Hiring & Retention
August 29, 2022

How to Prepare for Open Enrollment: Month-by Month No-Stress Strategies

Two words that have the potential to ruin any HR professional’s end-of-summer vacation? Open enrollment. While the annual window where employees can make changes or opt in to new benefits has the potential to be incredibly stress-inducing, it doesn’t have to be. Read on to discover strategies that can make year-round planning a little smoother.

First: View Open Enrollment as a Secret Retention Strategy

Before we get to our checklist of how to prepare for open enrollment, a quick reminder: as the labor market remains tight, open enrollment can (and should!) be a key piece of your retention strategy. The benefits you offer your employees—and how well you explain them—can be your not-so-secret weapon in boosting retention and making you the MVP of employee satisfaction. View this upcoming season as a chance to re-engage your current employees and shore up your offerings to attract new ones.

Open Enrollment Planning Checklist


Though you've probably already selected most of your benefits, now's the time to shore up your offerings and lay the groundwork for a successful season. Here are some steps to take as summer draws to a close:

  • Conduct competitive research. Take a look at some of your competitors and see what they’re offering employees. While most benefits may have already been selected, there’s likely still time to add additional offerings to your package. If you’ve heard of companies that are using financial wellness benefits like earned wage access, now may be the time to explore these and look into how financial wellness benefits impact retention.
  • Conduct employee listening sessions. What do employees feel is missing from their benefits package or how their benefits have been communicated to them? Sometimes what HR teams find as valuable for their workforce is not something that their employees are really asking for. It’s helpful to take feedback from both employees who have been with your company a long time and new hires who may have a fresh perspective on what other companies are offering right now. Also ask about the best ways they’d like to stay informed.
  • Check for any gaps. As you assemble your benefits package, examine how the different offerings work together and what gaps may be missing. It’s no longer enough to think just about health benefits or financial wellness but a range of benefits that can complement one another. Providing meaningful benefits for your employees often boils down to choosing ones that actually have a tangible impact on their day-to-day lives, whether that’s promoting greater work-life balance, helping them expand their education, or supporting them through difficult times.


You’ve selected your benefits and you’re ready to get rolling! Here’s where fine-tuning your media plan comes in handy. How will you communicate information about your benefits to your employees? Remember that you can offer the best benefits in the world, but if your employees don’t understand them, they can’t take advantage.

  • Create a multi-media communications plan. People learn in different ways, and while one person may take the time to read a printed pamphlet, another may respond better to an in-person forum or event. Incorporate feedback from listening sessions. One of the cornerstones of how to plan for open enrollment should be strategizing the best ways to communicate with your workforce.
  • Hold a pre-enrollment Q & A forum. Whether you do this virtually or in-person, this is a great time to open up the floor to any questions employees have about existing or future benefits. Encourage people to come with whatever is on their mind and remind them that there are truly no stupid questions in the complex world of employee benefits. From health insurance and 401Ks to financial wellness benefits and beyond, taking the time to explain these different offerings can go a long way with enrollment numbers.
  • Remind your employees they can make changes. Open enrollment isn’t just a time for new employees to sign up for benefits, but for existing employees to evaluate whether or not they want to make changes to their plans. Encourage employees to attend information sessions where they can learn about everything you offer and re-evaluate if they’re taking advantage of the right options.

November - December

It’s go time! All your hard work and dedication have paid off and now it’s time to open the gates and let your employees sign up for benefits. Here are some last-minute ways you can make open enrollment season a success.

  • Make fielding questions easier. It goes without saying that when you launch enrollment, you’re likely to have a barrage of questions coming at you. Give people one streamlined way to ask questions, whether it’s only through email, strictly on Slack, or through a benefits portal. Keeping communications streamlined in one channel can help you and your team sort through questions faster and help employees find resolution.
  • Take feedback in real time. As the questions come in, start looking for comments, too! Consider sending out a survey asking employees both what they thought of the enrollment process and the benefits included. Make the surveys anonymous and straightforward so people aren’t hesitant to take a few moments to fill them out. 
  • Start thinking about next year! It's never too early to start reviewing employee feedback and fine-tuning your benefits for the following year. Using employee feedback is one of the best ways you can ensure your company is delivering what workers are demanding today, so take all the great feedback you collected and use it to make next year’s benefits even better.

Though we know open enrollment is always a huge undertaking, breaking your plan down into distinct steps can be helpful—as can listening to employee feedback and learning from your competitors. With a little planning, you’ll be on your way to a successful open enrollment season full of happy employees and less stress.

EWA: The in-demand benefit workers want NOW

As you review your company benefits, there's one competitive offering you can add to your package any month of the year: earned wage access (EWA). Branch’s responsible earned wage access can grant your employees up to 50% of their earned wages ahead of time in case an unexpected expense comes their way. We’re free for both employers and employees and have helped companies just like yours deliver a free benefit to their workforce that drastically improves their lives. 

See how EWA has helped one of our customers by clicking below.

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