the ultimate schedule imageMany of you have open enrollment periods that will start up in October, November and even early December. Which means that right about…oh…NOW, you’re probably trying to get all your ducks in a row when it comes to making, polishing, and scheduling your open enrollment messaging. You know: emails, posters, and the like.

This year, we’d like to help you out with that. Which is why we created the 6-week open enrollment schedule below.

Please use (and tweak) this as you see fit. And if you have any questions or comments, don’t be shy about reaching out in the comments section below.

Hope this helps!


What to Do: 6 Weeks Before OE

Now is a good time to start doing the following:

#1. Create an open-enrollment-specific messaging plan, if you haven’t already

What do you want to communicate, to whom, how, where, and when? Get together with your team and suss out the details.

#2. Nail down your needs for new and/or revised content

Set up a team meeting to break down all the content–print and digital–you’ll need to tweak or make from scratch. Keep in mind that everything that you message should tie back to your overall theme–and be as memorable as possible.

Begin reaching out to the artists, writers, UX designers, and other people who will need to update or create this content–and provide them with the necessary text or art guidance. (You might also consider passing along this eBook about creating super-engaging benefits communications written by Jellyvision founder, Harry Gottlieb.)

If you’re not sure where to look for outside talent, some national freelance talent agencies include Aquent, Creative Circle, The Boss Group, and Artisan.

#3. Plan live meetings and webinar events

When should you conduct your live meetings?

We’d suggest one week before the first day of open enrollment. Run the meeting too early, and folks will forget by the time it’s choosing time. Run it too late, and they’ll feel pressured and rushed.

For companies that have multiple locations around the country, make sure every HR representative on the ground is working off the same PowerPoint or talking points.

If possible, have the most knowledgeable members of your HR team call in to the live meetings elsewhere so they’re available to answer questions as well.

When should you run your webinar events?

Consider running a live webinar at least twice, at different times of the day, to increase the likelihood of employees being able to attend.

Try to conduct these webinars in the first few days of open enrollment, and provide the link to the recording of it throughout open enrollment.

If your company has employees working round the clock, make sure to account for their schedules, as well.

#4. Recruit employees to provide simple testimonials

Testimonials–honest, first-person accounts of using a product or service–are a super-powerful marketing tool not enough HR departments are using. Want to get new or hesitant employees to use a new benefits decision support tool? Put out a call for employees who had a good experience with it; interview them for ten minutes on camera, over the phone, or via email; and use their feedback in this year’s messaging. The wider variety of employee types you capture, the better.

What to Do: 4 Weeks Before OE

At this point, your communications can start focusing on the topic of open enrollment itself. You’ve already let employees know about important impending changes; now it’s time to tighten the messaging to concentrate on how employees can get the most out of their new benefits. And that starts with signing up for them at open enrollment.

#1. Publish a short article, list of FAQs, or Q&A on your company’s intranet

Regardless of the form it takes, this short piece should answer the biggest questions employees might have about open enrollment, be as lively as possible, and provide links to other relevant resources. Want to make sure folks take notice of the piece?

Give it an unconventional headline and pair it with an eye-catching visual.

#2. Publish intranet banner ads

If you used intranet banners last year, be sure to update them so they look and sound new. In addition to a single general banner ad, consider adding a variety of banner ads that appeal emotionally to various segments of your population.

#3. Add a note about open enrollment to your email signature

Ask everyone in your HR department to add a line like ‘Don’t forget: open enrollment starts [Month], [Day]’ to their email signatures.

Also, strongly suggest that the managers in your company do the same, so employees will see the message repeatedly from the people they interact with every day.

Here are a few ways you might approach this:

Mark Rader


Vice President of Global Benefits

Placeholder Industries

Don’t forget: open enrollment starts November 16.

Kimberly Galitz


Shift Supervisor

Placeholder Industries

Need help picking your benefits this year? Talk to ALEX!

#4. Start making a manager’s toolkit

Don’t overlook one of the most effective communication channels you have at your disposal–employees’ bosses. The manager’s toolkit should provide basic talking points and FAQs managers can use to help deliver your OE message to employees.

But don’t just drop this on your managers and say ‘Good luck!’ Provide them with some ideas of when and how to share the information; the easier you make it for them, the more likely they’ll actually do it.

What to Do: 1-2 Weeks Before OE

Holy smokes! Open enrollment is just around the corner!

The communications you send out during this time should remind your employees it’s coming up, and give them the information they’ll need to make the best possible choices.

#1. Conduct your benefits webinars or live presentations

Want to encourage folks to watch or attend? If you have the budget for it, consider offering a small incentive–say, a $5 Starbucks gift card to everyone who participates or the chance to win a free day off in a webinar attendance raffle. It might help move a few people off the fence and into a folding chair.

#2. Put up on-site posters, fliers, and table tents

Print assets like posters, fliers, and table tents can be remarkably effective at grabbing employee attention in a cost-effective way. Break rooms, cafeterias, and parking structures are great choices, and a strategically positioned flier next to a time card machine, office copier, or water cooler can work wonders.

#3. Create a list of this year’s likely FAQs

If you haven’t already done so, compile a list of what you anticipate this year’s FAQs to be, and answer them as clearly and succinctly as possible. This will both prepare you for the emails and calls you’ll be getting and provide you potential content for the reminder emails you send during OE.

Here are a few common open enrollment FAQs and one approach to answering them:

Q: What happens if I don’t sign up for anything during open enrollment?

A: Oh, no! Don’t do that. Placeholder Industries uses an active enrollment, which means you can’t just let your choices roll over from year to year. You have to log into our enrollment system and make your selections before [Date here].

If you don’t make your choices by [Date here], you’ll have to wait until next year’s open enrollment period before you can sign up for benefits.*

(*Unless you experience a qualifying life event like getting married or divorced, having a baby, or if your spouse loses his or her job.)

Q: Why are we getting rid of the HMO plan?

A: We understand that the HMO was a popular plan (20% of Placeholder Industries employees were enrolled in the HMO last year), but the current health care environment is making it impossible for us to keep offering it at an affordable rate. Instead of increasing everybody’s premiums (the amount you contribute toward the cost of the plan), we decided to replace the high-premium HMO with a low-premium PPO with HSA account.

Q: Can somebody help me pick the right benefits?

A: Of course! That’s what we’re here for. We suggest you talk to ALEX first. ALEX is an easy-to-use interactive benefits counselor who will explain all your benefit options and help you figure out which ones will be best for you and your family. If you have questions that ALEX can’t help with (like questions about specific medications or health care services you require), you’re welcome to contact the Benefits Help Desk at 312.555.1212.

Q: Will my prescription be covered under our prescription plan?

A: In a word, yes. Our prescription drug plan will cover the cost of your prescribed medications, but the cost of your copay may vary. Retail prescription copays are $10 for generics, $35 for brand formulary, $60 for brand non-formulary, and $150 for specialty drugs.You can get more information on drug copays at or by calling the Benefits Help Desk at 312.555.1212.

Q: What if I make a mistake? Will I be able to fix it after open enrollment closes?

A: Yes. Our company does allow employees to make corrections to open enrollment elections, but you must do so before December 15, 2015. All corrections must be made via the Benefits Help Desk at 312.555.1212. You cannot make changes through the enrollment platform after [Date here].Please note, the correction period is not meant as an extension of the open enrollment period. Only corrections will be accepted during this period.

Q: I will be on vacation during open enrollment. Can I make elections when I return?

A: No, you must make your elections during the open enrollment period, which is [Date here].

Q: Why am I being prompted to provide a Social Security number for my dependents?

A: Centers for Medicare and Medicaid Services (CMS), the agency that monitors the claims collections from employers for Medicare, requires all employers and retirees to provide the social security number of any employee/retiree and dependent covered through an employer sponsored medical plan. CMS uses this to cross reference any Medicare participant who also has coverage through an employer, as the employer plan becomes primary. The prompt is an alert that information is missing for an enrolled dependent.

#4. Send first postcard if you’re doing a postcard campaign

If you’re thinking about doing a two-postcard send, in order to reach partners and spouses at home, aim to have your first ‘Your benefits decision support tool is available’ postcard hit mailboxes the day the resource is made available (which should fall about 1-2 weeks before enrollment season officially begins).

What to Do: During Open Enrollment

Now’s the time to gently and tactfully pester your employees about enrolling by the deadline–and provide them the resources they need to do so.

#1. Send out at least three company-wide emails

Email #1 – Announcement Email (First Day of OE)

Email #2 – First Reminder Email (Halfway through OE)

Email #3 – Second Reminder Email (The day before OE ends)

Tip: Make sure to indicate the negative consequences of not enrolling in time, especially in the final two emails.

#2. Schedule a postcard to arrive a few days in

If you’re planning on sending postcards to people’s homes reminding them to enroll, schedule one to arrive a few days after open enrollment has begun.

If you send the postcard too early, people might want to take immediate action, and not be able to–which is a missed opportunity.

#3. Celebrate that it’s over! Wooo-hooo!

On the last day of your benefits enrollment period, we’d recommended you enjoy one of our delicious benefits cocktails or mocktails. For example:

The Coinsurance Cosmopolitan

Allowed Amount Ingredients (80%)

2 ounces vodka

1 ounce Cointreau

1 ounce cranberry juice

Member’s Contribution Ingredients (20%)

1 ounce Rose’s lime juice (reserved)


Combine the Allowed Amount ingredients into a cocktail shaker and mix well with ice. Strain into a chilled martini glass, then invite your guest to add his or her 20% contribution. Garnish with a slice of lime.

The Coinsurance Cosmo is awfully tasty, but if your coworker has had enough after their first serving, you can always switch them over to an alcohol-free version of the drink called ‘The Out-of-Pocket Limit.’


3 ounces lemon-lime soda

1 ounce cranberry juice

1 ounce Rose’s lime juice


Combine ingredients into a cocktail shaker and mix well with ice. Strain into a chilled martini glass. Garnish with a slice of lime.

Did you find this schedule helpful? Want a boatload more OE communications tips and templates for free RIGHT NOW?

Download The Ultimate Open Enrollment Communications Playbook