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Surviving Open Enrollment: 20 when everything works
together.
Tips and Quotes From HR Pros
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By Rebekah Cuevas | Published on August 16, 2023 | 7 min read

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Table of Contents

5 Practical Methods for Combating Stress

7 Ways to Curb Stress with a Proactive

Communication Plan

3 Reasons to Stop, Drop, and Survey

2 Reminders to Seek Support From Brokers

Every autumn, there’s a chill in the air that has nothing to do with the weather—it’s the and Benefits Providers
arrival of open enrollment. 3 Ways HR Technology Can Make Open
Enrollment Easier
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:

● I manufacture my own commute. Because I’m steps from my kitchen to my office,

lines can get blurred and stress can follow me home. To combat this, I manufacture an
end-of-day commute. I get in my car, go get a coffee, hop on my bicycle, or just go for
a walk when I’m ready to end my day. Having that physical act helps me make the
mental separation that lets me function well in other areas of my life.
● I listen to podcasts. In between meetings, I pop in my earbuds in and listen to a
favorite podcast. I’ve found this to be more effective at lowering my stress levels than
music, and I give myself bonus points as they’re usually related to professional
development!
● I connect with my colleagues. Each day, I try to link up with a different colleague and
take a lunchtime walk. Not only does this build trust and resiliency in the team, but it
helps to get up and get moving on a day that’s otherwise fraught with meetings.”

—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:

● Communicating annual price changes. They are usually up (and almost never down!)
and people have a lot of feelings.
● Making sure you didn't miss anyone who wanted to add benefits.

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:

● Communicate constantly. Even when you’re tired of hearing or reading your own
messages, you can’t communicate enough about the purpose of open enrollment, the
actions employees need to take during this period, and the final date to submit
changes.
● Keep it simple. Your messages and instructions need to be easily accessible and easy
to understand.
● Reach out directly to employees that haven’t responded. Set up an automation
that sends a personalized message to each employee that hasn’t responded or
submitted enrollment documents within one week of the due date.

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

bambooHr

OPENENROLLMENT
Ifyoucansurvivethis,youcansurviveanything.

Don’t lose track of another open

enrollment to-do.

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cracks with these free pre and post
enrollment checklists.

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Rebekah Cuevas
Rebekah Cuevas is first-generation Latinx, LGBTQ+ author and editor with over a decade of experience. As a copywriter at BambooHR,
she’s obsessed with empowering the “human” in human resources, connecting HR pros to impactful HR advice and solutions. Her research
spans workplace wellbeing, progressive performance reviews, pay equity, and how DEI initiatives build stronger, safer, and more profitable
workplaces for all. Rebekah's work has appeared with Torrey House Press, and she holds a B.A. in English from Utah Valley University.
Connect with Rebekah on LinkedIn.

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