What a Global Digital Transformation Taught Me About Leadership (Part 1)

Author's Note: Throughout my career, I've had the privilege of leading creative and digital transformation initiatives across hospitality, financial services, retail, and consumer brands. Looking back, no experience shaped my leadership philosophy more than helping transform Best Western Hotels & Resorts' global digital experience.

This two-part series isn't intended to be a case study about a website redesign. It's a reflection on the leadership lessons I gained through that experience—lessons about collaboration, organizational change, Agile, people development, and continuous learning that continue to influence how I lead creative teams today.

While these experiences were shaped by my time at Best Western, the principles extend well beyond a single organization and remain just as relevant in today's rapidly evolving digital landscape.

Part One: Building Teams Before Building Technology

When people hear the phrase digital transformation, they usually think about technology.

Cloud migration. Platform modernization. Artificial intelligence. Automation. New content management systems. While those elements certainly matter, I've come to believe they're only part of the story.

The most successful digital transformations aren't defined by the technology they implement—they're defined by how effectively they bring people together around a shared vision.

That realization came during my time at Best Western Hotels & Resorts, where I had the opportunity to help lead one of the organization's most ambitious digital initiatives: bringing country-specific websites together into a single global digital platform.

The technical challenge was significant. Every market had its own business priorities, customer expectations, languages, workflows, and stakeholders. Success required much more than replacing dozens of websites with one platform. It required aligning people from around the world around a common purpose while still respecting the unique needs of each market.

Looking back, I'm incredibly proud of what our team accomplished. But the greatest outcome wasn't the platform we launched.

It was how the experience transformed me as a leader.

Much of that growth was influenced by two exceptional leaders—Greg Adams, Senior Vice President & Chief Digital Officer, and Felipe Carreras, Managing Director of eCommerce. They challenged me to think beyond design and technology and demonstrated that lasting digital transformation begins with leadership, communication, and trust.

Digital Transformation Is Really Organizational Transformation

Technology is often the most visible part of a digital transformation, but in my experience it's rarely the most difficult. The real challenge is aligning people around a shared vision.

Our global website initiative wasn't simply about consolidating country websites into one platform. It required balancing global brand consistency with local market needs, establishing governance without creating unnecessary bureaucracy, defining shared design standards, and building trust among teams that had previously operated independently.

As a UX and Creative leader, I learned that success wasn't measured solely by how polished the interface looked. It was measured by how effectively people collaborated to create it.

Working alongside stakeholders across England, France, Italy, and Germany taught me that successful collaboration extends far beyond project plans and status meetings. Every market brought its own language, cultural nuances, business priorities, customer expectations, and communication styles.

I learned to adapt how I presented ideas, listen carefully to local concerns, build trust across diverse teams, and navigate conversations with senior executives whose perspectives were shaped as much by their local markets as by the needs of the global brand.

Some stakeholders were direct and decisive. Others valued discussion and consensus before making decisions. Some focused on protecting local business requirements, while others prioritized global consistency, operational efficiency, or speed to market.

Those experiences strengthened my ability to influence executive stakeholders, balance competing priorities, and lead with empathy while still moving complex initiatives forward.

Perhaps the most important lesson was this:

Digital transformation is as much about cultural transformation as it is about technical transformation.

Technology creates the opportunity for change.

People determine whether that change succeeds.

That lesson has stayed with me throughout every leadership role I've held since.

Agile Isn't About Speed—It's About Learning

Before joining Best Western, I viewed Agile primarily as a project-management methodology.

During my time there, the organization made a significant investment in transforming how we worked by embracing Agile across our technology and digital teams. This wasn't simply the introduction of a new process—it represented a fundamental shift in culture. Product managers, developers, UX designers, business analysts, QA engineers, and digital leaders all learned together as we adopted Agile principles and built a common language around collaboration, planning, transparency, and continuous improvement.

Experiencing that transformation firsthand changed the way I think about leadership.

I realized Agile isn't really about moving faster.

It's about creating an environment where teams can learn faster.

Rather than attempting to define every requirement upfront, Agile encourages teams to establish a clear vision, break large problems into manageable pieces, gather feedback early, and continuously improve based on what they learn.

Working alongside cross-functional teams reinforced something I still believe today: iterative progress consistently outperforms the pursuit of perfection.

Quality doesn't come from predicting every answer before the work begins. It comes from learning continuously, adapting quickly, and creating feedback loops that allow teams to improve over time.

More importantly, Agile changed my understanding of leadership.

A leader's role isn't to control every decision or prescribe every solution. It's to create clarity around the objective, remove obstacles, empower people to solve problems, and foster an environment where experimentation and learning become part of the team's culture.

I've carried those principles into every creative organization I've led. Whether launching omnichannel campaigns, improving customer experiences, implementing creative operations, or building UX programs, I've consistently found that teams who learn together outperform teams that simply try to execute faster.

CliftonStrengths Changed How I Lead People

One of the most influential experiences during my time at Best Western had nothing to do with technology.

It was being introduced to CliftonStrengths.

Like many managers earlier in my career, I believed leadership meant identifying people's weaknesses and helping them improve.

CliftonStrengths challenged that thinking.

Instead of asking, "How do we fix people?" it encouraged us to ask, "How do we help people do more of what they naturally do best?"

That simple shift transformed how I build creative teams.

I stopped trying to make everyone think alike. Instead, I began looking at teams as collections of complementary strengths.

Some people naturally excel at vision and strategy. Others thrive on execution and operational excellence. Some bring structure and organization. Others generate ideas, challenge assumptions, or build relationships with remarkable ease.

Creative organizations need every one of those strengths.

Over time, I became much more intentional about assigning work, coaching employees, building cross-functional partnerships, and helping people find opportunities that aligned with their natural talents rather than forcing everyone into the same mold.

Just as importantly, CliftonStrengths helped me better understand my own leadership style.

It taught me that self-awareness is one of the most valuable qualities a leader can develop. Understanding where I naturally added value also helped me recognize where I needed to rely on others. That perspective made me a more collaborative leader and reinforced the importance of building teams with diverse perspectives rather than identical skill sets.

The best leaders don't surround themselves with people who think exactly like they do.

They build environments where different strengths come together to produce better ideas, stronger collaboration, and better outcomes than any individual could achieve alone.

Looking Ahead

The lessons I learned through digital transformation, Agile, and CliftonStrengths fundamentally changed how I build teams and approach leadership.

But they were only the beginning.

In Part Two, I'll explore how The 7 Habits of Highly Effective People, leading people through organizational change, and embracing continuous learning shaped the leadership philosophy I continue to apply today.

Because while technology will continue to evolve, the principles of great leadership remain remarkably consistent.

They begin—and end—with people.

Next in the Series: What a Global Digital Transformation Taught Me About Leadership – Part Two: The Leadership Principles That Endured