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Why Successful Open Enrollment Begins 90–120 Days Before Enrollment

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Employer Services

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When Enrollments Go Sideways: Building a Year-Round Communication Plan

by Brian Hugger | Sep 16, 2026 | Benefits, Workforce | 0 comments

Three men in suits collaborating at a modern office desk with computers and documents.

Communication, Communication, Communication:   A communication action plan with clients throughout the year is the best way to optimize the relationship. This can be broken into various stages: client acquisition, pre-enrollment, enrollment, post-enrollment communications, and ongoing servicing.

In-order-to maximize outcomes and client satisfaction, brokers and carrier reps must take care in being diligent communicators and focus on offering personalized benefits to the diverse needs of varying clients. Communication is the most important skillset a broker or carrier rep can develop tomaintain a fruitful and high-satisfaction relationship with a client and its employees or members. It is important to ask consultative questions, and to be creative in addressing and meeting the needs of each client. This means avoiding the temptation to cookie-cutter solutions across all clients, and to carefully develop a benefit strategy that fulfills each of their unique needs. This involves a consultative approach, being careful not to “sell” the solution.

Since communication is perhaps the most important function of the sales and client servicing process, this is where most of the energy, both pre and post-enrollment should be devoted. In today’s market there are very high expectations and many tools available to meet them. Below are some strong examples of methods of optimizing open enrollments for employee benefits. Prior to enrollment, utilize multiple channels, utilizing various communication methods, including emails, webinars, breakroom flyers, website banners, texts and voicemail reminders when appropriate, along with face-to-face meetings, to reach employees effectively and on a more personal basis when possible or appropriate. Live interactions can have a profound positive impact on engagement, encouraging personal interactions, as they can significantly improve message retention and engagement.

Collaboration and consulting, rather than selling in today’s marketplace, is vital. To properly consult, you have to ask questions to discover the needs of a client and the individual needs of its employees or members. Once the needs and values of an organization are known, only then will be appropriate for the client to consider the potential solutions.

It is best practice to communicate upcoming enrollment dates regularly, with teasers of plans available, and reminders of enrollment dates and deadlines. During the enrollment window, agents and brokers should be prepared to answer client questions quickly to assist with the decision-making process. All communications should be in simple terms with easy to comprehend and concise language. Consider tiered options for benefits with voluntary benefits to mitigate first dollar expenses like co-pays and deductibles, as well as fill gaps of potential lost work to care for loved ones etc. Ensure that enrollees comprehend how to utilize the coverages, and the general claims process and timelines.

When enrollments go sideways, it isn’t always that communication has failed, but when communication fails, the enrollments will go sideways. The best way to maximize the relationship with the client and the employees or members, is to have a strong communication plan. Being sure to communicate the: what, where, how, when, why, etc prior, and throughout the enrollment will help produce more positive results.

Up next: Part 3 of 4, “Educate, Simplify, Automate: Making Open Enrollment Easy for Employees.” With a communication plan in place, the enrollment itself is next. We’ll cover how education and the right technology make the process easier for everyone involved.

Author: Brian Hugger

With over 25 years experience in various leadership roles, Brian has developed a keen instinct and advanced skills making him an effective leader and communicator across many industries. Experience in Employee Benefits, Human Resource, Recruiting, Insurance, Retail management, Manufacturing, Project Management, Customer Service, Data Integrity, Analytics, Consulting, Sales management and Insurance Sales. This experience has developed Brian to relate with the needs and find creative solutions of various clients. Brian is a strong communicator and exemplifies ethical leadership with honesty, integrity, and compassion.

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