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It’s that time of year again, when those eagerly anticipated benefits enrollment guides will soon arrive in mailboxes (and inboxes) around the country.


Employees and their family members have been waiting patiently all year, and soon they’ll be reading those enrollment guides cover to cover, feeling more ready than ever to make informed choices that match their needs exactly…Right?

Okay, that might just be my dream. Engaging employees in benefits is tough, and sometimes the engagement dream never comes down from the clouds to acknowledge the realities of the employee experience on the ground. 

For a while now, I’ve heard about the idea of delivering a benefits shopping experience. Sounds good on paper, but the problem is that employees don’t really like to shop for benefits. And it’s understandable. Filling a shopping cart with a high-deductible health plan, long-term disability coverage and optional life insurance isn’t quite as satisfying as discovering a great pair of boots during a Cyber Monday online sale. Shopping for those boots online is, well, just different than choosing benefits.

To find the boots (and the price) you like best, you might visit several different websites. You might put something in your cart. You might even buy it. But you might not, happy enough to let the cart sit there for a while as you continue shopping around for the best deal. After all, there’s probably no rush. As a friend of mine says (she’s a website user experience testing pro), this is a “frequent but non-critical task.”

With choosing benefits, it’s a little more complicated because while the things you’re choosing are going to protect your health and well-being throughout the year, none of it feels like a bargain. And of course, there’s a ticking clock—the enrollment deadline—which can feel especially stressful when you’re not even sure what you’re buying. My user experience friend calls this an “infrequent but critical task.” It’s only once a year, but there’s big money involved and important protections to choose. But even so, a lot of employees would like to avoid annual enrollment altogether.

But there’s a lot we can do to make it a better experience, and to help employees through this infrequent but critical task with more understanding and confidence. Here are some tips to consider:

  1. Start with a goal. If you are thinking about changing your approach to annual enrollment communication, start with small steps. Do you have a goal that’s specific about what you want your investment in communication to achieve? Here are some questions to consider:
  • Is it a status-quo benefits year when not much is changing, or are there important, new program details to explain to your employees?
  • Are enrollment patterns across plans right where you want them, or are many of your employees over-insured in higher-cost plans that include benefits that often go unused?
  • If you offer an HSA-based medical plan, are employees making the most of the HSA’s many tax advantages, or are many leaving those opportunities on the table?
  • Do your employees know how to make informed enrollment decisions, or is it more of a guessing game that involves random advice from co-workers—or perhaps in extreme cases an astrologer?

These are just a few examples, but the answers to questions like this can help you sharpen the focus of your communication strategy, and create new opportunities for outreach that’s more personalized and relevant.

  1. Make it a conversation, not a speech. Is your communication plan a one-way street, without feedback channels or dialog with your employees? If so, consider developing an employee listening strategy. It’s a great way to understand employee concerns and discover any disconnections in engagement. Plus, it will help you evolve your strategy and target your investments with employee concerns and preferences in mind.
  2. Focus on the “why” as well as the “what. Are you devoting enough energy and content to explaining why your organization offers the benefits you’re writing about? Employees need to understand the context for all the details you communicate, and it’s even better if they can see how those details fit into your broader total rewards strategy. 
  3. Look beyond the enrollment guide. After all, there’s only so much a benefits guide can do. While it’s a great resource for all the details, the information can be challenging to absorb. For every employee who reads it cover to cover, there are probably ten who are skimming it (at best). So, consider a slimmer guide and think about delivering content through other touch points—like SMS text, social media, artificial intelligence-powered assistance and mobile apps. They’ll help you meet employees where they are and engage them more like consumers.
  4. Build in a few surprises. When it comes to benefits, the word “surprise” might not seem like a good fit. After all, there’s serious money attached to benefit programs, for you and for your employees. But that doesn’t mean you can’t do the unexpected. Whether it’s different content choices, a fresh graphic design or a new communication channel, your annual enrollment story is sure to be more compelling if there’s some element of your engagement strategy that your employees don’t see coming.

Ready to flip the employee experience through better engagement? Get started with Businessolver.

Want more information on how you can harness the power of AI for better benefits engagement? Check out our e-book below. 

AI and empathy

View all Posts by Mike Shepherd