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What does it take to step into your first leadership role when the safety net disappears almost immediately?
In this episode, I'm joined by Cosimo Maiolo, a qualified actuary whose career has taken him from Sydney to London to Dublin, and through just about every leadership challenge you can imagine along the way. Cos was nominated as one of our greatest actuarial leaders of 2026, and it's easy to see why. He's someone who's thought deeply about what it means to lead people well, and he's generous enough to share the moments that tested him most.
We cover a lot of ground. Cos shares what it was like to step into his first management role, only to have his own manager leave two weeks later. He talks about what moving overseas taught him about humility and influence, including how building a simple tool for a client in Ireland became the foundation for real credibility. And he opens up about a performance management experience that reshaped the way he gives feedback, including a lesson that many of us in the profession need to hear.
Key takeaways:
- Say yes, even when you're not ready. Leadership opportunities don't come around often, and feeling uncomfortable is usually a sign you're about to grow. -
- Your success as a leader is tied to the success of your team. Getting to know what motivates your people isn't a nice-to-have, it's the job.
- Humility is a leadership skill. The willingness to step back, listen, and earn credibility from scratch (especially in unfamiliar territory) can separate good leaders from great ones.
- Direct feedback is a kindness. The "compliment sandwich" sounds nice but often means the message gets lost. Clear, unequivocal feedback (delivered with care) is
what actually helps people grow.
- Unaddressed performance issues affect the whole team, because your other direct reports are watching! Kicking the conversation down the road is rarely the neutral choice it feels like.
What's the feedback conversation you've been putting off, and what's it actually costing your team?
Cosimo is the Chief Actuary & Product Officer at Teachers Health, an Australian-based not-for-profit private health insurer.
His team oversees Actuarial, Pricing, Business Intelligence, Product, and emerging member health initiatives, with a focus on delivering meaningful, sustainable value for Teachers Health members.
A Fellow of the Institute of Actuaries of Australia, Cosimo brings over 15 years of experience across life insurance, superannuation, and health insurance. He has more than a decade of leadership experience, having led diverse teams across Australia, the UK, and Ireland.
Connect with Cos on LinkedIn.
Connect with Julia on LinkedIn.
Click here to learn more about the Guardian Actuarial Leadership Program.
Read Julia’s leadership development books written especially for actuaries:
- For new and aspiring managers: "Aspiring Actuarial Leaders: The Modern Manager’s Toolkit"
- For new and aspiring senior leaders: "Senior Leadership: An Essential Guide for Actuaries"
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Thank you for listening to the We Are Actuaries podcast. Connect with Julia and Guardian Actuarial on LinkedIn. For more interviews and articles, visit our website.
