095: Are you waiting to feel ready or will you put yourself forward anyway?
Thank you to BCH for sponsoring this episode.
Summary
In this episode, Sandra speaks with Caroline Wagstaff, about accidental careers, bold decisions, and why putting yourself forward often matters more than feeling ready.
Caroline shares her journey into insurance from a marketing background, describing it as a mix of choice and serendipity. From building her own successful business to stepping into one of the most influential leadership roles in the market, her career is a reminder that not every step needs to be perfectly planned.
Together, they unpack what leadership really looks like at the senior level. The shift from “doing” to listening, influencing, and creating space for others. And why many people struggle with this transition, often feeling like they are not adding value when in fact, that is the role.
The conversation also dives into one of the biggest challenges facing the industry today:
Talent.
Caroline shares honest insights on the imbalance between supply and demand. From overwhelming volumes of applications to a lack of structured entry pathways and an ageing workforce creating a future gap.
They challenge the idea that the problem is simply attracting talent, and instead explore whether the real issue is what happens after talent arrives.
This is a conversation about confidence, curiosity, and building a career that is intentional, not accidental.
Key Takeaways
You don’t need to feel ready to take the next step.
Careers are often shaped by opportunity and action, not perfect planning.
Leadership at senior level is about listening and influencing, not just doing.
The insurance industry may have a demand problem, not just a supply problem.
Community is one of the strongest retention tools in the industry.
Flexibility and trust are essential for modern ways of working.
Social media is one of the most powerful (and underused) tools to attract talent.
You either trust your team or you don’t. There is no middle ground.
About the Guest
Connect with Caroline Wagstaff on LinkedIn.
About the Host
Connect with Sandra Lewin on LinkedIn
Sign up to ‘Coffee with Sandra’ newsletter to stay up to date on all things 100 Women in Insurance.
Join ‘The Pink Book’ Collective — a private LinkedIn group connecting women in insurance to find mentors, speaking opportunities and more.
About Sponsor
BCH is a multidisciplinary Chartered Building Consultantancy.
