How to Plan Your 2027 Employee Wellbeing Strategy & Calendar
If you’re starting to plan your 2027 employee wellbeing calendar, you may be starting with questions like: What should we focus on each month? Which wellbeing topics should we cover? When should we schedule workshops, challenges, or benefits campaigns?
These questions are useful, but they might not actually be the best place to start.
A strong employee wellbeing strategy is more than a calendar of activities. It’s a plan for how your organization will support employee wellbeing throughout the year, connect employees to the resources you already offer, and use wellbeing to support larger workforce priorities like engagement, retention, healthcare costs, manager effectiveness, and employee experience.
Your annual wellbeing calendar is one part of that strategy, not the strategy itself.
So whether you’re building a workplace wellbeing program from scratch or trying to bring more structure to an existing one, here’s what should go into your 2027 employee wellbeing plan.
What Is an Employee Wellbeing Strategy?
An employee wellbeing strategy is the framework that guides how your organization supports employee health, wellbeing, and day-to-day work experience in ways that also contribute to business and workforce outcomes.
Your strategy should answer a few key questions:
What are our business goals for the year?
Which employee needs and workforce priorities matter most when it comes to achieving those goals?
What resources and programs do we already have?
Where are the biggest gaps or opportunities?
What will we actually do throughout the year?
Who will manage and champion each element of the strategy?
How will employees hear about and engage with it?
How will we know if it’s working?
Instead of treating wellbeing as something that exists separately from the rest of the organization, start by asking what your business needs from its workforce and where wellbeing can realistically make an impact.
That might mean improving retention, increasing employee engagement, supporting managers, helping employees better navigate benefits, or reducing some of the productivity and cost pressures associated with poor employee wellbeing.
At On the Goga, our wellbeing expats often work backward from four questions: What does the organization need to accomplish? What needs to be true of the workforce to support that? Where can wellbeing influence those outcomes? And what should be measured over time?
1. Align Your 2027 Wellbeing Strategy With Business Goals
Before you choose a wellbeing theme for January, start with your organization’s priorities for 2027.
What is the business trying to accomplish?
Maybe your organization is:
Growing quickly
Trying to reduce turnover
Managing rising healthcare costs
Navigating organizational change
Focused on employee engagement
Investing in manager development
Trying to improve the employee experience
Supporting a distributed or frontline workforce
Then ask:
What needs to be true of employees for the organization to succeed?
For example, if retention is a major priority, your wellbeing strategy might focus on manager support, belonging, employee experience, and access to resources.
If healthcare costs are rising, the opportunity might be to help employees better understand and use benefits the organization already pays for while supporting healthier workplace conditions over time.
If engagement is low, the problem may not be a lack of programs. It may be that employees don’t see those resources as relevant, accessible, or connected to their day-to-day experience.
This gives your wellbeing strategy a reason to exist beyond “we want to offer wellness programming.”
2. Audit Your Existing Employee Wellbeing Programs and Benefits
Most organizations already have more wellbeing resources than they think.
Your benefits team may manage:
An EAP
Mental health support
Financial wellbeing tools
Caregiving benefits
Preventive health resources
Fitness or wellness platforms
Family-building benefits
Health coaching
Leave programs
Other teams may also be supporting wellbeing without necessarily calling it “wellbeing.” For example, Learning and Development may offer manager training. Employee Resource Groups may run events related to belonging, identity, caregiving, or community. Internal Communications may already have annual campaigns. HR may have initiatives related to engagement, culture, recognition, or employee experience.
So before adding anything new in 2027, take inventory of what already exists. Then ask three questions:
What should we keep?
Which resources or programs are working, strategically important, or already well established?
What is underused?
What are you already paying for that employees may not fully understand, know about, or use?
What is actually missing?
Only after reviewing the first two should you decide where new investment is necessary.
Reviewing existing benefits, vendors, communications, survey data, employee feedback, and other materials is a core part of our Wellbeing Pulse process because it helps surface where resources are working, where they may be underused, and where communication or access is breaking down.
3. Choose a Few Strategic Wellbeing Priorities for 2027
A common mistake in annual wellbeing planning is to mistake a wellbeing theme for a wellbeing priority. Themes, like "February is Heart Health” or “May is Mental Health,” are important for content organization, but they’re not going to help you achieve your business priorities for the year. What you really need, are a few simple employee wellbeing priorities that align to your business goals.
For example:
Priority 1: Make wellbeing resources easier to find and use.
Priority 2: Strengthen manager support for employee wellbeing.
Priority 3: Help employees build sustainable wellbeing habits.
Now your monthly themes have a purpose. Your February newsletter on heart health can support Priority 1 by pointing employees to your gym reimbursement membership. A manager toolkit during Mental Health Awareness Month can support Priority 2. The monthly calendar becomes the activation plan for your strategy rather than the strategy itself.
4. Understand What Different Employee Groups Need
Your workforce probably doesn’t experience wellbeing, or work, in one uniform way. A corporate employee working remotely can click an email and join a lunchtime webinar. A retail employee may never see that email. A manager may need tools to support employees rather than another employee-facing program. As you build your 2027 wellbeing roadmap, define the major employee audiences you need to reach.
That may include:
Corporate employees
Frontline or deskless employees
Remote and hybrid employees
People managers
Different shifts or locations
International employee populations
Employees with different access to technology
Employees at different stages of life
You don’t necessarily need a different wellbeing strategy for every population. What’s important is to have a shared strategy that can be activated differently depending on how employees actually work.
5. Build Your 2027 Employee Wellbeing Calendar
Once you know your goals, priorities, audiences, and existing resources, you can start building the calendar. Year-round visibility is one of the hallmarks of a connected wellbeing strategy, and a calendar can help accomplish that.
A practical 2027 wellbeing calendar might include:
Monthly or quarterly wellbeing themes
Regular employee communications
Live or on-demand workshops
Wellbeing challenges or campaigns
Strategic promotion of existing benefits
Manager resources
Seasonal wellbeing moments
Signature wellbeing events
Employee listening or feedback moments
Major internal wellbeing projects
Instead of simply asking, “What wellness activity should we do each month?” Look back at your priorities, and ask: What are we focused on, and how can that show up throughout the year?
Not everything has to happen every month, and not every month needs a brand-new campaign. The goal is to create enough consistency that wellbeing stays visible throughout the year without overwhelming employees or your HR team.
6. Connect Wellbeing Programming to Existing Benefits
This is one of the easiest ways to make an employee wellbeing program more valuable. Imagine you host a workshop on stress management. Employees attend. They like it. They leave with a few practical tools. Great! But what happens next?
If your organization already offers therapy, coaching, an EAP, mindfulness resources, caregiver support, or another related benefit, your workshop can become an entry point into those resources.
The same approach can work across your wellbeing calendar. A financial wellbeing campaign can point employees toward your financial coaching benefit. A sleep workshop can connect back to behavioral health or preventive care resources. A manager training can reinforce mental health, leave, or employee support resources. A caregiving campaign can surface benefits employees may not realize they have.
Instead of asking employees to engage with one more disconnected thing, use wellbeing programming to make the broader benefits ecosystem easier to understand and use. For organizations with a large number of existing vendors or benefits, this can be more valuable than simply adding another resource.
At On the Goga, we sync our clients' benefits into their wellbeing hub, so employees can access everything in one palace, aligned to their calendar.
7. Build Communications Into Your Wellbeing Plan
Employee wellbeing programs don’t work if employees don’t know they exist. That sounds obvious, but communication is often treated as something that happens after the strategy is built. It should be part of the strategy itself. For every major initiative, consider:
Audience: Who needs to know about this?
Message: Why should they care?
Channel: Where will they actually see it?
Timing: When does promotion need to begin?
Call to action: What do you want employees to do?
Follow-up: How will you remind or re-engage them?
Your communications plan may also need to vary by workforce. Corporate employees may respond well to email, Slack, Teams, or an intranet, where frontline employees may be better reached through manager cascades, breakroom signage, SMS, QR codes, an employee app, or shift-based communication.
A complete 12-month wellbeing roadmap should account for those audience and communication differences. Our roadmap process includes guidance on channels, timing, message types, and ways to make existing resources easier to find, understand, and use.
8. Include the Bigger Projects Behind Your Employee Wellbeing Program
Your 2027 wellbeing roadmap shouldn’t only include employee-facing programming. Some of the most important work may happen behind the scenes. Your annual roadmap might include projects like:
Creating a central wellbeing resource hub
Improving benefits navigation
Establishing a cross-functional wellbeing committee
Creating a manager wellbeing toolkit
Developing workforce-specific communication plans
Consolidating overlapping vendors
Improving wellbeing measurement
Conducting employee listening sessions
Establishing clearer ownership and governance
Building a shared annual wellbeing calendar across teams
These projects may not produce the same immediate engagement numbers as a workshop or challenge, but they are often the projects that help most to achieve your wellbeing priorities and business goals.
9. Define Ownership and Be Realistic About Capacity
This is where many wellbeing strategies break down. The ideas are good, the calendar looks great, and then nobody has the time to execute it.
For each major initiative in your 2027 plan, decide:
Who owns it?
Who needs to support it?
What needs to happen first?
What resources are required?
Are there dependencies?
What could prevent it from happening?
Does your internal team realistically have the capacity to execute it?
A roadmap should reflect the organization you actually have. If your internal capacity is limited, that doesn’t mean your strategy needs to be small. It means you need to make clear decisions about what your team owns, what vendors own, what managers help activate, and what simply doesn’t make the cut this year. Need a partner, or an extra set of hands? We can help.
10. Decide How You’ll Measure Employee Wellbeing
Finally, decide how you’ll know whether your 2027 wellbeing strategy is working. That doesn’t mean every initiative has to tie directly to healthcare savings. Different goals require different measures. Depending on your priorities, you might track:
Program participation
Monthly active engagement
Workshop registrations and attendance
Benefit or resource utilization
Communication reach
Click-through rates
Employee awareness of available resources
Manager participation
Employee feedback
Wellbeing sentiment
Engagement trends
Retention indicators
Absence or productivity signals
Progress against key implementation projects
Your measures should follow your strategy. If your goal is increasing resource awareness, measure awareness and utilization. If your priority is manager capability, look at manager participation, adoption, and employee experience. If your goal is creating a more connected wellbeing ecosystem, track whether resources are becoming easier to find, more consistently communicated, and better used.
A strong roadmap defines success before implementation begins. Depending on the strategy, that may include participation, engagement, utilization, employee feedback, manager adoption, communication reach, sentiment, and other indicators tied to organizational goals.
What Should a 12-Month Employee Wellbeing Roadmap Include?
By the time your 2027 wellbeing roadmap is complete, you should have:
Clear business and workforce goals
An understanding of employee wellbeing needs
An audit of current benefits, vendors, and programs
A small number of strategic wellbeing priorities
Defined employee audiences
A 12-month employee wellbeing calendar
Planned workshops, campaigns, communications, and key activities
A strategy for promoting existing benefits and resources
Major infrastructure or strategy projects
Clear owners and responsibilities
Implementation considerations and dependencies
Measures of success
A full roadmap brings those pieces together into a month-by-month plan showing what to focus on, when to focus on it, who it’s for, how it connects to existing resources, and what it will take to execute.
Your 2027 Employee Wellbeing Strategy Should Answer One Big Question
Ultimately, your roadmap should make it easy to answer: What are we trying to improve, what are we going to do about it, and how will employees experience that strategy throughout 2027?
When that answer is clear, building your annual wellbeing calendar becomes much easier. You know which programs belong, and which ones don’t. You know which benefits need more promotion, and where different employee groups need a different approach. And instead of looking for another wellness idea every month, your team can spend the year executing against a plan, and driving meaningful results.
Need Help Building Your 2027 Employee Wellbeing Strategy?
On the Goga helps organizations turn scattered benefits, programs, employee needs, and communications into a practical employee wellbeing strategy.
For teams that need a starting point, our Wellbeing Pulse helps assess the current wellbeing landscape, identify strengths and gaps, and prioritize what to focus on next.
For organizations ready for a more complete plan, our Wellbeing Roadmap turns that discovery into a practical 12-month strategy with priorities, a month-by-month implementation timeline, employee audiences, communications, resource integration, implementation guidance, and measures of success.
Planning your 2027 employee wellbeing strategy? Talk to On the Goga about building a roadmap your team can actually use.
