What if one wrong move during open enrollment could cost you your top talent? Nearly half of employees, approximately 40%, say they would leave their jobs for better benefits. That is a wake-up call for any business offering employee benefits. Open enrollment is more than just paperwork. It’s a chance to strengthen loyalty, boost morale, and show your team they matter.
Let’s review some of the employers’ most common (and avoidable) mistakes and how employee benefits consulting can help you turn enrollment season into a strategic win.
Why Strategy Matters
Open enrollment is not just an annual task; it’s a strategic opportunity. A well-planned approach helps employees better understand their options, feel more confident in their choices, and appreciate the value of their benefits. Low engagement, miscommunication, and costly oversights become far more frequent without a solid strategy.
Treating It Like a One-Off
Many employers treat open enrollment as a once-a-year obligation rather than part of an ongoing strategy. This reactive approach limits employee participation, creates confusion, and often results in rushed decisions or missed opportunities.
Employees may feel overwhelmed or uninformed when benefits communication only happens during enrollment season. A thoughtful, year-round strategy helps keep your team prepared, engaged, and more likely to make confident, informed decisions when it matters most.
Rushing the Process
Waiting until the last minute to decide about benefits can be costly. Employers who rush the open enrollment process often end up with plans that do not truly fit their workforce’s needs, resulting in low satisfaction and unnecessary spending.
Without adequate time to review options, communicate changes, and answer employee questions, confusion and missed deadlines are almost assured. Taking a proactive, well-paced approach improves outcomes and helps businesses use their benefits budget more effectively.
Poor Communication
Even the best employee benefits plan can fall short without consistent and clear communication. When employees do not understand their options or what is changing, they are less likely to engage and more likely to make choices that do not serve their needs.
Poor communication during open enrollment can lead to frustration, underutilized benefits, and unnecessary strain on HR. Fortunately, there are ways that businesses can improve communication so that their team feels more informed, supported, and confident in their benefits decisions.
Overwhelming or Confusing Language
Benefits materials packed with jargon and complex terms can quickly overwhelm employees, especially those unfamiliar with insurance or financial concepts. When communication is unclear, employees may tune out entirely or make errors that impact their coverage and costs.
Jargon-heavy content can also create barriers and misunderstandings, leading to frustration and disengagement. To drive better outcomes during open enrollment, it is essential to simplify the language, break down core concepts, and make benefits information as accessible and user-friendly as possible.
Lack of Guidance Tools
Without the proper support, employees are left to make complex benefit choices independently, often leading to stress, confusion, and costly mistakes. Guidance tools, such as decision aids, comparison charts, and personalized recommendations, can help employees better understand their options and make informed, cost-effective choices. When these resources are missing, participation rates often drop, and the actual value of the benefits package may go unrecognized or underused.
Outdated Processes
Relying on manual, paper-based, or outdated enrollment systems can slow everything down and increase the risk of errors. These legacy processes often frustrate HR teams and employees, making enrollment feel more like a burden than a benefit. As workplace expectations evolve, so should how benefits are managed and delivered.
Manual Enrollments
Handling open enrollment through forms and spreadsheets may seem manageable, but it often leads to unnecessary administrative burdens and costly errors. Manual processes are time-consuming, more complex to track, and prone to data entry mistakes affecting coverage and compliance.
For HR teams, this means more follow-up, corrections, and frustration. Shifting to digital platforms reduces risk, saves time, improves accuracy, and creates a better experience for both workers and administrators.
No Tech Integration
Without modern technology and system integration, open enrollment becomes a fragmented, inefficient process. Lack of automation means missed opportunities for real-time insights, data accuracy, and streamlined workflows.
HR teams are left juggling disconnected platforms and manual updates, which slows decision-making and increases the chance of errors. Integrating benefits platforms with payroll, HRIS, and other systems saves time and enhances transparency, compliance, and overall effectiveness of your benefits strategy.
Build a Smarter Employee Benefits Strategy With New City Insurance
Don’t think of open enrollment as just another annual task. It’s a chance to demonstrate value, retain talent, and strengthen your overall employee benefits strategy. By avoiding common pitfalls, such as poor communication, outdated processes, and rushed planning, you can create a smooth and more effective experience for your team and your business.
Ready to take a more strategic approach to open enrollment? Contact New City Insurance today to learn more about our services and get the most out of your benefits investment.