Roadmaps: the value of an uncertain plan

A product roadmap is an uncertain journey.

Most companies never manage to launch the big, innovative services that they dream of. Often that’s because either they don’t have a roadmap, or they misuse it.

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If you don’t have a roadmap, then the story of ApplePay is a great illustration of how a roadmap gets you from the middle of nowhere, to where everyone else wishes they could be. 

When smartphones started to become popular, lots of firms began trying to create ‘digital wallets’. Mostly, those firms were banks and financial services companies with great advantages in this space.

Apple didn’t have such a history. It began with a password manager: Keychain. At the turn of the century, Apple introduced it to store wifi and email passwords so you didn’t need to retype them every time you connected.

In 2011, it introduced iCloud which synchronised those passwords between your Mac and iPhone, no need to retype passwords on your tiny smartphone.

Then, in 2013, Apple expanded Keychain to autofill credit card details into web forms, saving typing and teaching users to trust their phones with payment details.

The same year, it replaced the iPhone’s master password with a fingerprint sensor making it effortless to access secure data.

Then in 2014 it added NFC technology to the iPhone and launched ApplePay.

While most of the competing services failed, ApplePay was soon adding a million customers each week.

A roadmap from Keychain to ApplePay.

That timeline is Apple's roadmap. The roadmap is the embodiment of Apple's plan, its strategy to get to ApplePay. Look along the roadmap and you can see Apple piecing together the technology, operational know-how, and customer insight to launch a successful service.

Now, the above is a simplification - I don’t know what Apple’s complete product roadmap looked like. By its own admission, Apple spent years buying and refining enabling technology, honing the user experience, and creating the operational capability.

But the story shows two things. First, you go a long way even if you start in the wrong place. Second, delivering requires focus and discipline.


A great product roadmap does that - it's a visualisation of strategy that helps an organisation maintain focus and discipline over years.

The roadmap marks out intermediate steps that deliver value to the organisation and its users.

If your organisation is always delivering ‘low hanging fruit’ projects, and never getting to the big stuff, this shows how you can use those smaller steps to get to the big goal.

Instead of trying to pick all the low-hanging fruit, you need to select the ones that get you closer to your goal. Start by defining that goal.


Most product roadmaps lack vision. They’re lists of ideas and opportunities graded by complexity - a prioritised list of quick wins.

To lead your organisation into a distant future, you need to have a vision that’s big enough to excite your team and credible enough for them to believe. The journey needs to be worth it.

Instead of grading opportunities by complexity, sort them into themes.

Each theme will be a focussed subset of opportunities. Each will contain its share of quick wins and complex challenges. But within each you’ll discover a coherent customer proposition, and a clear vision.

Deciding what not to do

A great strategy helps you decide what not to do. The ‘quick wins’ strategy is ‘do everything that’s easy’, which isn’t much of a strategy at all.

When you look at the themes, you now have a choice of customer propositions. Your strategic choice becomes: ‘how do we want to deliver value to our customers?’ A much stronger approach.

Pick one theme.

Often the right one is the one that has the best combination of customer value, business value, and feasibility.

At cxpartners we make a first pass at this by getting stakeholders to rate customer value, business value, and feasibility using a ‘red, amber, green’ rating. The winner is the theme that avoids red flags and maximises number of greens.

Making the vision feel real

We believe it’s important to bring the theme to life.

When people can experience a taste of the future they get excited and motivated. That motivation helps to give them the discipline they need to see through the roadmap.

An elevator pitch (verbal description) is okay. A storyboard or video is better. An interactive mock-up is best of all.

We’ve moved from ‘do what’s easy’ to a compelling vision. Now we need a plan to get there. This is where most product roadmaps go wrong.

Just enough planning

Too many product roadmaps look like a project plan. The wider organisation wants to know when a particular feature will be launched. So the roadmap becomes a list of promised features, each with a delivery date.

But the further ahead you plan, the more assumptions you need to make. Each assumption increases risk. Once you get more than a few months ahead, the promises in the plan are so risky that no one trust them.

Product roadmaps stretch out for years. They’re a higher level planning tool than project plans. A series of objectives. The detail required to create a delivery plan doesn’t belong in a roadmap.

The value of an uncertain plan

Instead think of product roadmap as the choices facing a rock climber. The goal is somewhere over thataway. The route is visible. But only the next few hand holds can be safely identified.

Product roadmaps tell you three things: where you’re trying to go, the most likely route, and the next step.

Roadmaps are about grasping nearby opportunities to reach a goal.

Like a rock climber, you can only be certain of a hand hold when you get close enough to feel it. And you may discover that you need to change direction, back-track, or re-think your destination. The most realistic roadmap is that one that acknowledges that uncertainty.

Our roadmaps do that by offering detailed descriptions of the vision in the coming phase, with less detail in successive phases - it’s clear what we do and do not know.

It's not about the document

Writing a good product roadmap is as much about what you keep out (promises that can’t be kept) as what you put in (vision, waypoints, and next steps).

By doing that, a good roadmap encourages teams to focus on the right things.

The problems that undermine roadmaps come about when stakeholders ask product teams for more detail and certainty than anyone can promise.

The marketing department needs to create a launch campaign - so it demands details on features and deadlines. The board wants to know whether it is spending money wisely, so it demands to know the market size for a product that’s never been seen before. A senior manager wants to know how the product will turn out, so demands that the team incorporates his untested idea.

Each of those problems can blow up a product roadmap. Anxiety, and a desire for certainty is at the heart of each one.

The real skill in delivering a product is in managing that anxiety. That requires listening and empathy.

Stakeholders’ demands and questions tell you something about the jobs they’re trying to do. Each one is a call for help and engagement.

Instead of trying to push away those ‘unreasonable’ demands, it’s better to explore where they come from. How could the marketing team promote the product without a feature list? How could the board be confident in the value of what’s being produced? Why does that senior manager fear the product will turn out wrongly?

Answering those questions takes time. But since each stakeholder has something valuable to offer, and is part of a larger team, it’s time well spent.

It's about coaching

Strategy and roadmaps are really about a kind of leadership.

Not the 'my way or the highway' kind of leadership. But the kind that listens, involves, and binds people to a common cause - coaching a team to success.

So when we’re creating roadmaps, our real focus is on coaching and building trust, flexibility, and cooperation across organisations. The design activities we choose, and the conversations we have are all done to create alignment.

That is how organisations find the discipline to deliver on the roadmap, and make the journey from the middle of nowhere to where everyone else wishes they could be.

Giles founded cxpartners with Richard Caddick in 2004. He's author of 'Simple and usable' and an invited speaker at design conferences around the world.