Keeping your team engaged and connected is harder than ever. Between packed schedules and remote work, it’s easy for meaningful conversations to slip through the cracks. And if you’re not careful, you can lose track of how your employees are actually doing. Asking the right questions—and showing you care—can make all the difference. Here are the questions to start with:

How are you showing up today on a scale of 1–10? Simply asking “How’s life?” can lead to short, unspecific answers. A numerical score invites self-reflection. Follow up with, “What’s contributing to that score?” to dig deeper, especially for remote employees who may feel disconnected or lonely.

What’s something you’re excited about outside of work? This simple question builds rapport and uncovers personal passions. Don’t push if someone is hesitant to share—trust takes time to build. But over time, these conversations create space for openness and connection.

Do you derive meaning from your work? If not, what changes could help? Understanding what motivates your team members is essential. Ask about the highs and lows of their role, and listen without interrupting. Small adjustments could make a big difference in their fulfillment and productivity.

What could make this job or organization more compelling for you in the long run? Understanding what drives long-term commitment helps you retain top talent. Be open to their ideas, and if something isn’t feasible, be honest. Collaborate on solutions to show you value their perspective.
 
What makes you feel depleted or drains you at work, and what can I do to support you? Every team member faces unique challenges. Ask about roadblocks or tasks that feel like time-wasters, and explore how you can help. Be careful not to come across as micromanaging—this is about support, not control.
 
What are your career goals and dreams? How can I help you move toward them? Take the time to understand their ambitions beyond their current role. Whether it’s suggesting training, offering stretch assignments, or simply listening, showing investment in their growth fosters loyalty and engagement.
This tip is adapted from “6 Questions to Find Out How Your Employees Are Really Doing,” by Rebecca Knight.
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