Evaluating Digital Transformation Efforts

Digital Transformation

Today’s businesses are nearly all in a period of transition. If you aren’t old enough to have lived it, all you need to do is stream a few episodes of just about any ’90s sitcom to realize that business has changed at an overwhelming pace since then. This change continues today. Companies are all at varying points on the journey of digital transformation. Some are on the bleeding edge, while most are taking a cautious or catch-up approach. A few remain blissfully unaware, but these aren’t likely to last much longer.

Doing Digital Transformation Right

Digital transformation sounds great, and I’ve already implied that it’s essential. That’s not quite accurate, though. What’s essential is doing it right. A poorly executed digital transformation can be just about as harmful as burying your head in the sand and hoping things will stay just as they are. (They won’t.)

Digital Transformation as a Journey, Not a Destination

One of the first aspects of a good digital transformation plan is to understand its nature. Digital transformation isn’t a one-and-done initiative. How do we know? For starters, we aren’t using Windows XP (or, shudder, the dreaded Windows ME) anymore. Technology will continue to evolve, and your digital transformation will continue as it does.

It’s better to think of digital transformation as a journey. Where are you right now? Where are your competitors? What do you need to do, procure, or implement to catch up with (or better, pass) your competitors? Once you’ve implemented those steps, start to look at what’s next.

Digital Transformation as Mission Critical

Businesses today must understand that digital transformation is mission critical. It’s not something you spend money on when business is booming and squeeze out of the budget when money is tight. As soon as you stop failing to innovate, you give your competitors an open door to squeeze you out of the marketplace. Keep up with your digital transformation journey and stay competitive.

Digital Transformation as a Monitored Initiative

Many companies that do form a digital transformation plan fail to follow through in some way. It’s important to regularly evaluate the progress of your company’s digital transformation plan (be it quarterly or monthly). If digital transformation is a journey rather than a destination, a company working from a 3-year-old digital roadmap is doing it wrong.

Evaluating Your Company’s Digital Transformation Efforts

Evaluating your company’s digital transformation is a complex process. If your company doesn’t have an evaluation plan in place, you might be wondering where to start. Here’s how to get started evaluating your company’s digital transformation.

Ask Questions

It’s easy to assume that a process or plan that’s not making too much noise is working well, but doing this is a mistake. As you should with any process or plan, ask plenty of questions at regular intervals. What is and isn’t working? What new implementations are causing friction among the staff? Is that friction due to lack of training or because the technology solution is failing to deliver? Is the plan sticking to budget? What new technologies or platforms are developing that should be added to the company’s digital transformation journey? What is the right time to add those technologies? Is a particular technology failing to deliver or costing more than you’d budgeted for?

Asking good questions of the right people can greatly improve your digital transformation efforts. Don’t be afraid to include a wide range of departments and seniority levels in your questioning, either.

Review Business Needs

Just as available technology changes over the years, so do your business needs. A piece of software that was mission critical in Accounting 10 years ago may be peripheral or even obsolete today. Similarly, the business needs of your Data and Analytics department today are likely quite different (and far more evolved) than they were 20 years ago. That’s assuming you even had a data and analytics group 20 years ago!

An important part of reviewing your digital transformation efforts, then, is reviewing each department’s business needs and processes. Providing new solutions to long-solved problems isn’t the best bang for your buck. Be sure you understand the problems and processes of each business unit so you can focus your digital transformation efforts in the areas that matter most.

Get the Right People in the Room

A digital transformation plan that no one really knows about isn’t going to accomplish much. A review of that plan that no one knows about won’t, either. Your digital transformation evaluation efforts should include a pretty decent cross-section of organizational leadership. The CFO and CIO (or their delegates) are key stakeholders, as are the leaders of various business units. The CEO must be informed and on board for this to be effective, though of course the size of your organization will likely guide the CEO’s level of real involvement.

Buy-In Is Key

You need the right people in the room, but you also need buy-in from those people. If digital transformation evaluation is a new concept (or a loathed one), you may need to educate first. Get the key stakeholders in a room and use points like these (not this one, of course) to help them understand the mission-critical importance of this process.

Data Is Everything (Else)

You don’t want your review meetings to be based solely on feeling. If your meetings sound a lot like “Well, Jane in Accounting is frustrated using this new software” and “I believe implementing this new platform will really help!”, you need a heaping helping of data. Task your analytics group with researching the effects of a new software suite, for example, so you have real data to go along with feelings.


The digital transformation journey is never-ending, and your efforts to evaluate that journey are as important as they’ve ever been. If you could use a hand, whether with the journey or its evaluation, let’s start a conversation today.