Companies everywhere are scrambling to retain their best employees – and many are still getting it wrong. As reported by the Wall Street Journal, the traditional playbook of bigger salaries, fancier job titles, and purpose-driven mission statements isn’t cutting it. People are leaving jobs more frequently than ever, often for reasons that go far deeper than money.
If you’re serious about keeping your top talent, you need to stop guessing and start asking. Researchers Ethan Bernstein and Michael B. Horn have developed four deceptively simple questions that can help managers uncover what really motivates employees to stay or go. Used effectively, these questions are the first step in building real loyalty.
The Four Questions That Can Save Your Team
These four questions aren’t about cornering your employees – they’re about understanding them. They offer a way to open honest conversations and uncover the hidden forces that drive people to leave or stay.
1. When was the last time you almost quit?
This question gets to the heart of dissatisfaction. It encourages employees to reflect on real moments of doubt, helping managers identify what’s broken. It’s not about forcing confession – it’s about opening space for honesty. To get real answers, you need to create a safe environment and follow up with actions that show you’re listening.
2. When was the most recent time that work didn’t feel like work?
This question highlights what energizes and engages your team. It helps you identify the kinds of tasks, environments, or teams where your employees thrive. When you know what makes your people come alive, you can give them more of it.
3. What trade-offs are you making to stay in this role?
Every job has compromises. This question helps managers understand what sacrifices their employees are silently making—whether it’s missing family time, delaying career growth, or tolerating micromanagement. Once you know the trade-offs, you can reduce the cost of staying and increase the reward.
4. If this job disappeared tomorrow, what would you want to do next?
This question reveals true aspirations. Not everyone wants a promotion—some want lateral moves, new skills, or more autonomy. By knowing where people want to go, you can help them grow in ways that align with their vision and your needs.
These questions, used regularly and sincerely, shift the conversation from “How do we keep them?” to “What do they really want?” They are the foundation of real retention.
From Insight to Action: 30 Proven Strategies to Keep Your Best Employees
Once you’ve asked the right questions, what comes next? A wealth of research and expert advice offers actionable strategies to create an environment where great people want to stay. Here are 30 proven ways to turn insight into retention:
- Personalize career paths – Help each employee chart a unique path based on their goals and skills.
- Offer flexible work models – Hybrid or remote options show trust and reduce burnout.
- Recognize regularly – Frequent, specific praise increases morale and loyalty.
- Invest in mentorship programs – These build skills and deepen organizational connection.
- Use real-time feedback – Ongoing feedback beats annual reviews for engagement.
- Design “critical experiences” – Create high-value stretch assignments aligned with employee ambitions.
- Foster a culture of appreciation – Make gratitude part of daily management.
- Be transparent about promotions – Let people know what it takes to grow.
- Give employees autonomy – Micromanagement drives talent away.
- Train managers to coach, not control – Leadership style is a top driver of retention.
- Support emotional well-being – Create programs for mental health and stress management.
- Make onboarding personal – Customized onboarding improves early retention.
- Improve internal mobility – Promote from within to show growth is possible.
- Encourage innovation time – Let employees pursue passion projects.
- Use data-driven segmentation – Treat employees like customers, not averages.
- Provide clear vision and purpose – Help employees see how their work matters.
- Celebrate milestones – Recognize birthdays, work anniversaries, and big wins.
- Host career progression meetings – Discuss where employees want to go long-term.
- Involve employees in decision-making – Engagement rises with ownership.
- Address burnout early – Teach managers to spot and respond to warning signs.
- Adapt benefits to actual needs – Survey employees and tailor perks accordingly.
- Encourage team bonding – Positive peer relationships are a retention multiplier.
- Model work-life balance – Leadership must walk the talk.
- Provide growth budgets – Give employees funding for courses, books, and tools.
- Invest in leadership development – Grow tomorrow’s leaders internally.
- Offer meaningful work – Tie tasks to a larger mission.
- Create psychological safety – Make it safe to fail, speak up, and disagree.
- Use technology for support, not surveillance – Tools should empower, not micromanage.
- Give employees a say in change – Let them help shape new initiatives.
- Track and analyze retention trends – Use data to improve and adapt continuously.
Retention isn’t about perks and pizza parties. It’s about understanding your people deeply—and designing systems that support who they are and who they want to become. Ask the right questions, take real action, and you won’t just keep your best employees—you’ll build a place where they want to stay.
The future of talent retention lies in personalization, trust, and purpose. Companies that embrace this now will be the ones thriving while others struggle to catch up.
FAM Editor: I seems to me that as a boss, you would probably not ask these questions yourself. In a larger organization you would want your HR folks to ask them. Depending on the state of your company, good luck getting real answers. That said, there are many ways to ask these questions and many other suggestions included.
