Building IT leaders for an AI-driven future

Since joining Travelers in 2018, Mojgan Lefebvre has been a driving force behind the company’s digital and operational transformation, modernizing core platforms, strengthening customer experience, and enabling business growth through technology. As executive vice president and chief technology and operations officer, she leads the global technology and operations organization, spanning cloud, cybersecurity, data, AI, digital platforms, customer service, billing, and business resiliency.

Lefebvre’s career story spans senior leadership roles across healthcare, consulting, and technology, with a perspective that’s been informed and expanded by her board experience and her passion for developing future-ready talent. On a recent episode of the Tech Whisperers podcast, she drew from those experiences to explore how CIOs can lead at speed and scale without sacrificing reliability, accountability, humanity, and heart.

Lefebvre has developed a leadership style grounded in three attributes that increasingly define top-tier CIOs: ambition, adaptability, and accountability. After the podcast wrapped, she spent some time discussing how those qualities were forged early on, how they guide her decision-making today, and how they shape her approach to preparing people to thrive in an AI-driven future. What follows is that conversation, edited for length and clarity.

Dan Roberts: You’ve spoken openly about how growing up in a family that moved frequently made you feel different and required you to adapt quickly to new environments. How did those early experiences shape your leadership style, particularly your ability to navigate ambiguity and help others feel steady during change?

Mojgan Lefebvre: Growing up, change was constant. Because of my father’s work, my family moved frequently, and I was often the new person in unfamiliar environments, whether it was new countries, new cultures, or new expectations. At the time, it simply felt disruptive. But in hindsight, it built a deep comfort with uncertainty and an instinct to adapt rather than to resist change.

Those early experiences taught me to listen carefully, to observe before acting, and do my best to find my footing quickly. I attended a British school in Tel Aviv, learning a new language, navigating cultural differences, and all of this reinforced how critical communication and empathy are when you’re facing change. And then later, living through periods of upheaval and making the decision to leave my home country of Iran to pursue opportunities somewhere else certainly required resilience, self-belief, and a willingness to move forward without any sort of perfect clarity.

That’s the mindset that has stayed with me throughout my career. As a leader, I don’t view ambiguity as something I want to eliminate; I view it as something to manage thoughtfully. When the team sees their leaders as grounded, honest about what’s known and what’s unknown, and really clear about direction, that creates clarity, even in moments of disruption and ambiguity. Those early experiences really shaped my leadership style that is rooted in adaptability, resilience, and helping others move forward with confidence when the path is not fully defined.

Can you share an example where a difficult moment or even a setback ultimately led to a better outcome?

Early in my career, I learned an important lesson about authenticity from a moment that

felt small at the time, but it’s stayed with me. When I was in college, my name, Mojgan, was often difficult for others to pronounce. It still is. And so, wanting to make things easier, I started introducing myself as Megan.

I thought, okay, this is going to remove friction, and it’s going to help me blend in. But it actually had the opposite effect, because each time I heard the name, I totally felt disconnected from who I was, and I really felt like I’d compromised something essential for the sake of others’ convenience. I went with it, though, for six months, and then I realized that the discomfort was about the name itself and about misalignment. I wasn’t showing up as myself, and that just made it harder to lead with confidence, to be myself, and to feel like I had integrity.

So I went back to my name and I said, my name is my name, and hopefully people who care will try their best to say it. That experience really shaped how I think about leadership to this day. Authenticity is not just a personal value; it’s a leadership strength. When you feel comfortable bringing yourself as who you are to the table, you’re creating space for others to do the same thing. It leads to stronger teams, better ideas, diversity of perspective, and diversity of who you are. Showing up in a real way leads to a far more resilient organization.

It started as a very small personal setback, but it became a lasting reminder for me that real leadership is staying true to yourself and showing up as who you truly are.

From being valedictorian at Georgia Tech to choosing a demanding, problem-solving role early in your career at Bain Consulting, ambition has clearly been a throughline. How do you think about ambition today, not just personal ambition, but growing organizational ambition in a world where AI is raising expectations for what’s possible?

Over time, my understanding of ambition has shifted quite a bit. Early in my career, as you noted, ambition was much more personal. It was about proving myself, tackling hard problems, pushing my own limits. But today, ambition is far more collective. It’s less about what I can achieve individually and far more about what an organization can become when it sets a bold, shared aspiration.

In today’s world, AI is fundamentally raising the bar for what’s possible, but truly ambitious organizations won’t only measure their success by how quickly they adopt the tools. They’re going to measure it by how deeply they rethink their value propositions around human and AI collaboration, and that’s really about asking the harder questions of, how do you use AI

to extend expertise, not just automate tasks? How do you elevate decision-making? How do you elevate customer experience and drive productivity at the same time?

Growing organizational ambition requires leaders who are explicit about their expectations and courageous about the trade-offs that they can make. Ultimately, they create a culture that believes bigger outcomes are possible while also investing in capabilities like talent, data platforms, and more.

You’ve emphasized the importance of balancing empathy and humanity with accountability and performance. In your experience, where do leaders most often get that balance wrong, and what guidance would you offer CIOs who are trying to lead with heart without losing the discipline required to deliver results?

Leaders can get the balance wrong if they treat empathy and accountability as opposing forces when, in reality, they are deeply connected. Some leaders may over-rotate towards results, believing that pressure and pace alone are going to drive performance. In the short term, maybe that can produce outcomes, but over time, it erodes trust, engagement, and, ultimately, retention. People leave.

Other leaders can lean too heavily into empathy only, avoiding the hard questions or decisions in an effort to protect people. As Kim Scott explains in “Radical Candor,” which she also calls “compassionate candor,” if you don’t have those tough conversations while caring personally, that’s when you’re going to end up with perhaps having to let people go, putting jobs at risk, and really doing the wrong thing for the organization — not only for the people, but also for the organization.

Leading with heart does not mean lowering expectations. It means being clear about outcomes, holding people accountable, and making the difficult decisions while you also care personally about them as they’re doing the work. The discipline comes from clarity, from clear goals, clear ownership, and honest feedback delivered with love and respect.

For CIOs, the guidance is simple — it’s not easy, but it’s simple: Care deeply, challenge directly, and be consistent. Because when people know where they stand, when they understand what’s expected, and when they trust that the leaders have their back and their best interests at heart,

then accountability becomes a source of strength rather than fear. And then everything else, including performance, follows from that.

You recently shared this advice with graduates of Travelers’ Engineering Development Program: Ask questions, build a strong foundation, and stay connected. As AI reshapes work and careers, what additional guidance would you offer emerging technology leaders to help them stay relevant, resilient, and fulfilled over the long term?

The advice I’ve been giving recently is simple but important: Build for scale but govern for trust.

In a large enterprise and, frankly, in any meaningful leadership role, it’s not enough to show what AI can do. You have to prove it can be trusted to operate responsibly, consistently, and at scale.

That mindset matters early in your career, because the habits you build around rigor and responsibility are really what stay with you throughout your career. Practically, that means investing time in building strong foundations and understanding data, architecture, security, ethics, not just learning the latest tools. AI that scales without trust becomes a risk very quickly. AI that earns trust can become a competitive advantage.

I also encourage emerging leaders to stay relentlessly curious and connected, ask questions, learn how the business actually works. It is absolutely not enough just to understand how the technology works. And then build relationships and build that across disciplines, build it across the product teams, operations, risk, and all different parts of the business, because the most impactful AI leaders are the ones who can bridge all those roles.

Finally, I would tell them, fulfillment will come from impact. When you focus on building things that are trusted, useful, and meaningful, you can stay energized and relevant regardless of how hard you’re working. That’s what allows people to grow resilient careers in a field that’s going to keep changing and is going to keep requiring showing up with a lot of energy.

One of your teachings around taking risk is this mindset of asking, “Why wouldn’t you?” If you could go back and offer advice to your younger self at a moment when taking a risk felt uncertain or uncomfortable, what else would you say?

I would tell my younger self that the discomfort you’re feeling is a signal, but it isn’t a stop sign, so don’t stop what you’re doing. Early on, I often overestimated the downside of taking a risk

and underestimated my ability to adapt if things didn’t work out. With experience, I’ve learned that the worst-case scenario is rarely as bad as we imagine, and that growth comes from stepping into the unknown.

The mindset of “Why wouldn’t you” isn’t about being reckless; it’s about being intentional. Take risks that are aligned to where you want to go, prepare as best as you can, and then trust yourself to learn along the way. Then, even when something doesn’t work, you’re going to learn from it. It’s rarely wasteful, and it will become information. Your failure can become information that you can leverage and that others can leverage as well.

That way of thinking has shaped how I lead today, and it’s made me more willing to place thoughtful bets, to try new approaches early on, and to give others permission to do the same. By modeling the way, and by modeling confidence in learning, not just in success, you’re creating that culture where people are willing to stretch, willing to innovate, and willing to take the risk that you absolutely need them to be willing to do in today’s world.

Looking back, the moments that felt uncertain or uncomfortable were often the ones that mattered the most. Knowing that now, I’d tell my younger self, “Take the step. You’ll figure out the rest.”

As Mojgan Lefebvre shows us, the leaders who will thrive in an AI world aren’t choosing between speed and humanity, innovation and reliability, or heart and accountability. By mastering the balance, they’re enabling their organizations to go fast and to go far. For more insights from Lefebvre’s leadership playbook, tune in to the Tech Whisperers.