Open enrollment season is a pivotal time for small businesses in Wisconsin, but it often feels like a burden for business owners and employees alike. Navigating complex benefits options, managing tight deadlines, and ensuring employees understand their choices can be overwhelming.  The 2025 enrollment period is just around the corner, and now is the time to prepare. By addressing common challenges, using efficient tools, and providing clear guidance, you can transform open enrollment into a smoother, more efficient process for your business and your team.

1. Evaluate Current Enrollment Processes

How to Improve Employee Benefits Open Enrollment 2025 Process | Sustainable HR PEO

The first step to improving open enrollment is to assess how things went last year. Were there frequent questions from employees about benefits options? Did you experience bottlenecks in getting everyone enrolled on time? Identifying these pain points will help you create a plan to prevent the same issues from happening again.

Gathering feedback from your employees is essential in this process. Surveys or one-on-one conversations can uncover the areas where employees felt confused or overwhelmed. For example, were they unsure about the differences between health plans or the availability of wellness benefits? This kind of feedback will guide your adjustments to the 2025 process.

As a small business owner, it’s important to recognize that you don’t have to handle this alone. Partnering with a PEO like SustainableHR gives you access to resources, expertise, and tools that streamline the entire benefits process.

2. Utilize a Centralized Benefits Platform

Technology can be your greatest ally during open enrollment. Rather than relying on manual processes or paper forms, use a centralized platform where employees can easily review, select, and submit their benefits choices. SustainableHR PEO offers a seamless online system that simplifies the entire process for both employees and HR staff.

Employees can log in to review benefits options, make changes, and submit their selections online, while HR teams can monitor progress in real-time, ensuring all deadlines are met without the need for constant follow-up. This reduces errors, saves time, and makes the process much smoother for everyone involved.

3. Simplify Communication

Communication is often one of the most overlooked areas during open enrollment. Employees are bombarded with information about various benefits, yet they don’t always understand what’s being offered. By simplifying how you communicate benefits options, you can make the process much easier for them.

Clear, jargon-free language should be the foundation of all benefits materials. Instead of long, dense emails or complicated brochures, break down the information into digestible pieces. Use different formats, such as videos, webinars, or Q&A sessions, to make it easier for employees to understand their options. SustainableHR PEO can provide resources and expertise to help you create communications that engage and inform your employees, making open enrollment less stressful for everyone involved.

Learn more about gaining enhanced benefits with a PEO

4. Offer Personalized Support

How to Improve Employee Benefits Open Enrollment 2025 Process | Sustainable HR PEO

One of the biggest challenges during open enrollment is ensuring that every employee fully understands their benefits options. Employees come from different backgrounds, and not everyone is familiar with the details of health insurance plans, retirement benefits, or wellness programs. Offering personalized support during the open enrollment process can help mitigate confusion and reduce mistakes.

Setting up a help desk or offering one-on-one consultations can significantly enhance the enrollment experience for employees. During these consultations, employees can ask specific questions about their personal situations, such as which health plan is best for their family or how to maximize retirement contributions. Having knowledgeable staff available to address these queries provides employees with peace of mind and empowers them to make informed decisions.

5. Train Managers and HR Staff

While personalized support for employees is crucial, training your managers and HR staff is just as important. These are the people who will be on the front lines during open enrollment, answering employee questions and resolving issues as they arise. Providing them with proper training will ensure that they can confidently handle inquiries, assist employees with decision-making, and troubleshoot any problems that come up during the process.

Consider organizing a few training sessions before open enrollment begins. Focus on educating your managers and HR team on the various benefits options, the enrollment software, and the best practices for assisting employees. The more prepared your team is, the smoother the process will be for everyone involved. 

6. Create a Timeline and Checklist

Preparation is the key to a successful open enrollment, and having a clear timeline and checklist will keep everyone on track. This should include all key milestones, such as when to start communicating with employees, deadlines for submitting paperwork, and when to schedule follow-up reminders. A well-structured timeline ensures that there are no last-minute surprises or missed deadlines, reducing the stress of the process.

Providing a checklist to both HR staff and employees will also help them stay organized. Employees, in particular, will appreciate having a simple document that outlines what they need to do, when they need to do it, and who to contact with questions. For business owners, a checklist will ensure that all necessary steps are taken on time, leaving no room for error.

SustainableHR PEO can assist by providing templates, timelines, and checklists that are tailored to your business’s specific needs, making the entire process smoother and more manageable.

Conclusion: Setting the Stage for a Successful Open Enrollment

By offering personalized support, training your staff, and creating a clear timeline, you can greatly improve the 2025 open enrollment process for your employees. Planning early and using the right tools, like those provided by SustainableHR PEO, will reduce stress, streamline the process, and make it easier for your team to navigate. Take the opportunity to improve your open enrollment strategy now, so when the time comes, your business and your employees will be prepared for a successful enrollment season.

The team at SustainableHR PEO is here to simplify your open enrollment process. With our expertise and tools, we’ll help you navigate HR complexities with ease. Book a call today to get started!

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