadmap.

It all begins with the end in mind. Take your product vision and ask questions like:

  • How might we get a step closer to our vision?
  • What’s standing between us and our vision?
  • What would help us stand out?
  • What’s holding us back from growing?

You want to have discussions based on outcomes to product the strategic roadmap. Without that, you will end up creating a trap map instead.

Keep it short and simple. You’ll find billions of templates for strategic roadmaps and two hundred million tools. But if you get it wrong, it doesn’t matter. Never forget GIGO: garbage in, garbage out.

I’m not telling you to ignore all those resources; you may find cool things to help you, but the key is to foster a value-driven mindset. Focus first on collaboration and clarity, then think about tools and templates.

Strategic roadmap example

I ask myself the aforementioned questions several times before crafting a roadmap. Let me share a quick story with you.

When I was working at an online shop with the mission of making young parents’ lives easier, I got myself into a trap map discussion.

Management presented 15 items they wanted to be delivered. I knew that would trap us, so I played my madman game. The conversation went like this:

Me: “I see you’ve put a lot of work into this plan, and I’d like to understand how you came to these features. What do you expect them to generate that will help us stand out?

COO: “These features are missing in our product. Once we have them, our retention will grow.

I heard a word I like: retention.

Me: “Does that mean we have a retention problem now?

COO: “Sadly, yes. Customers don’t return to our shop after the first purchase. We think it’s because we lack these features. That’s why it’s important to deliver them fast. On top of that, our acquisition cost is skyrocketing. We better deliver.

Me: “Alright. I understand that we have a retention challenge combined with an unsustainable acquisition. Now, I’d appreciate learning from you what gives you confidence that those initiatives will solve these problems.

COO: “Well, I simply know that. My experience tells me that.

Me: “I understand, but customers are tricky; they surprise us with their behavior. Would you give me two weeks to work with the team to come up with evidence from our customers? I will make my top priority increasing retention rate and decreasing acquisition costs.

COO: “Two weeks. No more.

After this exchange, I ran experiments with the team and learned what customers cared about. It was enough to present to management and show that those initiatives wouldn’t solve our problem.

So we crafted a simple strategic roadmap that looked like this:

  • Milestone 1 — By the end of Q2, we have increased our retention rate by 30 percent while maintaining profitability. That will enable us to grow sustainably
  • Milestone 2 — By the end of Q3, we have created an organic customer acquisition channel representing 10 percent of our general acquisition. That will help us unburden our acquisition costs

It sounds too simple to work, but it was all we needed.

We shared the milestones with all directors and managers. We continuously updated them on our progress. Ultimately, we reached both goals, but I must confess that our first attempts failed. Fortunately, we were empowered to pivot as long as we needed.

Final thoughts

A great strategic roadmap will pave the way for your team to thrive.

A flawed strategic roadmap will diminish their potential and will cause waste.

I cannot state enough the power of simplicity. If you’d be willing to simplify what everyone else is complicating, you can be surprised by the results you can generate.

Featured image source: IconScout

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David Pereira Product Leader with 15+ years of experience. Partner at Value Rebels and interim CPO at omoqo. Almost every product team is trapped somehow; untrapping them is what drives me.

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