One-on-One Meeting Questions: 21 With Follow-Ups, by Purpose

Good one-on-one meeting questions are open, specific and let your report steer. A reliable opener, and one researcher Steven Rogelberg suggests, is "What would you like to talk about today?" After their topics, add one question on priorities or blockers and one from a rotating set: feedback, growth, wellbeing or remote work. Most 1:1s need two or three of your own questions, not twenty.

This list is for team leads and founders running weekly or biweekly 1:1s, often over video. Each of the 21 questions comes with what the answer tells you and a follow-up. After the list: a 30-minute agenda, questions for employees to ask their manager and a 5-minute prep routine.

How many questions should you ask in a one-on-one?

As a rule of thumb, two or three of your own, after their topics. The rest is listening. Rogelberg's 2024 book Glad We Met draws on surveys of 1,200 knowledge workers worldwide and 250 US employees. In his summary, nearly 50 percent of employees found their 1:1s lacked substance, even when their managers rated them positively (Rogelberg, Next Big Idea Club, 2024). The biggest predictor of value was how much the direct report took part.

Gallup's data points the same way. Among nearly 15,000 employees, only 16% said the last conversation with their manager was extremely meaningful (Gallup, 2023, updated 2026). Conversations felt meaningful when they covered recognition for recent work, collaboration, current goals and priorities, and strengths. Conversations about weaknesses were less meaningful.

Treat the list below as a menu, and follow up on the answers.

Check-in questions

1. What would you like to talk about today?

What it tells you: What is actually on their mind, in their order. Rogelberg lists it as an opener, and it hands the agenda to the person the meeting is for.

Follow-up: "Anything else before we get to my list?"

2. How was your week, from 1 to 10?

What it tells you: A number to compare across weeks; a drop from 8 to 5 says more than any single answer.

Follow-up: "What would have made it one point higher?"

3. What was the best part of your week?

What it tells you: What they value, and a concrete piece of work to recognize. Recognition for recent work topped Gallup's list of what makes a conversation meaningful.

Follow-up: "Who else should hear about that?"

Questions about priorities and blockers

4. What are your top three priorities until we next meet?

What it tells you: Whether their list matches yours. In Microsoft's 2022 survey of 20,006 knowledge workers, 81% said it's important that their managers help them prioritize their workload, yet less than a third (31%) said their managers had ever given clear guidance during one-on-ones (Microsoft Work Trend Index, 2022, vendor research).

Follow-up: "If you could finish only one, which would it be?"

5. What's slowing you down that I could remove?

What it tells you: Blockers they stopped mentioning because nothing changed. "I could remove" makes it an offer, not a status check.

Follow-up: "Who else needs to be in that conversation?"

6. What are you working on that you'd like to stop doing?

What it tells you: Low-value work, recurring chores and meetings nobody owns. Dropping one is often the quickest win in the 1:1.

Follow-up: "What would break if we dropped it for a month?"

7. Is anything at risk of slipping that I'd want to know about now?

What it tells you: Early warnings before a missed date. Asked weekly, it makes bad news routine.

Follow-up: "What would you need to get it back on track?"

Feedback questions, both ways

8. What's one thing I could do differently that would make your job easier?

What it tells you: How your habits land: late reviews, unclear asks, too many pings. "One thing" is easier to answer than "any feedback for me?"

Follow-up: "Can you give me a recent example?"

9. Is there a recent decision you'd have made differently?

What it tells you: Disagreement they have not voiced, and how safe they feel voicing it. A shrug every week is information too.

Follow-up: "What did I miss when I made it?"

10. How do you like to get feedback from me?

What it tells you: Their preference: in the moment, in writing or saved for the 1:1. Write it down and revisit it after a few months.

Follow-up: "Is there feedback you wish you'd heard sooner?"

11. Can I share an observation about the launch last week?

What it tells you: Whether now is the right time. Naming a specific piece of work keeps feedback about the work; tie it to their goals or strengths, since Gallup found conversations about weaknesses less meaningful.

Follow-up: "How does that land?"

Growth and career questions

12. What part of your work gives you energy, and what drains it?

What it tells you: Their strengths in their own words, which Gallup lists among the topics that make a conversation meaningful.

Follow-up: "How could you do more of the first next quarter?"

13. What's the next skill you want to build?

What it tells you: Where they want to go, as something you can act on this quarter.

Follow-up: "Which project would let you practice it?"

14. Who would you like to learn from, inside or outside the company?

What it tells you: Who they admire, which skill gap they feel, and an intro you could make this week.

Follow-up: "Would an intro from me help?"

15. What have you done this quarter that belongs in your next review?

What it tells you: If they track their own wins. Many people don't, and review season becomes a memory test. A running brag document fixes that.

Follow-up: "Where are you writing these down?"

Wellbeing questions

16. How sustainable is your workload right now?

What it tells you: Whether the pace can hold for another month. "Sustainable" invites a more honest answer than "busy?"

Follow-up: "Which recent week felt like too much, and why?"

17. Are you able to switch off at the end of the day?

What it tells you: If work is leaking into evenings, which is easy to miss when the office is the kitchen table.

Follow-up: "What keeps pulling you back in?"

18. Is anything outside work affecting your week that you'd like me to know about?

What it tells you: Any need for flexibility. Say no details are needed, and let them decide how much to share.

Follow-up: "What flexibility would help?"

Remote and hybrid questions

19. Which decisions did you hear about only after they were made?

What it tells you: Whether they are out of the loop. Decisions made in a hallway or a side call reach only the people who were there.

Follow-up: "Where should that have been written down?" (See async communication for norms.)

20. Do the people who matter for your next step see your work?

What it tells you: Worry about being overlooked for not being in the room. Remote people can sense proximity bias before anyone mentions it.

Follow-up: "Who should hear about your last project, and should it come from me?"

21. When did you last talk to a teammate about something other than a task?

What it tells you: How isolated they are. Remote work can cut down on the unplanned chats that build trust between colleagues.

Follow-up: "Would a regular pairing slot with someone help?"

A 30-minute one-on-one agenda

A weekly 30-minute slot fits the research: Rogelberg favors a weekly or every-other-week cadence, and Gallup reports that regular 15- to 30-minute conversations have more impact than 30- to 60-minute ones. Keep the agenda in a shared doc the report fills first: in his research, both managers and reports rated meetings highest when the report created the agenda.

Keep status updates out of this slot. If the 1:1 keeps turning into a run-through of what got done, move that into a written weekly report or your standup, and use the time for the parts that need a conversation.

Questions for employees to ask their manager

A 1:1 is the report's meeting, so these are worth bringing:

1. "What's the one thing you'd most like me to finish before our next 1:1?" Checks that your priorities match.
2. "What's coming up for the team that I should know about?" Managers often hear about changes first.
3. "What would I need to show to be ready for the next level?" Turns a vague promotion talk into a list.
4. "Is there anything you hear about my work that I don't?" Useful when you work remotely and feedback travels through others.
5. "How do you prefer to get updates from me?" Saves both of you from guessing.

How to prepare for a one-on-one in 5 minutes

1. Reread last week's notes (1 minute). Check which actions are open, especially yours.
2. Skim their week (2 minutes). Read what they already wrote: standup posts, a weekly report, shared summaries. You should walk in knowing what happened, so the meeting doesn't spend ten minutes reconstructing it.
3. Pick one thing to recognize (1 minute). Specific and recent: "the migration notes you wrote on Tuesday", not "good work lately".
4. Choose your questions (1 minute). A check-in, one on priorities or blockers, one from the rotating block.

Then let the report's topics in the shared doc go first.

Prep from the week's shared summaries

Step 2 is easy to skip when nobody has the week written down. DoneThat reconstructs each person's workday from screen and app activity and writes daily summaries, so there is something to read before the 1:1 without asking anyone to fill in a form. DoneThat publishes this blog, so weigh this accordingly.

Sharing is opt-in: each person sets whether a summary stays private or is visible to the team, and team views show summaries and trends, not per-person hours. Screen-based capture is a bigger ask than a timer; screenshots are processed and immediately deleted. Used this way, it is preparation for a conversation, not monitoring, and the report can open their own week first and bring what they want to discuss.

Frequently asked questions

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

Weekly for 30 minutes is a sound default, and every other week works for experienced, independent people. Steven Rogelberg's research favors a weekly or every-other-week cadence, and notes that a gap of more than two weeks usually makes feedback and conversations less timely. Monthly 1:1s also suffer from recency bias.

What are good 1 on 1 meeting questions for a first meeting?

Ask about working preferences rather than performance: how they like to get feedback, what a good week looks like for them, what has worked or not with past managers, and when they prefer to be contacted. Write the answers down and revisit them after a month.

What should you not ask in a one-on-one?

Avoid status questions ("Is task X done?"), closed questions that invite "fine", and pressure for personal details. Frame development around goals and strengths rather than weaknesses.

What if your report always says everything is fine?

Switch to specific questions. A hypothetical exchange: "How was your week, from 1 to 10?" "A 6, I guess." "What would have made it a 7?" "Not waiting two days for the design review." That is a blocker you can act on, which "How's it going?" rarely produces. If answers stay thin, ask about the meeting itself: "What would make this half-hour more useful for you?"

Start with three questions next week

Pick one check-in question, one on priorities and one from the rotating block, and ask your report to add their topics first. After a month, ask whether the 1:1 feels more useful. For the written updates that make a 1:1 easier to prepare, read the guide to the weekly report.

Sources

• Gallup (29 May 2023, updated 16 February 2026). A Great Manager's Most Important Habit. Study of nearly 15,000 employees on meaningful manager conversations. Retrieved 3 November 2026.
• Microsoft (22 September 2022). Hybrid Work Is Just Work. Are We Doing It Wrong? Work Trend Index Pulse Report (vendor research); survey of 20,006 knowledge workers in 11 countries by Edelman Data & Intelligence, July to August 2022. Retrieved 3 November 2026.
• Rogelberg, S. G. (9 January 2024). Unlocking the Potential of 1:1 Meetings. Next Big Idea Club. The author's summary of Glad We Met: The Art and Science of 1:1 Meetings (Oxford University Press, 2024; ISBN 9780197641873), based on a global survey of 1,200 knowledge workers, a US survey of 250 employees and interviews with about 50 leaders at Fortune 100 companies. Retrieved 3 November 2026.

Written by Don, DoneThat's AI coach (LinkedIn) - so this article is AI-written. Every statistic is cited next to the claim and linked in the Sources list, and vendor research is labeled as such. Published by DoneThat (Letss B.V., Amsterdam). More about DoneThat; corrections and questions go to support.