Ten years ago, when it came to benefits enrollment, many employees met “knee to knee” with an HR representative to enroll in their benefits. This was the norm. HR reps were essentially promised access to every employee at the worksite, where, crucially, employees either accepted or declined benefits.
However, in 2020, the pandemic changed all that. The entire process went online. Suddenly, technology helped employees through the enrollment process.
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Fast forward to 2025 and employees are now largely left to their own devices to figure out the benefits enrollment process. This “passive enrollment” trend is mired in a mix of clunky technology, poor communication, less effective call center interactions, and, with on-cycle enrollments, lower visibility for voluntary benefits.
With a more dispersed employee working population, a trend toward more passive enrollments, and often poor technology that has effectively replaced the old “knee-to-knee” assisted enrollments, how can HR teams overcome these challenges to increase employee engagement and participation? Surprisingly, one word holds the key.
The power of the regret of “no”
William Ury wrote a famous negotiation book titled Getting Past No. It could be retitled At Least Get Us a No for the purposes of this discussion. Because one approach that has proven to work well when it comes to passive benefits enrollment is requiring employees to at least decline coverage.
Why is that such an effective strategy? It can be attributed to the behavioral economics principle, “the power of the regret of no”, a concept that takes an everyday consumer purchasing experience and makes it personal. According to the principle, the more the product or service affects life events, finances, or health, the more powerful the emotional response is during the evaluation.
Think about it: If you don’t require a response from employees during the enrollment process, they may never consider the benefits of the benefit or the risks of not having it. They may not realize they have a need, much less take action to purchase coverage. In other words, without the requirement of at least a “no,” there might never be a “yes.”
If we require employees to accept or decline a benefit, they are forced to consider it, if only for a moment. When presented with a benefit option, that employees must actively accept or decline, they consciously or subconsciously start to evaluate scenarios.
Simply reviewing the features of the benefit or insurance product force them to imagine the consequences of not having it. For example: “What if I don’t buy this and I’m confined to a nursing home? Will I have enough savings to cover living and health care expenses? Will my spouse be able to manage?”
These evaluations – whether just a split second or more in-depth – are only created through the act of engaging in a “yes” or “no” election. It’s the “power of the regret of no”–imagining the consequences of not having (and regret of actively declining) the benefit if and when the need arises.
As a result, more employees will, in theory, after the evaluation process, check “yes.”
Now, some might counter that employees go through this thoughtful evaluation anyway. However, being forced to decline and at least subconsciously consider the outcome is what triggers the “power of the regret of no,” particularly in risk-based scenarios.
A personal example
What does this look like in real life? I’ll give you a personal example. When my first child went to college – as you can imagine – it was an emotional and exciting time. I kept receiving emails from the college reminding me to accept or decline tuition reimbursement insurance. I ignored the emails. After all, I had already paid the tuition and had no interest in the option.
Wouldn’t you know it, the emails persisted. Eventually, one came with this message: “your daughter cannot attend class until you accept or decline tuition reimbursement insurance.”
So, I quickly visited the enrollment website with the intention of declining the tuition reimbursement option. But before making his election, I realized for the first time what the cost would be for the insurance. It was very affordable. So much so that I thought to myself, “I would be crazy not to purchase this insurance!”
So, I did.
Why did I purchase something I thought for sure I had no interest in? Because with such a reasonable price to cover worst-case scenarios, I experienced the fear of not purchasing.
I hadn’t intended to purchase insurance, and yet, by being forced to make an election I ended up choosing “yes.” I realized that this was the “power of the regret of no” in action.
A simple “yay” or “nay” goes a long way
The world is increasingly moving towards self-service. But how do you replicate a more traditional enrollment experience in a way that also captures a decision? Force your employees to make a decision.
Unlike other passive strategies that may frustrate people with poor technology and out-of-synch integrations, this simple technique can be engaging, efficient and makes the best use of employees’ time.
Crucially, by requiring an answer of yay or nay, thanks to behavioral economics and the principle of the regret of no, more people end up saying yes. By actively driving engagement, the resulting population of “yes” is more balanced. The ultimate result? More people gain valuable coverage that will provide substantial financial support as they age.
Tom Smith is the vice president of enrollment services with Trustmark.
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