The Manager's Playbook #3 - Using "random" questions
Struggling to get your direct reports to share more during 1:1s? Are your 1:1s feeling a bit quiet? Do you wish your team would open up more?
It’s a common challenge, especially when working with introverted or newer team members who you are still building trust with. But here’s one simple change that can make your 1:1s more reflective and meaningful:
End each 1:1 with a “random” question.
Not a “how’s the project going?” kind of question, but something that invites them to think, reflect, or share a personal insight.
When I first started managing, my team was full of introverts. They were quiet and hesitant to share. Introducing a different question each week broke that silence and helped them be more reflective.
It often wasn’t that they weren’t willing to share; it was more about not having the insight of what to focus on. The questions encouraged them to think about different topics and voice their opinions on them.
Scenario: Asking random questions in 1:1s
You want your 1:1s to go beyond status updates, but when you ask open-ended questions like “What’s on your mind?” or “How are things going?” you’re met with short answers. It’s not that your team doesn’t want to talk. Sometimes, they just need a nudge in the right direction.
🎯 Tip 1: Introduce a weekly question
Ask a different question at the end of each 1:1. Think of it as a conversation starter: something unexpected, thoughtful, or even a bit silly.
Example: “If you could instantly learn a new skill, what would it be?”
🫶 Tip 2: Set a safe tone
Begin by emphasizing that these questions are meant to be a judgment-free and fun way to learn more about them. You’re not looking for a “right” answer: you’re looking for honest ones.
✔️ Tip 3: Adapt it to the individual
Choose questions that suit the personality and comfort level of the person you’re speaking with. Some people might enjoy philosophical questions. Others prefer lighthearted ones.
⏰ Tip 4: Give time to reflect
Share the question at least a day or two in advance so they have time to think and reflect. Many people (especially the introverts on your team) will appreciate the time to think on their own first.
🤔 Tip 5: Lead by example
Go first. Be open. Show vulnerability. Your willingness to share signals that it’s okay for them to do the same. Answer the question to show your human side as well.
🎭 Tip 6: Make it both fun and serious
Use a mix of fun and serious questions. Don’t limit yourself to just work-related topics. You’ll be surprised what comes from a well-timed “What fictional world would you love to live in?”
💖 Tip 7: Switch it up
Take turns picking the question. I normally introduce this after having done the format a few times. Encourage your direct report to bring along their own questions. See what they are curious about!
📌 Tip 8: Follow up on previous answers
Bring up past responses in future 1:1s to show you’re genuinely listening and to encourage deeper conversations.
For example, some of my favourite questions:
“What’s one thing most people don’t know about you?”
“What’s your favourite way to treat yourself?”
“What fictional place would you most like to visit?”
“Who has influenced you most when it comes to how you approach your work?”
If you want to start creating your own questions, I’d recommend following Priya Parker on LinkedIn. Every week, she has a weekly LinkedIn post about the techniques of coming up with “magical“ questions and helps you understand what makes a question magical!
Need more examples? Use these resources for inspiration:
These questions help your team build self-awareness, reflect on what matters to them, and bring more of themselves to the conversation. Over time, you’ll find that your 1:1s shift from check-ins to more human conversations.
It’s about finding that balance between work insights and personal stories. Finding those questions that work for that specific person.
The right question can unlock a great conversation.
How do you encourage your team to open up? What are your favourite questions for 1:1s? Drop a comment below or reach out: I’d love to hear your ideas and experiences!
Se you next time,
Melinda
