Week 19: One Size Does NOT Fit All

Most of us remember the game Perfection. You’re given a tray full of oddly shaped pieces and a board full of holes, and each piece fits in one and only one place. With the clock ticking, the challenge isn’t just speed; it’s recognizing which piece belongs where. Try to force a piece into the wrong hole, and it simply doesn’t work.

Interestingly, health insurance strategy works exactly the same way. Clients are the pieces, strategies are the openings, and while there may be several workable options for a particular client, there is usually one approach that fits better than the rest.

We hear a lot these days about how artificial intelligence is especially good at pattern recognition. It can look at large amounts of information, identify similarities, and quickly narrow in on likely outcomes. It turns out that experienced insurance agents aren’t all that different.

Seasoned professionals tend to see the right fit faster than newer agents, but that difference isn’t about intelligence or effort. It’s about intuition, and that comes from exposure.

Over time, experienced agents have seen more client profiles, more unusual situations, and more cases that didn’t quite fit the standard approach. That repeated exposure builds pattern recognition, allowing them to eliminate poor fits more quickly and focus their attention on strategies that are more likely to work.

Newer agents aren’t doing anything wrong. They simply haven’t seen as many shapes yet. And until you’ve encountered a wider range of scenarios, it’s hard to recognize which options truly belong on the table and which ones don’t.

Whether new or experienced, problems arise when an agent’s toolbox is limited. There’s an old saying that when you’re a hammer, the whole world starts to look like a nail—and the same thing happens in benefits. When you only know one or two strategies well, every client starts to look like a candidate for those same approaches. That’s when perfectly capable, well-intentioned advisors find themselves trying to make a solution work simply because it’s familiar, not because it’s the best fit.

This can show up in many ways: defaulting to the same funding method for every group, overlooking coordination opportunities with Medicare, or never even considering reimbursement-based or alternative strategies. It isn’t negligence. It’s the natural outcome of working with a narrow set of options. Square pegs end up in round holes not because agents don’t care, but because they don’t always know another hole exists.

Over the years, I’ve asked dozens (and probably hundreds) of poll questions in CE classes about attendees’ familiarity with different benefit strategies, and the results are remarkably consistent. Many agents report that they are not familiar with – or have never even heard of – strategies like:

• Medicare Premium Reimbursement Arrangements (MPRAs)

• Captive solutions

• Medical Expense Reimbursement Plans (MERPs)

At the same time, other agents say they use these strategies regularly and have clients who benefit significantly from them. The difference isn’t regulation, market, or intelligence – it’s exposure. Two agents can operate in the same environment and have completely different strategic toolkits.

It’s important to be clear here. Knowing about a strategy does not mean you need to recommend it, sell it, or even like it.

In many cases, the right answer really is a traditional approach. But understanding that alternatives exist, and knowing when they might or might not apply, makes advisors more confident in the recommendations they ultimately make.

That confidence matters. Clients can feel the difference between a recommendation that’s chosen because it’s familiar and one that’s chosen because it’s been thoughtfully considered against other viable options.

This is why, heading into 2026, we’re intentionally shifting toward deeper conversations with subject matter experts and solution providers. Rather than offering surface-level overviews or quick summaries, the goal is to explore when a strategy actually makes sense, when it doesn’t, and what real-world implementation looks like. These conversations aren’t about adding complexity for the sake of it; they’re about helping agents recognize more shapes so they’re less likely to force a fit.

The more strategies you understand, the easier it becomes to rule out the wrong ones and feel confident in the right one – even when that right answer is simple.

When advisors broaden their understanding, clients receive recommendations that feel tailored rather than templated. Trust deepens, renewals become smoother, and agents gain confidence in their role as problem-solvers rather than product-pushers.

One size does not fit all in health insurance. The more shapes you recognize, the better your chances of finding the right fit (before the clock runs out).