Leading Into the Unknown: A Lesson in Risk, Innovation, and the Futures We Build

Lately I’ve been reflecting on leadership and how it can drive or hamper innovation. I was going back through my journals from 5 years ago and had time to reflect on a key learning moment. In early January 2020, my risk radar picked up on something subtle but unsettling. At that time I was the Head, Innovation and Strategic Projects for a top private school in Toronto. A few fragmented mentions of a respiratory illness emerging in Wuhan had made their way into the global news cycle, tucked between updates on trade policy and holiday season retrospectives. At the time, there wasn’t a name for what we would all come to know as COVID-19—but the indicators were enough to trigger a sense of unease. I was responsible for analyzing the risks of an upcoming international student trip, and the variables were beginning to shift. What had been a low-probability outlier was edging closer to center stage.

This is not a story about the pandemic. We’ve read volumes on that already. Rather, this is a story about a leadership lesson that has shaped how I view risk, innovation, and the responsibilities of futurist thinking. It is a story about a moment when foresight met decisiveness, and what happened when leadership created the conditions for something extraordinary to emerge.

It was Karen Jurjevich, my former boss and a leader of uncommon wisdom, who recognized that my analysis wasn’t just identifying risk. It was creating the conditions for accelerated innovation. What followed was one of the most meaningful leadership interactions I’ve had in my career.

The Risk We Don’t Yet Understand

Great leaders often recognize signals others miss, not because they have a crystal ball, but because they know how to pay attention. I brought my early concerns to Karen with the kind of cautious precision that comes with good analytical practice. I laid out what we knew, what we didn’t, and the implications for the student experience and institutional liability. The goal wasn’t to predict the future, it was to prepare for a range of possible futures.

What struck me was not just her receptivity, but the way she used that moment to pivot. Karen didn’t react with fear or bureaucracy. She listened carefully, then shifted the conversation. “So,” she asked, “what would we do if we had to cancel the trip? If school wasn’t in person? What would that look like?”

The shift from problem-identification to solution-acceleration was immediate. She wasn’t looking to slow things down or wait for more data. She was looking to speed up the right experiments and she knew I already had one underway.

Building the Future Before You Need It

Long before Zoom became a household word, I had been experimenting with virtual environments. I was particularly interested in Virbela, a platform that allowed for immersive collaboration in a digital campus. In 2019, this was still fringe territory—something between a curiosity and a forward-looking prototype. But in a world where flexibility, engagement, and global reach were becoming strategic priorities, it felt like an important area to explore.

When I mentioned the project to Karen, she didn’t just support it. She told me to go faster. The same was true for Zoom, which we had already deployed in a limited fashion for internal collaboration. Her message was clear: the signals were strong enough, the foundation was already there, and the time to scale was now.

By the time closures began rolling in March of 2020, we weren’t scrambling to stand up new systems. We were optimizing what we had already built. The acceleration she enabled in January became a strategic differentiator just a few months later.

Risk as a Catalyst for Innovation

One of the most misunderstood aspects of risk is the idea that it’s something to be managed away. In practice, risk is a lens—a way to view not just what might go wrong, but where value might be created in the face of uncertainty. Karen’s leadership modeled this beautifully. She didn’t just see risk as something to contain. She saw it as an opportunity to do something better, faster, and more aligned with where the world was headed.

That mindset—of using risk analysis as a springboard rather than a stop sign—is a hallmark of leaders who operate with a futurist orientation. It requires the humility to act before you have full certainty and the confidence to invest in ideas that aren’t yet validated. It’s not reckless. It’s rigorous. And it’s rare.

The Power of Experimental Capacity

In retrospect, what made this leadership moment so powerful was that the experimentation was already happening before the pressure hit. We weren’t reacting. We were responding, building on prototypes and pilots that had been quietly developed in the margins.

This is one of the critical lessons I share with organizations today: your capacity for innovation in a crisis is directly proportional to the quality of your experiments before the crisis. If you want to be ready when the world shifts, you need to be exploring the edges of what’s possible long before the need becomes urgent.

Karen didn’t tell me to pause. She told me to push. She created a leadership context where the perimeter of the organization—the place where innovation often begins—was not only safe to explore, but strategically important to accelerate.

From Trendspotting to Organizational Readiness

Futurist thinking is not about predicting the future. It’s about preparing for multiple versions of it—and ensuring your organization has the capacity to adapt, absorb, and act. What distinguishes strong futurist leaders is their ability to turn early signals into institutional readiness.

By January 2020, it was already becoming clear that the future of education needed to be more hybrid, more resilient, and more globally agile. COVID-19 simply forced the acceleration of those truths. The organizations that thrived were not those who had the best contingency plans. They were the ones who had been building toward the future before the contingency arrived.

Karen Jurjevich modeled that posture in how she led our conversation, and in how she empowered experimentation as a strategic asset.

What This Teaches Us About Leadership

Leadership, when done well, is about more than steering. It’s about cultivating a culture where ideas are tested early, risk is examined with nuance, and readiness is built from the edge in. Too often, we associate leadership with stability and predictability. But in moments of inflection, the real measure of leadership is adaptability—and the ability to reframe uncertainty as possibility.

Karen’s leadership in that moment gave me a living example of how to create that frame for others. It showed me how to use foresight to accelerate meaningful experimentation and how to turn quiet projects into strategic pivots. It reminded me that leadership is not about being the smartest person in the room. It’s about seeing the emerging horizon and asking the right people to sprint toward it.

Innovation Requires Sponsorship

The truth is, most innovation fails—not because the idea is flawed, but because it lacks sponsorship. Karen gave me something more valuable than funding or resources. She gave me belief. And that belief was catalytic.

When leaders demonstrate belief in their people’s forward-looking experiments, they do more than de-risk innovation. They make it contagious. The result isn’t just better preparedness. It’s a culture where strategic imagination has room to breathe—and where people are willing to bet on the future because they know their leaders already are.

Looking Forward

Today, as I guide organizations through their own transformations—whether driven by AI, data strategy, or macro uncertainty—I find myself drawing on that leadership moment more often than I expected. It reminds me that risk is not the enemy of progress. It’s the compass that points us to where progress is most needed.

It also reminds me that the future is already being built, quietly, in the experiments we support or suppress. Leadership is the deciding factor in whether those experiments stay dormant—or become the differentiators that carry us through change.

The lesson from that January isn’t about how we responded to COVID-19. It’s about how one leader saw the signal before the noise—and helped accelerate the future before the world caught up.