One on One Meeting Questions for Both Sides of the Table

Good one on one meeting questions are open-ended, tied to a purpose, and asked from both chairs. Managers should ask about priorities, blockers, growth and how they themselves can improve; employees should bring decisions they need, feedback they want, and career topics. Pick questions by the meeting's job, not from a random list.

That last point is where most question lists fall short. A first meeting with a new report needs different questions than the twelfth weekly check-in, and a conversation about promotion needs different ones than a conversation about a project that's slipping. So this guide is organized by what the meeting is for, with questions for the manager and for the employee under each heading. It closes with structure, because a meeting's format usually matters more than any single question you ask in it.

What a one on one is actually for

A one on one is a recurring private conversation between a manager and a direct report, and its job is everything that doesn't fit anywhere else: concerns, half-formed ideas, friction, career direction, and early warning of trouble. It is not the place to recite what you did this week. Status belongs in a tool or a standup.

The best-known writing on the format agrees on one thing: the meeting belongs to the employee. In High Output Management, former Intel CEO Andy Grove described the one on one as the subordinate's meeting, with its agenda and tone set by them, and argued that the manager's role is to learn and coach. Ben Horowitz, writing for Andreessen Horowitz, made the same point more bluntly, saying the manager should do 10% of the talking and 90% of the listening. You don't have to follow those ratios literally, but the direction is right: if the manager is doing most of the talking, the meeting has stopped doing its job.

The first 1:1 with a new report or a new manager

The first meeting is about learning how the other person works, not about work itself. You're building a small user manual for each other: how they like feedback, what motivates them, what has gone badly before. Write the answers down, because you'll need them months later when feedback or recognition is due.

Lara Hogan, a management coach and author, published a widely shared set of first 1:1 questions in 2016 that covers exactly this ground, including how someone prefers to receive feedback and recognition. She also keeps a file for each person she manages, with the answers as its starting point. The lists below draw on that idea and extend it to the employee's side.

Questions a manager should ask

• What did your best manager do that you'd like me to keep doing? What did a manager do that you never want to experience again?
• How do you prefer to get feedback: written or spoken, in the moment or saved for our 1:1s?
• Do you like recognition in public, in private, or not much at all?
• What kind of work gives you energy, and what kind drains you?
• When you're stressed, how would I be able to tell? What helps?
• What do you want to be doing in two years, even if it's vague right now?
• Is there anything about how you work, such as hours, focus time or caregiving, that I should know?

Questions an employee should bring

• What does a great first 90 days look like from your point of view?
• How do you prefer to be updated: messages, a doc, or saved for this meeting?
• Which decisions can I make on my own, and which do you want to see first?
• What's the most important thing the team is trying to get right this quarter?
• How will my performance actually be evaluated, and by whom?
• What's one thing previous people in this role struggled with?

If you're the new person on a remote team, the first meeting often happens on camera before you've met anyone in person, so first impressions carry more weight than usual. Our guide to lighting for Zoom meetings covers the cheap fixes that make you easy to read on screen.

Weekly check-in questions that don't turn into status updates

Routine check-ins are where one on ones quietly die. After a few weeks the conversation drifts into a project readout, both people feel it's pointless, and the meeting gets cancelled. The fix is to ask questions that can't be answered with a status report, and to move the status itself somewhere else.

For the manager

• What's on your mind this week?
• What's the thing you're most worried about right now, even if it's small?
• Is there a decision you're waiting on from me or anyone else?
• What took longer than it should have this week, and why?
• What's something you did recently that you're proud of and that I may have missed?
• Is there anything you're working on that you think we should stop doing?

For the employee

• Here's what I need a decision on, and my recommendation.
• Here's a risk I see coming in the next few weeks.
• Is my current priority order the same as yours?
• I heard about a change; what does it mean for our team?
• I'd like a second opinion on how I'm approaching this problem.

Notice the employee items are statements, not questions. Arriving with a recommendation rather than an open problem is the single habit that makes a report's 1:1 time most valuable, because it turns a vague discussion into a quick yes, no or adjust.

Career-growth conversations

Career topics get crowded out of weekly meetings by whatever is urgent, so they need protected time. Some managers reserve one meeting a month for them; the Manager Tools podcast's widely used 30-minute format sets aside its last ten minutes for the future every week. Either works if it actually happens.

For the manager

• Which parts of your job would you like to do more of, and which less?
• What skill do you want to be noticeably better at a year from now?
• Is there someone in the company whose job you find interesting? Would an intro help?
• What would make you feel ready for the next level, and do you agree with what the leveling criteria say?
• What's a stretch project you'd take on if it came up?

For the employee

• What's the gap between my current work and the next level, in concrete examples?
• Who decides on promotions here, and what evidence do they look at?
• Is there a project coming up that would give me visibility on the skill I'm building?
• What would you want to see from me in the next six months to support a raise or a title change?
• Can we revisit this in a month and check progress against what we agree today?

When a growth conversation turns into a compensation discussion, it usually benefits from being written down afterward. Our salary negotiation email templates cover how to put the ask in writing once you've raised it face to face.

Feedback, in both directions

Feedback is the topic both people avoid most, which is exactly why the 1:1 is the right place for it: it's private, regular and low-stakes by design. The trick is to make asking for feedback routine enough that it stops feeling like an event, and to ask questions that can't be answered with a polite "all good."

Kim Scott, author of Radical Candor, recommends that managers ask for feedback before giving it, and her own go-to wording is "What could I do or stop doing that would make it easier to work with me?" She also warns against yes-or-no versions such as "Do you have any feedback for me?", which almost always get a reflexive no, and encourages people to find phrasing that sounds like themselves. After you ask, stay quiet long enough for the other person to actually answer.

Manager asking for feedback

• What's one thing I could do differently that would make your week easier?
• Was there a moment recently where I got in your way?
• Is there anything I say I value that my actions don't back up?
• How clear are my requests? Give me an example of one that wasn't.

Employee asking for feedback

• What's one thing I should do more of on this project?
• If you had to pick one skill that's holding me back, what would it be?
• How did that presentation land with the people in the room?
• Is there feedback about me that you've heard secondhand but haven't passed on?

When feedback needs to go upward from an employee, anchoring it to a specific moment and its effect on the work is safer and clearer than a general judgment: "When the deadline moved on Tuesday without a message, I lost a day of work" lands better than "communication could be better."

Workload and blockers

Overload rarely announces itself. People keep saying yes until something breaks, and by then the manager learns about it from a missed deadline. Workload questions work best when they ask for specifics, such as hours, trade-offs and what got dropped, rather than asking how someone is coping in general.

1. 1Map the load. Manager: "If you listed everything you're on right now, what's on it?" Employee: "Here's my current list. Can we rank it together?"
2. 2Find the constraint. Manager: "What's the one thing that, if it were removed, would speed up everything else?"
3. 3Name the trade-off. Employee: "If I take this on, which of these should slip?"
4. 4Check the invisible work. Manager: "What are you doing that doesn't show up in any tracker, like reviews, onboarding or answering questions?"
5. 5Agree on the unblock. Either side: "Who's doing what before we next meet?"

The last step matters most. A blocker that gets discussed but not assigned will be discussed again next week, which is how 1:1s earn their reputation as meetings where nothing happens.

Wellbeing without prying

Managers should care how people are doing without turning into an amateur therapist or pressing for personal details. The balance is to ask questions that offer an opening but make it easy to decline, and to focus on what you can actually change: workload, schedule, deadlines and support.

• On a scale you choose, how is your energy this week compared with usual?
• Is there anything outside work that's making this stretch harder, that you'd want me to know about? No details needed.
• Would any flexibility on schedule or deadlines help right now?
• What's one thing that would make next week feel more manageable?
• Is there anything you'd like me to stop asking about?

For employees, it's reasonable to share only what's useful for planning: "I have a family situation for the next few weeks and may need to shift some meetings" gives your manager what they need without disclosing more than you want to. Lara Hogan has also published a shorter set of check-in questions for periods of crisis, which is worth bookmarking for weeks when a standard agenda feels tone-deaf.

Remote 1:1s, when you can't read the room

In an office, a manager notices a closed door, a long lunch or a tense exchange in the hallway. Remotely, most of those signals are gone, so the 1:1 has to carry more weight. That means asking directly about things that would otherwise be observed, and making sure the video call itself doesn't get in the way.

Questions that replace the hallway

• Who on the team have you actually talked with this week, beyond messages?
• Is there anyone you're waiting on who's hard to reach across time zones?
• Do you feel you know what's happening in the rest of the company, or does news reach you late?
• Is anything getting lost in written communication that we should talk through live?
• What does a typical day look like for you right now, hour by hour?

Practical habits for remote 1:1s

• Keep cameras on by default for 1:1s, but agree that a voice-only walk-and-talk is fine when both people prefer it.
• Close other tabs and silence notifications. On a call, glancing at a second screen reads as disinterest.
• Put the running doc on screen so both people can see notes being written.
• If you work across time zones, alternate who takes the inconvenient slot rather than always defaulting to headquarters time.

Being easy to see and hear is part of being present. If the person on the other end is squinting at a backlit silhouette, the conversation is harder than it needs to be; our guides to Zoom lighting and a professional Zoom background cover the fixes. 1:1s also can't do the whole job of connecting a distributed team: they build the manager-report relationship, while virtual team building activities and employee spotlight formats build connections across the team.

On that point, a consistent set of profile photos across Slack, the HR system and the team page quietly helps remote colleagues put faces to names. Our piece on team headshots for remote teams covers how to get a matching look across every city.

Structure: agenda, running doc and cadence

Questions only help if the meeting around them is set up to use the answers. Four structural decisions do most of the work: who owns the agenda, where notes live, how often you meet, and how you keep status reporting out. Get these right and even an average set of questions produces a useful meeting.

Who owns the agenda

Following Grove and Horowitz, the employee's items come first. A common arrangement is that the report adds topics to a shared doc before the meeting, the manager adds theirs underneath, and anything unaddressed rolls to next time. Manager Tools popularized a fixed version, a 30-minute weekly meeting split into ten minutes for the report, ten for the manager and ten for the future. It's a useful default if your meetings tend to drift.

Why a shared running doc beats memory

Use one document per relationship, newest meeting at the top. It fixes three problems at once: commitments stop getting forgotten, both people can add topics during the week when they come up, and when review season arrives there's a written record of feedback, wins and growth goals instead of whatever the manager happens to remember from the last month. Keep each entry short, with topics, decisions, and action items with owners.

Weekly or biweekly?

The two best-known sources disagree here, which is a useful reminder that there is no single right cadence. Manager Tools argues for short and frequent; Grove argued for long, at least an hour so that thorny issues have time to surface, with frequency set by how experienced the person is in their current role.

• Weekly, around 30 minutes: better for new reports, new managers, remote teams and fast-changing work. Small issues surface while they're still small. The cost is more calendar time, which adds up for managers with large teams.
• Biweekly or less often, 45 to 60 minutes: works for experienced reports in stable roles and leaves room for deeper topics. Grove suggested weekly meetings for people new to their work and perhaps once every few weeks for seasoned ones. The risk is that one cancellation turns into a month without a conversation.
• Whichever you pick: reschedule rather than cancel. Repeatedly cancelled 1:1s tell a report their concerns are the first thing to go when the week gets busy.

The status-update failure mode

If the first fifteen minutes are always a recap of tasks, move that recap into a written update the manager reads before the meeting, and open with a non-status question instead. A useful test: could this conversation have been an async message? If yes, it should have been, and the time should go to something that needs a live conversation.

When a 1:1 surfaces something serious

Sometimes the question lands harder than expected, and a report describes burnout, a conflict with a colleague, or signs they're thinking of leaving. The goal in the moment is not to solve it on the spot. Listen, confirm you've understood, agree on a next step and follow up when you said you would.

Signs of burnout

• Thank them for saying it, and avoid minimizing it ("everyone's busy") or rushing to fix it.
• Ask what would help first. Often it's removing or delaying a specific piece of work, which a manager can actually do.
• Make a concrete change to workload or deadlines before the next meeting, and say what it is.
• Point to whatever support your company offers, such as an employee assistance program or leave options, and involve HR where company policy calls for it.
• If someone says anything suggesting they may be at risk of harming themselves, treat it as urgent rather than as a work topic. In the US, the 988 Suicide & Crisis Lifeline is available by call or text at 988.

Conflict with a colleague

• Get specifics: what happened, when, and what the effect on the work was.
• Ask what outcome they want. Sometimes it's advice, sometimes it's intervention.
• Don't promise confidentiality you may not be able to keep if the issue involves harassment, discrimination or safety; say that some things you'd have to escalate.
• Agree whether you'll talk to the other person, coach them to do it, or watch and revisit.

A resignation signal

• Ask directly and calmly: "It sounds like you might be weighing other options. Can we talk about what's behind that?"
• Separate what's fixable (project, manager friction, growth path, pay) from what isn't (relocation, a career change).
• Don't make commitments on pay or promotion you can't deliver. Say what you'll find out and by when.
• If they're leaving regardless, the goal becomes a good handover and a relationship that survives it.

For employees raising something serious, the same principle applies from the other chair: say what's happening, say what you need, and ask what the next step is. "I'm running on empty and I think it's the on-call rotation. Can we look at alternatives this week?" gives a manager something they can act on.

A one-page starting agenda

If you want something to paste into a new running doc today, this template covers most weeks. Rotate the career and feedback prompts rather than asking all of them each time, and let the employee's section expand when they need it to. The template is a floor, not a script.

1. 1Employee's topics: what's on your mind, decisions needed, risks.
2. 2Manager's topics: context from above, requests, recognition.
3. 3One rotating prompt: growth, feedback in either direction, or workload.
4. 4Action items: who, what, by when.
5. 5Carry-over: anything not covered moves to the top of next week.