Open enrollment going imperfectly is the normal experience — what separates the HR teams that handle it well is not that they avoid problems; it is that they have a plan for when problems arrive.
Every year, HR teams spend weeks preparing for open enrollment. The communications go out, the portal is set up, the deadlines are marked on the calendar. And then the window opens and something goes sideways.
It might be the employee who missed every communication and is now panicking with three days left. It might be the technology that is not syncing the way it was supposed to. It might be the flood of questions about a plan change that was not communicated clearly enough. It might just be the general sense that the whole thing feels harder than it should, even when you did everything right.
Open enrollment going imperfectly is not a failure. It’s the normal experience of running a complex administrative process under a deadline for a workforce with different circumstances, different levels of engagement, and different levels of comfort with the decisions they are being asked to make. What separates the HR teams that handle it well from the ones that don’t is that the former avoid problems; it’s that they have a plan for what to do when problems arrive.
The most common open enrollment problem is employees who haven’t yet made their elections with the deadline approaching. Some of them are genuinely stuck on a decision. Some of them got busy and put it off. Some of them did not realize the deadline was as close as it is.
The most effective thing HR can do at this stage is not another mass reminder. It’s a targeted outreach to the specific employees who have not yet enrolled, ideally with a direct line to someone who can answer a question or help them through the portal in real time. Employees who have not enrolled by the last few days of the window often just need someone to remove a single point of friction; be that a question that has been sitting unanswered, a portal login that is not working, or confusion about which plan to choose.
If that’s not possible to do individually, a communication that directly addresses the most common reasons people get stuck—“not sure which plan to pick,” “think my current plan carries over automatically,” “was waiting to talk to my spouse”—will reach more of the right people than a generic deadline reminder.
Portal issues during open enrollment are more common than anyone likes to admit. Things like employees being unable to log in, elections that aren’t saving, and dedication previews that show the wrong amounts can erode confidence in the process and create extra work for HR on top of everything else that is already happening.
The most important thing when a technology issue surfaces is to have a clear escalation path:
If the answer to any of those questions is unclear, that clarity is worth establishing before the last few days of the window, not during them.
High question volume during open enrollment is almost always a signal that the communications that went out before the window opened did not answer what employees actually needed to know. The questions coming in now are the questions the communications should have answered three weeks ago.
That’s useful information for next year. For right now, the most practical thing is to identify the three or four questions that are coming in repeatedly and send a targeted communication that answers them directly and clearly. One well-timed email that addresses the questions everyone is actually asking will do more to reduce inbound volume than any number of general reminders.
It happens. Despite communications, reminders, and follow-up, some employees will miss the enrollment deadline. The answer for most of them is that they will remain on their current plan if they were already enrolled, or they will have no coverage until the next open enrollment or a qualifying life event if they were not.
That’s a difficult conversation to have, but it’s a much easier one when it is handled clearly and promptly rather than discovered weeks later. The employee who finds out in December that they missed enrollment is in a better position than the one who finds out in March when they try to use coverage they thought they had.
Being direct with employees who miss the deadline is the most useful thing HR can do for them at this point, including what it means, what their options are, and what to watch for in terms of qualifying life events that could open a special enrollment period.
Open enrollment being hard is not a sign that something is wrong. It’s, unfortunately, the nature of the work. We work with HR leaders across industries, and those who handle this period of time well aren’t the ones burying their heads in the sand. They’re the ones who have clear responses at the ready when problems inevitably arise.
~
Brian Allen | President, evco | Managing benefits for 36,000+ lives since 2005
The founders who consistently get better renewal outcomes started thinking about next year in November — and the planning that happens now is what determines how much leverage they have when renewal arrives.
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.
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.