Is A × B the Same as B × A in Digital Transformation?
I recently added another question to my ever-curious mind: When it comes to digital transformation, is A times B the same as B times A? Does the order really matter?
As I progress through the Innovation Leadership Course, part of the Digital Transformation in the AI Era Certification at MIT Professional Education, I’ve made a striking discovery: the journey toward digital transformation doesn’t always start from the same point.
In many digital transformation programs I’ve attended, the topics of culture and leadership are typically addressed at the end. I don’t know the reasoning behind that design, but to me, it subtly suggests something about how these elements are prioritized.
At MIT, however, the experience is quite different. After nearly three months in the program, we haven’t yet started studying AI technologies or digital systems. Instead, we’ve been focused on leadership, culture, and human dynamics—the core principles behind any transformation.
For me, these subjects feel natural; they’re part of my daily work. But as I engage with my classmates—most of whom come from technical and IT backgrounds—I’ve realized how challenging these areas can be. One of my peers shared candidly, “These topics are very difficult for me.” Yet she quickly added that she sees their value, because one of her greatest challenges in transformation projects isn’t technology—it’s people: aligning diverse stakeholders, each with their own perspectives, toward a shared vision.
In our leadership module, we’ve dedicated time to exploring our own leadership skills. I was pleasantly surprised to see how many of my classmates—experienced professionals—were willing to be vulnerable by admitting they struggle with receiving feedback or sharing meaningful personal moments. It reinforced something I’ve always believed:
Leading transformation is not just managing change.
It’s about leadership, relationships, communication, and empathy.
These human elements are not always reinforced when organizations face the daunting task of becoming more digital and agile—but they should be.
Three Insights to Start Digital Transformation on the Right Foot
So here are three things organizations can do to address the cultural and leadership variables of digital transformation at the beginning of the equation—not at the end.
1. Evaluate More Than Readiness—Evaluate Trust
Beyond assessing organizational readiness or digital literacy, organizations should also take time to evaluate how people truly feel about leadership, communication, and trust.
Experts such as Patrick Lencioni and Frances Frei have demonstrated that trust is central to successful teams. As Frei states, leaders who start by earning trust enable others to take the risks that change requires. (Adapted from Frances Frei’s TED Talk, “How to Build (and Rebuild) Trust”)
Trust enables people to voice their concerns, share their fears, and engage meaningfully in change. Without trust, even the most advanced technology will have trouble taking hold.
2. Adopt a Strategically Pessimistic Mindset
Prevention is key.
Organizations should cultivate what I like to call a strategically pessimistic mindset—deliberately using premortem strategies to anticipate potential challenges before they arise.
I recently talked with a client who mentioned that their company spent over 400 hours of manpower fixing issues that came up after a digital transformation rollout. Of course, premortems can’t catch all problems—but the process itself encourages creative thinking. It helps teams identify potential pitfalls and develop preventive or corrective action plans beforehand.
Being strategically pessimistic isn’t about expecting failure—it’s about preparing for it with insight and imagination.
3. Manage the Extremes of Reaction Effectively
In transformation projects, leaders often encounter two extremes:
Those who believe that technology—or AI—will magically solve everything, creating unrealistic expectations.
And those who resist change entirely, holding fast to the way things have always been.
Both extremes can be harmful. Our recommendation is to involve experts in group dynamics, leadership, and change psychology from the beginning of innovation projects. Because innovation doesn’t happen in isolation—it occurs through teams.
Teams that communicate openly, navigate conflict effectively, and align around a shared purpose don’t form “by osmosis”. They are the product of intentional, guided interventions that strengthen collaboration and trust.
While some leaders naturally balance technology and people, that combination of talents is rare. Partnering with external experts who can observe, coach, and support both individual and team dynamics can make the difference between a transformation that thrives—and one that falters.
In Conclusion
Digital transformation isn’t a simple formula where A × B always equals B × A.
When culture and leadership come first, transformation stops being just a technological project—and becomes a human journey of adaptation, connection, and growth
Written by Annie-Mariel Arroyo, PH.D
Dr. Annie-Mariel Arroyo-Calixto is a practiced organizational psychologist with more than 28 years of professional experience in organizational change and leadership development. Dr. Arroyo is the founder of Culture To Fit, where for the past 22 years, she has helped leaders build or reshape their organizational culture and lead transformation. She is a seasoned leadership educator and a renowned executive coach known for her ability to guide leaders in gaining deeper insights and self-growth.
