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Somewhere in your benefits package is a perk that has outlasted three executives and helped approximately four people.
And you’re about to renew it again! 😬
Open enrollment is right around the corner, which means HR is approaching that magical season when everyone urgently needs the info they ignored three months ago.
Before the reminder emails take over your inbox, though, there’s a bigger convo worth having:
📣 What are we actually offering people, and does it still make sense?
As you’ve probably experienced, some benefits get stale over time.
A vendor renews, and suddenly a decision made for a very different workforce has tenure.
Meanwhile, employees have become caregivers or moved somewhere their doctor takes exactly none of their insurance options.
Your benefits stack carries a huge chunk of your employee value proposition, ya know! People experience that promise through what they can afford and how easily they can get help. I care about that gap, especially when a lean HR team is expected to close it between an employee relations situation and somebody’s urgent question about parking.
Betterment at Work’s 2026 Open Enrollment Season Planning Guide offers a framework for getting ahead of the rush, including reviewing retirement benefits. If changes to your 401(k) are on your mind for next year, this is a useful moment to start asking questions! 💡
Let’s give the whole stack some attention and cover some important reminders before we’re all communicating exclusively through FINAL REMINDER subject lines.
❓❓I’d start by asking, if you were building this package today, which benefits would you choose again?
For a company with 50 to 200 employees, every addition has a cost, including the time someone (usually you) spends administering it:
- Start with health insurance: Which means looking at what employees pay through premiums and when they use care
- Review network changes: If you offer a high-deductible health plan with an HSA, examine whether employees understand the pairing and can manage the upfront expense
- Look across the stack: Maybe your mental health platform overlaps with support already available through another vendor. Perhaps caregiving assistance would address a need employees keep raising
👀 I think low utilization deserves investigation before cancellation.
A benefit can be valuable to a small group, especially when life gets complicated. Ask whether people need it and can access it without sacrificing their lunch break to a password reset!
Betterment’s 2025 retirement readiness research explores employees’ financial stress. Use that as a convo starter, then ask your own people where money feels difficult. Budgeting support or financial coaching may deserve consideration alongside retirement savings.
🎨 Creative benefits design can mean redirecting dollars toward something more useful. You have my enthusiastic permission to question a vendor’s place in the stack, even if their account manager sends excellent holiday cookies.
Also, look at how the pieces work together. Offering therapy support means less if employees struggle to find an available appointment.
Retirement education can feel frustrating when someone needs help managing immediate bills.
Ask vendors where their service ends and where employees are supposed to go next. The answer occasionally involves another login and a very optimistic assumption!
I’d rather fund a package people can navigate than win an imaginary award for having the longest benefits page. Nobody is framing that award!
Sixty days before open enrollment is a useful planning checkpoint. Put it on the calendar while you still have a personality outside this project!
Betterment’s guide uses that window to review offerings and vendor changes, test the enrollment experience, and get internal stakeholders aligned.
🙃 Payroll connections deserve attention here too. Discovering an issue after deductions begin is an especially unpleasant group activity.
Some changes might need a lil longer. For example, a 401(k) provider transition has its own implementation requirements and deadlines, so confirm timing with your provider well before promising a launch date.
At 30 to 45 days out, employees should start hearing what’s coming. Give them a CLEAR summary of changes and the dates that matter, then reserve space for questions.
During enrollment, make the portal easy to reach and follow up with people who still need to act.
Afterward, check elections and payroll accuracy, and document the confusing bits while they’re fresh.
Bring finance into the choices early, with the employee impact attached to each dollar discussion. If a change saves money, explain who absorbs the difference.
If it adds cost, show the need it addresses. That makes the convo considerably more useful than asking HR to somehow make everything better with the same budget.
Unfortunately, an employee can complete enrollment perfectly and still have absolutely no idea what they selected!
That probably happens more than you think, although I’m lowkey afraid to know exactly how much. 🫣
We ask people to make decisions involving their family’s care and their paycheck, then hand them language that sounds like it was assembled during a legal department escape room. My worst nightmare.
Please explain the deductible in a sentence someone would say out loud.
I think it would be helpful to use specific situations employees recognize. For example, someone expecting a baby may want help comparing coverage and likely costs, or someone approaching retirement may have questions about their contributions.
Offer ways to explore those questions privately, without announcing personal information in a team meeting.
Managers can remind people to review their options and point them toward qualified support, since their role has boundaries.
(I have several concerns about Brad from sales developing strong opinions on anybody’s healthcare elections)
For retirement education, Betterment shares low-lift ways to help employees engage with their 401(k), including drop-in office hours. Give people room to ask the question they think everyone else already understands!
Then, ask what remained confusing, and those answers should influence the benefits stack itself.
Repeated questions about accessing care might point to a vendor experience that needs fixing, even when your comms are excellent.
🥴 Health insurance can consume the entire benefits convo, which is totally understandable. After all, there’s a lot happening there!
Still, you’ll want the retirement plan on the agenda too, with enough time left to actually discuss it.
For employees trying to build long-term savings, the plan’s costs and design matter.
Review the employer match, if offered, and whether eligibility or vesting rules fit your workforce. Ask what employees experience when they enroll or need help.
Then get specific about fees:
- Who pays which charges?
- What services do those charges cover?
- How do investment expenses compare?
Betterment does a good job of explaining why a cost-efficient 401(k) deserves scrutiny.
Fees reduce the money remaining invested, and their effect can build over time.
Compare costs alongside service quality and investment options, because a cheap plan that creates endless confusion has its own consequences!
I think HR’s workload belongs in this review, too. A benefits stack held together by your manual fixes has a capacity limit, and I would prefer you reach retirement before reaching your limit.
Betterment offers paperless enrollment and 350+ payroll integrations, alongside retirement guidance and support for employees and plan sponsors.
Their compliance services can also help with plan administration. Ask which responsibilities remain with your org and what any guarantee covers.
📝 One important clarification though: employees can generally adjust 401(k) contributions throughout the year, subject to plan rules. Open enrollment provides a useful reminder to review retirement savings…health plan deadlines shouldn’t imply otherwise.
Open enrollment has a funny way of feeling months away until suddenly a dozen employees are bombarding you with questions! 😬
Before the annual inbox apocalypse begins, use Betterment’s 2026 Open Enrollment Season Planning Guide to pressure-test your plan.
It gives you a practical framework for reviewing your benefits, mapping out key deadlines, communicating changes, and catching the tiny administrative surprises that love to become enormous problems at the worst possible moment.
This is also your opportunity to give retirement benefits more than the polite little nod they usually get.
Ask your provider to explain the fees, employee experience, admin responsibilities, and any upcoming requirements that could affect your plan.
Betterment’s retirement legislation hub can help you start convos about SECURE 2.0 without reading federal retirement legislation recreationally, which I assume was not on your vision board.
Your entire benefits stack does not need to be reinvented by Friday. Pick one area that feels confusing and start there.
Download Betterment’s guide now, while your calendar is still asking nicely!
Disclosures:
Paid non-client. Views may not be representative. See G2 reviews. Learn more.
Information provided about SECURE 2.0 reflects Betterment’s current understanding and analysis but may change as additional regulatory guidance becomes available. Provisions may require plan amendments before they can be implemented. This content is for informational purposes only and is not legal or tax advice.
