05/04/2026
“Never discuss religion, politics… or insurance at Thanksgiving dinner.”
One of my newest clients recently had one of the hardest business conversations they’ve ever faced — breaking up with the same insurance agent their company had worked with for nearly 50 years.
Think about that.
Generational relationships.
Holiday cards.
Claims calls.
Renewals year after year.
At some point, the relationship became personal.
But as the business evolved, so did the risks, exposures, and insurance needs.
These conversations are emotional. Awkward. Often avoided for years because nobody wants to feel like they’re betraying someone who’s been there forever.
But if a major uninsured or underinsured loss happens, the breakup suddenly becomes much easier — because the question changes to:
“Why didn’t we address this sooner?”
The best insurance relationships don’t just provide comfort. They challenge your strategy, evolve with your business, and make sure your protection keeps pace with your growth.
Because insurance isn’t about avoiding difficult conversations.
It’s about surviving the difficult moments.
Marshall+Sterling