Adapting Retention Strategies: How Businesses Are Addressing the Changing Needs of Their Workforce

At Legacy Online School, I’ve discovered that retention doesn’t mean just keeping people; it means keeping them engaged. One moment that made us reconsider how we were retaining people occurred when several team members shared that remote education created a feeling of “always on”. While this wasn’t the traditional burnout, it was the emotional burden of being so intimately involved with students’ lives without enough opportunity to reset.

So we quickly adjusted. First, we established Focus Weeks where we have no internal meetings and minimise Slack, just time to think and create. Second, we restructured professional development into small innovation pods where teams co-created solutions as a group rather than through passive professional development. Third, we established brief asynchronous audio touchpoints which are human, quick and natural in place of superficial status checking meetings.

The change was real. Engagement increased, but more than that, the energy of the group changed. People felt trusted, less overwhelmed, and more connected. Retention followed.

My belief is simple: retention shouldn’t be a defensive strategy. It should be a design choice. When you build an environment that respects how people actually work and feel, you don’t have to fight to keep talent—they choose to stay because the culture makes sense for who they are today, not who they were last year.

We completely changed our retention strategy to focus on structural equity rather than surface-level connections. We discovered that virtual happy hours and swag boxes were not retaining employees during the height of the remote work boom. Workers in different time zones preferred autonomy and benefit parity over forced socialization.

As the CEO of Wisemonk, working with international teams on a daily basis, I observed a distinct trend in which foreign hires felt inferior to headquarters employees. We made the decision to audit all of our benefits. We shifted our attention from “fun” to making sure an Indian developer had the same level of parental leave and health insurance as a San Francisco designer.

In particular, we dealt with a high-churn problem with a Southeast Asian team. Although they received good compensation, they were required to spend their evenings at meetings. We upgraded their local insurance to a premium tier and moved to a strictly asynchronous model. It had an instant effect. We haven’t lost a team member in that area since we made the change, and their stress levels have clearly decreased. Respect, not benefits, is the key to retention.

When two high performers left in the same quarter, it forced me to rethink what leadership actually looked like. This happened in one of my previous companies, where I believed that frequent check-ins and close tracking would help people feel supported.

Instead, it had the opposite effect. Conversations became about updates, not honesty. People stopped sharing what was really going wrong.

That experience changed how I approach retention. I rebuilt one-on-ones around problem solving, asking where people felt blocked instead of what they had finished.

The shift was small, but the impact was clear. Engagement returned, collaboration felt easier and the team began to trust leadership again. Retention followed naturally because people finally felt like the system worked for them, not against them.

We noticed our team needed more flexibility as workloads and personal commitments shifted, so we adapted our retention strategy around autonomy rather than perks. We introduced clearer project ownership and more control over how people structured their weeks, paired with shorter, more focused check-ins. This change gave individuals space to manage intense periods without feeling monitored. The outcome was higher engagement, fewer burnout signals, and stronger accountability across projects.

When scaling Jungle Revives from a founding team to a distributed workforce managing wildlife expeditions across multiple regions, I recognized that traditional retention strategies, competitive salaries and standard benefits, were insufficient for retaining passionate conservation-minded team members in a mission-driven organization.

The Challenge:

Initially, I applied IT agency retention models: competitive compensation, performance bonuses, and career progression paths. However, Jungle Revives team members, guides, naturalists, content creators, and logistics coordinators, had different motivations. They joined not primarily for salary but for alignment with conservation mission and meaningful wildlife engagement. Yet the operational demands of tourism logistics created burnout: guides working 15-hour days during peak season with minimal downtime, content teams producing constant material without creative autonomy, and administrative staff managing logistics without visibility into impact.

Specific Adaptations I Implemented:

1. Mission Visibility and Direct Conservation Impact:

I restructured communication to show how each role directly supported conservation.

2. Seasonal Flexibility and Extended Breaks:

Rather than year-round 40-hour weeks, I implemented seasonal contracts with extended recovery periods. Peak season (October-March) involved intensive 50-60-hour weeks, but April-September offered reduced hours, sabbatical options, or project-based work. Guides could shift to naturalist training, content creation, or conservation research during off-season, preventing burnout while building skills.

3. Wildlife Engagement as Compensation:

I formalized wildlife research participation time (20-30 hours monthly) as paid work, allowing team members to engage in birdwatching expeditions, habitat restoration, or wildlife monitoring alongside commercial tours.

4. Peer Learning and Expertise Development:

Created internal certification programs where guides developed specializations.

5. Community and Belonging:

Implemented monthly “Jungle Revives Collective” gatherings where team members shared wildlife observations, conservation challenges, and personal experiences.

Outcome:

Turnover dropped from 35% annually to 8% in year two. More importantly, retention quality improved: people staying longer and more engaged. Guide satisfaction increased substantially; they reported feeling like “conservation partners” rather than “service workers.”

At EVhype, we noticed retention challenges particularly affecting our customer service and technical teams. By analyzing exit interview and engagement survey data, we identified that career development opportunities and work-life balance were the primary concerns. We responded by implementing targeted career development programs, establishing mentoring relationships, and rebalancing workloads across these teams. These changes resulted in a 20% reduction in attrition for those groups.

During COVID, I realized our traditional retention playbook (raises, bonuses, career paths) was suddenly irrelevant. My team’s needs shifted overnight from “how do I advance?” to “how do I survive?” We had to completely rebuild our approach.

The wake-up call: Three of our best property analysts quit in one month – not for more money, but for “better work-life balance.” Exit interviews revealed burnout, anxiety about health risks from property showings, and frustration that we hadn’t adapted to their new reality.

Here’s what we changed:

1. Flexible Scheduling Based on Life Stage

Instead of 9-5 in-office, we created three tiers:

– Parents homeschooling kids: 6-10 AM + 3-7 PM work blocks

– Caregivers for elderly parents: Fully async with 48-hour response windows

– Standard: Flexible hours with core 10 AM-2 PM availability

This wasn’t “work from home” – it was acknowledging people’s lives had fundamentally changed.

2. Mental Health Budget

Every employee got $100/month for mental health – therapy, meditation apps, gym memberships, whatever helped. No questions, no receipts required for amounts under $100. Trust over tracking.

3. “No-Contact Showings” Premium

Property showings were our biggest COVID anxiety driver. We paid 20% premiums for virtual showings and hired contractors for in-person work. Team safety trumped short-term profits.

The outcome:

– Voluntary turnover: 35% annually – 8% in 12 months

– Employee satisfaction scores: 6.2/10 – 8.7/10

– Applications for open roles: 3x increase

– Productivity per person: Actually increased 15% despite “flexible” hours

The lesson: Retention isn’t about perks – it’s about acknowledging reality. When your workforce’s needs fundamentally shift, old playbooks fail. Ask, listen, adapt.

I experienced a situation where I had to adapt retention strategies when a team I supported began experiencing burnout due to workload changes and shifting expectations. It became clear that the existing approach to retention, which focused mainly on competitive compensation, was no longer enough. I began by gathering feedback through informal conversations and short surveys to understand what employees felt they were missing. The common themes were flexibility, clearer communication and better growth opportunities. In response, we implemented more flexible scheduling options and encouraged managers to set clearer weekly priorities so workloads felt more structured. We also introduced regular check-ins that focused on wellbeing rather than only performance.

To address development concerns, we created a simple framework for skill building that included job shadowing and optional workshops. These changes led to a noticeable improvement in morale. Employees felt heard and appreciated, shifting toward a more supportive environment. Over time, turnover decreased and engagement survey results showed higher satisfaction with work-life balance and communication. This experience reinforced the importance of staying responsive to changing employee needs and understanding that retention is not a one-size-fits-all strategy but something that evolves with the team.

About two years ago, we simultaneously had changing needs from two valuable team members: A writer/admin needed to become the caregiver for her ailing grandmother, but wanted to stay with the company by working nights and weekends. An editor/admin had health issues involving surgeries and recoveries, so she needed extensive time off and wanted to stay with the company in a reduced capacity.

We adapted our retention strategies by prioritizing employee well-being and offering flexible work arrangements. We also provided an opportunity for professional development by reaching out to other team members to gauge interest and identify who would be willing to step up and take on training for additional duties.

Our strategy was a win-win, keeping the writer and editor happy and employed, promoting two other team members, and giving more work to another two team members looking for more hours.