Many people, myself included, have a recurring dream where they show up for a college exam, but have either forgotten to attend the requisite class or completed any of the coursework. The dream always leaves a pit in my stomach, realizing how terribly underprepared I am for some crucial exam. Though it’s been a while since my last midterm, the lesson remains the same: being unprepared isn’t fun, and frankly, it can be terrifying. It’s one of the many reasons why I tell employers — as well as vendors and brokers — that they need to prepare for enrollment strategies.

Now, you may think preparation means coordinating communications and resources for an upcoming enrollment, and that’s certainly accurate. But this step needs to be taken even further. Employers shouldn’t just be preparing for their next enrollment, they should plan for their next several enrollments.

Doing so allows all parties involved — including employers, employees, brokers and vendors — to map out the best course of action for workplace benefits, related employee communications and engagement goals and the actual enrollment solution that’s being set-up. And, best of all, it means employers are always prepared for what comes next year after year. As a matter of fact, when one year’s messaging is completed and evaluated, you’re starting to plan for the following year’s messaging and enrollment process.

Here’s how to help create this strategy.

A multi-year enrollment strategy for benefits

A solid multi-year enrollment strategy starts with the benefits strategy for the employer and their employees. Too often, enrollment strategies miss their intended mark when employees are overloaded with benefits and, especially, multiple voluntary benefits all at one time. While insurance professionals live and breathe insurance daily, it’s likely that employees are only thinking about their benefits during enrollment or when they need to file a claim. Rather than bombarding workers with a massive voluntary benefits package, it’s more effective to prepare, and to plan a multi-year strategy for unveiling employees’ benefit options.

As an example, employers may want to introduce just one or two new voluntary benefits in the first year. Then, the next year, those benefits will be serviced with a re-enrollment. And the year after that, introduce new benefits during enrollment. This multi-year approach saves employees from being overwhelmed and lets them absorb the value of the benefits year-over-year.

This way, employees can make a more informed decision about their benefits and what is important for themselves and their families. This strategy also helps establish a roadmap for a long-lasting relationship between employers and advisers — a win-win all around.

A multi-year enrollment strategy for communication

If you’re going to have a plan for introducing new benefits throughout the year and, most importantly, want employees to understand those benefits, you need to have a plan when it comes to communication. A multi-year enrollment strategy must, in turn, encompass a communication strategy to deliver information on what benefits are being offered, how their benefits work in conjunction with each other and when employees will have an opportunity to enroll.

The benefit strategy you painstakingly created will only take you so far if you don’t have regular communication to make employees aware of the benefits and ultimately help these employees appreciate their value. Treating communication as a one-off project just before enrollment begins does not work effectively; it needs to be a concerted effort that occurs throughout the year.

Ongoing communications about benefits is fantastic for helping employees understand their benefits, but it also offers a solution for employers. Employers may have a wide range of topics they want to address with employees in addition to their complete benefits package such as high-deductible health plans, dependent audits, well-being programs, corporate strategy communications to all employees, customer service initiatives, 401(k) education and many, many more. Employers can use their multi-year enrollment strategy as a tool to piggy back on their benefits communication to address these important corporate initiatives or messaging. Especially at time of enrollment, this is a great way to keep employees engaged and drive home important topics that employers need to address.

A multi-year enrollment strategy for one-on-one enrollment


Of course, if you want to use enrollment as a vehicle to drive important company initiatives, you need to conduct regular, active enrollments. In an ideal world, this would mean that on an annual basis, producers and employers collaborate on a plan to initiate one-on-one employee benefits enrollment.

About 90% of employees who enroll one-on-one with an insurance representative express high levels of satisfaction with their enrollment, according to a Trustmark study. And it’s not just our research that bears this out: we’ve seen time and time again that this kind of one-on-one engagement drives the strongest results in terms of participation. For employees who need guidance on the right protection or for employers looking to engage employees on important topics, planning an annual one-on-one enrollment as part of your multi-year enrollment strategy will work wonders for delivering results on both of these goals.

Both employers and advisers look toward enrollment to provide education on, appreciation for and participation in benefits. And a properly executed multi-year enrollment strategy can help both meet these shared objectives. Beyond that, a multi-year enrollment plan sets employers up for long-lasting success. It’s a long-term strategy that helps to make sure that the nightmare scenario, where you show up unprepared on the day of the exam, remains nothing more than a bad dream.

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Dan Johnson

Dan Johnson

Dan Johnson is vice president of sales and marketing for Trustmark Voluntary Benefit Solutions and has more than 30 years of experience in the insurance industry. Dan has spoken to various industry groups such as Voluntary Employee Benefits Board, National Association of Health Underwriters, and Million Dollar Round Table. Dan was elected into the Workplace Benefits Hall of Fame in 2013. Dan can be reached at dan.johnson@trustmarksolutions.com.