Dancing with Paradox to Navigate Digital Transformation
Dear friends,
Welcome to the second issue of our newsletter, the Threshold.
We live in a world of mounting tension and accelerating change. Global headlines remind us daily: polarization, disruption, and uncertainty are no longer the exception—they are the environment we operate in. What happens on the world stage—wars and alliances, breakthroughs and breakdowns—is mirrored in boardrooms, in teams, and in every digital transformation journey.
In the face of such complexity, it’s tempting to search for simple answers. But transformation isn’t linear—and neither is leadership. It requires holding paradoxes: speed and reflection, structure and fluidity, ambition and humility.
This is the work of Digital Wisdom.
It’s the glue that connects the human to the technological, the visionary to the practical, the individual to the collective. It’s what allows us to not only navigate polarities—but to embrace them as a source of creativity and transformation.
And while we may not be able to change the course of world events, we can begin with one—ourselves. One person shifting perspective. One team practicing a new way of working. One leader choosing wisdom over reactivity. These are the ripples that move outward—and become waves of change.
In this issue, we explore how to step into that tension with clarity and courage—so we can lead not from fear or force, but from grounded awareness and forward wisdom.
Barbara Wittmann & The Digital Wisdom Collective Team
This is a sneak peek at my upcoming blog series about what I learned as an interim Global IT Director. Stay tuned for more...
I’ve partnered with IT and business leaders for over two decades—first as an implementation consultant, then as a strategic advisor and coach. Last year, I stepped into the role of Interim Global IT Director for a fast-scaling global company. This experience didn’t just confirm what I already knew—it challenged my expectations, opened up new levels of understanding and, in many ways, transformed how I think about leadership and technology. In my next couple of blogs, I’d like to share some insights that I picked up along the way, beginning today with a focus on the polarities we face as digital leaders.
Common polarities we encounter in IT
My experience at the helm showed me that some core polarities run deep in IT leadership, and how essential it is to consciously navigate them. I learned that when you truly embrace the complex, the contradictory, the confusing—magic can happen.
🔥 COST OR CATALYSTIn my first CEO meeting, I faced a familiar question: "How does IT save us money?" This challenge reveals a fundamental tension that every IT leader faces: are we merely a cost center, or are we truly a catalyst for transformation? To begin to answer this question, we began a careful analysis of redundant tools and forgotten licenses, a process which uncovered millions in potential savings through a 10% reduction in software spending.
It turned out that this process wasn’t just about cutting costs—it was about earning the right to tell a bigger story about our team and its impact. As we got more comfortable with and familiar in big picture spaces, our capacity for affecting org-wide impact grew.
🧰 FIX OR BUILDIT leaders and teams feel a constant pull between two critical functions. On the one hand, these teams are field urgent technical issues and requests in the immediate term from a huge variety of internal customers. On the other, they need to build and implement strategies and roadmaps that bring align the organization around consistent strategies and systems that support sustainable growth. Neither of these core functions can live without the other, and balancing this was a central theme and challenge in my time leading the IT team.
🙌 OWN OR COLLABORATEMy time serving as Interim Global IT Director obviously coincided with an explosion in new technology, concentrated in the generative AI space. This meant that our team was flooded with requests and ideas for new pet projects and transformation initiatives coming from all corners of the company. While this initially felt overwhelming, we quickly learned that we needed to build a balanced approach that both encouraged innovation and initiative, while creating some structure to manage the innovation process, especially as it impacted our team’s strategies, budget and roadmap.
📚 INDIVIDUAL OR SHARED NARRATIVESCommunication and storytelling can make or break any transformation initiative. While we were able to achieve a lot as a team, I knew that impact would be super-charged if we could more meaningfully align across the company. We aimed to aligning our strategies and goals with those of the company, and other teams, to make sure we were all speaking the same language. This allowed us to clearly tell the impact story of our work and ideas in ways that resonated across the company, building support and momentum from within.
The power of one
As Interim Global IT Director, I became living proof that one person can shift the narrative. My aim was to bring a refreshed mindset to the team: one focused on possibility rather than limitations. In taking this approach, we were able to transform:
A cost conversation into a value creation opportunity
Siloed thinking into cross-functional collaboration
Reactive responses into strategic leadership
The key wasn't having all the answers. It was having the courage to ask different questions and the wisdom to invite others into a new way of thinking.
A new paradigm for leaders
Do you want IT to be seen as a cost center or as a catalyst?
Do you want a seat at the table or to stay stuck in the back office?
Do you want to wait for change or shape it?
Digital transformation starts with these choices.
It was with these principles in mind that drove me to create the six-month Digital Wisdom Collective program, which is designed for leaders who are ready to dance with these polarities. We don't offer simple answers—we offer the wisdom to navigate complexity with confidence. The question isn't whether your organization faces these tensions—it's whether you're ready to lead through them.
Get in touch to learn how you or your team can join our program's June 2025 cohort and master the art of navigating polarities in digital transformation.
News & updates
New cohorts kick off in Summer 2025! The next cohort for our six-month Digital Wisdom Leadership program starts in June ☎️ Learn more and set up an intro call here
Want to get a glimpse into the Digital Wisdom Collective? This month we’ll kick off regular Digital Wisdom Circles, diving into special topics around wise & authentic leadership for the digital age. Read on and register here.
New podcast interview 🎙️ Barbara was featured on Christopher Salem’s Sustainable Success Show talking about Why Digital Transformation Fails—And How Digital Wisdom Can Save It. Check it out here.
From our blog ✍️ Check out our Mindset Monday deep dives about the transformative power of Openness and Active Listening in leadership and in life.
New Forbes Features ✅ Barbara was featured in two Forbes Business Council articles on sustainable practices in retail and the secret to thriving innovation teams.
What we're reading & listening to
From CIO: Don’t underestimate the power of mindset and non-technology factors in digital transformation efforts. Read more here…
From CIO, nearly half of IT leaders operate within a culture of fear. What might this do to innovation and growth? Read more here…
The Business Movers podcast goes deep to explore how successful entrepreneurs built their business. We’re inspired by stories like that of Richard Branson, who found new ways to navigate the paradox of market expectation and innovation opportunity. Listen here...