What makes a great reinsurance leader – and how can leaders prevent themselves from falling into an echo chamber of consensus? This was among the questions put to a panel of reinsurance leaders by ABIR CEO John Huff at the 2025 Bermuda Risk Summit.
Offering his perspective on how to encourage diversity of opinion among a team, reinsurance stalwart and Convex CEO Stephen Catlin emphasized the importance of CEOs being good listeners. “Leadership starts with listening, and you can’t be a good leader if you don’t listen,” he said. “I think if you start by encouraging others to listen, you will have people around you who will offer opinions, and that is healthy.”
Catlin said that building out a team in which people are unafraid to have – and to voice – their opinions, including their differing opinions, is critical to effective leadership. That quality of collective thought leads to better decision-making, he said, and it should be embraced. Adding to this, Kathleen Reardon, CEO of Hiscox Re & ILS shared the business’s twin ambitions to ensure that its team are deeply knowledgeable about the business and the market, and that they have access to leadership at every level.
“I think you can still motivate your team to push for excellence as a leader at the same time as investing in their career,” she said. “The way I handle this at Hiscox Re is that I have one-to-one meetings with the team, and skip-level meetings so I can hear what the next generation of talent has to say… It’s very much about having a level-playing-field-type environment.”
Nicolas Papadopoulo, CEO of Arch Capital Group, noted that encouraging diverse voices to have their say within a business all starts with creating the right culture. Creating alignment is all about engagement, he said, because people tend to be happier when they feel they can contribute to an organization, and that this contribution will be recognized. “So you have to create this environment where people can challenge the decisions that are made, and you have to be willing to change. Because listening is one thing, but active listening is about [being] willing to incorporate what you’re listening to into your mindset, and to potentially change your mind.”
From the perspective of Christian Dunleavy, group president and CEO of Aspen Bermuda, being thoughtful about who you hire into an organization is essential – as is adopting a “hire slow, fire fast” philosophy. He shared that Aspen Bermuda brought somebody to come in and work with its executive team who introduced them to the approach of not being able to say what you think for the first 20 or so minutes of a meeting but instead only ask questions.
“So, you would spend the first 15 or 20 minutes in a discussion essentially just probing and learning and trying to understand,” he said. “… And then at the end of it, you sometimes reach a different conclusion in your own mind than you thought going in. And so you should try it. It's harder than you think, and it's actually quite a good way to challenge your own thinking.
“Because we have a lot of people in all our teams who are super smart people who have accomplished a huge amount in their careers and who really have the courage of their convictions and believe that what they think makes a lot of sense. But when you get that collective group in the room and ask questions and really try to kind of interrogate the issue, sometimes you come out in a different place.”
Another core element of this is about building an environment where people are encouraged to voice their opinions but there’s a commitment to making a decision by the end of the discussion. “Disagree but commit is how I think about it,” Dunleavy said. “The most toxic thing that can happen is you make a decision as an executive team, and then somebody's out there saying, ‘That wasn’t my call. I didn’t agree with the decision but that’s the way they wanted to go’.
“That’s really corrosive to an organization and to a culture. So that collective responsibility to be able to disagree but to commit on the way forward is, I think, really critical to being able to run a good organization and build a good culture. It’s about having the ability to say, ‘Actually, I've changed my mind, and I'm going to go in a different direction than I expected.’ So, it’s about getting the right people in the room and everybody really trusting each other, I think it's critical.”
