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Build a digital transformation roadmap in 8 steps + free template

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Digital transformation roadmap overview

Global spending on digital transformation topped $1.3 trillion in the wake of the pandemic. But much of this spending will go to waste because the efforts are led by the ill-informed. Why? Because they don’t have a digital transformation roadmap.

Okay, let’s back up. What is digital transformation?

Digital transformation is the adoption of new technologies, tools, and modern practices into every aspect of an organization. As you overhaul how you do business, right down to how your people think, you transform your organization to be more successful in the digital age. 

Many companies think they must ditch everything they’ve ever known. In reality, this evolution of your business is more about re-orienting your strategy to make sure you get the most value from your resources. 

And there’s no better way to guarantee success than with a digital transformation roadmap. 

Execute your digital transformation in Cascade! The #1 Digital Transformation Platform.

Here’s what you will learn from this article: 

  1. What is a digital transformation roadmap? 
  2. Why do you need a digital transformation roadmap? 
  3. How to build it in 8 super easy steps
  4. 5 common challenges to avoid in your digital transformation roadmap
  5. 3 examples of successful digital transformation

So, let's get things straight before your team dumps the company’s entire corporate strategy resources into a burning barrel in the parking lot. 

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What is a digital transformation roadmap?

A digital transformation roadmap is a defined process that explains how an organization can embrace digital technology to achieve its business goals and ultimately become a more sustainable, future-proof business. 

Your roadmap is an essential—but separate—aspect of your digital transformation strategy. Whereas a strategy is a blueprint that creates a clear vision of where you want to be in the future and why, the roadmap is a visualization of your strategy. It defines all activities you will need to complete within a given timeframe to achieve your goals. 

Why do you need a digital transformation roadmap? 

Many companies have a strategy. Sure, it might be stuffed away in an old Dropbox folder somewhere, but it exists (somewhere). At least you’ll always have faint memories of that big presentation, right?

In truth, it’s the roadmap that really makes the difference—that’s where you detail how you will take ideas to implementation. Without a plan, your project relies on hope (and that’s never a good place to be in business!)

Here are three benefits of a digital transformation roadmap:

    • Clarity: It's one thing to have an idea, and it's another thing to implement. A roadmap makes it crystal clear for your people on exactly what to do, when, and how. That way, your organizational goals remain in reach.

    • Inclusivity: No one wants to feel left out. When you only have a handful of decision-makers in the boardroom directing everyone else, it causes friction. Bring your team together by ensuring everyone has a say and everyone knows the value and purpose of their role.
  • Effectiveness: Using a roadmap is the most effective way to help people prioritize their daily actions. With a clear plan, your business can stay on track to your ideal destination, with the fewest number of detours in between.

Let’s imagine you want to build a house. You’ve got a general idea of what you want it to look like. It’s a two-story home with four bedrooms, five and three-quarter bathrooms, a kitchen, pool, and a partridge and pear tree.

Great. That's the plan. Let's get started.

Wow, big fella. Not so fast.

The problem with a bare-bones strategy is that a simple list of goals doesn’t include the context you need to guide decision-making. People can see what you want, but they don’t know how they’re supposed to make it a reality. 

Without clarity and direction, your project can quickly go off the rails. 

How to build a digital transformation roadmap

Okay, so you want to make this change happen. It's time to create your digital transformation roadmap. Let's walk you through the process by considering one of the most extraordinary transformations in history. That's right. We're talking about Walter White becoming the bad guy in Breaking Bad. 

1. Define your vision, mission, and values

Before you can set off on your digital transformation journey, you need to get clear on the destination. First, analyze the current state of your organization. The starting point is to plot your course with a defined company vision and values. What does the big picture look like? How do you want to achieve it? 

vision statement in digital transformation roadmap

A vision statement lays the foundation for your business strategy. Make sure that it’s on top of everyone’s mind with Cascade

When Walter White realized he needed to make bank before popping his clogs, he had a vision. Sure, his goal of becoming the crystal meth kingpin of Albuquerque isn't something that we recommend, but that grit and focus helped encourage his associates to work with him. 

2. Unite your people with your plan

To create a digital transformation plan that actually leads people to the promised land, you need company-wide buy-in. That means everyone from your C-suite to the janitor’s breakroom has to be on board. How can you do that?

  • Share information with everyone
  • Listen to concerns and questions
  • Take note of employee feedback

As you maintain open communication throughout the ranks, you can foster a close-knit culture that fuels happier employees and more productive action.

Contrary to Walter’s authoritarian approach, we recommend you present your vision in a way that is more inclusive and welcoming, as that will help unite your team. After all, people must support you before they can support your ideas.

Legendary management genius, Peter Drucker, hit the nail on the head when he said that “culture eats strategy for breakfast.” Strategy is vitally important. But if your organizational culture isn’t aligned with what you want to achieve, it doesn’t matter how good your strategy is—your people won’t make it happen. 

3. Set Key Performance Indicators (KPIs)

It’s 2022. If your business doesn’t measure its strategic initiatives, you’re missing out. Whether you’re in the business of NFTs, non-profit, or narcotics distribution, you should set targets and measure engagement. How else can you gauge progress and be sure you’re on track to your goals?

The best way to set KPIs is to use the SMART criteria framework:

  • Specific. Avoid a vague goal—be specific about the desired outcome. For example, Walter White knew he needed $737,000 to provide for his family after he was gone.
  • Measurable. From cash to conversions, pick a metric that makes sense and is easy to track over time.
  • Achievable. Walter figured out it would take 11 more dodgy deals. Make sure you set something your team can deliver. 
  • Relevant. Don’t track KPIs that aren’t related to your goals or vision. Just as Walter turned a blind eye to the mounting body count, you shouldn’t worry about missing office pens. Just keep your eyes on the prize.
  • Time-based. Everything should have a deadline. Whether it’s a terminal diagnosis or a big product launch that lights a fire under your collective rear ends, align your KPIs with a timeline that makes sense.

digital transformation roadmap reportingCreate real-time visualizations and automated reporting of your KPIs within Cascade.

4. Break it down and map your resources accordingly 

On your digital transformation roadmap, you should break the process down into a series of mini-projects. You can then assign resources to each project and think about how best to optimize your use of time, money, and people on each step. 

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5. Establish accountability

Digital transformation will thrive upon the shoulders of motivated key stakeholders who believe in what you're trying to achieve and their role within the cause. You can create these champions in your organization by giving employees ownership of specific missions or digital transformation initiatives.


Make sure your employees are aware of their responsibilities within Cascade.

Engaged employees understand how their work impacts the bigger picture and connects to the company's vision. And there is no better way to keep people engaged and improve work performance than to empower them with responsibility. When Walter entrusted Jesse to take on a more significant role in the cooking, it kept his reluctant protege onside to grow the business (and keep Walter out of prison). 

6. Analysis and feedback

After your team takes your ideas to implementation and much of the transformation is complete, you must evaluate their efforts. Ask yourself questions like:

  • How successful have you been? 
  • How has the transformation impacted internal stakeholders?
  • What external outcomes have happened?

If you are now the market leader you set out to be, you might call it a success. But if your team hates your guts, there may still be some work to do—remember, buy-in is crucial. Gather feedback, and refine your business processes and practices to make sure this transformation sticks.

7. Celebrate the little wins

As mentioned, digital transformation can be a long road. When you’re lost in the desert with no gas, you could lose sight of the vision. Without excitement, you only have hard work, which can dent morale and motivation. 

It’s crucial to take note of the micro goals and achievements in the journey, as these moments can encourage people to dig deep when the going gets tough. Whether you just hit a new monthly revenue record or completed a 4-day cookathon that could net you millions in illicit narcotics sales, celebrating the milestones matter.

8. Ride the momentum

Digital transformation is not a set-and-forget process. It's an evolution of your business and the springboard to embrace new ideas, technologies, and practices.

Your digital transformation roadmap will help you plot the course, define the actions and mini-projects, and tackle challenges along the way. Moreover, it will give you momentum to drive game-changing innovation as you move forward to the next stage.

You might find that your goals and end vision shift over the journey. You might set your sights on bigger ambitions, from simply having a sustainable business to building what Walter calls “the empire business.” 

5 common challenges to avoid in your digital transformation roadmap

If you want to survive any journey, you must avoid the pitfalls. Here are five challenges to be aware of when you create your roadmap:

1. Lack of collaboration

When you lack team alignment, it doesn’t matter how amazing your business strategy seems on the surface. The people responsible for on-the-ground execution must share your vision, and they must embrace open communication and collaboration. Walter’s undoing was rooted in an inability to get everyone in line. 

2. Lack of specificity

Failure to be specific on the details leaves things open to chance. People might run with their initiative, but if this is misguided, you could be left with a mess (like if you fail to mention budget limits on a paid advertising campaign or why someone shouldn’t pour hydrofluoric acid into a bath). In your digital transformation roadmap, you must set clear directions to your final destination—the details matter.

3. Lack of monitoring

Another trap that many companies fall into is that they forget (or neglect) their monitoring duties. You can decide how often you analyze the progress on your goals and how often you compile reports. Maybe it's weekly, perhaps it's monthly. Just make sure you set your KPIs and track progress over time. If you don't, you could waste a lot of time, effort, and money.

digital transformation roadmap dashboard reporting

Monitor your progress in real-time with personalized and automated reports within Cascade. 

4. Lack of risk management

Every company must know what risks lie ahead. Simply putting your head down and hoping for the best isn't a strategy that will get you across the finish line. You might dodge a few bullets, but eventually, the lack of forward-planning will catch up with you. Think about everything that could threaten your progress or prevent you from making your transformation—internally and externally.

5. Lack of Tools

It’s not easy to manage customer expectations, new products, new workflows, let alone do it all while your team embraces a new way to do everything. When you have the right tools, it’s much easier to make every day count as a bigger step toward the organizational goals.

Cascade simplifies strategy execution by connecting all projects and KPIs in one place. It helps your entire team collaborate across your digital transformation initiatives to carry out the essential daily actions in a more fun and effective way.

3 examples of successful digital transformation

Successful digital transformations require significant cultural change. You might have the aim of greater strategic alignment, a competitive advantage, or it could be a complete redefinition of your customer journey. 

Here are some great examples of companies that must have an excellent digital transformation roadmap:


The global courier company could see the importance of delivery speed and data analytics in the modern age. Not to wait around for an emerging startup to usurp them, UPS was able to pre-empt disruption. 

Its focus on artificial intelligence, automation, and big data analytics led to real-time package tracking. Ultimately, this innovation paved the way for a better supply chain, quicker delivery times, and a better customer experience. 


Furniture is something most people want to shop for in person. Still, IKEA didn’t let that stop them from going gung-ho with digital transformation. 

The Swedish furniture giant used fun branding on its website to connect its audience and tapped into augmented reality to provide a more immersive, interactive shopping experience. Customers can visualize items in their homes through the app or use their smartphones to scan items while they shop to speed up the checkout process.


If you want to be a high-impact brand, you need to make high-impact changes. For many years, Nike has invested heavily in its digital ecosystem to help engage employees and customers alike.

A focus on lean manufacturing techniques and digital strategy helped Nike remain profitable and competitive in 2021 and beyond, despite supply chain issues during the pandemic. It’s just the latest chapter in one of the most innovative brands in history—you can learn more by checking out our case study in the Strategy Factory.

Transformation takes time

Digital transformation isn't a sprint, and it isn't even a marathon—it's an epic adventure that could last years. If you don’t have a solid strategy that explains what you want to achieve, how to do it, and who will be responsible, there’s no chance of success.

Clarity, context, and step-by-step directions are just the basics. A proactive attitude to KPIs, analysis, feedback, and iteration are critical elements to ensure you don't get stuck. 

With a digital transformation roadmap, you can lay the entire strategy out in an intuitive way that makes it easy for your entire team to get on board and stay on track. 

Free Template Download our Digital Transformation Strategy template Download this template



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