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

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 known for.

The conversation explores the power of difficult conversations and the everyday courage it takes to advocate for yourself at work. Crystal offers practical insight into how to prepare, stay grounded, and revisit conversations when they do not go to plan. She also reflects on the role of informal mentorship, the importance of self-reflection, and how learning to speak up has shaped both her professional and personal confidence.

This is a story about awareness, growth and the clarity that comes from doing the work to define success on your own terms.

Takeaways

• Exploring different roles in insurance can help you understand where you truly thrive
• Recognising when you feel stuck is a sign to pause and reflect
• Networking and mentorship are key to navigating career challenges
• Difficult conversations, though uncomfortable, often build trust and respect
• Preparation is essential for having difficult conversations
• It's okay to revisit conversations if they don't go as planned.
• Personal and professional growth often intertwine in the workplace
• Learning from both positive and negative experiences is valuable
• Confidence can be built through experiences in the industry

About the guest

Connect with Crystal Riley on LinkedIn

About the host

Connect with Sandra Lewin on LinkedIn

Learn more about the 100 Women in Insurance Collective: www.100womenininsurance.com/collective