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As artificial intelligence transforms the insurance industry, we may be overlooking one of its greatest challenges: Who will teach the next generation what experience has taught us?
Think back to when you first entered the insurance business. You probably learned the fundamentals by reviewing policies, reviewing loss runs, handling claims, or working alongside someone who had been doing the job for years.
And when something didn't look quite right, there was usually an experienced colleague who could explain why. Those everyday interactions were more than just getting the work done. They were how insurance professionals developed the instincts, judgment, and expertise that made them valuable.
Now, AI is beginning to take over many of those routine responsibilities. That's good news for productivity, but it raises an important question: If AI does the work that once taught people the business, how will the next generation gain the experience they need?
The Experience Gap Nobody Is Talking About
AI can review documents, identify inconsistencies, analyze information, and recommend decisions in seconds. But knowing what to do with that information still requires judgment. Consider a young commercial lines underwriter reviewing an unusual risk. AI may identify the exposures and recommend a course of action. But will that underwriter recognize when the recommendation doesn't tell the whole story? Will they know which questions to ask, what exceptions matter, or when to challenge the results?
Those skills aren't learned simply by reading a procedure manual. They're developed through experience, mistakes, conversations, and guidance from people who have encountered similar situations before. And that guidance may be harder to find than we think.
A 2026 report from the Chartered Insurance Institute's New Generation Broking Group found that only 11% of surveyed insurance professionals reported having a formal knowledge-transfer program. Research from SHRM revealed a similar problem across industries, with most HR professionals reporting that their organizations weren't formally documenting critical industry or relationship knowledge.
In other words, we're automating work faster than we're developing ways to pass along the knowledge behind it.
The Value of Experience Has Never Been Greater
For decades, the insurance industry has relied on experienced professionals to mentor younger colleagues, often informally. A senior claims examiner explains why a seemingly minor detail changes the outcome. An experienced account manager recognizes a coverage gap before it becomes a problem. A veteran underwriter knows when a risk deserves a closer look.
These are lessons that can't always be captured in a system or replicated by an algorithm. And as more experienced insurance professionals approach retirement, the industry risks losing not only their expertise but also the people best equipped to teach it.
The solution isn't to resist AI.
It's to recognize that technology and human experience are most powerful when they work together.
Organizations need to be more intentional about knowledge transfer. That means creating opportunities for experienced professionals to coach newer employees, review complex cases together, explain the reasoning behind decisions, and share the lessons that only years in the business can provide.
Keeping Experience in the Workforce
At WAHVE, we've always believed that retirement shouldn't mean the end of a valuable insurance career.Through our Vintage Contract Staffing solution, experienced insurance professionals can continue contributing their expertise while helping organizations meet their staffing needs. Just as importantly, they can serve as valuable resources to less experienced colleagues, sharing the knowledge and perspective developed over decades in the industry.
Of course, that knowledge transfer doesn't happen automatically. Employers need to create the opportunities for mentoring, collaboration, and learning. AI will undoubtedly change how insurance work gets done. But it doesn't eliminate the need for experienced professionals. In many ways, it makes their contributions even more important.
The real question isn't just what work AI can do for us. It's how we ensure the next generation learns what AI can't teach.
Because the future of insurance won't depend on technology alone. It will depend on the people who know how to use it wisely—and the experienced professionals who help them get there.
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