The Three Ts of Digital Transformation

The saying "Culture eats strategy for breakfast" has been around for decades, but when it comes to digital transformation, it's the cultural and human factors that are often overlooked and under-planned. In our race to modernize processes and transform customer experiences, understanding the cultural impact of changes and how to address them is 90 percent of the game. But what does that really mean? In talking with successful leaders about digital transformation efforts, I've found the most common cultural shifts in successful technology leadership fall into three categories: timing, testing, and trust.

Without changing how they think about timing and decision making, companies will just be delivering new technology, not digitally transforming. Accelerating development cycles and increased user expectations require a rethinking of how user testing, input, and feedback are involved in the project management process. More than even before, the uncertainty of technology and the potential impact of artificial intelligence and other technologies demand more than just credibility but trust in leadership for digital transformation to be successful.


How quickly will decisions be made and how often will they be reevaluated? For companies that are serious about digital transformation, technology project budgeting and evaluation is moving from an annual to a quarterly cadence. The advantage of this approach is that it gives greater flexibility and ability to adapt to both changes in the market and evolutions in technology on an ongoing basis. The challenge is that it requires business cases, objectives, key performance indicators, and milestones to be more streamlined and easily measurable so progress on an evolving project can be tracked with limited pain and suffering for the team. Otherwise, you risk analysis paralysis.

Keys for setting a new timing cadence include focusing on a few key metrics, automating the data gathering and measuring for those metrics as much as possible, and, up front, setting a threshold—either in budget dollars or volume of staff or transactions impacted—for what is a big decision or change in direction.


In line with a more accelerated decision timeline is making user testing more of an ongoing feedback loop. I've never heard a technology leader say he wished he'd gotten user feedback and input later or less often. In contrast, I often hear that user testing is separate from the overall planning and deployment process, which is a mistake. Involving nontechnical users throughout the requirement defining, planning, and development processes does more than just help with buy in and user adoption. It helps tech leaders identify blind spots that they might have missed and reduces the risk that big gaps between what is needed and what is actually delivered aren't discovered before go-live.

For some companies, this means shifting from a presenting mind set to a proposing mindset, bringing a broad group of constituents into the process before a plan is fully designed, and including them on an ongoing basis. For effective transformation to happen, you need not just user buy-in but user championing.


Finally, and perhaps most importantly, vital to the success of any digital transformation journey is trust. Trust is far more than the ability to deliver as promised and on schedule. It's the willingness of your team—and those not on your team—to take a leap with you even when they're not sure what lies ahead.

In talking with successful leaders, I've found there are simple things they do consistently to build trust and win the benefit of the doubt. First, they're authentic human beings, sharing enough of who they are as people to make them more than a title or an email address. Second, they take responsibility for their mistakes and are sometimes willing to fall on the sword, even when it's not necessarily their fault. Third, they admit weakness, making it clear when they don't have a good answer to a question, don't know something, or are facing a big challenge and need help. Being authentic, fallible, and sometimes uncertain leads by example and provides a more open environment where concerns, complaints, and risks can be more openly raised and resolved.

Every company's definition of digital transformation is different, and so are their measures of success. However, it's obvious that transformation is about much more than technology, and subtle shifts in culture can be the difference between real success and just checking the boxes. Timing, testing, and trust are key stepping stones for a successful journey.

Rebecca Wettemann is CEO and principal at Valoir (, a technology industry analyst firm focused on the connection between people and technology in a modern digital workplace.