October exposes everything a benefits program got away with during the quieter months — and the mistakes that surface are almost always ones that started in the preparation, communication, and accountability decisions made long before renewal arrived.
Benefits management is one of those employer must-dos that feel seasonal, but are actually a monthly commitment. We’ve seen firsthand how a lack of urgent calls to HR can make the process complacent. But October is where the hard work really pays off.
When your renewal and open enrollment arrive at the same time, the invisible gaps during the quieter months suddenly have consequences. Below, we’re outlining the specific line items that can go astray this month. Most of them are predictable and, better yet, understanding is the first step toward not repeating them next year.
The most consequential mistake employers make is the absence of decisions they should have made in July and August.
Specifically: not reviewing utilization data before the carrier finalizes their renewal analysis, not modeling alternative plan structures before the renewal number arrives, and not having a real conversation with their broker about what the renewal outlook looks like while there is still time to do something about it.
By the time October arrives, the carrier has already done their analysis. What they send over is an output of months of data review, not just a preliminary estimate. So when an employer sees this number for the first time in October, they’re reacting to a conclusion that wasn’t built with their input.
Conversely, an employer who spent September (and even earlier) reviewing the same data, modeling alternatives, and working with their broker to build a strategy is evaluating a proposal against something concrete.
The bottom line: You work with whatever you built before it, or you work without it.
Now comes the hard truth: open enrollment communications that go out the week before the enrollment window opens are not communications. They’re notifications.
A notification tells employees that something is happening and asks them to take action by a deadline. A communication tells employees what is changing, what it means for them specifically, and what they need to do to make a good decision for their family. The first produces a flood of questions during enrollment. The second answers those questions before they get asked.
The mistake most employers make is treating open enrollment communication as an administrative task rather than a strategic one. They send the plan comparison document, they post a reminder in Slack, they set up the enrollment portal. And then they wonder why the same questions come in every year from employees who clearly didn't absorb any of it.
The reason is not that employees don't care. On the contrary, they care a lot. But when communications aren’t designed around what they actually need to know, they’re a missed opportunity for collaboration.
When something goes wrong during open enrollment (and something always does), we’ve found that the employers who resolve it quickly have one person they can call who knows their account and can act on it.
The opposite side of things is an employer who spends three business days waiting for a carrier to call back, or who discovers that the enrollment change they submitted was processed incorrectly, or who finds out that a dependent was not added to the plan because the paperwork went to the wrong place. Unfortunately, these aren’t unusual situations. They’re the predictable output of a benefits program where accountability is diffuse, and no single person owns the outcome.
Having one point of contact who takes ownership of problems when they surface is a structural requirement for a benefits program that works under pressure.
Preparation that makes October manageable happens in the summer, not in October itself. The utilization review, the alternative modeling, the communication planning—all of it has more value at 90 days than at 30.
Invest in your broker beyond a twice-a-year transactional check-in. Rather, begin an ongoing engagement where the broker knows their plan, knows their team, and is actively working on their account throughout the year. That relationship is what makes it possible to move quickly when October requires it.
Employee communication is a core part of open enrollment management, not an afterthought. The employers who run the cleanest enrollments invest in helping their people understand what they have before they're asked to choose. That investment pays back in fewer questions, better decisions, and a smoother close to the enrollment window.
October doesn’t have to be the hardest part of the year. But it rarely gets easier on its own. The conditions that make it manageable are built in the months before it arrives. When you’re ready, the evco team of experts is here to guide you through the process and avoid these typical pitfalls.
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Brian Allen | President, evco | Managing benefits for 36,000+ lives since 2005
Open enrollment communication fails when it's designed around what HR needs to say rather than what employees need to understand. Closing that gap is what separates a clean enrollment from a chaotic one.
The most useful thing a CFO can do before October arrives is get specific about what they actually know going into renewal. If you can answer these questions, you’re in a different position than most.
What most employers don’t realize is that the renewal conversation they’re having in October was largely decided before it started. By the time you see the number, they’ve already done their homework. September is when your homework needs to happen.