25 Check-In Questions to Use in Your Next 1:1

Nov 10

A good 1:1 isn’t just a status update.
It’s a regular place to see what’s really happening beneath “I’m fine” and “all good.”

The questions you ask shape the answers you get.
Small shifts in language can turn a polite catch-up into an honest check-in that surfaces confusion, tension, and needs early—before they solidify into bigger problems.

Below are 25 check-in questions you can use in your next 1:1. You don’t need all of them at once. Pick one or two that fit your context and stay with them long enough to really listen.

How to Use These Questions

Don’t stack them. One strong question, explored fully, is more useful than five rushed ones.
Signal your intent first:
“I’d like to use this time to check how things are really going for you, not just the tasks.”
Make it normal to come back to the same question over time:
“Let’s revisit this next week and see what’s shifted.”
When someone answers, resist the urge to solve immediately. Start with:
“Say a bit more about that.”
“What’s the part that matters most to you here?”

Use these as invitations, not interrogations.

Questions About How Work Feels Right Now

What’s one thing that’s going well for you at work this week, and one thing that needs attention?
Simple, balanced, and opens the door to both pride and concern.
What’s taking up the most mental space for you right now?
This often surfaces the real agenda, which may not be on your meeting notes.
On a scale of 1–10, how clear do you feel on your priorities this week? What would move that number up by one?
Combines a quick pulse check with a concrete next step.
Is there anything you’re worrying about that we haven’t talked about yet?
Makes room for the thing that hasn’t felt safe or important enough to name.
If you had to name the “headline” for your week so far, what would it be?
A light way to get a snapshot of mood and focus.

Questions About Support and Needs

Is there anything you need from me that you’re not getting?
Clear, direct, and ownership-oriented.
What’s one place where a small change from me would make your work easier?
Keeps it practical and specific.
Where do you feel well-supported right now, and where do you feel a bit on your own?
Helps you see both strengths and gaps in your support.
What’s one resource, tool, or piece of information that would make this week easier?
Turns vague frustration into concrete asks.
When you think about the last month, is there a moment where you thought: “I wish I’d had backup there”?
Good for catching missed support after the fact.

Questions About Workload and Capacity

How sustainable does your current workload feel over the next 4–6 weeks?
Keeps you out of the “this week only” trap.
What are you doing right now that someone else could reasonably own?
Surfaces delegation opportunities and role clarity issues.
What did you say yes to recently that you’re not sure you actually had capacity for?
Opens a conversation about boundaries without blame.
If you had 10% less on your plate, what would you remove first?
Reveals what feels heaviest or least aligned.
Where are you at capacity, and where—if anywhere—do you still have some space?
A more nuanced answer than “busy” or “not busy.”

Questions About Clarity and Direction

What’s one thing about our direction, strategy, or priorities that still feels fuzzy to you?
Invites questions people often feel they “should” already know.
Is there a recent decision you’d like more context on in order to do your best work?
Links clarity directly to performance.
What question about our work have you been holding back from asking?
Gives permission to name the “quiet” question.
What assumptions are you making about this project or team that we should check together?
Assumptions drive behavior; naming them prevents misalignment.
Where do you see a gap between what we say we value and what you see day-to-day?
One of the most powerful ways to surface culture issues.

Questions About Relationships, Repair, and Growth

Is there anyone on the team you feel a bit out of sync with right now?
You don’t need details, just enough to know whether support or repair is needed.
Is there anything you’d like to clear up or repair—with me or anyone else—that we haven’t made space for?
Signals that repair is welcome, not taboo.
What’s something you learned or were stretched by in the last month?
Keeps growth visible, even when it was uncomfortable.
If we did a quick retrospective on the last few weeks, what would you say we should keep doing, stop doing, and start doing?
Brings a simple team tool into the 1:1 setting.
What’s one thing you appreciate about this team right now, and one thing you wish we’d do differently?
Holds appreciation and critique together, without canceling either out.

What to Do With the Answers

A powerful question is only half the work. The other half is how you respond.

Start with reflection, not fixing.
“Let me make sure I’m hearing you…” is often better than “Here’s what we’ll do.”
Name what you’re taking away.
“I’m hearing that your workload is technically manageable, but the constant context switching is draining. That’s the part I want us to focus on.”
Be honest about constraints.
If something can’t change right now, say so directly and explain why. Clarity is better than vague reassurance.
Close the loop.
In the next 1:1, return to what they named:
“Last time you mentioned X. Here’s what I did with that, and I’d like to hear how it’s feeling now.”

Over time, these questions do more than generate good conversations. They teach your team that naming reality is a normal, expected part of working together—not a last resort.

Pick one question for your next 1:1.
Ask it with genuine curiosity.
Stay long enough in the answer to learn something you didn’t already know.

Want Help Building This Into Your Routine?

Tools like these work best when they become part of the rhythm of how your team operates—not just something you try once and forget. If you’d like support designing check-ins, reflection structures, or feedback systems that make honesty and connection routine, reach out to us at hello@humanrepair.org.

Monica Rodriguez