Why insurance mentorship should be a two-way street

By Alyssa DiSabatino, | December 1, 2025 | Last updated on December 12, 2025
3 min read
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People say mentorship makes better brokers. That can apply both to mentees and mentors, says Michael Boynton, vice president of business insurance at NFP Canada.  

“I’m at that mid-stage of my career where I’m able to look at it both ways. It’s not just about senior people teaching junior people. I think mentorship is a two-way relationship; top down is the transfer of experience, and bottom up is the transfer of new ideas,” he says. 

“When you have both working together, you build a brokerage that protects clients today, stays relevant for the future and ultimately promotes a healthier work culture.” 

Boynton recalls being mentored by his father and older brother, and several older colleagues, when he first entered the industry.  

Now, he’s doing his part by mentoring two new producers at NFP. He also regularly supports newer brokers and account managers with their work. 

Mentorship, he says, can help young brokers hone key skills like organization, sales strategy and how to ask the right client questions.  

Another lesson Boynton tries to instill in his mentees is to be well-prepared — that’s especially important ahead of tough client conversations, like claims losses or premium increases.

“I encourage brokers to over-prepare. I coach new brokers to approach those difficult conversations with preparation, transparency with the client, and empathy,” he says. “I think even when the news isn’t easy, when brokers communicate clearly and confidently, clients can trust the process.” 

But for mentors, there’s another added benefit to helping the younger cohort: brokers can deepen their own customer communication skills by explaining products or policy wordings to their junior colleagues. 

“When you help someone else develop, you end up raising your own standards as well. So for example, when you’re explaining coverage to someone, that process sharpens your own thinking,” he says. “It’s made me a better communicator with clients, because you learn how to…translate those complex risks into plain language.” 

Closing the mentorship gap 

But senior leaders are retiring industry-wide, and they’re taking years of specialized knowledge with them. 

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Specifically, 8.5% of the industry is expected to retire by the end of 2026, according to the Insurance Institute of Canada’s 2023 demographic report.  

One solution to this widening knowledge gap is developing a two way mentorship dynamic. 

“Younger people are strong with technology. Senior brokers have decades of nuanced judgment. So the gap is in connecting those two groups,” Boynton says. “When mentorship is missing, you end up with tech savvy brokers who lack depth and experienced brokers who aren’t adopting new tools. So, we need both working together.” 

How technology can play a role

Plus, technology can help younger brokers learn the nuances of the products they sell. 

For example, Boynton regularly uses AI as a mentoring tool at his brokerage to help brokers work through client problems.

“They’ll put in…some simple company details…and it can spit out all the emerging risks that might be in that industry, and then provide claims examples.” 

And the tool allows their mentors to step in at the end and assess how their mentees approached the problem.  

“AI can document patterns and summarize complex wordings. It can highlight what questions to ask based on similar risks that we handled in the past. So when you combine that with human coaching, you get kind of the best of both worlds. New brokers grow faster, and senior brokers can spend more time on high-value teaching instead of repetitive instruction.” 

And, because AI systems can capture and organize information, it also retains institutional knowledge.  

That doesn’t mean it’s replacing senior brokers. Rather, it can support younger brokers by handling repeatable tasks, says Boynton. 

“The best outcomes come from combining human mentorship and smart technology.”

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Alyssa DiSabatino

Alyssa Di Sabatino has been a reporter for Canadian Underwriter since 2021, covering industry trends, market developments, and emerging risks.