Raises. Titles. Benefits. Perks. Purpose.
It’s the standard playbook for keeping top talent—and according to a recent Wall Street Journal article, it’s not working.
In “The Secret to Retaining the Best Employees,” authors Ethan Bernstein and Michael B. Horn share insights from 15 years of research and over 1,000 job changes. Their takeaway? Employees don’t leave just for more money or flashier titles. They leave when hidden push-and-pull forces inside and outside your organization go unaddressed.
For small business owners, this is especially critical. You often don’t have the budget to “buy loyalty.” But you do have the ability to lead with empathy and curiosity—if you ask the right questions early and often.
Here are four simple, smart questions that can help you understand what really matters to your employees—and keep them from walking out the door.
1. When was the last time you almost quit?
It’s bold. But it opens the door to honest feedback.
This question helps surface unresolved frustrations—maybe about feeling disrespected, overlooked, or burned out. According to the WSJ article, one CFO uses this during performance reviews to uncover workplace friction before it festers.
Tip: Frame it as “What can I do differently to make your job better?” before asking. Then really listen.
2. When did work last feel easy or energizing?
We often overlook what’s working. But employees remember when they felt in flow—when their work clicked.
These moments are more than happy accidents. They reveal what motivates someone: teamwork, autonomy, recognition, creativity, or impact. Use that insight to design better roles and avoid disengagement.
Tip: Dig into why that moment felt good. It’s usually not just the task—it’s how it made them feel.
3. What trade-offs are you making to stay in this role?
Everyone sacrifices something to keep a job. For some, it’s flexibility. For others, it’s growth or work-life balance.
This question uncovers hidden pain points—and helps you respond before they become deal breakers. The WSJ points out that many employees don’t have the language to ask for what they need constructively. You can help.
Tip: Pay attention to shifting priorities over time. Trade-offs change as life changes.
4. If your job disappeared tomorrow, what would you do next?
This one’s not about encouraging someone to leave—it’s about uncovering aspirations you might otherwise miss.
Not everyone wants your job. The all-star developer might want deeper technical training, not a promotion. Asking this helps you invest in the right career paths—ones your employees will actually stick around for.
Tip: Use this to fuel internal mobility, mentorship, or upskilling opportunities.
Smarter Questions, Stronger Retention
We get it. These questions can feel uncomfortable. But so is reading a resignation letter from your best employee.
Employees now change jobs every 3.9 years on average, and younger generations switch even more frequently. Retention doesn’t always come down to compensation or perks. More often, it’s about whether employees feel seen, heard, and supported.
You don’t need a huge HR department to start asking better questions. You just need the willingness to listen—and the courage to act.
At Focus HR, we specialize in helping small businesses create the kind of workplace people want to be part of. If you’re ready to rethink retention, we’re here to help.
