7 Questions Every Organization Should Ask Before Planning 2027 Wellness Strategies

7-minute read

A full wellness calendar doesn’t mean your organization has a wellness strategy.

As you begin mapping out 2027, it’s tempting to cram your organization’s calendar full of challenges, campaigns, and wellness activities. Instead, take a step back and consider what your employees would find most valuable.

You don’t need a new activity every single week to keep wellness participation going strong. A few well-designed experiences will give your employees something to look forward to while allowing your team to focus on execution and building momentum.

You can start by using these 7 questions to outline a wellness strategy that benefits your people and your organization.

1. Are We Building a Strategy or Just Selecting Activities?

You don’t have to do it all. Walking challenges, yoga classes, and nutrition campaigns, all support employee wellbeing. The key is connecting them to a larger purpose.

Start by choosing 2-3 priorities. Maybe you want to encourage movement or support emotional wellbeing. Great. Focus on that and then connect each activity to a specific goal.

For example, a workplace walking challenge encourages movement while giving coworkers a reason to spend time together. Plan a mix of additional activities throughout the year (like a spring seasonal challenge or short educational sessions) with time between major initiatives so your team can review results and prepare for what’s next.

Wellness doesn’t need to run at full speed every week to remain relevant.

2. What Specific Problem Are We Trying to Solve?

Your wellness strategy should reflect your organization’s goals and your employees’ needs. Start with the information you already have.

Review surveys, program feedback, participation trends, and benefits utilization. These sources will reveal what employees value and where additional support is needed.

One person might enjoy wellness challenges but want more opportunities to participate with coworkers. Another employee might request practical resources to manage stress and improve wellbeing.

Use these insights to set clear priorities and be specific about what you want to accomplish. “Making wellness more accessible to frontline employees” details a clear direction. After that, you can explore scheduling, communication, and formats that fit employee workdays.

Participation data shows what’s happening. But the employee feedback tells you why it matters.

3. What Are Employees Telling Us They Need?

Some of the best wellness ideas start with a simple question: What would make your workday better?

One employee enjoys friendly competition, while another prefers a walk with a coworker. Someone else appreciates practical ideas for taking a mental break.

Ask your employees what interests them before you finalize any plans. Make sure to include employees who rarely or never participate. Their feedback will reveal new ways to make wellness more welcoming.

Look for common themes rather than trying to accommodate every single request. If employees want more connection, consider walking groups or team challenges. If they want flexibility, offer activities they can complete on their own time.

Close the feedback loop by sharing what you learned and how their suggestions will shape the program. Employees are more likely to keep sharing ideas when they see their input is put to use.

Related: How to Engage Employees Who Never Participate in Your Wellness Programs

4. Are Our Programs Accessible Across All Locations, Shifts, and Work Environments?

Wellness should fit into employees’ lives, not require them to rearrange everything to make it work.

Office employees may have time for a lunchtime activity, but many frontline employees need options that fit into breaks. Remote employees might appreciate virtual activities, and shift workers need more flexible windows.

Accessibility also means offering different ways to participate, whether that’s a competitive leaderboard or a casual experience minus rankings and performance goals. Make room for both.

Walking is one flexible option. Employees can join a group walk, take a short movement break on their own, or participate in a step challenge at their own pace. Everyone shares the same goal while choosing how they participate.

Clear instructions, convenient schedules, and options for different abilities and interests make activities easier for everyone to join.

5. How Does Financial Wellbeing Fit Into Our Strategy?

Financial wellbeing is an important part of the wellbeing experience. Start by reviewing the financial resources your organization already offers. These might include retirement education, budgeting tools, financial counseling, or guidance on managing debt.

Then ask whether employees know about these resources and find them easy to use.

A benefit doesn’t have to be new to be valuable. Clearer explanations, timely reminders, and easier access help employees make better use of existing resources.

Ask employees if there are any financial topics they’d like to understand better. Keep these resources confidential and easy to access. Employees should be able to explore their options without feeling pressured to share personal details.

6. What Capacity and Resources Do We Realistically Have?

A wellness strategy should energize your team, too. Planning activities, coordinating communications, tracking participation, and managing vendors take time. Assess your team’s capacity before committing to a full calendar.

Review your budget, staff time, and existing tools. Identify tasks you can simplify or share with other departments, then prioritize the activities that best support your goals.

You don’t need something new every month to keep wellness engaging. A seasonal walking challenge paired with a few focused campaigns creates variety without overloading your calendar. Build in time to gather feedback, celebrate successes, and prepare for new initiatives. That way your team will be better equipped to deliver each activity.

7. How Will We Measure and Evaluate Success?

Success looks different for every wellness program. Choose specific goals and data that reflect what you want employees to gain from each experience.

Decide what to measure before launching an initiative. If your goal is to encourage movement, track participation in fitness activities. If you want to strengthen social connections, ask employees if they enjoyed spending time with coworkers. If you want to reach more of your workforce, review participation across locations, functions, or departments – however your workplace is organized.

Be sure to include both participation and employee experience. Attendance shows how many people joined, but a short survey and a few informal conversations reveal what people enjoyed and what they’d change.

Participation inevitably varies throughout the year. Some employees join multiple activities, others prefer a particular challenge or season. Offer opportunities that allow everyone to return when an activity interests them.

Related: How to Create a Wellness Challenge Employees Look Forward To

Make 2027 a Year of Meaningful Wellness Experiences

A successful wellness strategy starts with clear priorities, detailed employee feedback, and a plan your team is excited to deliver.

Wellness doesn’t require a never-ending stream of challenges and campaigns. Thoughtfully timing activities will give employees something to look forward to and anticipate what will come next time.

Ultimately, the best wellness strategy is one employees want to be part of and your team can sustain.

Ready to Plan Your 2027 Wellness Strategy?

HES helps organizations of all sizes create wellness experiences that encourage healthy habits and bring people together. From walking challenges to programs that support connection and participation, HES will help you build a strategy that fits your workforce and your goals.

Connect with HES to discuss how to make your wellness programs more engaging, inclusive, and successful.

Frequently Asked Questions About Wellness Strategies

What should a workplace wellness strategy include?

An effective strategy includes clear goals, employee feedback, accessible activities, realistic resource planning, and ways to measure success. It should connect specific initiatives to broader wellbeing priorities while still giving employees flexible ways to participate.

How can organizations improve workplace wellness participation?

Start by asking employees what interests them and what makes participation difficult. Offer activities that fit different work schedules, environments, abilities, and interests. Walking challenges, team activities, and flexible individual options are meaningful ways to get more people involved.

How often should organizations offer wellness activities?

There is no single schedule that works for every organization. Rather than filling your calendar with new activities every week, consider implementing a few well-designed initiatives throughout the year. Pausing between major activities gives employees a chance to recharge and wellness teams time to evaluate results.

How can organizations prevent wellness burnout?

Keep activities manageable, offer variety, and avoid overwhelming employees with constant campaigns and communications. Employees will participate when an activity interests them, and use that feedback to shape future offerings. A sustainable approach supports long-term engagement without requiring year-round participation.

How can organizations measure wellness strategy success?

Choose data points that align with each initiative’s goals. Track participation, review engagement across locations and employee groups, and gather employee experience feedback. Regularly review these findings to help wellness teams identify what works, improve future activities, and use resources effectively.