Do your 1:1s feel like a checkbox exercise? Are you walking away from these conversations, wondering if they really made a difference? (Or canceling them because they feel like a waste of time?) You’re not alone—and it doesn’t have to be this way.
It’s All in the Questions
Asking more questions can transform a routine check-in into a powerful tool for engagement, growth, and mutual understanding. Here’s the catch: you don’t need to have all the answers ready. Your role is to listen, understand, and partner with your team members to create their ideal work environment.
While there is no single “right” question, here are 26 to help you get started and build your Question Library:
🤝 Building Authentic Connections
- What recharges your batteries outside of work?
- Which activities from your past would you love to revisit?
- How do you maintain work-life balance?
- For remote teams: What helps you feel connected to your colleagues?
🔥 Understanding Motivators
- What gets you excited about coming to work?
- When do you feel most energized in your role?
- If you could wave a magic wand, what would you change about your job?
- What’s your superpower?
- What new superpowers would you like to develop?
- Which of your contributions deserve more recognition?
- How can we better leverage your talents?
📈 Fostering Development
- Tell me about a recent challenge that taught you something valuable. What would you do differently next time?
- How stretched do you feel in your role (1-10)?
- How could we stretch you more?
- What’s the most significant thing you’ve learned lately?
- Which parts of our business intrigue you?
- What skills are you eager to develop?
- Who here inspires you professionally? Is there someone you’d like to learn from?
- What learning opportunities interest you?
- Let’s map out the key skills for your role—where do you see yourself?
🚀 Supporting Career Growth
- How are you tracking against your big-picture goals?
- What could accelerate your professional journey?
- How does your current role align with your career vision?
- Which projects light you up?
- What’s your dream next move?
- What achievement here are you most proud of?
💡 Pro Tip: Handling Tough Conversations
When faced with requests you can’t fulfill, don’t dodge the conversation. When an employee requests something that is unlikely to happen, try:
“I hear how important this is to you. While we can’t make this specific change right now, I’m committed to finding other ways to support you. What else could make a meaningful difference?”
Great 1:1s aren’t about having all the answers—they’re about:
- Building genuine trust
- Developing relationships
- Uncovering what matters most
- Creating partnerships that help everyone thrive
Remember: The goal isn’t perfection. It’s progress, understanding, and creating an environment where both you and your team can do your best work.
