When people hear I’ve led digital transformation initiatives totalling over $20 million, they often ask about the technology—what tools we used, what systems we implemented. But the real story isn’t in the tech. It’s in the people, the networks, and the meticulous planning that fuels innovation. Building high-performing teams, staying connected to industry leaders, and always having contingency plans have driven my success.
Transformation isn’t just a shiny presentation of results; it’s a gritty, complex process filled with unforeseen challenges, tough decisions, and relentless problem-solving. Let me share some lessons I’ve learned along the way.
Lesson 1: Always Have Plans A, B, and C
The hard truth about high-stakes projects is this: 90% of the time, things don’t go as planned.
I’ve seen it all—subject matter experts resigning mid-project, consultants backing out, and internal politics derailing change management efforts. The reality of transformation is that you deal with moving parts, human emotions, and unforeseen roadblocks.
This is why I’ve always approached projects with not just a Plan A but also Plans B and C. It’s not about being pessimistic; it’s about being prepared. For instance, our vendor failed to deliver key integrations on time during a significant PMS migration project. Because we had a contingency plan, we could pivot to a workaround that kept the project on track and minimized disruption to operations.
Having multiple plans isn’t just about logistics—it’s about mindset. When you think ahead and anticipate challenges, you build resilience. You’re not caught off guard; you’re ready to adapt. And just as importantly, you gain credibility with your stakeholders. When they see you’ve thought through the risks, you get their buy-in from day one.
Lesson 2: Evaluate Strategic Fit and Remove Resistance
Transformation starts with the people. Early in my career, I inherited a team with a mix of talent, enthusiasm, and resistance. One individual stood out. He had the most institutional knowledge—years of experience and an intimate understanding of the systems. But there was a problem: he resisted every change we tried to make.
Managing him out of the team was one of the most challenging decisions I’ve ever made but also one of the most important. Without his resistance, the team began to flourish. Fresh ideas emerged, and collaboration became the norm. It wasn’t just about removing a blocker but creating an environment where innovation could thrive.
Lesson 3: Leverage Your Network
Your network and connections are your greatest assets in transformation. Knowing who’s innovating, which products are game-changing, and which are just hype can save you from costly mistakes.
Early in my career, I made poor decisions—not by choice, but due to internal politics. I deployed solutions that looked great on paper but weren’t fit for purpose, all because of the pressure to be seen as “innovative.” These were solutions chosen for headlines, not utility.
However, every misstep taught me the importance of validating solutions thoroughly. I lean heavily on my network to stay ahead of the curve. Whether identifying the best vendors or learning from peers who’ve tackled similar challenges, being “in the know” is invaluable.
Lesson 4: Empower Thinkers and Problem-Solvers
Once the right people are in place, the next step is empowering them. Thinkers and problem-solvers thrive when given autonomy and trust.
I recall one project integrating a cloud-based PMS across multiple properties. It was a mammoth task with countless moving parts. One team member—a relatively junior analyst—came up with a bold new approach to structuring the data migration process. It was a risk, but the data supported it.
I backed him, and his solution saved us weeks of effort. It was a turning point, not just for the project but also for his career. By giving him the opportunity to make an impact, we unlocked his potential and delivered incredible results.
Lesson 5: Continuously Optimize
Transformation isn’t a destination; it’s a journey. Even when a project is complete, there’s always room for improvement.
One example is the Gen AI task force I led. In six months, we achieved a 20-30% increase in productivity across key roles. But we didn’t stop there. We dug deeper, refining processes, exploring new use cases, and ensuring data security. That relentless focus on optimization is what turns good teams into great ones.
Lesson 6: Plan for Resistance in Change Management
Change is hard. It’s human nature to resist it, especially when it feels like it’s being imposed from above. Successful transformation requires not just technical solutions but also cultural buy-in.
One strategy I’ve found effective is involving key stakeholders early and often. When people feel heard and included, they’re more likely to embrace change. And when resistance does arise, having backup plans allows you to address concerns without derailing progress.
Lesson 7: Prioritize Attitude Over Capability
Skills can be taught, but attitude and hunger for growth are irreplaceable. Some of the most impactful team members I’ve worked with started with limited experience but brought an unmatched drive to learn and contribute.
One standout hire was a junior analyst who lacked technical expertise but had incredible curiosity and determination. Within a year, she led a critical initiative and delivered results that exceeded expectations.
The Greatest Compliment
One of the proudest moments of my career came when a senior executive told me this:
“The progress and innovation we’ve achieved under your leadership in the last few years is more than the company has seen in its history.”
It wasn’t just about technology—it was about people, preparation, and a relentless commitment to excellence.
Final Thoughts
Digital transformation isn’t easy. It’s messy, unpredictable, and full of challenges. But with the right team, a strong network, and a commitment to planning for the unexpected, you can achieve extraordinary results.
So, my advice? Be bold, think ahead, and always have a Plan A, B, and C because uncertainty is the only certainty in the world of transformation.
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