100 One-on-One Meeting Questions

A one-on-one is the most leveraged half-hour on a manager’s calendar, and the one most often wasted. Run badly, it becomes a verbal status report — information both people already had. Run well, it’s where you build trust, clear the blockers nobody raised in standup, develop people for the role after this one, and hear the feedback that would otherwise reach you too late to act on.

The questions below — around 100 of them — are grouped so you can pick a handful to match what this week needs, not read them out like a checklist. They’re framed in both directions: questions managers ask their reports, and questions reports should bring to ask their manager. Start with the short guide to running a great 1:1, then help yourself to the banks, and finish with a reusable agenda template you can run live in TeamRetro.

How to run a great 1:1

The format matters far less than the habit. A few principles make almost any set of questions land.

What a 1:1 is for

A 1:1 exists to do four things a status meeting can’t: build a genuine working relationship, surface and clear roadblocks, develop the person, and give them a safe channel to give you feedback. If your 1:1s mostly cover “what did you ship, what’s next”, you’re spending premium time on something a written update would do better — and skipping the part that only a conversation can.

How often and how long

Weekly is the right default for most direct reports; fortnightly works once the relationship is well established and the person is senior and steady. Thirty minutes is plenty if you protect it. The cardinal rule: it’s the report’s meeting, not yours. Let them set much of the agenda, do most of the talking, and never quietly let the 1:1 become the first thing you cancel when you’re busy — a repeatedly-cancelled 1:1 tells someone exactly where they rank.

How to use these questions

Don’t fire the whole list. Pick two or three per session, rotate categories week to week, and let the answers lead — a good follow-up question beats moving to the next prompt. Keep a shared running agenda both of you add to during the week so the meeting starts with real material instead of a cold “so, how’s things?”.

Check-in and rapport questions

Open the meeting as a human, not a manager. These warm the room and read the person’s state before you get into the work. They’re close cousins of our check-in questions — borrow from there too.

How are you, really — not the standup version?
What’s your energy like this week, on a scale of one to ten?
What’s something good that happened since we last spoke?
What’s been on your mind that has nothing to do with work?
What are you looking forward to this week?
If this week had a weather forecast, what would it be?
What’s one word that sums up how the last sprint felt?
What’s something you’re proud of recently that I might not know about?
Is there anything you wish I’d asked you about?
What would make this week a good one for you?
Outside work, what’s keeping you busy at the moment?
What’s the best thing about your work right now — and the most frustrating?

For lighter openers when the team’s a bit flat, our icebreaker questions for work and funny icebreaker questions work just as well in a 1:1 as in a group.

Work, priorities and blockers

The heart of most 1:1s: what they’re working on, what’s in the way, and what they need from you. Your job here is to unblock, not to inspect.

What are you focused on this week, and is that the right thing to be focused on?
What’s slowing you down or getting in your way right now?
Where are you stuck, and what have you already tried?
Is anything taking longer than it should? Why?
What’s the one thing you most need from me this week?
Are your priorities clear, or are you guessing at any of them?
Is anything on your plate that someone else should really own?
What are you working on that you don’t think matters? Let’s question it.
Where are you waiting on someone else, and how long have you been waiting?
What decision are you stuck on that I could help you make?
Is there a meeting or commitment we could drop to give you more focus time?
What’s a small thing that’s annoying you that we’ve never bothered to fix?
What would you tackle first if you had an uninterrupted day tomorrow?
Is there anything you’re worried might slip, so we’re not surprised later?
What’s going better than expected right now?

Growth and career development

These are the questions reports remember. They signal you’re invested in the person after this role, not just this sprint.

What do you want to be doing more of — and less of?
Which part of your work makes you lose track of time?
What skill would you most like to build over the next few months?
Is there a project coming up that would stretch you in a good way?
Where do you want to be in two years? What would get you closer?
What’s something you’ve always wanted to try but never had the room to?
Who in the organisation do you learn the most from? Should we get you more of that?
What would “a great year” look like for you?
Is there a skill you have that we’re not using enough?
What’s the next level for you, and what’s the gap between here and there?
What kind of work do you want to be known for?
Is there feedback you’ve had before that you’re still trying to act on?
What would make you feel like you’re growing, not just delivering?
What’s a stretch you’d take on if you knew it was safe to fail at?
Is there a mentor or a conversation that would help you right now?

Feedback — in both directions

The hardest and most valuable category. A 1:1 should carry feedback both ways: yours to them, and — just as importantly — theirs to you. Ask for upward feedback often, and make it safe to give.

Feedback for the report:

What’s one thing I think you do really well that you might underrate in yourself?
Here’s something I’d love to see you try — how does that land?
Where do you think you could have more impact than you do today?
Is there a pattern you’ve noticed in your own work you’d like to change?

Upward feedback — what they think of how you manage:

What could I do differently to support you better?
What’s something I do that gets in your way?
Am I giving you too much direction, too little, or about right?
Is there anything I’ve said or done that didn’t sit right with you?
What’s a decision I made recently that you’d have made differently?
Where am I not giving you enough context?
If you could change one thing about how our team works, what would it be?
What’s something you’ve been meaning to tell me but haven’t found the moment for?
How could our 1:1s be more useful to you?
Is there feedback you’re holding back because you’re not sure how I’ll take it?

Wellbeing, workload and engagement

Read the sustainability of the work, not just the output. Burnout rarely announces itself — it shows up in these questions first.

How’s your workload — sustainable, or are you running hot?
Are you taking proper breaks and actually switching off?
What’s draining your energy at the moment?
On a scale of one to ten, how motivated do you feel right now? What would move it up one?
Is there anything about your work that’s stressing you out?
Do you feel recognised for the work you’ve been doing?
When did you last feel genuinely proud of your work here?
Is there anything making you think about whether this is the right role for you?
Are you getting enough heads-down time, or is the day all interruptions?
What would make your day-to-day a bit easier?
Is there support you need that you haven’t asked for?
Do you have what you need to do your best work — tools, access, clarity?

Workload and engagement are individual signals; to read the same things across the whole team, pair your 1:1s with a regular team health check.

Questions employees can ask their manager

The 1:1 is the report’s meeting, so come with your own questions. If you manage people, share this list with your reports — a 1:1 they help drive is far more useful than one they sit through. These capture the “questions to ask my manager” intent directly.

What are the most important things for me to focus on right now?
How am I doing against expectations — honestly?
What’s one thing you think I should start doing, and one I should stop?
What would it take for me to get to the next level?
Is there anything you need from me that you’re not getting?
What’s coming down the line that I should be aware of?
How does what I’m working on connect to the bigger picture?
Where do you see my biggest opportunity to grow?
Is there a skill you think I should be building?
What’s a blind spot you’ve noticed in how I work?
How do you prefer I bring problems to you — early and rough, or worked-through?
What’s keeping you up at night about the team right now?
Is there a project I should be putting my hand up for?
What does success look like for me over the next quarter?
How can I make your job easier?

Questions for remote and distributed reports

Distance hides things that a shared office surfaces by accident — isolation, drift, ambiguity. These questions do deliberately what proximity used to do for free.

Do you feel connected to the team, or a bit on an island?
Is there enough context reaching you, or do you feel out of the loop?
How’s your home setup — do you have what you need to work well?
Are the async expectations clear, or are you guessing when a reply is “late”?
Is there a decision that happened without you that you wish you’d been part of?
How are the meeting times working across your timezone?
Do you get enough informal contact, or is it all scheduled calls?
When you’re stuck, do you know who to reach and how?
Is anything about working remotely wearing on you?
What would make you feel more part of what the team’s doing day to day?

Skip-level meeting questions

A skip-level — meeting someone who doesn’t report to you directly — reads the health of a team and the wider organisation, not an individual’s performance. Ask about the experience, never to go around their manager.

What’s working really well in the team right now?
What would you change about how the team works if you could?
Is there anything getting in the way that I might not be able to see?
How well do you understand where the wider organisation is heading?
What’s a decision recently that you didn’t understand the reason for?
Is there anything your manager does that you’d like more — or less — of?
Do you feel you can speak up when something’s wrong?
What’s an idea you have that hasn’t found a home yet?
Is there something the leadership team should know but probably doesn’t?
What would make this a better place to work?

First 1:1 with a new report

The opening 1:1 sets the tone for the whole relationship. Spend it on them and how they work, not on your plans for them. These cover the “first one-on-one with an employee” intent.

How do you like to work, and when are you at your best?
How do you prefer to receive feedback — in the moment, or considered and written?
What’s the best manager relationship you’ve had, and what made it work?
What’s something a previous manager did that you’d rather I didn’t?
How do you want to use this time together?
What do you need from me to do your best work?
What are you hoping to get out of this role?
Is there anything I should know about how you like to communicate?

Closing and action questions

End every 1:1 the same way: clear on what’s next and who owns it. A meeting with no agreed action is a meeting you’ll repeat.

What’s the one thing you’re taking away from this conversation?
What can I do, specifically, before we next meet?
Did we miss anything you wanted to cover?
What’s the most important thing for you to act on this week?
Is there anything we should put on the agenda for next time?
On a scale of one to ten, how useful was this — and what would make it a ten?

Your 1:1 meeting agenda template

A light, repeatable structure keeps 1:1s on track without making them rigid. Copy this as a shared running agenda you both add to through the week, then work down it in order — the report’s topics first, because it’s their meeting.

Check-in — a genuine “how are you?” and a quick read of energy and workload.
Their topics — whatever the report brought; blockers, decisions, things on their mind.
Your topics — context, priorities, feedback, anything you need to flag.
Growth — a rolling thread on development, not every week but never neglected.
Action items — one or two clear commitments, each with an owner and a date.

The point of an agenda is consistency, not ceremony. Keep it short, keep it shared, and protect the time. If you want to make your 1:1s a deliberate habit rather than a recurring calendar slot, our guide to running effective retrospectives and our team charter guide both cover turning loose intentions into agreements a team actually keeps.

Run better 1:1s and team check-ins with TeamRetro

Great 1:1s read the individual; a healthy team needs you to read the whole as well. TeamRetro is built for the team-level half of that picture — silent input, anonymous voting and tracked actions on a shared board. Pair your recurring 1:1s with regular team health checks to sense the team’s wellbeing, alignment and morale over time, and use the retrospective templates for the team-level reflection that turns what surfaces in your 1:1s into changes the whole team owns. For a format that doesn’t exist yet, generate a custom board in seconds. More conversation starters live in our icebreakers hub.

Frequently asked questions

What questions should you ask in a one-on-one meeting?

Ask questions that open up connection, surface blockers, support growth and invite upward feedback — not a status update you could read in a ticket. A reliable rotation is a short check-in (“how are you, really?”), one on current work and roadblocks (“what’s slowing you down?”), one on growth (“what do you want to be doing more of?”), and one inviting feedback on you (“what could I do differently?”). Pick two or three per session rather than firing the whole list.

What are good questions for employees to ask their manager in a 1:1?

The 1:1 belongs to the report, so come with your own questions. Strong ones include “what are the most important things for me to focus on right now?”, “how am I doing against expectations, honestly?”, “what would help me get to the next level?”, “is there anything you need from me?”, and “what’s coming that I should know about?”. Asking for context, priorities and feedback turns the meeting from a check-up into a conversation you steer.

How do you structure a one-on-one meeting?

Keep a light, repeatable shape: open with a genuine check-in, then cover the report’s topics first (it’s their meeting), then yours, then growth or development, and close on clear action items with owners. A shared running agenda both people add to during the week beats improvising. The structure matters less than protecting the time and never letting it collapse into a status report.

How often should you have one-on-one meetings?

Weekly for most direct reports, or fortnightly once a relationship is well established and the person is senior or steady. The cost of cancelling is higher than the cost of a short meeting, so default to keeping it and ending early when there’s little to discuss. Pair the personal rhythm of 1:1s with a regular team-level health check so you read the whole team as well as each individual.

What should you not do in a 1:1 meeting?

Don’t turn it into a status update, do most of the talking, cancel it repeatedly, or save all your critical feedback for it. It also shouldn’t be the only place issues get raised — surprises in a 1:1 usually mean feedback was held too long. Treat it as the report’s time to be heard, unblocked and developed, and keep status reporting to the channels built for it.

What are good skip-level meeting questions?

In a skip-level — meeting someone who doesn’t report to you directly — ask about the team’s experience rather than individual performance: “what’s working well in the team right now?”, “what would you change if you could?”, “is there anything your manager could do more or less of?”, and “what’s getting in the way that I might not see?”. The aim is signal on the team and the wider organisation, not to go around the person’s manager.