For about three months after I became a manager, every 1-on-1 I had followed the same script. I’d sit down, smile, and ask: “So, how’s it going?”
“Good.”
“Anything you need from me?”
“Nope.”
“Cool. Well, let me know if anything comes up.”
Meeting over. Five minutes. Both of us relieved.
I thought I was doing fine. I thought no news was good news. Then two people on my team quit within three weeks of each other. One of them told me in the exit interview that she’d been frustrated for months and didn’t feel like I ever asked the right questions to figure that out.
She was right. I wasn’t asking the right questions. I was asking the easy questions — the ones designed to get a quick “fine” so we could both move on. Research from HBR confirms that the quality of your questions directly determines the quality of your 1-on-1s. If you want them to actually do something, you need to ask questions that invite real answers. Here are 25 that work.
Why “How’s It Going?” Is the Worst 1-on-1 Question
Before we get to the good questions, let’s talk about why the default ones fail.
“How’s it going?” is a social greeting, not a real question. It’s the verbal equivalent of a head nod in the hallway. People are trained from childhood to answer it with “Good” or “Fine.” You’re not going to get “Actually, I’m drowning and I’ve been thinking about quitting” in response to a throwaway opener.
The same goes for “Any updates?” and “Anything I can help with?” These questions put the burden on the other person to identify their own problems, articulate them clearly, and feel safe enough to share them — all in the span of about three seconds. That’s asking a lot, especially from someone who might not fully trust you yet.
Good 1-on-1 questions share a few traits:
- They’re specific enough to prompt real thinking. “What’s your biggest frustration this week?” beats “How’s it going?” every time.
- They’re open-ended. Open-ended questions for employees get real answers. Yes/no questions get yes/no answers.
- They signal that you actually want the truth. Some questions create permission to be honest.
- They uncover things you wouldn’t learn in a team meeting. That’s the whole point.
If you’re still figuring out how to structure your 1-on-1s, start there. Once you’ve got the basics down, these questions will make each meeting count.
Opening & Check-In Questions (5)
The first few minutes set the tone. These questions move past small talk without being weirdly intense.
1. “What’s been on your mind this week?”
Why it works: It’s open enough to go anywhere — work stress, a personal thing, a random idea they’ve been chewing on. It signals that you care about them, not just their output.
What to listen for: Hesitation. If someone says “Nothing, really” too quickly, they might not feel safe yet. That’s okay. Keep asking over time. Trust builds slowly.
2. “On a scale of 1-10, how are you feeling about work right now?”
Why it works: Numbers are easier to give than paragraphs. And the follow-up is where the gold is: “What would make it a point higher?” Now you’re talking about something specific.
What to listen for: Trends. A consistent 7 is fine. A drop from 7 to 4 needs attention. A 9 followed by a 3 means something happened — ask about it.
3. “What’s one thing that went well for you since we last talked?”
Why it works: Starting with a win creates positive momentum. It also tells you what your team member values — which might be different from what you’d assume.
What to listen for: Whether they struggle to name anything. That’s a sign of either low morale or someone who doesn’t recognize their own contributions. Both are worth exploring.
4. “What’s been the hardest part of your week?”
Why it works: It normalizes struggle. Asking about hard things says “I know this job isn’t always easy, and I want to know about the rough parts too.”
What to listen for: Patterns. If the hardest part is always the same thing — a difficult colleague, a broken process, an unclear priority — that’s a systemic issue you need to address.
5. “Is there anything you’ve been wanting to bring up but haven’t?”
Why it works: This gives explicit permission to raise uncomfortable topics. Some people carry things for weeks, waiting for the “right moment.” This question creates that moment.
What to listen for: Body language. Even if they say “No,” watch for a pause, a look away, a shift in posture. Sometimes “No” means “Not yet.” Revisit it next time.
Work & Blockers Questions (5)
These questions help you uncover the stuff that’s slowing your team down — before it becomes a crisis.
6. “What’s the thing you’re spending time on that feels like a waste?”
Why it works: Everyone has tasks they think are pointless but do because they assume they have to. This question gives them an opening to challenge that. Sometimes you can actually remove the blocker right there.
What to listen for: Processes you own or created. If the “waste” is something you implemented, don’t get defensive. Ask more. They might be right.
7. “Where are you stuck right now?”
Why it works: “Stuck” is a friendlier word than “failing” or “behind.” It implies the problem is the situation, not the person. People are more likely to admit being stuck than to admit they’re struggling.
What to listen for: Whether they have a plan to get unstuck or need help. Some people just need to vent. Others need you to unblock them. Ask: “What would help?“
8. “What decision are you wrestling with?”
Why it works: New team members especially sit on decisions because they’re afraid of choosing wrong. This question surfaces those moments so you can coach them through the decision instead of making it for them.
What to listen for: Decisions they should be making without you. If someone is wrestling with something well within their authority, that’s a confidence issue worth addressing. Let them know: “That’s your call. I trust your judgment.”
9. “Is anything unclear about what you’re working on or why?”
Why it works: Lack of clarity is one of the biggest silent productivity killers. People waste hours going in the wrong direction because they didn’t want to ask a “dumb” question. This gives them a safe way to ask.
What to listen for: Confusion about priorities. If they’re not sure why something matters, they’ll have a hard time making good tradeoffs when things get complex.
10. “If you could change one thing about how we work as a team, what would it be?”
Why it works: It positions them as an expert on the team’s problems — because they are. The people doing the work usually know what’s broken better than the person managing the work.
What to listen for: Ideas you can actually implement. When someone gives you a suggestion and you act on it, it sends a massive signal: “Your input matters here.” That’s how you build real trust with your team.
Career Growth Questions (5)
Most new managers forget this category entirely. Don’t. Your people are thinking about their careers even if they’re not talking about it. These career development conversation starters open the door to discussions that matter far more than any status update. As Kim Scott emphasizes, the best managers use 1-on-1s to understand where their people want to go and help them get there.
11. “What part of your job do you wish you could spend more time on?”
Why it works: This tells you what energizes them. If someone loves data analysis but spends most of their time in meetings, there might be a way to rebalance. Even small shifts matter.
What to listen for: Misalignment between what they enjoy and what their role requires. Complete misalignment is a flight risk. Partial misalignment is an opportunity to reshape the role.
12. “What skill do you want to develop this year?”
Why it works: It shows you care about their growth, not just their current output. And it gives you concrete things to help with — training budgets, stretch assignments, introductions to people who have that skill.
What to listen for: Vague answers like “leadership” or “communication.” Push for specifics: “What does that look like? Can you give me an example of someone who does it well?“
13. “Is there a project or responsibility you’d like to take on that you haven’t had the chance to?”
Why it works: High performers especially crave new challenges. If you don’t give them opportunities, they’ll find them at another company.
What to listen for: Ambition level. Some people want a stretch assignment. Others want to lead something. Match the opportunity to where they are.
14. “Where do you see yourself in two years — and what can I do to help you get there?”
Why it works: The second half of this question is what makes it powerful. Lots of managers ask about career goals. Few follow it with a genuine offer to help. That follow-through is what separates good managers from forgettable ones.
What to listen for: Whether their two-year goal aligns with staying on your team. If it doesn’t, that’s okay — but you need to know. Helping someone grow out of your team is one of the best things a manager can do.
15. “What feedback have you gotten in the past that you found most useful?”
Why it works: This tells you how they receive feedback, what kind of feedback resonates with them, and what they’re actively trying to improve. It also opens the door to a deeper conversation about how to give effective feedback.
What to listen for: Whether they can name specific feedback at all. If they can’t, they probably haven’t been getting enough of it. That’s something you can fix.
Feedback & Relationship Questions (5)
These questions strengthen the trust between you and your direct report. They’re also the scariest ones to ask — which is exactly why they matter.
16. “What’s one thing I could do differently as your manager?”
Why it works: It demonstrates vulnerability. You’re saying: “I know I’m not perfect and I want to improve.” That’s powerful coming from someone in a position of authority.
What to listen for: The first time you ask this, you’ll probably get “Nothing, you’re great.” Don’t accept it too easily. Try: “I appreciate that, but there must be something. Even small things count.” Over time, as people see you actually act on their feedback, the answers will get more real.
17. “Do you feel like you’re getting enough feedback from me?”
Why it works: Most people want more feedback than they’re getting. This question opens the door to figuring out what kind of feedback they need and how often.
What to listen for: What kind of feedback they want. Some people want frequent, informal check-ins. Others want detailed written feedback after big projects. Knowing their preference makes your feedback land better.
18. “Is there anything I’ve done recently that was frustrating or unhelpful?”
Why it works: This is more specific than “What can I do better?” and more time-bounded. “Recently” makes it feel safe — you’re not asking them to catalog every grievance, just whatever’s fresh.
What to listen for: Specific examples. If someone says “When you jumped into my meeting last Thursday and took over the conversation,” that’s gold. It hurts to hear, but now you know something concrete to fix.
19. “Do you feel like your work is recognized?”
Why it works: Feeling invisible is one of the top reasons people leave jobs. This question directly addresses it. And the answer might surprise you — your idea of recognition and theirs might not match.
What to listen for: Whether they feel recognized by you specifically, by the broader team, or by leadership. Each gap requires a different fix.
20. “How do you prefer to communicate — and am I doing that?”
Why it works: Some people want Slack messages. Others want face-to-face conversations. Some hate being put on the spot in meetings. Knowing their preferences helps you work with them more effectively.
What to listen for: Frustrations with your current communication style. If they prefer async communication and you keep scheduling calls, you’re creating friction without realizing it.
Big Picture Questions (5)
Use these when you want to zoom out and check on the broader stuff — motivation, alignment, and overall satisfaction.
21. “What’s something about this company or team that you think we should change?”
Why it works: It invites strategic thinking and shows you value their perspective beyond their immediate tasks. It also surfaces cultural issues that might be brewing under the surface.
What to listen for: Whether the thing they want to change is within your power to change. If it is, take action. If it isn’t, be honest about that — and advocate for them where you can.
22. “What motivates you most right now — and is your current work aligned with that?”
Why it works: Motivation shifts. What excited someone six months ago might bore them now. Regular check-ins on motivation prevent the slow drift into disengagement.
What to listen for: Disconnects between motivation and reality. This kind of question works well alongside employee engagement survey questions — it gives you the qualitative story behind the numbers. If someone is motivated by learning and they’re doing repetitive work, you’ve got a problem to solve before they solve it by leaving.
23. “If you were in my position, what would you focus on?”
Why it works: This flips the perspective and often surfaces insights you’d never get from a direct question. People are surprisingly good at seeing blind spots from outside the role.
What to listen for: Problems they’ve been hesitant to raise directly. Framing it as “If you were me” gives them psychological distance that makes honesty easier.
24. “What’s something you’re proud of that you think I might not know about?”
Why it works: In busy teams, good work gets overlooked constantly. This question catches the wins that fell through the cracks and gives your team member a moment to own their accomplishments.
What to listen for: Hidden contributions. The bug they fixed on a weekend. The new hire they mentored. The process they quietly improved. These are things you should be amplifying.
25. “Is there anything else you want to talk about that we haven’t covered?”
Why it works: Simple and essential. Some of the most important things come out in the last two minutes when someone finally feels comfortable enough to say the thing they’ve been holding back.
What to listen for: The “doorknob confession.” In therapy, this is when the patient drops a bombshell on the way out. In 1-on-1s, it sounds like: “Oh, one more thing…” Pay attention. That “one more thing” is often the real reason they came.
How to Use These Questions: Practical Tips
You don’t ask all 25 in one meeting. That would be an interrogation, not a conversation. Here’s how to actually use this list.
Pick 3-5 per meeting
Choose one from each category that feels relevant. Rotate through the list over time. Your direct report shouldn’t be able to predict exactly which questions you’ll ask — that keeps the conversation fresh.
Match questions to the situation
- First few 1-on-1s with someone new: Lean on Opening and Feedback & Relationship questions. You’re building trust, not optimizing productivity.
- Busy sprint or stressful period: Focus on Work & Blockers and Opening questions. People need to feel supported, not interrogated about their career goals.
- Quarterly or end-of-cycle: Go heavy on Career Growth and Big Picture. This is when people are naturally reflective.
- After a conflict or tough feedback: Use Feedback & Relationship questions to repair and strengthen the connection.
Let them lead
The best 1-on-1s are the ones where your team member drives the agenda. Share this list with them. Say: “Here are some questions I might ask. You’re welcome to pick the ones that feel most relevant to you each week.”
Actually listen to the answers
This sounds obvious, but it’s the part most new managers get wrong. Think of these as coaching questions for managers — your job isn’t to solve every problem on the spot. Don’t ask a deep question and then immediately start problem-solving. Sit with their answer. Ask a follow-up. Let silence do some of the work.
The goal isn’t to check questions off a list. The goal is to understand what your person needs from you and to show them that you genuinely care. Questions are just the tool. Listening is the skill.
Follow through
If question #10 surfaces a broken process and you fix it, mention it next time: “You mentioned the review process was slowing you down. I talked to the design team and we’re trying a new approach. Let me know how it goes.”
That follow-through is what turns a good question into a trust-building moment. And if you’re in your first few months as a manager, building that foundation of trust early is one of the most important things in your complete guide to navigating the transition.
A Final Thought
The best managers I’ve worked for didn’t have some secret charisma or brilliant strategic mind. They asked good questions, they actually listened to the answers, and they did something about what they heard.
That’s it. That’s the whole trick.
Start with five questions from this list in your next 1-on-1. See what surfaces. Then adjust based on what you learn. Over time, you won’t even need a list — you’ll develop an instinct for the right question at the right moment.
But until then, this list is your cheat sheet. Use it.