Skip to the main content.

49 min read

The Future of Work: Flexible Benefits, Remote Policies, & Retention

The Future of Work: Flexible Benefits, Remote Policies, & Retention

On March 6, 2025, we hosted a webinar, "The Future of Work: Flexible Benefits, Remote Policies, and Retention in 2025," featuring HR expert Dan Evanoff. This conversation explored how small businesses can remain competitive by adapting to workplace changes. This article captures the core insights from that session, expands on the most impactful strategies small business owners can implement, and contains the recording and full transcript.

 

Watch the Webinar

🎥 Missed the live session? Watch the full webinar below!

 

 

Introduction

Small businesses are navigating a rapidly changing workplace. In the wake of the “Great Resignation,” the U.S. saw record-high voluntary turnover in 2022 – over 70% of all employee departures were by choice . At the same time, job openings hit all-time highs, meaning employees have more options than ever. For a business with fewer than 75 employees, losing even one key team member can be costly and disruptive. To stay competitive in 2025, small business owners must adapt to modern employee expectations. This means offering flexible benefits, embracing remote work policies, and doubling down on employee retention strategies. In this article, we’ll explore how these three areas can future-proof your small business workforce.

 

Flexible Benefits: Meeting Modern Employee Expectations

Today’s employees expect more than a paycheck – they want benefits and perks that support their lives and well-being. In fact, lack of flexibility and poor benefits are among the top reasons workers quit. A recent Pew survey found 45% of employees who left jobs in 2021 did so due to not having flexible schedules, and 43% cited inadequate benefits packages. Small businesses can compete with larger firms by tailoring a benefits package that addresses these needs without breaking the bank.

 

What Employees Want in 2025

Modern workers value benefits that provide flexibility, wellness, and personal growth. While health insurance and retirement plans remain important, other offerings can be just as impactful:

 

Wellness programs and mental health support

Services like employee assistance programs, gym membership reimbursements, or meditation apps show employees you care about their well-being. Nearly 80% of employers now offer wellness benefits of some kind.

Flexible work arrangements

The option to work remotely or adjust one’s hours is increasingly seen as a “benefit.” This perk directly boosts work-life balance and is highly valued by younger generations. For example, 76% of Gen Z and 74% of Millennials rate flexible schedules as very important, compared to 63% of Boomers.

Continuous learning opportunities

Offering stipends for courses, tuition assistance, or time for professional development helps employees grow. This not only improves their skills but also increases loyalty.

Personalized perks

Small businesses can be creative – think paid time off for volunteering, pet-friendly workplaces, or “birthday day off” policies. These low-cost perks can set you apart as a caring employer.

 

Cost-Effective Benefit Options for Small Businesses

You don’t need a Google-sized budget to offer great benefits. Focus on high-impact, low-cost options. For instance, if providing a full health insurance plan is too expensive, consider a Health Reimbursement Arrangement (HRA). A Qualified Small Employer HRA (QSEHRA) allows businesses with <50 full-time employees to reimburse employees tax-free for health insurance premiums, letting each employee choose a plan that fits their needs . This gives workers health coverage flexibility without the company paying for a one-size-fits-all group plan.

Other affordable benefits include generous paid time off policies (you control the amount), flexible schedules (which cost nothing but trust), and employee recognition programs (like monthly awards or public kudos). Even remote work itself is a cost-saving benefit – employees save time and money on commuting, and you may save on office costs.

 

Legal Considerations

When designing benefits, keep compliance in mind.

Healthcare Laws

Under the Affordable Care Act, companies with fewer than 50 full-time equivalents aren’t required to offer health insurance, but if you do, it must meet certain coverage standards. If you use HRAs or stipends, ensure they’re set up properly so that reimbursements remain tax-free and in line with IRS rules.

Employment Laws

Be mindful of federal and state regulations on benefits. For example, some states require even small employers to provide paid sick leave or family leave. If you offer a 401(k) or retirement plan, follow nondiscrimination rules so that benefits are offered fairly to all eligible employees

 

Also, maintain clear distinctions between employees and independent contractors – offering an employee benefit to a contractor could blur classification lines and lead to legal trouble. When in doubt, consult a human resources expert or labor attorney to review your benefits plan. With a bit of planning, small businesses can provide flexible, compliant benefits that make employees feel valued.

 

Embracing Hybrid and Remote Work 

The shift to remote and hybrid work is one of the biggest workplace transformations of recent years – and it’s here to stay. Flexible work arrangements went from a nice-to-have to an expectation: 80% of companies now allow employees to work from home at least part of the time, and many small businesses have gone fully remote. To remain competitive as a small employer, it’s crucial to have clear remote work policies that leverage the benefits of remote work while avoiding potential pitfalls.

Nearly half of employees who can work from home say they’d be unlikely to stay at a job that eliminates remote options. In Pew Research Center’s October 2024 survey, 46% of workers who work from home at least sometimes indicated they would be “very or somewhat unlikely” to stay if their employer no longer allowed remote work . Younger workers and those who currently work fully remotely were especially likely to say they’d quit  This underscores how vital remote flexibility has become for retention.

 

The Case for Hybrid and Remote Work

Does remote work actually work? Research and recent experience say yes. Multiple studies have found that allowing remote or hybrid schedules does not hurt productivity. For example, a 2024 study reported in Harvard Business Review showed “no measurable difference” in productivity between hybrid workers and fully in-office workers . In fact, the hybrid group had higher job satisfaction and lower quit rates than their office-only counterparts . From a business perspective, remote work can even improve the bottom line – one analysis found companies with flexible work arrangements (like part-time remote schedules) are 21% more profitable on average than those that are fully in-person. The reasons are clear: remote work can reduce overhead costs, expand your talent pool beyond your local area, and keep employees happier.

Employee demand for remote work is high. We’ve already seen that nearly half of employees might leave if remote work is taken away. Other surveys echo this: about 57% of workers say they’d look for a new job if they cannot work remotely or on a hybrid schedule. Particularly in tech and professional fields, talented people often prioritize flexibility over other benefits. For a small business, offering remote work can be a competitive advantage to attract skilled employees who might not consider you if you required 100% on-site attendance. It’s also a retention booster – employees with remote options tend to report higher loyalty. The key is to implement remote work effectively through smart policies.

 

Best Practices for Managing a Remote Team

Running a remote or hybrid team requires a proactive management approach. Here are some proven best practices for small businesses:

  • Set clear expectations and goals: Outline working hours or response times (if you need specific availability), productivity metrics, and project deadlines in your remote work policy. Managing by outcomes rather than hours is often effective – define what success looks like for a role and give employees autonomy in how they get there. This clarity prevents confusion and keeps everyone accountable.

  • Leverage technology for communication and collaboration: Equip your team with the right tools – video conferencing (Zoom, Teams), instant messaging (Slack, Microsoft Teams), and project management software (Trello, Asana, etc.) can recreate much of the in-office coordination. Make sure everyone is trained on these tools. Also, encourage the use of shared documents or cloud platforms so that information flows freely.

 
Protip

Over-communicate at first. In a remote setting, it’s better to clarify a task or follow up on a project status explicitly than to assume silently.

 

 

  • Maintain regular check-ins (but avoid micromanagement): Schedule routine team meetings (weekly or biweekly) and one-on-one check-ins between managers and employees. Regular video calls can keep people aligned and provide a forum to raise concerns. However, trust is critical – avoid the temptation to monitor every minute of your remote workers’ day. Focus on results. Many successful remote teams use a daily stand-up or an end-of-day report with key accomplishments and next-day plans, instead of constant supervision.

  • Foster team cohesion and culture remotely: Intentionally create opportunities for social interaction and team bonding. This could be a virtual coffee break, a fun Slack channel for non-work chatter, or occasional in-person meetups (quarterly team lunches or an annual retreat if feasible). Pair new hires with a “buddy” or mentor to help them integrate. Celebrating birthdays, milestones, or company successes via video call can also remind everyone that they’re part of a team, not just isolated individuals.

  • Provide the right equipment and ergonomic support: A remote employee’s home office is their workspace – make sure it’s set up for success. Over 56% of employers now offer subsidies for at-home work equipment, with an average reimbursement around $871 in 2024. A small business can offer a one-time stipend for a good chair, monitor, or help cover internet costs. This investment pays off in productivity and shows employees you care about their comfort and ability to work effectively.

  • Encourage work-life balance and model it: One risk of remote work is burnout – when home is the office, some employees struggle to unplug. Encourage your team to take regular breaks, stick to reasonable hours, and actually use their vacation days. As an owner, lead by example: avoid sending late-night emails and take time off yourself. Simple practices like setting “no meeting Fridays” or establishing that no one is expected to reply to messages after, say, 6 PM can help set healthy boundaries. By preventing burnout, you’ll have a more engaged and loyal team (and you’ll avoid the costly turnover that comes with overworked employees).

 

Pitfalls to Avoid (and How to Avoid Them)

Even with a good plan, remote work has its challenges. Here are common pitfalls small businesses face with hybrid or remote teams – and ways to mitigate them:

  • Isolation and communication breakdowns: Without water-cooler chats, remote workers can feel disconnected or misinterpret instructions. Combat this by keeping communication channels open. Encourage team members to pick up the phone or start a quick video chat to resolve issues that email or text can’t fully convey. As mentioned, regular video meetings can put faces to names and maintain human connection. Also consider implementing an “open virtual door” hour where a manager is available on call for anyone who needs to talk.

  • Proximity bias and inequality: In a hybrid setting, employees who come on-site more often might get more visibility, which can unconsciously lead to favoritism. To avoid this, establish equal opportunities for remote staff: ensure important meetings always include video dial-in, and consider using collaboration tools where everyone (remote or not) participates on equal footing. Evaluate performance based on results and contributions, not who you physically see in the office most.

  • Unclear remote work boundaries: Sometimes remote employees work too much, logging on early and late and feeling unable to disconnect. As a leader, make it clear that you expect employees to have personal time. For example, if someone consistently sends late emails, talk to them about managing workload or adjusting deadlines. Some companies set “quiet hours” (e.g., no internal emails after dinner time) to reinforce downtime. By preventing overwork, you’ll maintain productivity long-term and improve retention.

  • Security and data privacy risks: Remote work introduces IT considerations. Employees might be using personal Wi-Fi networks or devices. It’s worth investing in basic security measures: require strong passwords (and maybe two-factor authentication) for work accounts, have a VPN for secure access to any sensitive company data, and educate your team on phishing and cybersecurity best practices. If you handle confidential client information, ensure your remote policy covers rules on device use and privacy.

  • Compliance issues with remote employees: A less obvious pitfall is legal compliance when your employees work in different states. U.S. labor laws (and tax rules) often depend on where the work is performed. As a rule of thumb, if an employee works more than 50% of the time in another state, that state is considered their work location for tax and employment purposes . For example, if your Colorado-based company has an employee suddenly working from California most of the time, you likely need to register in California and remit state taxes, and you must follow California labor laws for that worker. Different states have different overtime rules, break requirements, and termination pay laws. To avoid nasty surprises, require remote employees to get approval before changing their home-base location, and consult with a payroll provider or HR expert to handle multi-state compliance. Also, make sure non-exempt (hourly) remote workers are tracking their hours accurately – not logging hours could lead to unpaid overtime claims if they end up working extra. By staying ahead on compliance, you’ll dodge fines and protect your business as you expand your remote team.

By following these best practices and watching out for pitfalls, even a small business can reap the rewards of remote work: greater productivity, happier employees, and a wider talent pool – all while minimizing risks. Remote work is a powerful tool in 2025; use it to your advantage.

 

Employee Retention Strategies for 2025

Retaining great employees is always important, but in 2025 it’s absolutely critical. Turnover is costly in both time and money, and it’s especially painful for a small business where each team member wears many hats. In this section, we’ll examine the impact of turnover and outline strategies to build a strong company culture and keep your people for the long run.

 

The High Cost of Turnover (and Why Retention Matters)

Employee turnover has a very real effect on your bottom line. When someone leaves, you incur expenses to find and train a replacement, and you lose the departing employee’s knowledge and productivity in the meantime. Research shows that replacing an employee can cost anywhere from one-half to two times that employee’s annual salary . For example, Gallup estimates a 100-person company with an average salary of $50,000 could spend $660,000 to $2.6 million per year on turnover costs. Even at a smaller scale, the numbers are eye-opening: if you have 10 employees and one leaves, you might be paying 50–200% of their salary to cover recruiting, onboarding, and lost output.

Beyond direct costs, high turnover hurts morale and productivity. Remaining staff often have to pick up extra work, which can lead to burnout or resentment. It can also impact customer relationships or project momentum if a key contributor exits mid-stream . And in a tight labor market, you might struggle to refill the role quickly, leaving your team shorthanded for longer than you’d like. All of this explains why improving retention is one of the smartest investments a small business can make. As one Gallup analysis noted, much of turnover is preventable: 52% of employees who quit said their company could have done something to keep them . In other words, with the right strategies, you can avoid becoming part of the $1 trillion annual turnover problem in the U.S. and keep your business running smoothly.

 

Building a Strong Company Culture in a Flexible Work Environment

One of the best retention strategies is cultivating a company culture where people actually want to stay. Culture might feel intangible, but it shows up in everyday behaviors – how your team communicates, collaborates, and supports one another. In a world of remote and hybrid work, building culture takes conscious effort, but small businesses have the advantage of agility and personal touch.

Start by articulating your company’s values and mission, and weave them into daily life. If your values include things like “ownership” or “teamwork,” recognize and reward those behaviors publicly. Ensure leaders and managers exemplify the culture you want – for instance, if you promote work-life balance but the boss is emailing at midnight, the message gets lost. Small actions, like a weekly shout-out in the team meeting for someone who went above and beyond, reinforce a positive culture.

Communication is the backbone of culture, especially with remote staff. Create rituals that bring people together: a quick Monday huddle to set priorities, or a casual Friday virtual hangout to relax. Invite feedback and listen to your employees – maybe it’s an anonymous survey or an open forum in a meeting. Showing that you take employee input seriously builds trust (for example, if people express feeling isolated, you might implement a buddy system or more team video chats to address it). Transparency from leadership is also key: share updates on how the company is doing, acknowledge challenges, and celebrate wins as a team. When people feel “in the loop,” they feel more connected to the company’s direction and success.

Find ways to bond that include both in-office and remote workers. If some staff are on-site and others are remote, make sure events (even informal ones like a lunch) have a virtual option or rotate activities so remote folks aren’t always left out. Consider periodic all-hands gatherings if budget allows – even an annual meetup can solidify relationships. If in-person meetups aren’t possible, get creative with virtual team-building (there are online escape rooms, trivia games, and other activities that groups can do via Zoom). The goal is to create a sense of community. When employees form personal connections and friendships at work, they are far less likely to leave just for a slight pay bump elsewhere.

Lastly, lead with empathy and support. In a flexible work environment, employees may be juggling family, health, or other personal issues along with their job. A culture that recognizes employees as whole people – by offering flexibility when someone needs to pick up a child or by simply checking in on workload and stress levels – is a culture where people feel valued. This ties closely into benefits and policies we discussed, like flexible scheduling and mental health support. They all feed into a supportive culture. When employees feel genuinely cared for and see that their company is willing to adapt to help them thrive, they tend to stick around.

 

Innovative Retention Strategies for 2025

Beyond the basics, what innovative tactics can small businesses use to boost retention? Here are a few ideas to consider in 2025:

  • Conduct “stay interviews”: Don’t wait for an exit interview to find out why an employee was unhappy. Periodically (say twice a year) have one-on-one conversations focused on what’s going well and what might entice them to stay longer. Ask questions like, “What about your job is most motivating? What would you change if you could?” This proactive approach can uncover issues early. Given that over half of people who quit said no one talked to them about their job satisfaction in the months before they left, simply starting that dialogue can set you apart.

  • Provide clear (and creative) career pathways: A common reason employees leave is lack of advancement. Small companies often have flat org structures with few formal promotions available. Combat this by creating growth opportunities in other ways. You might offer leadership of a new project, title changes to reflect increased responsibilities, or chances to develop new skills (for example, pay for a certification course and then allow the employee to take on work in that new area). Even lateral moves can keep things fresh – rotating an employee through different roles or departments broadens their experience and keeps them engaged. The key is to show a future: help employees see how they can develop with your company without necessarily needing a higher position to move into.

  • Recognize and reward contributions frequently: Don’t underestimate the power of appreciation. Implement regular recognition programs – monthly awards, peer-nominated accolades, or shout-outs in the company chat. Some companies give small spot bonuses or gift cards when an employee goes above and beyond. You can also reward longevity with extra vacation days at work anniversaries or a sabbatical after a certain number of years. These gestures build loyalty. Employees who feel seen and appreciated for their work are much less likely to job-hop.

  • Invest in management training: It’s often said “employees don’t leave companies, they leave managers.” Make sure anyone who supervises others in your business has the tools to lead effectively and empathetically. Provide training on giving feedback, coaching, and communication. A great manager will inspire team members to stick around and grow with the company. If you’re the owner managing everyone, seek feedback on your own management style and be willing to adapt – that’s an innovation in itself!

  • Flexibility as a perk: We’ve discussed flexible hours and remote work, but consider doubling down on flexibility to boost retention. Some cutting-edge small businesses are piloting 4-day workweeks (while still paying a full salary) or allowing employees to choose their own work schedules entirely. Surprisingly, trials of a four-day week have shown productivity can remain equal or even improve, and employee stress drops significantly. Even if you can’t do four-day weeks, offering an occasional extra day off (e.g. “Wellness Friday” once a month) or Summer Friday half-days can be a compelling reason for employees to stay. These initiatives signal that you trust your team and care about their quality of life.

  • Link performance to shared success: Small businesses can foster loyalty by giving employees a stake in the company’s success. This could be as formal as an employee stock ownership or profit-sharing plan, or as simple as team-based bonuses when certain goals are met. When your employees feel ownership – financially or emotionally – they are more invested in the long term. For example, if you hit an annual revenue target, you might promise a paid weekend retreat for the whole team. These kinds of rewards tie everyone’s success together and create a “we’re in this together” atmosphere.

Remember, innovation in retention isn’t about gimmicks; it’s about understanding your team’s needs and preferences and thinking outside the box to meet them. What works for one company might not work for another, so solicit feedback from your employees on which perks or changes they’d value most. You might be surprised – sometimes, flexible start times or a small development budget for each employee can matter more than a big salary bump. In 2025, the companies that retain talent will be those that stay attentive and adaptable to their people’s lives.

 

Key Recommendations for 2025

Keeping your small business competitive in the future of work means being proactive about benefits, flexibility, and retention. Here are the key takeaways and recommendations to implement in 2025:

  • Embrace Flexibility: Wherever possible, offer remote or hybrid work options and flexible scheduling. This is no longer a luxury – it’s a priority for many employees, and companies with flexible work see strong productivity and retention benefits.

  • Offer Meaningful, Customized Benefits: Go beyond the basics. Poll your employees (formally or informally) to find out which benefits and perks matter most to them. Whether it’s a stipend for health insurance via a QSEHRA, more robust wellness support, or education assistance, invest in things your team truly values. Remember, inadequate benefits can push good people out the door, so make your benefits a selling point for staying.

  • Strengthen Company Culture (Even from Afar): Be deliberate in building an inclusive, positive culture. Communicate openly, recognize achievements, and create opportunities for team bonding. Ensure remote employees feel just as involved as those on-site. A strong culture will glue your team together through changes and challenges.

  • Develop Your People: Show employees a future with your business. Provide growth opportunities, continuous feedback, and training. Great talent craves development – if they don’t get it with you, they may seek it elsewhere. Even without a corporate ladder, find creative ways to reward ambition and build skills.

  • Listen and Adapt: Finally, make retention an ongoing effort. Conduct stay interviews or pulse surveys to gauge morale. Pay attention to warning signs of burnout or dissatisfaction and address them promptly. By staying responsive to your team’s needs, you can correct course before losing valuable employees. In short, make your company a place where people want to build their careers.

By focusing on flexible benefits, smart remote work policies, and innovative retention strategies, small businesses can thrive in the 2025 world of work. These efforts will not only keep your employees happy and engaged – they will also save you costs in turnover and boost your company’s performance. The future of work is here; with the practical steps outlined above, even a 20-person or 50-person business in the U.S. can create a competitive, resilient workplace that attracts and retains top talent. Here’s to building a small business where people love to work, and a team that will carry your success well into the future.

 


 

 

From Startup to Scale: Financial Lessons from Xero's Founder [Listen]

From Startup to Scale: Financial Lessons from Xero's Founder [Listen]

In a candid conversation about building and scaling a global SaaS company, Xero founder Rod Drury shared invaluable insights about his journey from a...

Read More
Understanding the Process of Human Resource Management

Understanding the Process of Human Resource Management

Let's talk about something that's often overlooked but incredibly important for your company’s success—human resource management (HRM). Whether...

Read More
HR Best Practices for Remote Workers in Small Businesses

1 min read

HR Best Practices for Remote Workers in Small Businesses

Are you a small business owner struggling to manage remote workers effectively? You’re not alone. The shift to remote work has introduced new HR...

Read More