Skip to main content
Edit Page Style Guide Control Panel
Topographical Lines.
Benefits communication calendar showing employee benefits messages scheduled across the plan year

How Do You Build a Benefits Communication Calendar?

August 09, 2026

·

First Hill Trust

Key Takeaways

  • A benefits communication calendar lists every benefits message you plan to send during the year, with the timing, audience, channel, and owner for each.
  • Schedule each message for the point in the year when an employee can still act on it. Most calendars schedule by topic instead, which puts the message in the wrong month.
  • The FSA reminder is the clearest example. Sent in December, it reaches employees too late to use the money. It belongs in early fall.
  • Build the calendar around your plan year, starting from the enrollment window, and name one person as owner for every message.

Why This Matters

Picture a company that runs open enrollment well. HR sends the packet in October, holds two sessions, answers questions for three weeks, and closes on time with good participation.

Then nothing goes out until the following October.

In February an employee skips a physical because they assume it will cost them money. On most plans a preventive visit costs them nothing. In July someone who could have used the employee assistance program does not remember it exists. In December another employee forfeits a health FSA balance, because the reminder arrived with two weeks left and no appointments available.

HR never hears about any of it, because nobody complains about a benefit they forgot they had. The only measure anyone checked was enrollment participation, and enrollment went fine.

A communication calendar prevents all three, because each message is scheduled for the moment when the employee can still act. The rest of this post shows how to build one, and the kit above has the emails already written.


What Is a Benefits Communication Calendar?

A benefits communication calendar lists every benefits message you plan to send during the year, along with when each goes out, who receives it, which channel carries it, and who is responsible for sending it.

It is a working document, not a polished one. A spreadsheet is fine, as long as one person keeps it current and it lives somewhere the rest of the team can open it and see what is scheduled.

Required disclosures go on it as well. The summary plan description, the summary of benefits and coverage, and COBRA notices each have their own delivery deadlines. Put them on the calendar so they are not missed, and treat them as fixed dates you plan around.

What Should Go on a Benefits Communication Calendar?

Most published calendars organize by quarterly theme. First quarter covers financial benefits, second quarter covers health, third quarter covers family, fourth quarter covers enrollment. The themes are tidy, and they are built around subject matter rather than around whether an employee can still do anything about the benefit that month.

Schedule by action window instead. For each benefit, find the weeks when an employee can still do something about it, and put the message there.

  • Preventive care: right after the deductible resets. Under federal law, most health plans must cover recommended preventive services, including routine screenings and immunizations, at no cost to the employee even before the deductible is met. The start of the plan year is the moment to say so: the deductible has just started over, and these visits are not subject to it.
  • Health FSA spend-down: early fall, not December. A reminder sent in September or October reaches the employee while there is still time to book an appointment, order what they need, and spend the balance before the deadline. By December most of that room is gone, so December gets a short last call rather than the main push.
  • Life event information: at onboarding, and to everyone once mid-year. A marriage, a birth, or a spouse’s job change can allow an election change outside of enrollment, but only if your plan document permits it and only within the window that document sets. An employee who first hears this after the event has usually already missed the window.
  • Retirement contribution messages: timed to your payroll cutoff. January feels like the obvious month for these, but the date that actually matters is your payroll cutoff, the last day an election change can be processed in time for a given paycheck. Pick the paycheck you want changes to land in, find the cutoff for that pay period, and send the message at least one full payroll cycle before it, so an employee who wants to raise their contribution has time to make the change before the cutoff.
  • Open enrollment: the largest action window of the year. It is not a separate project. Put it on the same calendar and schedule everything else around it.

Awareness months fill gaps. They do not set the schedule. Build the calendar from action windows first, and if a month ends up with nothing in it, an awareness month is a fine way to fill it: February is American Heart Month, so heart content can take an open February. What an awareness month should never do is push out a message with a real deadline behind it.

How Do You Build It?

  1. Write out the twelve months of your plan year. A spreadsheet is fine. Then add two dates: when open enrollment runs, and when your deductible starts over, which for most plans is the first day of the plan year. Every other message gets scheduled around those two.
  2. Put each benefit in its month. The section above already gives you the send windows for the common ones: preventive care after the deductible starts over, the FSA reminder in early fall, and so on. Then add anything your plan offers that is not on that list, like a voluntary benefit or a wellness stipend, and ask the same question about it: when can an employee still act on this, and when is it too late? The answer is its month.
  3. Assign one benefit per message. A message covering five benefits gives the employee a list to think about. A message covering one gives them a single thing to do. A newsletter that mentions the FSA deadline, telehealth, the EAP, and open enrollment all at once gets skimmed and closed. An email that says check your FSA balance by Friday, with the link to check it, gets acted on.
  4. Pick the channel per message. Email reaches employees at a desk. Text reaches employees who are not at one. A home mailer reaches the whole household, not just the employee. And some employees never read any of it: they ask their manager. For them, give managers a short written answer sheet, the deadline, what to do, where to go, so the answer employees get is the right one.
  5. Name an owner for every message. Who writes it, who approves it, who sends it. A message with no name attached is the one that quietly does not happen.
  6. Review after enrollment closes. Look at what employees asked HR about most during the year. Every repeated question is a benefit that was not explained well enough, and that benefit belongs on next year’s calendar.

One check before the first send: your HR system, payroll, and carrier records have to agree on who is enrolled in what, because that is where every send list comes from. Mismatches between those systems are one of the five gaps that quietly create HR problems, and a calendar built on bad records sends the FSA reminder to people who do not have an FSA.

How Often Should You Communicate Benefits?

Send roughly one message a month outside enrollment, more during the enrollment window, plus required disclosures as they come due. That is more than most employers send, and it works because each message is short and covers one thing.

If you do not have the staff for that, run four messages a year, one per quarter, on the four benefits employees ask about most. A small calendar you keep up all year beats a twelve-month plan that stalls in March. Your broker should be able to supply most of the content, which is one of the things worth checking when you evaluate a benefits consultant.

Before You Plan Next Year’s Communications

Put your plan year on one page and mark the two dates that set everything else: your enrollment window and your deductible reset. Then go benefit by benefit and ask when an employee could still act on it, and when it becomes too late to matter. Answer that for each benefit and you have the calendar.

If you want the writing already done, our Benefits Communication Kit has nine ready-to-send email templates, one per benefit, each timed to the window when the employee can still act. Fill in your plan’s details and send.

If you would like to go over it with someone, you can schedule a brief review here or give us a call at (206) 625-1800.

Plan Sponsor FAQs

One named person, usually the HR manager responsible for benefits. Shared ownership between HR and internal communications tends to mean neither maintains it. Your broker or consultant can build it with you and supply content, but the person deciding what goes out should work for the company.

Shift the whole sequence. The anchor is your enrollment window and your deductible reset, not the calendar year. A plan year starting in July puts the preventive care message in July or August.

No. The calendar surrounds it. Enrollment communication stays as it is, and the other eleven months get covered too.

Sources

  • 45 CFR § 147.130 — Coverage of preventive health services (no cost sharing on non-grandfathered plans)
  • 26 CFR § 1.125-4 — Permitted election changes (mid-year changes after a change in status; plan document governs)
  • 29 CFR § 2520.104b-2 — Summary plan description (90-day delivery deadline)
  • 45 CFR § 147.200 — Summary of benefits and coverage (delivery timing at renewal and enrollment)
  • Important Disclosures

    First Hill Trust Company is a Washington State-chartered trust company. Investment advisory services are provided by BAC Capital Advisors, an SEC-registered investment adviser and a wholly owned subsidiary of First Hill Trust Company. Registration does not imply a certain level of skill or training. This article is educational. Neither First Hill Trust Company nor BAC Capital Advisors is acting as ERISA counsel or tax counsel to any plan or plan sponsor, and nothing here replaces advice from qualified counsel about your own plan.

    Accuracy and currency of information. The statutory provisions and regulatory descriptions in this article were verified against the cited primary sources as of the date of publication. Regulations and guidance change. Readers should confirm current requirements with qualified counsel.

    Educational purpose only. Provided by First Hill Trust Company for general informational and educational purposes only. It is not legal, tax, accounting, investment, or fiduciary advice, does not constitute a recommendation regarding any plan, investment, strategy, or course of action, and does not consider any recipient’s specific circumstances. Consult your own qualified advisors before acting.

    No offer, agreement, or commitment. Nothing in this material constitutes an offer, solicitation, agreement, or commitment to provide any particular service or to assume any particular responsibility. Descriptions of what a trustee, administrator, adviser, committee, employer, or other party “may” or “can” do are illustrative of how such arrangements commonly work and do not describe the terms of any specific engagement. The actual services provided, the allocation of responsibilities, the scope of any delegation, and the duties of any party are governed solely by the applicable plan documents, trust agreement, advisory agreement, and written service agreements. In the event of any inconsistency, those documents control.

    Services and regulatory status. First Hill Trust Company and its affiliates offer retirement plan services, recordkeeping and administrative services, trust and fiduciary services, investment advisory services, and group benefits services, in each case subject to applicable regulatory requirements and the terms of the relevant agreements. Not all services are offered to all clients, in all states, or in all circumstances. Investment advisory services are offered through an affiliated investment adviser; a copy of its Form ADV Part 2A is available upon request. Insurance and group benefits products are offered through appropriately licensed entities. The availability and scope of any service depend on eligibility and the applicable agreements.

    Fiduciary status under ERISA. Fiduciary status under the Employee Retirement Income Security Act of 1974, as amended (“ERISA”), is determined based on the functions performed and the authority exercised, not on titles or labels. Whether any particular party is acting as a fiduciary, and the scope of any related duties or potential liability, depends on the facts and circumstances specific to the plan and the relationship. Engaging a trustee, adviser, or other service provider does not eliminate a plan sponsor’s or committee’s own fiduciary responsibilities, including the duties to prudently select and monitor any party to whom responsibilities are delegated.

    Affiliated entities and conflicts of interest. First Hill Trust Company is affiliated with other entities, including an affiliated investment adviser and entities providing administrative, trust, or other services. These relationships may create conflicts of interest, including where an affiliate is engaged or compensated in connection with a plan. Such conflicts and compensation are described in the applicable service agreements and the affiliated adviser’s Form ADV Part 2A; fiduciaries should consider them when evaluating any engagement.

    Statutory and regulatory references. References to ERISA, the Internal Revenue Code, and related statutory or regulatory provisions are general summaries only. They are not a substitute for review of the actual statutory text, regulations, or guidance from the Department of Labor, Internal Revenue Service, or other relevant authorities, and they do not address how those provisions may apply to any particular plan, sponsor, fiduciary, or individual. Laws, regulations, and guidance are subject to change and to interpretation by the relevant agencies and courts. Examples, categories, and situations described are simplified for illustration and may not reflect the requirements or circumstances of any particular plan or person.

    No guarantee of results; investment risk. References to governance, fiduciary practices, risk reduction, or outcomes describe common industry approaches and potential benefits, not promises or guarantees of any result, of compliance, or of protection from liability, loss, or claims. All investing involves risk, including possible loss of principal; diversification does not ensure a profit or protect against loss. Past performance does not guarantee future results.
    For more information, contact First Hill Trust Company at (206) 625-1800.

    Related Articles

    Trees amongst fog.