
Digital transformation means a lot of different things to different people. But what we’ve found is that while the conversation often veers toward technology, technology is rarely the sticking point. The real challenge is that there’s not enough focus on the human element—the people leading the change in an organization. At SYPartners, we believe that transformation, digital or otherwise, is an ongoing pursuit—not an end game. As technology and the world continue to transform at an increasing pace, organizations need to build cultures that can constantly transform, too.

80 leaders joined us recently at our office in New York (as part of the Fast Company Innovation Festival) to investigate what it takes for a culture to thrive in today’s digital world, and discuss what gets in the way and how to get unstuck. Here is what we learned:
et’s start with the context: Digital transforms everything. It sparks new business models (e.g., Uber upended the taxi business by connecting people through their smartphones). It radicalizes our notions of speed and scale (e.g., in its first four years, Airbnb built the world’s largest hotel inventory across 89 countries, as compared to the several decades it took major hotel chains to do the same).
Digital transforms how companies create value (consider: the top five U.S. companies by market cap are all tech giants). And of course, digital transforms consumer expectations (Shouldn’t everything—from my banking experience to my thermostat—be beautifully designed, highly engaging, fast and convenient?).
All of these shifts have implications for how people and organizations must operate. And while each digital transformation is unique to the company undertaking it, we’ve found a common set of attributes that characterize a digital-ready culture:
When reflecting on their cultures against these four attributes, one-third of the leaders at our workshop said deep agency was what their culture most needed to work on. But perhaps what’s most interesting is what’s behind their answers. Some themes emerged across all four attributes when leaders elaborated on their responses.

For a group of leaders interested in trying new things and pushing the boundaries (they signed up for an innovation festival, after all), it’s clear that fear is a barrier in many of their organizations. Leaders shared concerns related to everything from fear of failure and not being perfect, to fear of change altogether, with statements such as: “People got used to hearing ‘no’ or ‘that can’t happen.’ They’re afraid to ask questions,” “There’s no appetite to do new things, or even old things in new ways,” and “We’re afraid of pushing things out too soon.”
As senior leaders look to transform their culture, this means mitigating fear is an important consideration, and it’s worth asking:
In any group of people, at work or otherwise, it’s hard to prevent silos from forming. Groups are how people bond and how work gets done. But as leaders expressed, the silos that crop up between functions—and even between leadership and everyone else—prevent the speed, ingenuity, agency and collaboration that are so critical today.
Sentiments like these were common among the group, and likely don’t feel foreign for many organizations: “Even in integrated teams, work gets siloed in functions, slowing us down,” and “Goals are closely held at the top, so it’s difficult to promote agency when few people have all the information needed.”
As a leader, ask yourself:

Culture can feel ambiguous—all encompassing and yet elusive. And that makes it hard to change. One starting point is through rituals: recurring acts that disrupt old patterns to shape new behaviors. Read more about building rituals in Fast Company’s article about our workshop.
And for a broader look at digital transformation, read our point of view on four critical steps leaders should take—from defining vision all the way to shaping culture.


