What a Global Digital Transformation Taught Me About Leadership (Part 2)

Author’s Note: his article is the second in a two-part series reflecting on the leadership lessons I learned while helping transform Best Western Hotels & Resorts' global digital experience.

In Part One, I explored how digital transformation, global collaboration, Agile, and CliftonStrengths fundamentally changed the way I build teams and approach organizational change. In this article, I shift from how we transformed to how those experiences transformed me as a leader.

The principles that follow continue to shape how I approach creative leadership, navigate change, develop high-performing teams, and build cultures rooted in trust, curiosity, and continuous improvement.

Part Two: The Leadership Principles That Endured

In the first article of this series, I shared how a global digital transformation changed my perspective on collaboration, Agile, and people development.

Those experiences taught me how to build stronger teams.

The lessons that followed taught me how to become a better leader.

Looking back, I realize the greatest investment Best Western made wasn't simply in technology. It was in developing leaders. Through mentoring, leadership development, and a culture that encouraged continuous learning, I was exposed to ideas that have influenced every leadership role I've held since.

The technology has evolved dramatically over the years. Platforms have changed. Customer expectations have shifted. Artificial intelligence is reshaping creative work in ways few of us could have imagined.

Yet the leadership principles I learned during that period remain just as relevant today as they were then.

The 7 Habits Made Leadership More Intentional

One of the most influential leadership development experiences during my time at Best Western was being introduced to The 7 Habits of Highly Effective People by Stephen Covey.

Like many professionals, I had heard of the book before. Reading it as part of a leadership culture, however, was an entirely different experience.

The principles quickly moved beyond theory and became practical tools that influenced how I approached projects, relationships, and decision-making.

"Begin with the End in Mind" became far more than a productivity exercise.

It became the foundation for every meaningful creative initiative.

Before discussing deliverables, timelines, budgets, or technology, I learned to start by asking better questions.

• What problem are we solving?

• Who are we solving it for?

• What business outcome are we trying to achieve?

• How will we know if we've been successful?

Those conversations created alignment long before the first wireframe, creative brief, or project plan was developed. Teams that understand the destination make better decisions throughout the journey.

Another habit that profoundly influenced my leadership was "Seek First to Understand, Then to Be Understood."

Creative leaders spend much of their careers presenting ideas, defending recommendations, and persuading stakeholders.

The best leaders I've worked with spent even more time listening.

That lesson became especially valuable while working with stakeholders across multiple countries. It was easy to assume that resistance to an idea meant someone didn't understand the strategy. More often than not, they understood something about their market, customers, or business that I hadn't fully considered.

Listening didn't mean agreeing with every request.

It meant understanding the motivation behind the request before deciding how to respond.

Over time, I learned to separate the solution someone was proposing from the problem they were trying to solve. That shift changed the quality of every stakeholder conversation I had going forward.

The habit of "Think Win-Win" also became increasingly important.

Balancing global brand standards with regional business needs wasn't about one side winning and the other losing. It required finding solutions that advanced the organization's broader goals while still respecting local expertise and customer expectations.

Leadership isn't about winning arguments.

It's about creating alignment.

Leading Change Means Giving People Context

One of the most important lessons I learned from Greg Adams and Felipe Carreras had very little to do with technology.

It was understanding that people rarely resist change itself. They resist uncertainty.

Every transformation creates questions.

• Will my role change?

• Will this make my job harder?

• Will my expertise still matter?

• Will local needs still be represented?

If leaders fail to answer those questions, uncertainty quickly becomes resistance.

The best leaders don't simply announce change. They explain it. They communicate the vision repeatedly. They provide context. They invite feedback. They acknowledge concerns instead of dismissing them.

Most importantly, they help people understand how their work contributes to something larger than themselves.

Throughout my career, I've carried that lesson into every organization I've helped lead.

Whether introducing Agile workflows, reorganizing creative teams, implementing new technologies, establishing governance, or launching new operating models, I've learned that communication is every bit as important as execution.

People don't commit to change because they're told to. They commit because they understand why it matters.

Leadership Is Built Through Trust

One lesson that isn't often discussed in project retrospectives is trust.

Large digital transformations involve uncertainty. Priorities change. Budgets shift. Timelines move. New information emerges.

When trust exists, teams adapt together. When trust is missing, every change becomes a negotiation.

The strongest leaders I worked with created environments where people felt safe asking questions, admitting mistakes, challenging assumptions, and offering better ideas.

That kind of trust doesn't happen by accident. It's built through consistency. Through transparency. Through keeping commitments. Through treating people with respect even during disagreement.

I've found that creative organizations are no different.

People produce their best work when they feel psychologically safe, understand the mission, and know their voices are valued.

Leadership isn't about having all the answers.

It's about creating an environment where the best answers can emerge.

Great Leaders Never Stop Being Students

When I reflect on my years at Best Western, one theme connects every lesson I learned.

Curiosity.

I arrived believing I was there to help build better digital experiences.

Instead, I found myself surrounded by leaders who cared just as much about developing people as they did about delivering products.

Greg Adams and Felipe Carreras created an environment where learning wasn't viewed as an occasional training event.

It was simply how we worked.

We learned Agile together.

We explored CliftonStrengths together.

We challenged ourselves through The 7 Habits of Highly Effective People together.

We talked about leadership as often as we talked about technology.

That experience fundamentally changed how I think about professional growth.

I stopped viewing leadership as something you eventually master.

Instead, I began to see it as a continuous practice of learning, adapting, and improving.

Every project became an opportunity to ask better questions.

Every stakeholder conversation became an opportunity to become a better communicator.

Every difficult situation became an opportunity to develop more patience, empathy, and perspective.

That mindset has stayed with me throughout my career.

When I later built UX organizations, established creative operations, introduced brand governance, implemented Agile workflows, or coached multidisciplinary teams, I wasn't simply applying technical experience.

I was applying a habit of continuous learning.

Today, we're entering another period of extraordinary change.

Artificial intelligence is transforming creative workflows.

Customer expectations continue to evolve.

Organizations are moving faster than ever before.

The leaders who succeed won't necessarily be the ones who know the most.

They'll be the ones who continue learning.

They'll remain curious.

They'll adapt.

They'll help others grow alongside them.

I believe that's the true competitive advantage of leadership.

Final Thoughts

When people ask me about my time at Best Western, they often assume the biggest takeaway was the successful launch of a global digital platform.

While I'm proud of what we accomplished, that's not the first thing that comes to mind.

I think about the mentors who invested in me.

I think about the conversations that challenged my assumptions.

I think about learning to lead across cultures, disciplines, and personalities.

I think about discovering that great leadership has far less to do with authority than it does with influence, empathy, and trust.

Years later, I've forgotten many of the project plans, meetings, and technical decisions.

I haven't forgotten the leadership lessons.

Those lessons influenced how I built creative organizations at Best Western, how I led brand and creative teams at Alliant Credit Union, and how I continue to approach every opportunity today.

Technology will continue to change. Platforms will evolve. New methodologies will emerge.

Artificial intelligence will reshape how creative work gets done.

But leadership is, and always will be, about people.

It's about creating clarity when others see uncertainty. It's about building trust before building solutions. It's about developing people while delivering results.

And perhaps most importantly, it's about remaining curious enough to keep learning long after the project is finished.

Because looking back, the most valuable outcome of that global digital transformation wasn't the platform we launched.

It was the leader I became.