Have you participated in or led a digital transformation at your organization? Was it really a transformation, or was it perhaps just a series of initiatives that sounded nice, felt good, and checked a few boxes?

I’ve seen many executives who’ve tried in earnest to digitally transform their organization, but were forced to settle for a set of random projects that don’t truly qualify as transformative. I’ve also seen some well-meaning but misguided initiatives fall short of embodying an effective transformation.

Sorry to break it to you, but swapping an analog clock for a digital clock in the lobby does not qualify as a digital transformation.

IT initiatives often disguised as digital transformations:

  • Programs made up of ERP upgrades, website updates, cloud migrations, or similar technology enhancement (the list is endless). These projects are typically operational, and not focused on the customer experience.
  • Technology projects solely picked up because they are funded, thus creating an opportunity for the delivery team to shine. A shrewd exec can scoop up almost any bankrolled program and, just because it’s the hot buzzphrase, call it a “digital transformation.”
  • Technology projects that neglect to change the organization’s business model. True transformations require breaking down legacy business silos. The customer doesn’t care about internal business divisions. They want a seamless experience. Give them one or they will go elsewhere.
  • Technology projects that overlook the hearts and minds within the organization. A close-minded organization doesn’t take the time to develop the skills required to enable the vision, and avoids making hard decisions about who to hire, who to retain, and who to let go in order to have the right people on the bus.

These examples and many others can materialize if an organization is accustomed to thinking “in-out” as opposed to “out-in.”

I once visited a small IT development consulting company that employed what they cleverly dubbed “Digital Anthropologists.” An anthropologist studies humans. This company sent their Digital Anthropologists into the field to study how humans interacted with their environment, digitally and non-digitally, and how those experiences impacted their feelings and behaviors. They sought to understand what the customers wanted to accomplish and how this could be done seamlessly. It was truly an “out-in” orientation. Unfortunately, this approach often is at odds with what business silos are trying to accomplish.

A real digital transformation includes:

“Out-In” Thinking

Garner a deep understanding of your current and potential customers. What might be important for you isn’t necessarily important for them, and vice versa. Get data whenever possible, and don’t limit yourself to analytics from your current digital footprint. Gut feelings are a good place to start, but data should drive decisions.

Envisioning the Organization’s Digital Future 

The most effective approach is to envision what the organization will look like in the future and plan your way backwards. The vision should build on the organization’s strengths, incorporate innovation, engage employees, consider external threats, and evolve over time. As with all visions, a digital one needs to be developed and executed methodically to ever be realized.

Reevaluating the Business Model

Given your new digital future, you will likely need to reinvent the business model of the organization. This is not for the faint of heart. The customer experience, internal operations, and the organization’s economic formula are all on the table. A few years back, Forester reported that almost 90% of customer experience executives believed customer experience is a top organizational strategic priority, but less than half had a company-wide program. A real transformation needs to reevaluate the business model, not just the digital silo.

Engaging the Organization

True digital programs can only succeed if they bring together people from across the entire organization. Small changes, like some of the fake digital transformations above, can be done within silos. But a real digital transformation must garner the hearts and minds of people representing the entire enterprise, if it is going to be truly meaningful and successful.

Entrepreneurial Design

Risks are high and funding is hard to secure. You have to keep the vision in mind, experiment, build prototypes, and prove out a market demand. You will pivot on a weekly basis as you will be learning what works and what doesn’t; what has changed internally and externally; and you may need to change the vision based on this learning. So, if you have secured a large sum of money for a large project, you are very possibly working on a fake digital transformation, like an improvement project.


To truly transform, you might need to give up some of what you currently have for the greater long-term good of the organization. The organizations who are willing to transform know that some sacrifice is needed. It is either that or let a current competitor (or rising star) eat your lunch. As a digital transformation champion, your role is to take strides towards a daring new future.