Great leadership isn’t about having all the answers, it’s about asking the right questions. If you want to build a high-performing, engaged team, the way you check in with your people matters.
Check-ins aren’t just status updates. They’re opportunities to build trust, deepen connections, and uncover what your employees need to succeed. The best check-ins don’t just skim the surface—they open the door to real, meaningful conversations.
So, how do you do it right? It starts with the right questions. Here are five powerful check-in questions every leader should be asking to create a more human-centered workplace.
1. On a scale from 1 to 10, how are you?
We’ve all asked, “How are you?” only to receive the automatic response: “I’m fine.” But what does that actually tell us? Not much.
By adding a scale—“How are you on a scale from 1 to 10?”—you get a meaningful data point. A seven tells you they’re doing okay, but you can follow up: “What would move you up to a nine?” If they say a two or three, that’s a clear signal they’re struggling. And now you can step in and ask, “What’s going on? How can I support you?”
This simple tweak transforms a check-in from a polite formality into a real opportunity for connection.
2. What’s the most important thing we need to talk about today?
Most one-on-one meetings start with an agenda—but whose agenda? If leaders dominate the conversation with updates and to-dos, they may miss the things that actually matter to their employees.
This question flips the script, putting the focus where it should be: on what’s top of mind for your people. Maybe it’s a major challenge they’re facing, a career concern, or something personal that’s affecting their work. By leading with this question, you ensure that your time together is spent on what truly matters.
3. On a scale from 1 to 10, how appreciated do you feel for your contributions at work?
Recognition is one of the biggest drivers of employee engagement. People want to know that their work matters. But appreciation isn’t one-size-fits-all—what feels meaningful to one employee might not work for another.
Asking this question gives you a pulse check on how valued your employees feel. If the response is low, follow up: “What would make you feel more appreciated?” Their answers will give you powerful insights into how to better recognize and support them.
4. How would you rate your career growth over the past year?
Career growth isn’t just about promotions. It’s about learning, challenges, and opportunities. And when employees don’t see a path forward, they disengage—or worse, they leave.
This question opens up an honest dialogue about career expectations. If someone rates their growth low, dig deeper: “What were you hoping for that didn’t happen? What kinds of opportunities would excite you?”
These conversations allow you to align growth opportunities with individual needs—before they start looking elsewhere.
5. How’s your head, heart, and health? (The 3H Check-In)
This question isn’t just about work—it’s about the whole person. Work and life are deeply intertwined, and when we acknowledge that, we create more supportive, human workplaces.
– How’s your head? (Mental clarity, focus, and workload)
– How’s your heart? (Emotional well-being and relationships)
– How’s your health? (Physical well-being and energy levels)
This check-in gives employees a space to share what’s really going on and allows leaders to offer the right kind of support. It’s a small act that can make a big difference.
Bonus Question: If you were to ever consider leaving, what do you think would be the reason?
This question is bold, but it’s also one of the most valuable conversations you can have with your top talent. Instead of waiting for an exit interview to understand why someone leaves, why not ask while they’re still here?
When you pose this question, you give employees permission to reflect on what might push them away. Maybe it’s a lack of career growth, flexibility, or a better financial opportunity elsewhere. Whatever they say, listen carefully—because this is your chance to address their concerns before they turn into reasons to leave.
Some leaders worry that asking this will plant the idea of leaving in someone’s head. But the reality is, people are already thinking about these things. Asking this question gives you the opportunity to retain and support your best people proactively.
The Bottom Line: Great Leaders Ask Great Questions
Check-ins aren’t about checking a box—they’re about fostering real, human connections. The best leaders don’t just talk; they listen. And the right questions make all the difference.
Try using these five questions (plus the bonus one!) in your next one-on-one. Your employees will thank you for it—and you’ll be one step closer to building a workplace where people feel seen, valued, and supported.
Want more insights on creating a better workplace? Stay connected for more leadership tips and strategies to build a truly engaged team.
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