Lessons Learned from Hiring a Director: Navigating Pitfalls in the Insurance Industry

Navigating the process of hiring a director-level employee in the insurance business can be tricky, as shared candidly by Joanna Wyckoff in the latest episode of the Insurance Business Babes podcast. This episode is packed with valuable lessons for both agency owners and aspiring directors about what to look for, red flags to avoid, and how to protect your business.

Red Flags and the Realities of Remote Work

Joanna recounted hiring a director of Agent Experience who was supposed to grow medical provider relationships and support the business during her absences. Despite the candidate’s impressive resume and persuasive interview, several red flags surfaced: lack of end-of-day reporting, limited presence at the office, and failure to log into key systems. Joanna admitted, “I had no way of measuring what they did that day because they failed to report any end of day activities like the rest of my staff does.” This lack of transparency was compounded by the employee’s use of a personal cell phone for business, eroding oversight and accountability.

Expensive Lessons: Pay and Expectations

Another major lesson was the cost of paying an employee during their licensing and contracting process—a stretch when the actual job tasks hadn’t even begun. Joanna paid several weeks’ salary for little to no business growth or value, a mistake Kathe summarized succinctly: “I would not pay people to do their contracting... they can come on board after their contracting is done.” Setting clear, measurable expectations from day one, including frequent check-ins, is crucial to avoid this pitfall.

Protecting Relationships and Company Assets

The most concerning outcome was the attempted transfer of business relationships to a competitor, highlighting the importance of contracts—not just with employees but with referral partners like doctor’s offices. As Joanna noted, “Now she's running around telling people crazy stories... when you let an employee manage a relationship, that doctor's office started seeing her every day and forgot about Joanna.” Owners must remain present in key partnerships and build contract protections into their processes.

Takeaways for Agency Owners

1. Vet Candidates Thoroughly: Assess real skills and demand proof—even from experienced hires. Personality and compatibility also matter.

2. Set Clear Accountability Measures: Require regular check-ins, system use, and task tracking from day one.

3. Don’t Pay for Licensing Time: Bring employees onboard only after they have their licensure completed independently.

4. Protect Relationships: Have strong, enforceable contracts for both employees and referral partners to prevent loss of business.

5. Stay Engaged: Even with trusted staff, maintain a visible role in key business relationships.

These hard-won lessons from the field will help you avoid costly hiring mistakes, protect your business relationships, and set up your next director for true success.

This episode is sponsored by ⁠CertifiedMedicareAgents.com⁠. Use the coupon code BABES2024 for a free lifetime BRONZE membership.