Editor's Note: Originally written July 17, 2025. Last updated: July 22, 2026.
Every July, I find myself watching the Tour de France.
At first glance, it's easy to focus on the dramatic moments: mountain attacks, breakaways, crashes, and spectacular stage wins. Those moments make the highlights, but they rarely tell the whole story.
Winning the Tour isn't about being the fastest rider on any single day. It's about navigating three demanding weeks with remarkable consistency. The yellow jersey rewards endurance, discipline, teamwork, and hundreds of smart decisions made over the course of the race.
The more I watch, the more I'm reminded of technology leadership.
Organizations often approach technology as a series of sprints—a major software implementation, a cybersecurity initiative, an AI pilot, a Microsoft 365 migration. Each project feels urgent and important.
But successful organizations aren't built by winning individual stages. They're built by steadily strengthening the organizational foundations that allow technology to create value over time.
Technology Isn't a Sprint
Technology leadership has always had a tendency to reward the next big initiative. Today it's AI. A few years ago it was digital transformation. Before that it was cloud migration, collaboration platforms, mobile strategy, or enterprise social networks.
The technologies change, but the pattern is remarkably consistent. Organizations naturally focus attention on the next visible project because projects have clear beginnings and endings. They create momentum, generate excitement, and give leadership something tangible to celebrate.
Strategy is different.
Good strategy is often less visible because it shapes the decisions that happen between major initiatives. It influences how technology investments fit together, how priorities are established, and how today's decisions will affect the organization several years from now.
The organizations that benefit most from technology aren't necessarily the ones moving the fastest. They're the ones building enough organizational capacity to continue adapting as technology inevitably changes.
The Difficult Stages Reveal the Strength of the Team
Watching the Tour, it's easy to appreciate an impressive sprint finish or a dramatic mountain attack. But over three weeks, those moments matter less than most people think.
The riders competing for the general classification are remarkably consistent. They avoid unnecessary mistakes, manage their energy carefully, rely on their teammates, and understand that one poor decision can erase days of strong performance.
Organizations face similar moments.
Technology strategies rarely unfold exactly as planned. Priorities shift. Funding changes. Key employees leave. Organizations acquire new business units or expand into unfamiliar markets. Regulatory requirements evolve. New technologies create opportunities that didn't exist when the original roadmap was developed.
Those aren't interruptions to the strategy—they're part of the environment the strategy has to operate within.
That's one reason FireOak spends so much time talking about governance, knowledge management, and organizational effectiveness. Those capabilities rarely attract the same attention as a major technology initiative, but they often determine whether an organization can adapt successfully when circumstances inevitably change.
Every Leader Needs a Strong Team
One of the things that makes professional cycling fascinating is that the winner is never truly riding alone.
Behind every rider wearing the yellow jersey is an entire team helping them succeed. Some riders set the pace. Others protect their teammate from the wind. Others sacrifice their own chances to keep the overall strategy on track.
Technology leadership works the same way.
Successful organizations don't depend on one visionary leader or one talented IT professional.
They depend on people across the organization who understand their roles, communicate effectively, share knowledge, and make thoughtful decisions within a common framework.
Technology teams, business leaders, operations, security, human resources, and executive leadership all contribute to the outcome.
The strongest organizations recognize that technology strategy is a team effort.
Knowing What Not to Chase
One of the things I've come to appreciate about professional cycling is how selective the strongest teams are.
Not every attack deserves a response. Sometimes another rider breaks away because they have little to lose. Sometimes the peloton lets them go because the move doesn't change the overall race. The best teams understand the difference between movement and meaningful change.
Technology leadership requires similar judgment.
Every year introduces new platforms, new AI capabilities, new productivity tools, and new predictions about how organizations should work. Some of those developments genuinely reshape the way organizations operate. Others generate far more discussion than long-term value.
One of the responsibilities of technology leadership is deciding which changes deserve immediate attention, which should be monitored, and which simply don't align with the organization's priorities.
That isn't about resisting change. It's about recognizing that every organization has limited time, limited resources, and limited capacity for change. Choosing where not to invest can be just as important as deciding where to move forward.
Consistency Creates Momentum
The winner of the Tour de France rarely dominates every stage.
Instead, they consistently perform well across very different conditions while avoiding the setbacks that gradually take other riders out of contention. Over time, those steady performances compound into a meaningful advantage.
Organizations often experience technology in much the same way.
Most successful technology strategies aren't built around one transformational project. They're the result of hundreds of thoughtful decisions made over time—establishing clear governance, improving information management, strengthening cybersecurity, documenting knowledge, modernizing infrastructure, and gradually reducing unnecessary complexity.
None of those decisions may feel particularly dramatic on their own. Collectively, they create an organization that's better prepared for whatever comes next.
Final Thoughts
One of the reasons I've enjoyed following the Tour de France this year is that it's a reminder that sustained success is rarely accidental.
Winning the overall race requires far more than physical ability. It depends on preparation, teamwork, discipline, adaptability, and making good decisions day after day—even when those decisions aren't particularly visible to anyone watching from the outside.
Technology leadership isn't very different.
The platforms organizations use will continue to change. AI will continue to evolve. New opportunities—and new distractions—will appear every year.
What tends to endure are the organizations that invest in the less visible work: building strong governance, maintaining institutional knowledge, creating clear decision-making processes, and developing the organizational capacity to adapt as circumstances change.
Like the Tour itself, technology strategy is ultimately less about any single stage than about putting together a long series of thoughtful decisions that move the organization steadily toward its goals.
