Just when you thought 2020 open enrollment was bananas, we’re coming upon a new year with a whole set of new challenges. As the pandemic winds down, companies are bringing employees back into the office, adopting hybrid work policies, and facing record levels of turnover amidst a highly unusual job market.   

All of these factors are piling on to the already difficult job of planning for open enrollment. In these rapidly evolving times, it can feel like an uphill battle to make your team members (remote and in-person, new and old) focus on benefits. On a positive note, your team members want more benefits education—91% of employees agree it’s important to understand their benefits. But our reports also show that more than half of employees (52%) feel that choosing benefits is stressful.

It all comes down to devising the perfect open enrollment strategy for your team. As such, we’ve created a step-by-step open enrollment communication timeline to manage and succeed with the planning process. Let’s get started! 

Planning and Strategy 

As Benjamin Franklin once said, “If you fail to plan, you’re planning to fail.” 

Okay, that’s the last cliche quote we’ll use in this guide—but it’s true! So, before we dive into the open enrollment timeline itself, you’ll need to lay the groundwork with a pre-enrollment strategy. 

We know it’s easy to get into the weeds when planning for open enrollment, especially for remote and hybrid teams, so we’ve broken this process down into five easy steps. 

Step 1: Identify changes for this year 

According to our HR Priorities Report, many HR teams reported doubling down on mental health benefits after a tumultuous year. Additionally, a worldwide pandemic highlighted shortcomings in the areas of healthcare and financial wellness. 

As a result of this and other shifts, you’ll need to take a second look at your current benefits offerings to see what’s working and what isn’t. Work with your HR team and managers to understand utilization of current programs and identify potential gaps. It could be that you have all the right benefits in place but need to better promote them during open enrollment. 

We interviewed 200+ real HR leaders to find out what their biggest priorities are this year.

Get the guide

Step 2: Review last year’s open enrollment strategy and materials 

There’s no better way to plan ahead than by looking back on past efforts. Take stock of the previous year’s open enrollment, including your plans, execution, resources, and results.

As you evaluate, ask yourself: 

  • What materials (digital and physical) did you send to employees last year? 
  • Which communication channels did you use?
  • Where did you see the most engagement or participation?
  • What went right/wrong? 
  • Did you have goals in place that you didn’t reach? If so, how could you avoid those roadblocks this year? 

Step 3: Establish clear goals 

How can you measure success without having set goals in place? (Hint: you can’t). Develop your open enrollment goals based on current benefits offerings with last year’s lessons in mind. 

The key is to make each goal quantifiable, so you can definitively analyze your performance post-open enrollment. 

Formula for writing open enrollment goals

“Accomplish [quantifiable goal] by [action].”


  • Increase HDHP enrollment by 30% by providing more personalized benefits education materials.
  • Reduce the amount of time spent answering benefits questions by investing in benefits engagement technology.
  • Achieve at least 20% enrollment in our new mental health benefit by sharing employee testimonials about why it’s helpful.

Step 4: Gather employee feedback on the process 

During the open enrollment timeline, it’s important to keep in mind the main objective—getting employees to understand their benefits. That’s what makes this planning step so important—to confirm they did indeed understand and engage with their benefits this past year. 

Send out a quick employee engagement survey to gauge the effectiveness of your past communications and ask for honest feedback on the overall process. Use this information to guide your strategy.

Download our State of Employee Benefits report to further understand employees’ expectations of their benefits for 2021 and beyond.

Get the report

Step 5: Choose your channels

Now that you’ve gathered needed improvements, lessons learned, employee feedback, and set clear goals, you can decide how to deliver your open enrollment messaging. 

We recommend a more virtual approach than you might be used to (more on that later). But understand every organization is different, so choose from the following channels to focus on: 

  • All-company meeting
  • Benefits guide
  • Email campaigns
  • Posters
  • Intranet ads
  • Postcards or other mailers
  • Brochures
  • Benefits fairs/vendor presentations
  • Benefits guidance tools, like ALEX

Make this year’s benefits presentation your best ever.

Learn how

Open enrollment communications timeline

Now, let’s get down to the nitty-gritty—executing your strategy. Follow this open enrollment communications timeline to ensure proper delivery of applicable resources and messaging to your people. You’ll note we’ve included links to additional resources for help along the way. 

8-12 weeks before

First stop: the benefits guide and resources. 

Embrace virtual 

Even if your team is back in the office or using a hybrid work model, there’s no reason to ditch the digital methods you adapted during the pandemic. Virtual open enrollment means less footwork for your HR team, lower expenses for print material, and increased access for your employees. 

In other words, your people don’t have to go searching through a pile of documents but instead can log on to your benefits dashboard and easily access open enrollment information at any place or time.

You need to meet your employees where they live, and for most, that’s on their digital devices.

For a successful virtual open enrollment, ensure you have these six must-have tools.

Read more

Update your benefits guide 

The benefits guide is the bible of your open enrollment process. But unlike testaments set in stone, you should update this resource yearly to reflect your latest offerings. 

Here are a few pointers to optimize your guide: 

  • Call out your most important info at the beginning. Greet the skimmers by dedicating one of your first pages/sections to a brief (bulleted list with any new details, what’s the same, and how to enroll). 
  • Use call-to-actions as much as possible, i.e., tell people the next steps to take and point them in the right direction. 
  • Link to or mention your decision support tool—a.k.a. your online benefits dashboard. 

Dust off the rest of your enrollment materials 

Time to pull out the enrollment materials you’ve used in the past. Here’s where you’ll make strategic cuts based on employee feedback. Don’t reuse any materials or content that saw little to no engagement. Make sure to audit and update anything you send it out.

No need to reinvent the wheel here! Use our easy, customizable templates to create common open enrollment materials.

Download now

4 weeks before

Publish intranet ads 

For those with an in-house intranet, create ads and announcements to remind your team that open enrollment is on the horizon. If you have a large headcount, consider targeting your ads to appeal to different audiences. 

Promote everywhere 

Your main objective a month out should be to raise awareness that open enrollment is happening. You want to explain to employees that it’s a critical time to get the most out of their benefits while reassuring them that your HR team and benefits support tools are there to help. 

Don’t forgo any opportunity to toss in a reminder, like your HR team’s email signature. 

Leverage managers and leaders

HR can’t reach all of your people alone. Enlist the assistance of leadership throughout your company to communicate important open enrollment messages and deadlines to their direct reports. 

But remember, managers and team leads are busy people too, so you want to leave enough time in your open enrollment communications timeline to warn them you’ll need their help. To make the process easier, offer them a toolkit that includes basic open enrollment talking points and FAQs.

To better connect with employees, share this resource with your HR team and managers: 7 Ways to Help Your Stressed-Out Employees Avoid Making Bad Benefits Decisions During Open Enrollment.

Read more

1-2 weeks before 

Mail out and distribute any physical resources 

While we can all try to go digital as much as possible, we know there are certain times when you might have to share physical resources. Since snail mail takes a little longer than virtual counterparts, plan for materials (like your physical benefits guide or postcards) to arrive one week before open enrollment. 

For those companies with in-office workers or hybrid teams, you can also hang up posters or on-site visual announcements to raise awareness the week before open enrollment. 

Send the open enrollment intro email 

The time has come to officially announce the kick-off of open enrollment. To get on your team’s radar, send a company-wide email with bulleted info. This communication should highlight need-to-know dates and essential details. 

Outline expectations for the following few weeks, including: 

  • Open enrollment start and end dates 
  • Invitation to company-wide meeting
  • Link to your decision support tool if you have one (Ask ALEX!) 
  • Links to any other open enrollment resources, like your benefits guide or FAQs 
  • Short but persuasive reminder that open enrollment is the one time per year when employees can make changes to their benefits

Pssst! Here are 6 ways to improve your open enrollment emails to employees.

Read now

Hold a company-wide meeting

Sometimes, all the communications and resources in the world can’t compete with good old-fashioned meetings. 

Assemble your employees for a company-wide gathering one week before open enrollment starts. For larger teams, consider hosting a few different time slots to fit within everyone’s schedule. 

And let’s be honest, there will be people who won’t make it or just won’t pay attention. C’est la vie! To address this inevitable issue, record at least one of your sessions so employees can reference it later. 

Want to level up the presentation for your company-wide? Check out our 7 Easy Ways to Improve Your Open Enrollment Benefits Presentations.

Learn more

Share FAQs

FAQ documentation is your best friend. It makes life easier for HR folks. And you can bet, if one person is wondering about something, others likely are too. So keep a running list of FAQs with clear and concise answers. Make the responses conversational and easy to follow, avoiding any jargon.  

You can share these in an FAQ page on your intranet or email them out to your team.

Guess what? ALEX can eliminate the need for FAQs. Book a demo and find out why!

Book a demo

During open enrollment 

Send email and text reminders 

Employees need reminders during the open enrollment process to, you know, actually enroll in their benefits plan. Most people equate figuring out and choosing health insurance to a trip to the dentist, so, unfortunately, they’ll likely put it off. Your job is to convince them it’s not nearly as bad. For instance, they can save money, invest more in their future, and access more robust benefits! How exciting! 🎉

Pro-tip: A benefits engagement tool like ALEX can help you make this process a little less tedious and highlight how to wisely navigate open enrollment. 

Send email reminders throughout open enrollment and especially in the days leading up to your deadlines. Encourage your team to access resources, ask for help, and use their decision support tool. If you can, consider sending text reminders or pinging them on your messaging platforms like Slack. This can help reach those remote team members and avoid over-stuffed inboxes. 

Our virtual open enrollment playbook has lots more tips on using texting and other tools in your approach. 

Learn more

Host office hours (virtual or in-person) 

Office hours offer a low-pressure way for your employees to ask questions, seek advice, and troubleshoot any issues. Scatter some time slots throughout the week where your HR team members are open for business. Remember, people will procrastinate, so you may want to increase office hours closer to your open enrollment deadlines. 

Learn more about how one of our clients used ALEX to tackle virtual open enrollment and boost HSA engagement by 86%.

Read now

Remind leadership to plug open enrollment 

You may have already asked them and sent them a tool kit—but you know that HR is all about that follow-up. So circle back with your managers, team leads, etc., and remind them to help you promote open enrollment. A simple mention in a meeting, a team slack, or even an email can go a long way with employees, especially when it comes from the people they work with and trust. 

After open enrollment


You made it! You deserve a pat on the back and a little R&R. 


We know, the last thing you want to do after the marathon of open enrollment is start planning for the next year. We get it! But it’s beneficial to quickly review your process and results while it’s still fresh in your mind so you can document for next year. It’s a lot easier to discuss what went wrong and right now than in eight months. 

To simplify this exercise, use our guide, 3 Things To Absolutely Do After Open Enrollment.

Read now

Empower employees to engage with their benefits all year long 

Your people can (and should) engage with their benefits all year long, not just at open enrollment. So once their new insurance and programs kick in, remind your employees to actually start using them. Encourage them to maximize their investment throughout the year!