7 Questions to Ask in Your First 1:1
Turning your first 1:1 from awkward silence into a trust-building conversation.
Why This Matters
Your first 1:1 can feel like a job interview you didn’t prepare for. You want to look confident, but inside you’re worried: What if I ask the wrong thing? What if they think I don’t know what I’m doing?
Here’s the truth: your first 1:1 isn’t about proving you’re the perfect manager. It’s about showing your team member that you care, you’re here to listen, and you’ll make their success a priority.
That’s it.
This issue gives you 7 copy-paste questions you can use tomorrow, plus a simple checklist to keep your 1:1 structured and stress-free.
Your 1:1 Starter Checklist
✔️ Book 30–45 minutes (not less).
✔️ Make it about them, not your to-do list.
✔️ Show up curious, not performative.
✔️ Write down action items—you’re modeling accountability.
✔️ End with clarity: who does what next?
The 7 Questions (Copy-Paste)
1. “What’s been the highlight of your week so far?”
→ Starts light, breaks the ice, and gives you insight into what energizes them.2. “What’s one thing that’s been frustrating or slowing you down?”
→ Signals that you want to remove blockers, not just assign work.3. “How are you feeling about your current workload?”
→ Opens space for honest conversation about balance and stress.4. “What part of your work do you enjoy most right now?”
→ Helps you spot strengths and motivation triggers.5. “Is there anything I can do differently to support you better?”
→ Models humility, builds trust.6. “What’s one thing you’d like to learn or get better at this quarter?”
→ Seeds career development early.7. “What’s one small change we could make as a team that would make your life easier?”
→ Turns the 1:1 into a team improvement lab, not just a status update.
🗣️ First 1:1 Conversation Flow (Copy-Paste Script)
Minute 1–3 → Break the Ice
Manager: “Hey, glad we could sit down. Before we dive into work, what’s been the highlight of your week so far?”
[Pause, listen, smile]
Manager: “Love that. For me, it’s [share something small/relatable].”
Minute 4–10 → Remove Roadblocks
Manager: “I want to make sure I’m not just adding to your plate. Is there anything that’s been frustrating or slowing you down lately?”
If they hesitate: “It could be tools, processes, meetings—anything that’s been a drag.”
Manager: “Got it. Thanks for sharing that. Let’s note it down and see what I can help with.”
Minute 11–20 → Growth & Support
Manager: “I also want to check in on your workload. How’s it feeling right now—manageable, or overwhelming?”
[Listen. Ask follow-up if needed: “What would make it feel more balanced?”]
Manager: “Looking ahead, what’s one thing you’d like to learn or get better at this quarter? Could be a skill, a project type, or even shadowing someone.”
Manager: “And for me—what’s one thing I could do differently that would make your life easier?”
Minute 21–30 → Team & Next Steps
Manager: “If you could wave a magic wand and change one small thing about how we work as a team, what would it be?”
[Listen → reflect back: “That’s a great point. Let’s test that idea out.”]
Manager: “Before we wrap up, here’s what I captured: I’ll [summarize your actions]. You’ll [summarize theirs]. Does that sound right?”
Manager: “Thanks again for being open. I really value your input—and I’m looking forward to our next chat.”
Quick Wins (Do’s & Don’ts)
Do:
Ask open questions.
Take notes (show you care).
Follow up on what they said next week.
Don’t:
Turn it into a status meeting.
Fill silence with nervous talking.
Promise fixes you can’t deliver.
Reflection (For You)
After your first 1:1, ask yourself:
What did I learn about them as a person?
What did I learn about their work?
Did I show them I’m here to support, not just manage?
Copy-Paste Tool: First 1:1 Agenda (Template)
Agenda
Check-in (personal highlight, mood)
What’s working well?
What’s challenging or blocking?
Support needed from me
Growth & learning goals
Team improvement ideas
Action items recap
(Drop this into your calendar invite or Notion doc. You now have a repeatable system.)
💡 Want to Go Deeper?
This issue gave you 7 starter questions and a simple script. But many of you have asked:
What if my team member doesn’t open up?
How do I handle 1:1s with senior/remote employees?
What’s the best way to track action items without making it feel like micromanaging?
How often should I run 1:1s, and what’s the ideal agenda?
I’m considering putting together a free deep-dive toolkit—a Complete 1:1 Kit with:
Agenda templates you can copy-paste into your calendar.
A question bank for different scenarios.
A scorecard to track progress across weeks.
Scripts for tricky 1:1 moments (when things get awkward or tense).
👉 If you’d love that, join the waiting list here: [link to waiting list].
💡 No payment required—just your email so I know who’s interested.
The more interest there is, the faster I’ll make it happen.
Final Word
Your first 1:1 sets the tone for your entire relationship. It doesn’t need to be perfect. What matters is that you show up, ask good questions, and listen with intent.
Next week, they’ll remember less about your exact words—and more about how you made them feel.
💡 Your Turn:
What’s one question you’ll use in your next 1:1? Hit reply and share—I might feature your story in a future issue.
Great artwork