
By Paul Cicco
Posted on: August 11, 2026
After enough enrollment seasons, it can be tempting to treat each one like the last. Same timing, same processes, same communication cadence – with success measured the same way it always has been: how many people enrolled.
But no two enrollment seasons are really the same. The economy shifts, workforce expectations evolve, and the way people want to receive benefits information changes right alongside. That means gauging success based on participation rates doesn’t always account for the more important objective, making sure employees understand what they applied for – and feel good about that decision months later.

As you help your clients plan for the upcoming season, here are three insights from the latest research to help you refine strategies and measure success.
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Build for understanding, not just enrollments
First, some good news. Interest in voluntary benefits has never been higher. According to our recent Pathway to voluntary benefits success report, 71% of working Americans* now say voluntary benefits are valuable or very valuable – up 12 points from last year.1 For an industry that's spent years telling employers and employees about the importance of these products, that's a real win.
Heightened interest is an opportunity to capitalize on during open enrollment, but it’s not as simple as it seems on the surface.
Forty-one percent of employees regret decisions they made about voluntary benefits during open enrollment, and 44 percent already plan to drop a benefit.1 Those aren't small numbers, and it's not a coincidence. Interest doesn't automatically translate into comprehension – and the products most likely to be misunderstood are often the ones with the most to offer. For example, based on a new LIMRA study, even among employees who are already insured, only about 6 in 10 say they understand group accident insurance, group critical illness insurance, or group disability income insurance well, compared to roughly 75 percent for medical and dental.2
Generic product feature descriptions don’t solve this challenge. What can work better is something concrete, such as product-in-action scenarios based on real-life situations, simple side-by-side plan comparisons built for the client's options, and short walk-throughs of how a claim really works. Tap into carrier resources to deliver tangible messages that go beyond status quo descriptions to highlight how benefits show up in moments employees recognize and relate to. Even better, showcase how coverages, like supplemental health products, work in tandem with other benefits to help reduce critical – and real – financial protection gaps.
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Design communication plans with reach – and staying power
You already know that workforces are more diverse than ever. So, it’s not surprising that no single communication channel effectively engages all employees. Understanding communication preferences is essential when tailoring each client’s open enrollment plan.
Conventional wisdom may be that younger employees may respond to something on a portal or app, while older generations rely on printed materials or a straightforward email. Overall numbers from the same LIMRA study help quantify employee preferences across a range of channels. Forty-three percent rely on email, 30% prefer online resources, 24% want printed materials mailed to their home.2
However, when you look at the numbers by generation, a more nuanced picture emerges:2
- Gen X leads the generations in preference for online benefits resources at 35%, compared to 23% of Gen Z.
- One-third of Gen Z likes to get text message communications, but the channel is favored by only 6% of Baby Boomers.
- Printed materials appeal to 30% of Baby Boomers – and, perhaps surprisingly, 22% of Gen Z employees.
Reaching employees is only half the equation – cadence and frequency are also key. Right now, 45% of employees say they only hear about benefits during open enrollment, even though most would welcome more frequent contact.2
Help clients think about open enrollment communications as part of a broader, year-round benefits communication effort. Employees who hear from their employer about benefits consistently, not only during the enrollment period, can come into enrollment already oriented and stay more confident in their choices well after it closes.
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Evaluate – and refine – the enrollment experience
Eighty percent of employees now prefer to enroll electronically, and 74 percent did during their most recent enrollment.2 That means most clients have a digital enrollment platform already in place. But even an established platform can have friction points that go unnoticed until an employee actually tries to use it – and that gap matters more for voluntary benefits than it does for medical.
Here's why: employees are motivated to push through a clunky process for medical coverage because the stakes feel high enough to justify the effort. Voluntary benefits don't always get that same built-in motivation. The friction that's a minor annoyance during medical enrollment – an extra click, a confusing screen, a hard-to-find detail – can be the deciding factor in whether someone finishes enrolling in supplemental health benefits at all.
Before the season opens, it's worth walking through the enrollment flow the way an employee would. How many steps does it take to complete? Is more information easy to find in the moment someone needs it, without leaving the flow entirely? Does it work as well on a phone as it does on a desktop? Flagging friction points and helping clients address them can ensure that a confusing enrollment moment doesn't undo all of the education and communication work that's come before it.
It's also worth the effort. Our latest Pathway to voluntary benefits success report also shows ease of enrollment is a growing factor in how employees perceive the value of their voluntary benefits, with related measures — like how easy the process felt — up 7 points year-over-year.1
Set your clients up for success
Participation will always be a key measure of enrollment success. But the real results come later when employees understand what they signed up for, see the value in it, and choose to re-enroll in the coverage next year. When you design enrollment strategies with those measures in mind, participation numbers tend to take care of themselves.
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* The MassMutual Workforce Financial Stability Score measures the changing attitudes and financial outlook of working Americans. Commissioned by MassMutual, the research began in June 2022 and is conducted online, monthly, among a nationally representative sample of 1,000 U.S. middle-market employees. For purposes of this research, MassMutual defines working Americans and middle-market employees between ages 22 and 67, working at firms with at least 25 benefit-eligible employees, with a household income of $40,000 to less than $150,000, and assets less than $300,000.
1 The pathway to voluntary benefits success, MassMutual Q1 2026 Report.
2 LIMRA 2026 BEAT Study, Benefits and Employee Attitude Tracker
Products and/or certain features may not be available in all states. State variations will apply.
Insurance products issued by Massachusetts Mutual Life Insurance Company (MassMutual) and its subsidiaries, C.M. Life Insurance Company (C. M. Life) and MML Bay State Life Insurance Company (MMLBay State), Springfield, MA 01111-0001. C.M. Life and MML Bay State are non-admitted in New York.
