Digital transformation: 5 ways to create a realistic strategy

Digital transformation requires organizational alignment and a shared vision. Consider this expert advice as you design your strategy
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Rocket coming out of computer to represent moving faster in digital transformation

Digital transformation is the giant umbrella that encompasses how people work in today’s economy. It’s typically a multi-faceted initiative that goes beyond simply modernizing applications. It encompasses everything that represents the way a business needs to operate in 2022 to deliver exceptional customer experiences.

This type of initiative is a shared responsibility. It starts with the CEO, who must be a champion of change, but it must also involve other leaders throughout the organization working together to make transformation happen. Sometimes it will require a Chief Digital Officer to coordinate the response, but one fact is consistent: Without alignment throughout the organization, the effort is likely to fail. And it might just take the company down with it.

[ Also read Digital transformation: 5 reality checks before you take the plunge. ]

That’s why successfully transforming your organization is a big task that can be tough to achieve. You need a plan, clear direction, and a way to make the journey less intimidating.

Here are five steps to get started.

1. Identify your long-term transformation goal

Where do you want your company to be in one, three, or five years? What’s your end target? What’s driving your desire to digitally transform?

Something like “I want to move to the cloud” is not an acceptable answer. Your goal must be unambiguous and easy to define, or you may end up moving in too many different directions. And don’t feel like you need to shoot for the stars; while having an ambitious goal is good, it’s also OK to identify something that may be “good enough” to give you an achievable objective.

Whatever goal you focus on, remember that getting to the heart of the why is important to formulating the how. You need to know where you’re going – and why you’re going there – to ensure you’re on the right path.

2. Assess the current state of your organization

Once you’ve determined the destination, perform an honest assessment of where your company stands right now. Don’t focus on individual business units. Instead, perform a holistic assessment of every area of your organization.


  • What tools are being used? Do they include modern SaaS applications, or are your teams still beholden to legacy applications and hardware? Who’s using them?
  • How do your teams work together (or do they)?
  • What processes are teams using? For example, are your teams using agile development methodologies or are they still practicing waterfall?

Assessments identify areas of need and improvement. Their duration depends on several factors, including the size of your organization and the number of solutions you use. For example, assessing a company of 80 people could take a week, while assessing an organization with 80,000 employees could take a year.

Regardless of the timeframe, assessments are essential. They will ultimately save you time and allow you to map out your digital transformation plan.

3. Simplify your efforts by setting short-term achievable goals

Businesses that practice agile, iterative approaches to software development will tell you that the best way to approach seemingly insurmountable undertakings is to break the effort down into achievable chunks. Digital transformation is no exception.

During the assessment phase, you will uncover areas of immediate need and opportunities for easy wins. You’ll also discover projects or technologies that are of lesser priority – things that will be nice to have but can probably wait a few months or even a year before implementation.

The best way to approach seemingly insurmountable undertakings is to break the effort down into achievable chunks. Digital transformation is no exception.

Use these findings to scale your efforts back into more manageable individual projects, each with its own timeframe for completion. For example, depending on your immediate needs, you may decide to overhaul your cloud infrastructure within the first year or invest in an agile development platform within six months. Meanwhile, you may opt to hold off on other lower-priority investments until year two or beyond.

All of these may be key components to reaching your goal, but some may be more important and easily manageable than others. Focus on those initially to get some quick wins that will help you build toward your end destination.

[ Read next: Cloud strategy: What CIOs really want from cloud providers ]

4. Budget appropriately

Digital transformation is a complex undertaking and developing accurate budget estimates can be challenging. Indeed, since many organizations tend to think of digital transformation solely in terms of its smaller pieces (cloud migrations, building modern applications, etc.), they tend to underestimate how much it will cost, only to be surprised later.

Your assessment can help you create accurate and realistic budget estimates. You’ll be able to determine which technologies you’ll need to invest in, for example. And you’ll get a good sense of how many teams you have in your organization, allowing you to budget for each and then scale that estimate up as necessary.

For instance, if your organization has ten teams, determine the cost it will take to transform one team and multiply it by ten. In short, apply the same rule you use to simplify your efforts to budget estimation.

5. Involve the entire organization

Finally, understand that digital transformation doesn’t just happen in the IT department; it happens in the C-suite, in cubicles, and in home offices. That means all stakeholders need to be aligned and in agreement with your company’s digital transformation goal.

The directive must come from management, but the work will happen throughout the company, often precipitating a major cultural shift toward new technologies and processes. In such cases, training and change management might be necessary to make users feel more comfortable with the new tools and processes. Leaders need to ensure that their teams are on board with the direction the company is moving in, and they should be willing to listen to feedback as the organization continues along its journey.

What that plan looks like is up to you. Digital transformation is different for everyone, and every company has its own objectives.

Meeting those objectives can be daunting. But by setting a goal, performing an assessment, breaking your plan into manageable pieces, budgeting realistically, and getting everyone to buy in, you will succeed.

[ Discover how priorities are changing. Get the Harvard Business Review Analytic Services report: Maintaining momentum on digital transformation. ]

Sarah McCasland is Chief Strategy Officer at Modus Create and an advocate of remote work, agile methodologies, and process improvement. Sarah has spent the last 10 years working with development teams to deliver products in a variety of industries while helping teams grow and excel.