How to Build a Digital Transformation Roadmap
May 10, 2018

How to Build a Digital Transformation Roadmap

by Brian de Haaff

There is a specific type of person who gets excited about looking ahead — far ahead. The type of person who enjoys challenging what is known to be true today. Big enterprise transformations require that type of forward-thinker.

Since you are reading this, you might be a product or company builder with this very mindset. But if major change concerns you, let me tell you something that might give you courage and maybe even a thrill. Leading an enterprise transformation is like being two superheroes at once.

Extreme exaggeration? You bet. But my point is this: When you are leading any kind of transformation, you need to get comfortable with the duality of executing against the existing strategy while working on the next-gen. And this is definitely true when we are talking about the most common transformation of all, digital transformation.

No matter your perspective, a digital transformation roadmap will help you balance these two worlds — the right now and the next future.

If you have built out innovative product plans in the past, you know that having a clear vision and distilled strategy is essential. So it may surprise you that this is often where digital transformations fail miserably — but not for the reason you may think.

People tend to judge the success (or failure) of these transformations against the near-term achievements of the existing, established business. They also want to see results — fast. That is just not very likely when you are investing now to unlock future business value.

There is no way that these new initiatives can stack up against the current business, at least not in the returns they initially generate. This is why it becomes difficult to compare them and justify the investment being made. But meaningful investment is required nonetheless because what you have now is unlikely to serve you and the customer well five years from now.

You need a set of strategic models and a roadmap that will help everyone around you see far ahead into the future.

If you want digital transformation to succeed at your organization, you need to apply your forward-thinking strategic mind. You need to think beyond the existing goals to create a strategy that considers what your customers will demand in three or more years, as well as what is possible over time.

Here are three areas to consider when building your longer-term digital transformation roadmap:


The first step should be setting relevant goals for what you want to achieve over a defined period. For a big transformation, this should be measured in years. Your goals need to be focused on how technology can improve your products and the customer experience. The hard part is to make sure these goals are independent of the current product and state of the business. Think deeply about the customer experience and company value that you want to deliver.


This work requires more than just technology. And it will require nearly everyone in the organization to be involved at some level. So you need to consider how everyone is connected. This includes the technology, the people that will deliver the customer experience you are after, and the dependencies between the two. For example, let’s say your company is about to webify formerly paper-based processes for customers. This is not as simple as turning on some new cloud-based forms. New ways of work need to be established and every group that serves customers needs to rethink what they do.


Transformations are often multi-year efforts for established companies, meaning progress will likely be slow and not immediately apparent. In order to show results to executives and internal stakeholders (and to keep the entire team motivated and on track), you need to create and celebrate key milestones along the way. Link these milestones to specific releases, epics, and major features that the team is delivering to show tangible progress. Using our new online services example from above, a milestone might be when the first internal test transaction is processed and received by an internal group that can deliver a service based on it.

Leading a digital transformation forces you to work within the present and future simultaneously.

Does the idea of major change seem a bit more exciting now? If not, that is okay. Just know that it is not something to fear — the challenge should be embraced. After all, what could be more exciting than dramatically changing the experiences of your team and customers?

Making that kind of impact is thrilling. Maybe not quite as thrilling as being a superhero with special powers, but I like to think it comes pretty close.

How does your company embrace major change?

Big transformation requires the right tool. Sign up for a free 30-day trial of Aha!

Brian de Haaff

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 roadmap software — and the author of the bestseller Lovability. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

Follow Brian

Follow Aha!

Related articles

January 8, 2018

The Product Plan vs. the Release Plan

Do you like to focus on the big picture — or get down in the details? It is true that our brains tend to favor one side or the other. But if you are a product manager…

January 23, 2018

User Stories vs. Requirements

Stories. You have hundreds of them if you are a product manager. Each one describes the awesome experiences you want your customers to have while using your product. And…

March 2, 2020

Agile vs. Roadmaps

Have you ever tried to follow a complicated recipe? Exotic ingredients, specialty cookware, and professional techniques — it takes more than instructions to cook a…

See why more than 500,000 users trust Aha! to build products customers love

Start your free 30-day trial

© 2021 Aha! Labs Inc.All rights reserved