Surviving Open Enrollment: 20 Tips and Quotes From HR Pros

Every autumn, there’s a chill in the air that has nothing to do with the weather—it’s the arrival of open enrollment.

For many in HR, this annual event brings stress, anxiety, and dread, and not just for those tackling benefits administration for the first time. Even seasoned HR pros aren’t immune to the yearly overwhelm of open enrollment—the hours and hours spent wrangling employees and their benefits data.

“Newbies in the field of HR are in for a crash course with the start of open enrollment. It’s a busy time of year for HR in general, but if you’re new to the field, it’ll be a wild ride," says Stefan Campbell, owner of The Small Business Blog.

But experienced pros often have time-tested tips and tricks up their sleeve that keep them grounded, organized, and effective in times like these, so we reached out through every channel we could find to ask for their advice. "Once you survive your first, they get easier as you learn more and more and have your company's benefits handbook basically memorized front to back,” Campbell says.

Here are 20 insights, encouraging thoughts, and practical tips we’ve compiled from those who've been where you are now—plus a few original motivational posters to help you waltz through open enrollment this year.

Quotes have been lightly edited for clarity and concision.

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5 Practical Methods for Combating Stress

“It’s tempting to just work harder during times of high stress, to let the ‘to do’ list steal the bookends of your day. But more is not better, and often only fuels the stress cycle. Instead, I opt for effectiveness over activity by maintaining balance. For me, that means gym and family time. These activities give me the energy to work through challenges and are a reminder of why I do it. The resulting calm also enhances my focus and fluidity, enabling me to handle unforeseen issues without added anxiety.”
—Tim Toterhi, CHRO at Plotline Leadership

“Personally, I manage stressful times like open enrollment by doing these three things consistently:

—Melina Gillies, CHRL, MAHRI, Head of Human Resource at FlexNetworks

“I manage stress during open enrollment by keeping a time-bound checklist, automating what I can, and never forgetting that someone will always miss the deadline. This keeps me on track, makes the process efficient, and keeps me grounded.”
—Tiffany Slater, Ph.D, SHRM-SCP, CEO and Senior HR Consultant at HR TailorMade

“I find that two of the most stressful things about open enrollment are:

Meditation, yoga, and exercise are good ways to spend time reminding yourself that you are the messenger of the stress, and the best you can do is be honest, straightforward, and empathetic with employees. Usually, at the HR level, you have nothing to do with the pricing and negotiations, but you're going to be the one to hear how people feel about it. Also, I try not to take on any big projects that either start or finish during the open enrollment month. Use your boundaries and set expectations, so you're not trying to accomplish a lot of other big things at the same time.”
—Jill Santopietro Panall, SPHR, SHRM-SCP, Owner and Chief Consultant at 21Oak HR Consulting

7 Ways to Curb Stress with a Proactive Communication Plan

“Plan before you do. That means testing your technology, leveraging available experts to explain plan details, and giving employees the gift of time via advance communication. Benefit decisions have significant cost implications. Making the right ones can help employees effectively care for themselves and their families. Yes, open enrollment is stressful, but the expertise provided by a sharp benefits professional makes an important impact. Knowing that will help you thrive when things get busy.”
—Tim Toterhi, CHRO at Plotline Leadership

“My advice for any admin—new or experienced—when it comes to open enrollment is to create a robust communication strategy. Similar to an employee journey map, admins can create an open enrollment communications map, which lists the timelines and touch points required for employees to make elections. From there, you can plan a series of communications to support these timelines (like FAQs, a user guide, or hosting a lunch and learn). Be sure to build in lots of follow-up with clear directives, as well as what to do if someone doesn’t want to make any changes.”
—Melina Gillies, CHRL, MAHRI, Head of Human Resource at FlexNetworks

“One thing you need to do to make both open and end-of-year enrollment run smoothly is to beef up your existing communications strategy. This strategy should also include a plan to maximize the web services you offer. Employees would rather go to their computers and have the information at their fingertips versus setting up a time to meet with you. That reduces your workload too. This works really well when you’re planning for a passive enrollment where most employees will keep the same benefits and they’ll just roll over to the new year.”
—Kamyar Shah, COO at Fractional; Owner of Kamyar Shah Consulting

“Annual open enrollment can be an overwhelming time that requires careful consideration to avoid chaos and potential noncompliance with state and federal laws (i.e., ERISA, ACA, COBRA, etc.) affecting employee benefits. Planning for the next open enrollment period should begin right after the last one ends to clean up any untidy processes. Plan out a series of employee communications to be provided before and during the open enrollment period."
—Angela Surra, Principal Benefits Expert for Mineral

“Three things, I think are essential to a successful open enrollment process:

No matter what you do, you’ll always have someone or several employees that miss the deadline and will be upset if they're unable to make a change. Prepare yourself and have a plan for self-care.”
—Tiffany Slater, Ph.D, SHRM-SCP, CEO and Senior HR Consultant at HR TailorMade

“When I worked in HR for Fortune 500 companies, open enrollment was usually a wild time. It's only 30 days long, so the best way to prepare is to put in a structured communication plan for the enrollment month and the month before with meetings, reminders, opportunities for employees to ask questions, proactive Q&A information that anticipates what they care about and will want to know. I typically do a fanfare when the period opens, then reminders at the end of the second, third and fourth weeks, with a special ‘two days left’ email before the end of the time period. The worst thing is when someone's spouse or partner calls in a rage because your employee didn't add them to the benefits in time. Don't let that happen to you!”
—Jill Santopietro Panall, SPHR, SHRM-SCP, Owner and Chief Consultant at 21Oak HR Consulting

“My advice would be to communicate—and then communicate some more! Start messaging as early as you can and simplify where you are able. Use all channels at your disposal like Slack, email, video messages, and live webinars with Q&A sessions. Publish FAQs ahead of time, and ensure you have a contact for detailed questions. If you plan ahead well enough with a great communication plan, I think open enrollment runs pretty smoothly and isn’t that stressful.”

Nicole Wosje, Senior HR Consultant

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3 Reasons to Stop, Drop, and Survey

“Remember, effective communication goes both ways, so no comms plan is complete without a way to efficiently and anonymously collect employee feedback on everything from open enrollment processes to what they think about the company’s benefits package. If you want your employees to truly hear you, start by listening just as closely to them.”
—Joey Tirado-Grundvig, Benefits Specialist at BambooHR

“Going it alone is the quickest and simplest way to get lost during open enrollment. The greatest strategies are those that take into account the particular requirements of your workforce (and their families). Find out what matters to your group by conducting surveys or focus groups. If you can, work with leaders to provide a range of possibilities. Include both basic and advanced options along with premium-sharing plans for employees that aim to strike a balance between the needs of both parties.”
—Olivia Parker, CMO of Better Days

Conducting an employee survey to gauge feelings about the benefits package can be very valuable to messaging. It will help you highlight any changes you made based on their feedback.”

Nicole Wosje, Senior HR Consultant

2 Reminders to Seek Support From Brokers and Benefits Providers

“To succeed during open enrollment, benefits administrators should rely on their broker as a trusted partner. We’re here to assist and should be available to help both admins and employees with any questions or concerns that arise during the crucial time of open enrollment. Leveraging our expertise can streamline the process and ensure a smooth experience for everyone involved.”
—George Beach Jr., Group Benefits Insurance Broker at George William Beach Insurance Services

Engage with the insurance broker to help facilitate open enrollment meetings and supply any needed materials. Advanced strategic planning is key to a calm and successful open enrollment period."

—Angela Surra, Principal Benefits Expert for Mineral

3 Ways HR Technology Can Make Open Enrollment Easier

“To keep communications relevant, it’s important to create an online space that includes everything benefits-related and keep it up to date year-round. This space should include every detail about their benefits and be accessible to everyone so that they can research and find answers independently.”
—Jovana Đurović, Editor in Chief at Home Grounds

“One of the biggest things that HR managers often overlook is the actual process in which employees can go through the enrollment process. If you’re not going to make this easy for the employees, then you’re making the job harder for yourself. Set up an online system that allows employees to take a closer look at their current healthcare insurance and other benefits, then allow them to make adjustments according to their needs easily. Get this data sent back to you, which you can then use for processing. It’s much easier this way and takes away many of the headaches.”
—Tina Grant, HR Manager at Aerospheres

“Using any automation or information that is built into the HRIS or benefits portal will really help streamline the process and track completion rates for a successful outcome.”
—Melina Gillies, CHRL, MAHRI, Head of Human Resource at FlexNetworks

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