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The ultimate guide to building a digital transformation strategy

January 26, 2022 - 33 min read


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What is a digital transformation strategy?

4 main areas of digital transformation

3 reasons why digital transformation is important

3 common challenges and roadblocks

How does digital transformation impact company culture?

6 types of digital transformation tools

6 steps to building a digital transformation strategy

How to build your digital transformation roadmap

In a recent survey, leaders were asked about the impacts of COVID-19 on their digital transformation strategy. According to Deloitte, 85% of CEOs accelerated their digital transformation strategy since the pandemic.

The result? Greater investments in technology that proved crucial for the business. But why? Well, many more people found themselves working remotely than ever before, and staying in business meant changing the way work got done. 

One learning we might not have anticipated around COVID-19 is rooted in how we do business. It’s taught us the importance of digitizing business operations to keep the company going. 

But digital transformation strategies aren’t just about technology. When a company makes a big change in the way an organization operates, human beings feel the impact. The flip side? Companies can’t actually make a big change in operations unless people change the way they work

And if we’ve learned anything about humans, we know that behavior change can be hard. But change isn’t impossible. With personalized coaching, navigating change and empowering transformation is possible. 

Let’s walk through what a digital transformation strategy looks like — and why it’s important. We’ll also talk about the impacts of digital transformation on company culture — and your organization’s success.

What is a digital transformation strategy?

As technology evolves, fast-moving businesses find ways to use technologies for a competitive advantage. After all, technology can make our lives easier. It can save time, energy, and work. 

Then all the other companies in the industry have to figure out how to integrate tech into their operations as well — or they fall behind. That fear of falling behind can create tunnel vision on the digital technology itself rather than the transformation.

But in today’s age, we know technology options are endless. There’s a reason why the saying, “There’s an app for that,” is so prevalent.

As business leaders, we know you have plenty of technology solutions to consider. We also know you have people and human beings behind those solutions. You have problems to solve to optimize your own customer experience. 

Before we get into creating a digital transformation strategy, let’s talk about its key components. 

4 main areas of digital transformation

According to Harvard Business Review, we can identify 4 main areas of digital transformation. Each area touches on a specific realm of your business in unique ways. 


There’s no shortage of new technologies these days. Take the Internet of Things (IoT) and cloud computing. Or machine learning, blockchain, and artificial intelligence. Or automation and the incredible growth of e-commerce (like Amazon).

We're living in an age of digital disruption. And emerging technologies are here to stay.

And while the technologies are changing, evolving, and innovating, there’s one thing that remains constant. Humans need technology to do their jobs well. And digital business is the future of business.

Dependent on your organization, you may be looking to adopt new technology into your business strategy. We know it’s not as easy as it sounds. Integrating a new initiative and technology into your organization can be messy. 

It can require overhauling a legacy system and modernizing it. It can involve months (and sometimes, years) of work to evaluate how to best plan for a big technology change. Not to mention months (and sometimes, years) of searching for the right technology in the first place. 

Technology is a massive component of a digital transformation strategy. Work with your organization’s digital leaders when selecting new technologies to install.


The second main area of a digital transformation strategy is data. Oftentimes, technology and data go hand-in-hand. In fact, the inability to look at the data you need might be a reason why you’re looking to implement new technology. 

When putting together a digital transformation strategy, consider the role of data. What time of information do you need to set your teams up for success? Is the technology worth implementing if you can’t access the data you need to measure your success? 

It’s unfortunately common that many companies aren’t receiving the data that they need. In part, it could be because feedback isn’t gathered from the ground up.

For example, your organization might be looking to implement a new IT system. This system is generally managed in day-to-day operations by frontline workers. Are those frontline workers being heard?

Again, make sure you’re working alongside your company’s leadership. But also, don’t underestimate the value of feedback. If your organization isn’t receiving the data it needs from technology, is it the right technology to implement? What does your digital transformation strategy need from a data perspective? What does success look like when it comes to data? 



You don’t transform anything by laying new tech on an old process. At best you gain a few efficiencies. To reap the benefits of digital transformation requires rethinking processes to focus on outcomes, not outputs. 

Processes are largely about what people do — changing processes means changing behaviors and mindsets. It requires time, a growth mindset, and rethinking how things work. So, it’s only natural that process is a big part of any digital transformation. This area of the digital transformation strategy is crucial to setting up your organization for success.

The process can look different depending on your organization. It can include any of the following: 

  • Aligning on the desired outcomes for internal and external customers
  • Streamlining work activities and teams to create an efficient, cross-functional process 
  • Putting together process management focused on customers and the end-user experience. This is especially if your organization builds mobile apps 
  • Improving existing processes to account for any newly adopted technologies 
  • Rethinking strategic decisions around company process, customer process, and more 

Collaboration plays a key role in creating more effective, outcome-oriented processes across the business. Make sure your teams are working together towards a shared goal. Clear communication and expectations are critical in this area of the strategy.

Organizational change 

This is where the magic happens. Organizational change is a huge undertaking, but it’s not impossible. 

Of all the areas of a digital transformation strategy, organizational calls on many key skills to successfully do well. Changing the way an organization operates requires leadership, teamwork, and emotional intelligence. It also requires strong, efficient communication — and courage

After all, at the root of any company are human beings. And humans can be resistant to change. Change is hard and uncomfortable. You might be implementing a new process for employees who are used to doing things a certain way.

In fact, many leaders themselves might be resistant to transformational change. This level of change can be threatening to power and budgets, status, identity, and security. Digital transformation can make some skills and expertise obsolete.

If you’re building out a digital transformation strategy, consider building a team of organizational change pros. A team of folks with strong people skills, the ability to influence and address underlying causes of resistance, and the ability to work alongside those impacted by the change is important.


3 reasons why digital transformation is important

Digital transformation is important for many reasons. In the era of digital transformation, we can outline three key reasons why any organization should consider a strategy.

It saves time 

This is the most common driver but also the tip of the iceberg for value. A digital transformation strategy can be time-saving, for workplace productivity and your customers. When technology is working for you, you save time. And we know time and productivity are valuable currency in today’s digital world. 

For example, you might be able to deliver solutions to your customer faster with new technologies. You might be able to streamline inefficiencies in your processes for your workers.

Good digital solutions can improve the employee experience, as a result. If you can save your employees valuable time to be able to focus on more impactful tasks, you’ll likely make them happier (and more productive). 

Agility and growth 

A digital transformation strategy is all about agility and growth. An agile, growth-centered mindset is critical to a successful strategy. 

From a cultural perspective, it can encourage innovation and growth. A company that accepts change, stays agile, and promotes growth shows its employees the importance of innovation. When employees are empowered to learn and grow (and challenge the status quo), the business benefits.

At BetterUp, we’ve found that a growth mindset and mental fitness go hand-in-hand. To be able to grow and stay agile, employees need to strengthen their mental fitness. We’ve found that resilient workers have more flexible thinking, contribute to more agile teams, and are over 20% more innovative.


It should be no surprise that agility and growth lead to innovation. This is yet another reason why digital transformation is so important.  

First, let’s talk about innovation in the context of our world. We know that pre-pandemic, only 1 in 5 workers worked remotely. Now, more than 70% of the workforce is remote.

And we see that employees want the flexibility of a hybrid workforce. According to our data, the shift to hybrid and remote work showed a 56% increase in creativity and innovation. 

We’re living in an age where we’re innovating where we work — and how we do it. At the core of this innovation is the digital transformation strategy. How are you best equipping your employees to innovate successfully? Are you setting up your workers for success? 

Consider the impact a digital transformation strategy can have on your organization’s ability to innovate. By empowering innovation and change, your organization will see more success.

When done right, digital transformation can impact your organization's revenue growth and profitability.

3 common digital transformation challenges and roadblocks 

We all know change comes with its own set of challenges. In fact, one study cited that 78% of organizations fail to scale their digital transformation initiatives. A digital transformation strategy isn’t exempt from roadblocks as it can be a huge change. But it’s possible to overcome those challenges with the right mindset and guidance. 

"When you think about it, it's always been human nature to be resistant to change because change feels like the intruder or trespasser in our comfort zone. And you fight it. It's important for company leaders to acknowledge and empathize with employees who are dealing with a lot of change, especially in situations like a digital overhaul." - Fiorenza Rossini, BetterUp Coach 

Here are some common challenges that we’ve witnessed — and how to overcome them. 

Resistance to change

If folks are comfortable where they are, you might run into this roadblock. People might not want to change how they do things. In fact, we find that resistance to change is more common than you may think.

At its heart, trust needs to be established to truly empower meaningful change. If an organization lacks trust, it’s unlikely that it’ll be able to make the change it needs.

If your organization seems resistant to change, try these tactics:

  • Involve employees from the beginning in creating the transformation. The frontline, the people doing the work — they often have a clear sense of what doesn’t work and ideas for how to serve the customer or their co-workers better. 
  • Communicate early (and often). Communication can make such a huge difference in building trust and transparency
  • Listen to your employees’ concerns. Gather feedback — and show vulnerability and a willingness to listen. Change can be threatening on a personal level because it has potential consequences for people’s financial and social well-being, as well as emotional. When you show your employees that you care, they’re more likely to be invested in the organization’s success. 
  • Educate your employees on the pros of the change. If your employees don’t understand why the change is happening, there’s a problem. Make sure you’re communicating what benefits they’ll get out of the change — especially if it’ll greatly improve their employee experience.


Lack of support from leadership

Sometimes, those resistant to change can be in leadership positions. If you’re a business leader, you yourself might be reading and wondering what value there is in making a big digital transformation. 

When leaders don’t show their support for change, it’s likely their employees won’t either. It’s critical that your organization’s leadership understands the importance of leadership support. Much like getting your employees on board, you should also educate your leadership team on the pros of the change. 

Listen to feedback and hear out your leadership. Everyone needs to feel a sense of responsibility and personal investment in an organizational change.

Not enough change management support

To help implement a wide-scale change, you need people who are good at doing it. That doesn’t mean people who are good at putting together messaging plans.

If you’re unable to assemble a team of people who really understand the value of the transformation and can make it relevant to those affected, you’ll likely find yourself at a roadblock.

Employees are largely not receptive to change. Without a dedicated team of people committed to leading and seeding change in the organization, your ability to affect change will be decreased. These people don’t need to be outside experts. In fact, examples such as Quest Diagnostics and ATB Financial suggest internally might be better. But they do need guidance, training, and support across the duration of a transformation.

In order to overcome this challenge, consider enlisting support from your leadership team. Can you secure buy-in from leadership to staff the needed support? By ironing out needs, duties, responsibilities, and team goals, you can use your influence to assemble a dream team.

How does digital transformation impact company culture? 

What does digital transformation have to do with culture?

Well, in today’s world, a lot more than you may think. We use technology to communicate, especially as our workforce becomes more and more remote. We use technology to track progress, streamline processes, and eliminate any bumps in our workstreams. 

And behind the technology are employees using it. Humans are the end-users of emerging technologies. Employees crave connection, that sense of belonging, and learning new things.

 In a remote work environment, how are employees connecting? How are employees learning? What platforms are employees leveraging to feel that sense of belonging? 

Quick answer: with technology. But that technology needs to work well and deliver desired outcomes for employees to thrive

With a successfully implemented digital transformation strategy, your employees should feel a positive impact. 

6 types of digital transformation tools

So, you might have a good understanding of what a digital transformation strategy is. You know why it’s important — and what you may come across while implementing it.

Do you have the right tools? Much like how you might approach mental fitness, your strategy should be a holistic reflection of your company's needs. Different tools will meet different needs — and it might take a suite of offerings to assemble your strategy.

Only after you get clarity on what you are trying to accomplish and the possibilities for better outcomes should you look at specific tools. Here are some common tools that you might consider:

    • Collaborative tools. Did someone say Google? A BetterUp customer, Google has long been a leader in building a suite of collaborative tools. But the keyword in this is “collaborative.” Folks need to be able to work together well in a hybrid and changing work environment — whether that’s in a Google document, Office365, or something else.
    • Ways to communicate internally. At BetterUp, we use Slack, email, and an internal intranet to house important resources. Depending on the size of your organization, you may need more internal communication support. Consider tools that’ll help increase communication between teams — and ask for employee feedback. 
    • CRM tools. For most (if not, all) businesses, a customer relationship management (CRM) system is crucial. A CRM helps your organization meet the needs of your customers. It can help automate tasks, streamline sales cycles, increase retention, and more. 
    • CMS tools. According to data, 70% of buyers fully define their needs on their own before engaging with a sales representative. Your web content is of the utmost importance to your digital transformational strategy. A content management system (CMS) houses things like your website, your blog, and other customer-facing content. 
    • Payroll and financial management tools. HR processes like payroll can be tedious and time-consuming. With the right tools, you can automate these processes so your HR team can focus on more impactful work. 
    • Human capital management tools. For any growing business, human capital management (HCM) is critical. From recruiting to employee experience to feedback, the right HCM tool can help empower your organization’s success. Some HCM tools also address other HR needs, like payroll. 

6 steps to building a digital transformation strategy

It’s time to start building your strategy. But where do you start?

Before you even think “technology,” align on a vision of how the world is changing,
where you want to play, and what kind of capabilities you’ll need to develop to get there. After that, we looked to McKinsey to help outline six steps to build your digital transformation strategy.


 1. Create a technology roadmap

We’ll get into the details of how to put together a roadmap in the next section. But this is a crucial first step to building out your digital transformation strategy. 

Your organization will need a very clear idea of what you want from a technology perspective — and where you’re going. This starts with evaluating where you’re starting from. From there, you can identify the steps needed along the way.

2. Develop and upskill talent

Before you implement your roadmap, your talent needs to fulfill your roadmap’s needs. As a leader, this means your organization needs to invest in upskilling your talent

Employees are craving the opportunity to learn. Whether you’re assembling a team from scratch or pulling existing employees into a new team, upskilling is crucial. 

Consider ways you can provide learning and development opportunities to your employees. Personalized coaching can help employees navigate change. With coaching, employees can meet challenges with grace and resilience. 

3. Implement an agile methodology 

Flexibility and agility are must-haves for any digital transformation strategy. But moving to an agile model requires collaboration, transparency, and change. 

But the benefits of an agile mindset far outweigh a static approach. Teams will be able to adapt more quickly, fix problems faster, and improve quicker. In the end, adopting an agile methodology can help manage risks, improve productivity, and inspire innovation. 

4. Shift to modern technology

If you’re thinking about digital transformation, you’re thinking about modern technology. New technology comes with a new host of capabilities that are critical to digital transformation.

But this means fully understanding what the new modern technology is bringing to the table. Enlist the help of your technology pros to evaluate new, modern technology. Make sure the tools and technology you select are going to meet your business needs.

Many organizations conduct testing and focus groups to help socialize new tools and gather feedback. In the end, it can help with the overall adoption rate of the technology in your organization. 

5. Look at the data and how to best manage it

If you’ve reached this step, you’ve likely selected what types of technologies you’d like to use. But before you implement, consider data and data management. 

How are the systems going to work together? What sort of data or insights can you mine from the tools you’ve selected? What data management gaps can you identify? 

Without robust data insights, your organization could suffer. Consider ways to build data management into your digital transformation strategy. By doing so, you’ll be able to find solutions that can meet your organization’s needs. 

6. Adopt, scale, and grow 

This is where your change management team will really shine. You might select new technology. You might have outlined a stellar strategy and roadmap. You might have everything about your digital transformation ready to hit the ground running. 

But if your organization doesn’t adopt the strategy, you’re stuck. 

Work with your change management team to drive adoption. From there, you’ll be able to identify ways to scale the digital transformation across your organization and continue to grow. 

6 steps to build a digital transformation strategy roadmap

McKinsey talks about the digital transformation strategy roadmap in three simple steps. If you’re at the beginning of your digital transformational journey, here’s how to get started on your roadmap. 

    1. Define the value of digital transformation. This can mean different things for different organizations. But at its core, this step of the roadmap should show your leadership why the investment is worth it. What goals do you have? How will digital transformation help your organization achieve those goals
    2. Organize your launch. Who are the key stakeholders? What role will change management play? What programs or initiatives need to be created? To successfully launch, the company needs to organize around the launch.

      This is likely a cross-functional effort that impacts all employees. Before starting the work, make sure you’re engaging with the necessary stakeholders. Build a network of digital transformation champions to help drive early adopters. Make sure you’re gathering feedback and adjusting to what you’re hearing from employees. 
    3. Scale. Once you’ve launched, the work doesn’t stop. It’s important to recognize that the launch is likely just the tip of the iceberg for your digital transformation strategy. The work begins at launch to drive adoption and scale initiatives to help meet your organization’s goals.

      For example, let's say your large-scale organization recently launched a new company-wide intranet. How are you supporting employees? Some organizations provide “office hours” to help answer any questions about a new tool and its goals.

      Others create plenty of resources, how-tos, and guides to using the tool. And still, others might offer training opportunities to upskill.

How to measure your digital transformation's success

Success looks different for each organization. It depends on your business goals, the tools you’ve selected, and the strategy you’ve implemented. 

But when it comes to measurement, we can outline key factors to consider. Outcomes — for the customer, for the employees, for the business —  should guide how to measure your digital transformation’s success. 

  • Customer experience and value. It’s likely that you’re already measuring customer satisfaction or customer experience. For example, are you seeing an increase in NPS scores since your digital transformation strategy? What feedback are you hearing from customers on the frontlines? What is your field team expressing? Work with your leadership team to develop KPIs around your customers to understand if you are delivering more value to them. 
  • Employee engagement (and performance). Digital transformation strategies can have an incredible impact on employee engagement and performance. With pulse surveys, open forums for feedback, and employee engagement tools, you can measure the impact of your strategy.
  • Agility and innovation. This can be hard to measure, but is the business more able to adapt and pursue opportunities in a rapidly changing and ambiguous environment? If the answer is no, the transformation is not a success.

The following are often used to assess technology implementations — and they can provide useful information. But, if transformation is your goal, these metrics will fall short.

    • Time saved. It’s probable that the technologies implemented will likely save your workers’ time. Perhaps you’ve set a goal around productivity and time saved. Consider measuring the before and after of your digital transformation. 
    • Usage and adoption. How many active users are you seeing? What’s the adoption rate look like for certain tools? Create a key performance indicator (KPI) around real-time usage and adoption.
    • Availability and reliability. Technical pros, this one is for you. Are you seeing a better flow efficiency? Maybe you’d like to measure the mean time to repair bugs and mean time to detect bugs? There are always new advancements coming out. Keep a keen on operational efficiency when trying out new advancements in technology.

Starting transforming your organization 

Digital business transformation starts with decision-making around what's best for your organization. You can examine your business processes to build an effective digital transformation strategy. 

We're living in an age of digital disruption — and change is more prevalent than ever. We know that the digital age brings some bumps in the road. But working with your business leaders, you can put your digital transformation efforts to the test.

And with the right resources, tools, and teams, you can create a successful digital transformation. Transformation can bring revenue growth, new products, and better business outcomes. But it starts with a solid digital strategy. 

When it comes to navigating a big change, we know it can be messy. Consider ways you can partner with BetterUp to help empower your workforce to better navigate uncertainty.

Your employees have the capability to reach their fullest potential to help drive positive change. 

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Published January 26, 2022

Madeline Miles

Madeline is a writer, communicator, and storyteller who is passionate about using words to help drive positive change. She holds a bachelor's in English Creative Writing and Communication Studies and lives in Denver, Colorado. In her spare time, she's usually somewhere outside (preferably in the mountains) — and enjoys poetry and fiction.

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