Reinvention is the defining skill for today’s CIOs, turning pressure, change and disruption into opportunities for leadership growth.
Engines dead. Five Beaufort winds. A patrol ship drifting in open water. Twenty men staring at me — waiting for direction, waiting for calm, waiting for a decision. In those thirty minutes, while we fought to restart the engines, I felt the weight of accountability in its purest form. Fear was on every face, including mine. My first job wasn’t to solve the problem — it was to steady myself so that I could steady them. Only then could we focus on the solution instead of the danger surrounding us.
Years later, as I led technology teams, I realized how familiar that feeling was. A system crash, a cyber incident, a project spiraling off-course — the team looks to the CIO in the same way my crew looked at me on that ship. The data is incomplete, the risks are real and the clock is merciless. And just like at sea, calm is contagious. If the leader panics, the team collapses.
My career has taken me from commanding a naval vessel to writing code as a junior engineer, to founding a company and eventually to executive roles leading global technology initiatives. Every stage forced me to reinvent myself, often painfully, always urgently. Reinvention isn’t optional — it’s the core skill that has kept me relevant across two completely different worlds.
That’s why I believe reinvention is the defining leadership challenge for today’s CIOs. Technology changes every day, regulations arrive faster than roadmaps and boards expect transformation without excuses. The leaders who thrive are the ones who can pivot, absorb pressure and help others rise to challenges they didn’t think they could handle.
Reinventing teams
On one mission, my crew and I were ordered to leave our base for more than two months, sailing to unknown ports with little certainty about what awaited us. At first, I worried about morale — long separations from home, new routines, constant change. I expected resistance, maybe even complaints. But something surprising happened. Once I set the expectation that this was our mission and we would succeed together, the crew adapted. More than that, they performed better than I thought possible.
It taught me a lasting lesson: people rise to the expectations you set. If you frame change as a burden, they’ll feel burdened. If you frame it as a mission, they’ll find the strength they didn’t know they had.
For CIOs, the same truth applies. Moving teams from on-prem to cloud, from waterfall to Agile or from manual workflows to AI-driven automation will always be uncomfortable. Leaders who over-index on empathy risk reinforcing fear. Leaders who set confident expectations create confidence in others.
Pivoting with discipline
When I left the Navy and entered the technology industry, I learned quickly that plans rarely survive the first contact. Early on, I embraced agile as a way to adapt. And while agile has undeniable value, I also saw how it can become an excuse for chaos. Too often, teams skipped preparation and architecture, assuming they could “pivot later.” The result wasn’t agility — it was debt.
As a CEO, I discovered the hard way that the quality of a Statement of Work (SoW) often determines the quality of the relationship. A strong SoW builds clarity and trust. A weak one breeds confusion and conflict. Agile doesn’t change that truth. Pivoting can be necessary, but without preparation and strong architecture, you’re not adapting — you’re gambling.
For CIOs, agility is vital, but it cannot replace discipline. The most vigorous transformations strike a balance between adaptability and structure, so pivots occur on a solid foundation.
The power of letting go
When I became CEO of my own firm, I thought the best way to protect the company was to be everywhere at once. In the morning, I was the project manager in the trenches with the client’s technical team. In the evening, I was the CEO negotiating with their executives. When a large customer tried to change the scope just weeks before delivery, I realized I had created the opposite effect. By being both PM and CEO, I blurred the lines, weakened our position and allowed the client to take us for granted.
We pulled through the project, but the lesson stuck: when leaders try to do everything, they actually harm the organization. They don’t give their teams room to grow, they dilute their authority and they create unhealthy dynamics with stakeholders.
CIOs often fall into the same trap. Out of responsibility, they insert themselves into every decision, every firefight, every meeting. But the higher the role, the more damaging this becomes. Authentic leadership is about empowering others while maintaining your authority for the moments that truly matter. Delegation isn’t abdication — it’s how organizations build strength.
Reinventing self
For years, I defined myself as an engineer. My job was to build what I was told to make. But over time, working side by side with customers, I realized the real value wasn’t in the code — it was in understanding what should be built. Customers didn’t always articulate needs in technical terms. Translating those fragments into real solutions was a different kind of leadership.
That was the moment I crossed the line from technologist to executive. Technology was no longer the end in itself — it was the tool. My responsibility had shifted from execution to vision, from building things right to creating the right things.
CIOs face a similar transformation. For decades, the role was centered on custodianship: maintaining systems, controlling costs and managing risks. Today, the CIO must be a strategist, shaping digital vision and influencing enterprise direction. Reinventing yourself from executor to visionary isn’t optional. It’s survival.
Staying relevant
When I transitioned from the Navy into tech, I didn’t have the luxury of endless resources. I had a 256MB USB stick and an internet café. I’d download documentation at night, study it after duty and repeat the next day — all while raising two young daughters. There was no shortcut, just focus and perseverance.
That discipline has been my most valuable asset. Today, I see professionals with smartphones, cloud platforms and AI copilots at their fingertips — yet many struggle to focus for more than a few seconds. The tools are better, but the mindset is weaker.
For CIOs, this isn’t just nostalgia. As Harvard Business Review has discussed, the half-life of knowledge is shrinking. What you know today may be irrelevant in twelve months. Reinvention requires continuous learning, the ability to block out noise and the discipline to focus when it matters. Tools change. Leadership discipline doesn’t.
My 5 rules of reinvention
Across both my naval and technology careers, I’ve found five rules that hold in any environment:
- Calm is contagious. Before addressing your team in a crisis, take two minutes to steady yourself — breathe, clarify the top priority, then communicate with focus.
- Expectations shape performance. Frame reskilling or transformation not as a burden, but as a mission. Instead of asking, “What worries you?”ask, “How will we make this succeed together?”
- Discipline anchors agility. When launching any major initiative, insist on a written “minimum viable architecture.” It doesn’t need to be perfect, but it must exist before pivots begin.
- Delegation builds authority. In your next project, identify one decision you usually make yourself — and assign it fully to a lieutenant. Then support their decision publicly.
- Focus is a superpower. Block two hours weekly in your calendar for uninterrupted learning or deep work. Treat it with the same respect as a board meeting — immovable and protected.
Reinvention as a leadership imperative
Leadership, in every chapter of my career, has been reinvention. On a ship with no engines, I had to reinvent fear into focus. On long deployments, I had to reinvent uncertainty into confidence. In technology, I’ve had to reinvent failed plans into disciplined pivots, personal failures into lessons and myself from engineer into strategist.
CIOs face the same reality every day. Systems will fail. Strategies will collapse. Regulations like the EU AI Act will reshape compliance. Teams will resist new directions. None of that is optional. What is optional is how leaders respond: whether they cling to old habits or reinvent themselves and their organizations for the next challenge.
Technology will keep evolving daily. The leadership challenge doesn’t change. Reinvention isn’t a one-time act. It is the CIO’s career. And those who embrace it won’t just survive disruption — they’ll define the future of their enterprises.
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