The CTO’s Edge: Leading Through Constraints

In the ever-evolving world of technology, the most powerful leadership lessons often emerge from adversity… those crossroads where economic turmoil, technical limitations, and human ingenuity collide.

I learned this firsthand in the mid-1990s during my time in the United States Air Force. At that time, I was stationed at Ramstein AB, Germany and working on the payroll system for Turkish nationals. The intersection of runaway inflation and legacy systems tested not only my technical abilities but also my potential as a future leader.

Today, as I coach aspiring technology leaders, I share this story not as nostalgia (okay, maybe a little since those were fun times), but as a reminder that resourcefulness under pressure is one of the most beneficial skills you can cultivate.

When Code Meets Crisis

Imagine maintaining a system when the ground beneath your code was shifting faster than any software update could keep pace. Sounds familiar?

Turkey, in the grip of hyperinflation, saw its currency’s value evaporate almost monthly. By 1995, one U.S. dollar was worth approximately 43,000 lira; by late 1996, it had surpassed 100,000. Even modest paychecks for our Turkish national staff ballooned into numbers our systems had never contemplated.

Our payroll software, built in Visual Basic 3.0 for Windows 3.1, was constrained by a 16-bit architecture: salary fields capped at 65,535. Currency realities soon dwarfed that limit. As overflows and errors crashed the payroll cycle, the need to upgrade was clear. Visual Basic 4.0, with its 32-bit support, could handle values in the millions. But our hardware lagged; many computers in the field still ran 16-bit Windows 3.1. And Yes, I was coding back before Long data types were mainstream.

Upgrading the code was the easy part. Replacing and upgrading workstations in another country, with limited budgets, strict procurement rules, and layers of bureaucracy…that was another story entirely. Preparations for Y2K finally forced widespread upgrades but that’s a story for another time…

We got creative: splitting lira figures into multiple fields, running calculations in U.S. dollars internally, and converting only for display. Each fix solved one problem and introduced another… and each one taught me something new about problem-solving under pressure.

Leadership Lessons from the Trenches

From these challenges came leadership principles that remain relevant today:

1. Embrace Constraints as Catalysts
   Constraints aren’t just obstacles…they’re catalysts for creativity. Instead of shielding teams from them entirely, use constraints to spark experimentation and unconventional thinking.
2. Balance Guidance and Autonomy
   High-stakes problems can be intimidating, but they’re also where growth happens. Provide context and mentoring, then step back and let the team wrestle with ambiguity.
3. Foster Systems Thinking
   The payroll problem wasn’t just about code. It was about hardware, workflows, and even economics. Great leaders help teams see and connect the bigger picture before acting.
4. Make Learning Visible
   Give space for learning. Document and share lessons as they happen. Retrospectives and storytelling ensure knowledge outlasts the crisis and strengthens the organization for the future.
5. Cultivate Resilience and Adaptability
   Rotate assignments, break down silos, and reward perseverance as much as eventual success. Resilience is as vital as technical skill.
6. Develop Problem Solvers, Not Just Coders
   Encourage your team to seek context, question assumptions, and challenge the how things have always been done. Problem-solving is a leadership skill, not just a technical one.

Coaching Takeaway: Building Teams Ready for Tomorrow

Looking back at those days, what stands out isn’t the technical upgrade…it’s the mindset it cultivated.

Today, we face different constraints: AI hallucinations, soaring cloud costs, new security threats. But the leadership requirement is the same…build teams and cultivate people that can adapt, reason, and solve when the easy answers run out.

Technology will keep changing. Constraints will keep showing up. The leaders who thrive are the ones who turn limitations into leverage.

Encourage the struggle. Support the journey. Celebrate the hard-won insights that last for decades.