You Love Benefits. Your Employees Just Need Them. That’s Why Your Open Enrollment Emails Don’t Work.

This site contains affiliate links. View the disclosure for more information.

Early in my career, at a company out in the field, I was so proud of my open enrollment reminder emails. They were cute. They were funny. I’d worked little jokes in, made them feel friendly instead of corporate, and I genuinely thought I’d cracked it.

People liked them. I got a few smiles in the hallway, a “hey, those emails are fun.” And then the numbers came in, and the elections hadn’t moved. Same low engagement, same wrong choices, same wave of confused questions after the deadline. The emails were a hit and a failure at the same time. Leadership noticed the second part.

It took me a while to understand what happened, and it’s the thing nobody tells you: I wasn’t writing for my employees. I was writing for me — the person who loves benefits. They didn’t need cute. They needed to know what to do, why it mattered to them, and that it would take less than five minutes. I’d made the emails enjoyable to the one person who already cared. Everyone else still had no idea what to pick.

If your open enrollment communication isn’t landing, this is almost always why. Not because your people are lazy. Because the message was built for the wrong reader. Let’s fix that.

The Real Problem Isn’t Confusion. It’s That You’re Not Your Reader.

Here’s the uncomfortable truth about benefits communication: the person writing it almost always cares about benefits more than the person reading it. You chose this work. You understand deductibles and HSAs and why the lower premium might cost more in the end. You find this stuff genuinely interesting.

Your employees don’t. The majority of people enrolling in benefits don’t love them — they have them because they know they need them. Benefits are a checkmark on a to-do list between a project deadline and picking up the kids. They’ll give your email about eight seconds before deciding whether it’s worth their attention.

That gap — between how much you care and how much they care — is the single biggest reason open enrollment communication fails. And the research backs it up: studies consistently find that most employees don’t fully understand the benefits they enrolled in, and the majority just re-pick last year’s choices rather than engage. The usual advice is “communicate more, on more channels.” But volume isn’t the problem. Translation is. You’re fluent in benefits. They’re not. Your job isn’t to say more — it’s to say it in their language.

How Adults Actually Take In Information (and How to Use It)

There’s real research on how adults learn, and it explains exactly why benefits messaging bounces off. Adults don’t absorb information the way kids in a classroom do. They engage when it’s relevant to a problem they actually have, on their timeline, in pieces they can use. Here’s how to turn that into messages that land.

1. Lead with their “why,” not your deadline.

Adults tune in when they know why something matters to them. Most OE emails open with “Open enrollment is November 1–15” — a deadline, which is your priority, not theirs. Flip it. Open with what’s at stake for them: “The choice you make this month decides what you pay at the doctor all next year.” Now they have a reason to keep reading.

2. Organize around their life questions, not your plan tiers.

You think in plans: PPO, HDHP, tier one, tier two. They think in questions: “What happens if my kid needs braces?” “What if I want to have a baby next year?” “What if I barely go to the doctor?” Build your communication around their questions and the right plan becomes the answer. Build it around your tiers and they glaze over.

3. Name what they already believe — then correct it.

Adults filter everything through what they already think they know. A lot of your people believe “the cheapest premium is the cheapest plan,” and they’re often wrong. Say it out loud: “The plan with the lowest paycheck deduction can cost you the most when you actually use it. Here’s how to tell.” When you name the belief they’re walking in with, they trust you enough to update it.

4. Deliver it in pieces, at the right moment.

A 20-page guide dropped a week before the deadline is information overload, and overloaded people freeze and default to last year. Break it up. One message about what’s changing. A separate one about how to decide. A reminder with the action step. Each one short, each one timed to when they need it — not all at once.

5. Give them a way to decide, not an order.

Adults want to make their own call; they resist being told what to pick. “Just choose the HDHP” backfires. Instead, hand them the question that leads to the answer: “If you rarely see a doctor and want lower paycheck costs, look here first. If you have regular prescriptions or kids in and out of the doctor, start here.” You’re guiding the decision, not making it for them. That’s what earns the click.

Forget Tailoring It by Generation

You’ve probably been told you need to talk to your Gen Z employees one way, your Boomers another, your Gen Xers a third. Put that down. When researchers reviewed more than twenty studies on generational differences at work, they found the meaningful differences mostly don’t exist — and that chasing them is closer to marketing than science. In one study, every generation ranked the same thing first: information shown simply and visually. They all wanted the same clear, plain, relevant message.

So you don’t need five versions of your OE email sorted by birth year. You need one version that respects how every adult takes in information: lead with the why, organize around real questions, keep it in pieces, make it plain. Chasing generational segments is how you end up exhausted and no clearer. Skip it.

So Should You Stop Being Fun? No.

Back to my cute, funny emails for a second, because the lesson isn’t “be boring.” Those emails got opened. People read them. Attention is the hardest part of this whole job, and personality is how you earn it — a warm, human voice will always beat corporate gray. That part was right.

What was missing wasn’t the warmth. It was the action. My fun emails entertained people and then let them go without telling them clearly what to do next. The fix isn’t to strip out the personality — it’s to attach every bit of that personality to one clear ask. Be the warmest, most human voice in their inbox, and make sure that voice points at a single next step. Voice plus action. Not one or the other.

What Usually Goes Wrong

Before the list, the short version: every one of these is the same mistake wearing a different hat — writing for the person who loves benefits instead of the person who just has them.

Where to Start This Week

If you do one thing: stop writing your next OE email from scratch. I pulled together the exact messages I use — the kickoff, the “what’s changing and what you do about it,” the reminder that drives action without nagging, and a plain-English plan-comparison one-pager — and wrote them so employees actually read them. Grab Steal My Open Enrollment Emails — five copy-paste templates, free.

For the visuals, build your one-pagers in Canva. A clean, plain-English benefit comparison your people can scan in thirty seconds beats a dense PDF every time — and Canva’s free templates make it quick. (Heads up: that’s an affiliate link, and I only point you to tools I actually use.)

And when you’re ready to run your whole open enrollment like a system — not just the emails, but the timeline, the rate math, and the decision tools — the Open Enrollment Mastery Kit is the full playbook: a 34-page plain-English guide, a 9-tab calculator, and a ready-to-use checklist.

Your employees are never going to love benefits the way you do. That’s okay. You love them enough for everyone — now let’s package that love so it actually lands.

This site contains affiliate links. View the disclosure for more information.