CIWA Q1 Future Newsletter 2026: Why Pros Ask Better Questions

CIWA Future member Sarah Bryant, CPCU, AU, Vice President in the Excess Casualty Division at Core Specialty, sat down with Todd Dixon, CRM, President of Excess Casualty at Core Specialty, for a thoughtful conversation on building a successful career in the insurance industry.
In this Q&A, Todd shares practical insight on embracing curiosity, navigating career paths, building strong relationships, and finding mentorship. His perspective offers grounded, real-world advice for professionals at any stage, especially those early in their careers.
Read on for Todd’s perspective, shaped by years of experience across multiple roles in the industry.
Why Pros Ask Better Questions: The Career Advantage No One Talks About
Sarah Bryant: What are the most important skills and qualities that you believe have contributed to your success in the insurance industry?
Todd Dixon: “The most important skill/quality that has helped me is being OK with not being the smartest person in the room. Be willing to ask questions, stay curious, and commit to continuous learning about the industry and the challenges we face. There is always something we need to understand better. In our roles, we will encounter challenges we haven’t faced before or topics we aren’t well-versed in. Being willing to seek out someone with experience and ask for advice or guidance is hugely important. It is acceptable not to know something you haven’t been exposed to, but having the curiosity to learn and grow is how you improve and advance.”
Sarah: How do you balance staying up-to-date with the rapidly changing insurance landscape while also staying grounded in traditional industry practices?
Todd: “There are fundamental tenets of the insurance industry that are timeless. The most important thing is that insurance is a people business, and building relationships is key to long-term success. You can stay up to date with industry changes by leaning into existing relationships to gain different perspectives and by building new relationships in areas where your network may be limited. This also ties back to curiosity and continuous learning through reading industry publications and listening to experts discuss topics like emerging exposures, claims challenges, legislative updates, and technological advancements that can improve efficiency and effectiveness.”
Sarah: What are the biggest challenges you faced early in your career, and how did you overcome them?
Todd: “The biggest challenge was figuring out where I fit best in the industry, given the many available career paths. Early in my career, I worked as a contract binding underwriter, marketing representative, insurance company underwriter, and wholesale broker. Each role provided valuable experience that I still use today. I kept learning, discovering what I enjoyed, what interested me, and where my strengths were. I also identified areas I didn’t want to pursue long-term. Many of the toughest challenges taught me invaluable lessons. Doing hard things may not be enjoyable in the moment, but working through them builds perseverance, which is essential for long-term growth.”
Sarah: How can young professionals find mentorship and build relationships with experienced leaders in the industry?
Todd: “There are many ways to do this, but the most effective is to ask questions of those with more experience. Start within your organization, then expand outward. Most successful people in the insurance industry are willing to share their knowledge with the next generation. Those who aren’t are likely not the right people to learn from anyway. Getting involved in organizations like CIWA and WSIA provides opportunities to connect with experienced leaders in a relationship-focused environment. In general, people enjoy talking about their experiences, including their career paths and advice. Asking thoughtful questions is one of the best ways to gain insight, build mentorship, and grow your professional network at the same time.”
Proud to have you with us in CIWA Future.
The future of the industry is stronger because you’re part of it.
Warm regards,
Jack Else & the CIWA Future Committee
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