Episode 8: An Open Enrollment Communications Playbook

Oct 10, 2023

Open enrollment can be intimidating for employees. An effective communications strategy can help them feel more prepared and informed when it comes time to make benefits decisions.

Invested at Work Podcast

Episode 8: An Open Enrollment Communications Playbook


Stephanie (00:00):

But I think we can all get bogged down when there are deadlines, when there are systems changes, when there are data challenges that have to be tackled. And it can be difficult sometimes to remember to just take that step back and think about the fact that you, as an employee, as well as all of the employees that you serve, are going to come out of this better if you've got a great plan for open enrollment that you can execute.

Rodney (00:30):

For HR leaders, open enrollment can be a year long commitment, but employees may not have thought about many of their workplace benefits options since the year before, and they might need some help getting up to speed and moving through the process. To learn more about common pitfalls when it comes to open enrollment communications and how HR professionals can avoid them, I spoke with Stephanie Glashow, Chief Marketing Officer of Morgan Stanley at Work. Stephanie lends us her insights on how to engage employees around open enrollment to help them feel more confident about their upcoming decisions. I'm Rodney Bolden, Head of Industry Engagement and Learning at Morgan Stanley at Work. This is Invested at Work.


Stephanie, welcome. I want to talk to you today about something that I know keeps HR leaders up at night, and that's open enrollment. As a workplace financial benefits vendor, how does Morgan Stanley at Work prepare your corporate clients for this time of year?

Stephanie (01:30):

Rodney, first, let me say it's great to be here. Enjoy listening to the podcast and I'm so happy to be one of your guests. I think that one of the best things we can do at Morgan Stanley at Work is help our corporate clients think about the way that communications can help facilitate a really smooth open enrollment experience. So I think it's really important for any communications to keep the recipient front and center, really taking the time to understand the needs of your employees.


It's funny that you mentioned that it can be a stressful time for HR professionals because I think open enrollment can also be very stressful for employees. Think about this. I remember the first time I had a full-time job that included benefits, and I needed to make those elections. And I did it and I got some input, and I felt pretty good about my choices. And then just a few months later, HR is knocking on the door again saying, "Do you want to rethink any of that? Do you want to make changes?" And I felt, honestly, a little anxiety about the fact that I now needed to reconsider all of these choices that I had just made. There's a certain sense that you may have made a mistake or that if you make the incorrect choice, you're stuck with it.


Now, I think that it's really important, of course, for employees to understand the deadlines that are associated with open enrollment. So you do want to create a sense of urgency. But at the same time, it's really important to make sure that people understand the benefits that are available to them. I think if you can work with all of your benefits providers to keep that in mind, remember that it's about the employee, demystifying the benefits for them, providing information to help them make good choices for themselves and for their families, then I think you'll have a certain sense of alignment across all of the communications that will really benefit the recipient.

Rodney (03:33):

Tell me a little bit more about how HR leaders should be thinking about not just the employees, but how do they make sure that those families that are covered under the benefits have that awareness of what is taking place and what is available for them to utilize?

Stephanie (03:50):

I think that any employee should have as much transparency as possible to the benefits that are available to them, and that those same sources of information should be easy for the employee to share with the people who are going to help them make the decision. It might be a family member who will also be covered by those benefits, or it could be a friend or another trusted advisor who's helping the employee make decisions about his or her own choices. And so things like FAQs, like a web portal where information can be readily seen, where choices can be compared to one another, provides an important source of information for the employees.


I also think that as you approach open enrollment, you have a really great opportunity to prepare people. Now, I'm sure you, like I, have sometimes received that postcard in the mail that says, "Hey, heads up. Open enrollment is coming. Stay tuned for more information." In my opinion, honestly, that's not a particularly successful communication vehicle because all you've done is told someone that more information is going to be coming to them at some point in the future, and you haven't given them anything tangible that they could do with that information.


So one thing I always advise is think about when it's appropriate to tell people to do certain things that they can do in the moment. So when you're announcing your open enrollment dates, perhaps you want to be as specific as saying, "Put these dates on your calendar." So now you're not just saying there's dates, you're tossing that postcard in a pile on your desk that you may or may not look at before November. You may look at it next March and realize that, "Yeah, open enrollment happened four months ago. Great."

Rodney (05:49):


Stephanie (05:51):

So just those simple suggestions sometimes will get people going.


But what I think is more important is helping them prepare for the things they need to think about. And to come back around to your question about others who may be covered by the plan benefits, that's the opportunity to start having those conversations. If you have a partner or spouse who also has benefits coverage, do you want to look at each other's options so that you know which plan you're selecting for which types of coverage, right? This is something that will take a little time. And so giving people those steps that they can take to say, "Hey, have a conversation with others who may be impacted by the choices you make during open enrollment. Think about what kind of coverage you need. Has it changed from last year?" And so I'm helping people really understand, "Oh, these are the questions I should be asking myself or the people in my life, and then I can be prepared when I enter that portal and have to actually start clicking buttons."

Rodney (06:53):

I always find the frequently asked questions, the FAQs, so helpful. But do you have any best practices for how companies can formulate those FAQs and make sure it's not just from the perspective of HR?

Stephanie (07:07):

What I recommend is creating actually a focus group or some kind of user group testing. And what you might want to do, and this takes a little bit of planning, is have somebody sit with you, somebody who's not one of your HR benefits buddies. You can't cheat on this test. But grab someone that you maybe see in the pantry or you run into in the elevator bank, and ask them if they will take 10 minutes and sit with you in front of the portal and pretend that they're going through their election. Tell them to ask you every question that comes to their mind as they're going through that experience. It could be something as little as, "Where do I find my password." Or, "What choices did I make last year? How do I find that? Or something much more complicated like, "How should I be thinking about what percentage, how many times of coverage life insurance do I need?" There's always that little thing like 1X, 2X, 3.73X. "How do I make that choice?"


Write those questions down and maybe do that with five people, or get your team to, everyone do it with one person. And take a look at those questions. Because to your point, an HR professional has the benefit, no pun intended, of being immersed in this topic a lot. Individuals who are coming to open enrollment probably haven't thought about this in about a year's time, and so capturing the questions that are really on their mind as they go through the experience can give you a great starter list of items to add to your FAQ.

Rodney (08:46):

As a workplace financial benefits vendor, you work with companies of all sizes, all industries, all demographics within those workforces. How do you determine the best mode of communication, and is it different for different demographics within the organization?

Stephanie (09:03):

100%, it is different for different demographics within the organization and different types of organizations, as you mentioned. I'm a believer in multi-touch, multi-channel communication, taking advantage of every channel that's available to you. So that could be everything from a leaflet that you're leaving on someone's desk. Could be digital signage or physical signage. And then of course, all of the electronic channels like email, messaging on the intranet. But don't forget about the human channels. Asking your managers to communicate if they have a weekly team meeting or in one-on-one communications. Remind people, "This is coming up. Here's where you can find the information." Human communication is always the most effective communication channel.


I also mentioned multi-touch, so different people will receive information and process it in different ways. I think that's well established science at this point. It might be demographically driven, but it might just be an individual thing. So you and I may share many preferences, Rodney, but you may be the guy who wants a text, and I may be the person who wants a phone call. And you would be hard-pressed to know that about one of us, or predict that about one of us, if you didn't ask directly. So using multiple channels of communication and repeating consistent messages through those channels will increase your odds of getting a message to someone in a way that works for them.

Rodney (10:39):

One channel we're starting to see in some companies, especially technology companies, is employee to employee communication about benefits via a Teams channel or a Slack channel. What are your thoughts on that?

Stephanie (10:52):

Everyone's got an opinion, right?

Rodney (10:54):


Stephanie (10:54):

And so creating an environment where people can share their opinions is of course valuable in many ways. But the big risk that I think companies need to watch out for is the risk of misinformation. And I'm not talking about anything malicious, but a simple misunderstanding by one person who then posts something on a Slack channel that is then read by hundreds, or in many cases, thousands of others, can be really disruptive to the HR team's process because now that phone call's coming in from all sides. Like, "What? I didn't know this." Or, "Why did this change?" And it might just be a simple misstatement of something or a true misunderstanding of something that's been set.


One thing that you can try to do to take advantage of that viral marketing for your benefits programs, if you will, is to create ambassadors. Identify employees who like to be someone who spreads the word or who are well-connected across the organization, and ask them if they would be willing to help you help their colleagues get set up with the right benefits for them at the time of open enrollment, and empower those individuals with the tools and resources that you and HR might have yourself. Whether it's that FAQ or the secret FAQ, or whatever it is that they can use. Or maybe you're giving them a message a week and just saying like, "Hey. This week, can you help us spread the word that we're having a webinar to help people prepare for open enrollment season?" That's a very easy task. It feels very manageable, but now you're using their networks to help encourage other employees to pay attention to what's going on. I think it's a great strategy.

Rodney (12:44):

Now, another thing I want to talk about is there are some benefits that are rolled out only at open enrollment, like healthcare. And there are other benefits that are talked about at open enrollment, but you can enroll in them throughout the year, like maybe an employee stock purchase plan or maybe a retirement plan. How does communication differ from those one-time enrollments as opposed to those ongoing enrollments? Or do they differ?

Stephanie (13:10):

They do differ. I would say that whenever you have an event or a point in time happening, you want to think about it in three stages. You want to think about the pre, the during, and the post. And we talked a little bit about the pre earlier, so communicating in advance, helping people understand what they can do leading up to the event rather than just saying, "Hey, something's coming," and having the conversations that they need to have so that they're ready so that when they enter the during period, they're prepared to do what they need to do, and they're not on the enrollment website at 11:58 PM and frantically calling their HR hotline because they don't understand one of the choices that's available to them. And I'm sure that never happens, but we would like to continue avoiding that.

Rodney (13:10):

Of course not. No, not at all.

Stephanie (14:04):

Never, never.


And then post, of course, you want to make sure that you're confirming people's choices back to them, that they know where to find the information about... Whether that's connecting them to the website for the different providers that they've selected or if you have that information on your own company portal, but just providing them with that ongoing information and support that they'll need.


Now, with an ongoing option, or a continuous enrollment type of option, you want to have continuous communication, but you do run the risk of losing people's attention if you're constantly sending the same message. So the way I would recommend thinking about that is what other events are going on that you can anchor to? What other messages might you anchor to? And so if there's an HR employee newsletter, having a little blurb that reminds people they're able to enroll in these programs at any time and giving them that next step. How do you do it? Do you call? Here's the number. Do you do it online? Here's the link, right? Making it very, very actionable. You can, again, leverage those human channels, and maybe each quarter, you pick a theme that you ask managers to cover off with their teams over the course of that quarter or that month, whatever you prefer, whatever cadence works for your company. But saying, "Hey, have you thought about this?"


You could tie it to external events. There are things like 401(k) day or 529 day. So if there are things that are going on in the external environment that maybe the media's picking up on, you can use those moments to remind your employees that your company is offering a way for them to take advantage of those programs as well.

Rodney (15:55):

Let's talk during open enrollment for a moment because I know you talked pre, during, and post. During open enrollment, if an HR leader observes that it's not going as planned and needs to pivot, what are some ways to identify that real-time feedback to understand that you need to pivot away from your predetermined strategy?

Stephanie (16:17):

One thing that's helpful for leaders in this situation is to think in advance about what they want to be watching out for and how they're measuring success. So success during open enrollment might be achieving certain levels of enrollment at certain points in time during the period. So one early indicator would be that people are not successfully completing the enrollment process at the rate that you would've expected. That's a sign that you want to start exploring why.


First thing would be, is the website working properly? Is that portal? Are there any technical issues that are going on? The second thing might be call some of those people who did successfully enroll and ask them, "Did you have any problems?" Going back to that idea of having your own internal focus groups. I think then knowing what your plan is, if enrollment is lagging. Think about, "Okay, what are we going to do? Are we going to hype that process every day? Are we going to send emails? Are we going to engage those employee ambassadors that we talked about, and say, 'Hey, walk the floor,' and remind everyone that it's open and they should get cracking? Are we going to do a sweepstakes where if you complete your open enrollment by such and such a date, you'll be entered in a drawing for something?" Right?


There are a lot of ways that you can motivate behavior, but you first have to understand what the problem is.

Rodney (17:48):

Let's talk about things that surprised you during an open enrollment. You and your team work on communications for thousands of companies. Is there any feedback that surprised you, something that came up that it's like, "Hmm, that's different"?

Stephanie (18:05):

People like to know what they need to do and also what they don't need to do. That was one key learning in a series of communications where we had been providing instructions and then also saying, "You don't need to change this thing. You don't need to worry about this." And then in communication four, we omitted that sentence and all heck broke loose. Now, it hadn't been intentional on our part. We really hadn't thought much about it. It was just trying back to that idea of different messages resonate in different ways. You don't want to be the broken record, so you try different language, you try different phrases. You're hoping to engage people in a new way. But all of a sudden people are like, "Wait a minute. You told me I didn't have to do anything about this and now this communication doesn't say that I don't have to do anything about this. Do I now need to?"


So when you think about the consistency of your communications, think about it from end to end. And if you are changing anything in the way that you communicate, be sure that that's intentional and that you're not going to create confusion. So I think that's one thing that I wouldn't necessarily have anticipated that caught us a bit off guard.

Rodney (19:26):

Now, post open enrollment, most HR teams will do an analysis. Any recommendations for practices that you've seen really get at the heart of how to improve a future open enrollment?

Stephanie (19:39):

With any kind of retrospective, it's important to leave emotion out of it and just focus on data. So the more data that you're able to capture and take a look at, I think the more likely you are to have an objective analysis that avoids any kind of defensiveness, finger pointing, hurt feelings, what have you that might cloud the ability to understand what really needed to happen differently.


I think secondly, setting the stage and reminding everyone that this is about the employees. This is about, your company has invested so much time, money, and resources in establishing a benefits program that is designed to really benefit the employee. And if those employees don't recognize and understand everything that they can avail themselves of, then that time, resource, and energy has been, I don't want to say wasted, but underutilized. And so keeping that as the focus or the North Star, if you will, can also help take some of the emotion out of that kind of retro analysis.


Another mistake that I think people make when they do those analyses is everyone's very diligent in the moment to think through all of the things that happened, look at the data, determine whether or not things were successful, identify opportunities for improvement. What happens to that list of things? What is the plan for how those observations and ideas for improvement become reality for next year's open enrollment? Some of them will likely be things that people can start working on right away, and they should. Others might not be things that you need for another 10 months or so. How do you not lose sight of those? So being very thoughtful, not only about conducting the analysis, but capturing and putting in place a roadmap for implementing any changes that you decide you'd like to implement is really critical.

Rodney (21:54):

Any final key takeaways, as the HR leaders are sitting there listening to the podcast, that you can impart to help them better prepare for future open enrollment?

Stephanie (22:07):

I think remembering that the employees want this to be as successful and easy as you want it to be for them.

Rodney (22:19):

Yes, we do. Yes, we do.

Stephanie (22:21):

Everyone's on the same side here. It can be frustrating when you're getting those 11:58 PM phone calls, and you feel that people haven't done maybe the prep that you would have hoped. But really thinking about the ways that you can help compel people to do that early prep, trying to leverage lots of communication channels, engaging that internal focus group, keeping your employees at the center of what you're trying to do. And reminding yourself of that, because I think we can all get bogged down when there are deadlines, when there are systems changes, when there are data challenges that have to be tackled. And it can be difficult sometimes to remember to just take that step back and think about the fact that you, as an employee, as well as all of the employees that you serve, are going to come out of this better if you've got a great plan for open enrollment that you can execute maybe flawlessly, maybe almost flawlessly, but certainly to the benefit of your organization.

Rodney (23:30):

One more question for you, Stephanie. What gets you excited about Work? In other words, what makes you invested at Work?

Stephanie (23:38):

One is the ability to use my communication skills and experience to help people understand how they can make great financial decisions for themselves and their families every day. And the second is that I am lucky enough to work with a team of incredibly creative and talented people. And so getting to do that every day in service of those clients that we support really is what gets me out of bed in the morning.

Rodney (24:11):

Stephanie, thank you so much for your insight today. Greatly appreciate you joining me.

Stephanie (24:15):

Thank you so much, Rodney. Great talking to you.

Rodney (24:24):

Invested at Work is brought to you by Morgan Stanley at Work, produced by StudioPod Media. Our executive producers are Fiona Kelsey, Lisa Boyce, and TJ Bonaventura. Our producer is Sterling Shore. Our engineer is Alejandro Ramirez. And our writer is Dan Pelberg.


Be sure to visit us at MorganStanley.com/atwork for more insights on workplace financial benefits, and I'll see you next time on Invested at Work.


Not all products and services are available in all jurisdictions. This material has been prepared for educational purposes only. Morgan Stanley Smith Barney, LLC, and its financial advisors and private Wealth advisors do not provide any tax or legal advice. Consult your own tax or legal advisor before making any tax or legal related investment decisions. Morgan Stanley at Work Services are provided by Morgan Stanley. Smith Barney, LLC, member SIPC, and its affiliates, are wholly owned subsidiaries of Morgan Stanley.



Your goal is to help your employees make more informed open enrollment decisions. But the process can be complex—for employees and employers alike—and it can be tough to break through the noise when it’s time to get critical information across. In this episode, we take a look at strategies for effective and clear communication before, during and after open enrollment that can help employees feel more supported and confident when making benefits decisions.

This is Invested at Work. Listen in.