Open enrollment 2026 will be here before you know it. But first, it’s worth taking a look at how your last open enrollment season went.
Did your staff feel informed or overwhelmed?
Did they actively engage with their options or default to the same plan as last year?
A recent HubSpot study found that 85% of employees are confused about their benefits. That stat is a clear signal that the current approach to OE isn’t working for most teams. Confusion can lead to indecision, frustration, and costly plan choices. It’s no wonder that many employees hate benefits open enrollment.
When you reflect on your last OE season and discover pain points, it’s not a bad thing. It’s an opportunity to learn from what didn’t work and build a stronger approach moving forward. With the right tools, messaging, and support systems in place, OE can transform into an engaging and empowering experience.
Let’s look into ways you can set yourself (and your employees) up for a smooth open enrollment.
Make Active Enrollment the Standard
Open enrollment shouldn’t be a passive check-the-box experience. Employees often skim an email (if that), assume nothing has changed, and stick with last year’s plan. They risk missing opportunities for savings or better coverage.
It’s best to start encouraging active enrollment. It’s a mindset that encourages employees to actively evaluate their current needs and make choices that align with where they are now.
Passive Enrollment Example: An employee with a new baby sticks with a high-deductible health plan they chose last year. They don’t realize that a PPO might offer more savings for increased pediatric visits.
Active Enrollment Example: The same employee receives a personalized video or text reminder highlighting potential plan options for a growing family. They take ten minutes to go over their choices and decide what makes the most sense for them in this stage of life.
How to do it:
- Send targeted text or email reminders.
- Use short explainer videos to walk through the plan changes.
- Offer decision-support tools that guide employees step-by-step.
Guiding employees through a more active open enrollment can help them make better-informed decisions. These decisions can lead to higher satisfaction, better outcomes, and fewer post-enrollment questions.
Prioritize Personalized Benefits Communication
Mass emails are easy to ignore. When a message feels generic or out of touch, it’s usually deleted without a second thought. Benefits communication needs to be more than an information dump. It needs to feel personalized.
What cuts through the noise is relevance.
Speak directly to the new hire, the remote worker, or those managing care for a family member. It cuts through the noise. It feels helpful. And most importantly, intentional.
Think for a moment about how different your workforce really is. A new hire might be overwhelmed and unsure where to start. A veteran employee with a growing family might be juggling dependent care, prescription coverage, and provider changes. Those two people don’t need the same messaging.
Even small touches, like referencing someone’s location or prior plan, can go a long way toward making messages feel tailored.
Take your communication beyond what you say to how you say it. A short personalized video can explain a plan change better than a long email. A digital postcard might get more attention than an intranet update.
Incorporating intentional digital solutions can help deliver content that resonates on a human level.
Expand Benefits Options
In 2026, employees are looking beyond medical and dental. Flexibility matters now more than ever.
Wellness stipends, learning allowances, childcare support, and mental health services aren’t fringe perks anymore. They’re a part of how employees evaluate if their employers support their lives outside of work.
At the same time, rising healthcare costs and the squeeze of inflation are making financial wellness a top concern. Educating employees on tools like HSAs and FSAs can help them stretch their dollars and plan ahead.
A strong communication strategy should:
- Highlight lesser-known benefits.
- Offer clear, accessible education before OE begins.
- Reinforce the value of financial planning tools year-round.
Digital benefits guides and microsites make it simple to educate employees on the full range of benefits available.
Lean into AI-Driven Support Tools
When employees are choosing between benefits plans, timing matters. So does accessibility to reliable information. But HR teams can’t be everywhere at once, especially during the busy open enrollment season.
That’s where AI support tools enter the chat. AI-powered chatbots, digital assistants, and interactive decision aids can give instant answers to common questions 24/7. No help desk ticket. No waiting on an email reply.
Let’s say you have an employee who is comparing two health plans. They have to decide by tomorrow’s enrollment deadline. Instead of reading through dense plan docs, they have an AI-guided comparison. Employees can make informed decisions quickly without the stress or back-and-forth.
Want to know more about this approach? A Scientific Approach to Open Enrollment breaks down how employees make decisions and how AI fits naturally into that process.
Design a Digital-First OE Experience
A digital-first approach isn’t just efficient. It’s expected.
Employees want mobile-friendly content they can access anytime. That means going beyond PDFs and links.
Imagine a mobile-optimized microsite where employees can:
- Explore plan options in plain language.
- Watch short explainer videos on new or updated benefits.
- Access links to enroll, ask questions, or schedule one-on-one support.
Layer in text updates and interactive digital postcards, and suddenly, OE becomes something employees actually pay attention to and engage with.
A streamlined digital experience tells employees you respect their time. It gives them the tools that make understanding their benefits simpler.
For more ideas on using the right channels at the right time, check out Open Enrollment Multi-Channel Messaging.
Extend Engagement Beyond Enrollment Season
Benefits education doesn’t end in January. Year-round communication is one of the best ways to reduce stress during OE and empower employees to make smarter decisions over time.
Implementing a year-round strategy doesn’t have to be complicated. Building consistent, bite-sized communication throughout the year makes it easier for employees to engage when it matters most.
1. Monthly Benefits Newsletters
Use a simple, branded email newsletter to keep benefits top-of-mind. Each month, highlight a topic and break it down. Some options could include preventative care in spring, wellness reimbursements before the end of the year, or a breakdown of HSAs and FSAs.
Promoting underutilized benefits and answering FAQs is another way to add value. Bonus: Include short employee stories or testimonials to make it more relatable.
2. “Did You Know?” Micro-Campaigns
Send out brief and focused messages that spotlight one benefit at a time. These could be emails, SMS texts, or digital postcards.
For example:
“Did you know your HSA can be used for dental and vision expenses?”
“You get three free therapy sessions through our EAP. No copay!”
This kind of micro-education helps employees rediscover the value of their benefits and encourages using them throughout the year.
3. Short Video Spotlights
Share quick 60 to 90-second videos that explain how to use a specific benefit or answer FAQs.
Topics could include:
- Understanding your deductible.
- How to submit an FSA claim.
- When to use telehealth.
You can host these videos on your benefits microsite and send them out via email or text. Flimp designs animated explainer videos to cover these topics. They’re visually engaging, easy to understand, and perfect for mobile. One less thing to add to your to-do list.
4. Seasonal Benefits Reminders.
Align benefits messaging with what employees are already thinking about. In Q1, talk about preventative care. In the summer, promote travel-related benefits like telehealth or ID theft protection. In the fall, remind employees to use their wellness stipends or FSAs before year-end deadlines. Make these links clear for them so the context sinks in.
5. Employee Surveys and Feedback Loops
Engagement goes both ways. Periodically check in with employees about how they’re using benefits, what’s confusing, or what they’d like to learn more about. Use quick pulse surveys or embed one-question polls in your newsletters. This input can act as a guide for your messaging while showing your employees that their voices matter.
More Than a Process, It’s a Message
Open enrollment is often seen as a logistical hurdle to get through. But it’s actually one of the most visible expressions of your company’s values. How you communicate about benefits, how accessible tools are, and how supported employees feel during the process all send a message about your culture.
Are you invested in their well-being or just checking a compliance box?
Employees should feel guided rather than overwhelmed. Benefits should feel tailored instead of transactional. When this happens, HR seems more like a trusted partner than a policy enforcer. That kind of trust ripples outward.
So, as you prepare for OE 2026, ask yourself: What kind of experience do I want employees to have? This goes beyond choosing a plan to include what it means to work there. Open enrollment isn’t just about benefits. It’s about belonging.