079: How to have difficult conversations at work with Crystal Riley

100 Women in Insurance · Aug 7, 2025 · 45m

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Summary

In this episode, Sandra is joined by Crystal Riley, who entered the insurance industry by chance and has since built a successful career across underwriting, broking and claims.

Crystal shares how exploring different roles helped her understand where she could thrive, and how feeling stuck prompted her to reflect on what she truly wanted from her career. She speaks openly about letting go of other people’s timelines, focusing on her strengths, and building a reputation around what she wanted to be…