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One on One Questions: 60 by Situation, and an Agenda

· 7 min read

On this page
  1. Why the meeting is worth keeping
  2. A 30-minute agenda
  3. First one-on-one with a new report
  4. A normal week
  5. Workload and blockers
  6. Career and growth
  7. Feedback, both ways
  8. After a hard week
  9. Skip-level meetings
  10. Questions to ask your manager
  11. Rotate the themes
  12. When the work itself is the topic
  13. Sources

The calendar says “1:1, 30 min” every Tuesday. By the third month it has become a status update: the person reads out what the board already shows, the manager says “great, anything else?”, and both leave five minutes early. The meeting exists, but it no longer does its job.

A good question fixes that faster than a new template. Below are sixty, grouped by the situation you are actually in, plus questions to ask your own manager, an agenda that leaves room for them, and a rotation so the same five questions do not come back every week.

Short answer: let the person set most of the agenda, keep status out, and pick two or three questions for the situation: a first meeting, a normal week, too much work, career, feedback, a hard week, a skip-level. Rotate themes so each comes back about once a month. Regular meetings matter: Gallup found employees whose managers meet them regularly are almost three times as likely to be engaged.

Why the meeting is worth keeping

Gallup’s numbers are the reason to protect the slot. In its State of the American Manager research, Jim Harter and Amy Adkins write that “employees whose managers hold regular meetings with them are almost three times as likely to be engaged as employees whose managers do not hold regular meetings with them”, and that “engagement is highest among employees who have some form (face to face, phone or digital) of daily communication with their managers” (Gallup). An earlier Gallup piece puts numbers on it: “only 15% of employees who work for a manager who does not meet with them regularly are engaged; managers who regularly meet with their employees almost tripled that level of engagement” (Gallup, 2014).

That is about meeting regularly, not about a particular script. The questions are there to make the regular meeting worth having.

A 30-minute agenda

MinutesPartWho leads
0 to 5How are you, really? One personal question, no work yetManager
5 to 20Their topics, in their orderThe person
20 to 27One theme question from the rotation belowManager
27 to 30What each of you will do before next timeBoth

Keep a shared note with the topics, written by either of you during the week, and the commitments from last time at the top. If the person has nothing for their part two weeks in a row, that is a signal too.

First one-on-one with a new report

  1. What did your best manager do that you would like me to do too?
  2. What did a manager do that you never want to see again?
  3. How do you like to get feedback: written, in the moment, saved for this meeting?
  4. When you are stuck, how will I know?
  5. What do you want to be known for on this team in a year?
  6. What is something about how you work that people usually learn too late?
  7. How often should we meet, and how long, for it to be useful to you?
  8. What should I never schedule over?

A normal week

  1. What is on your mind that is not on the board?
  2. What went better than you expected since we last talked?
  3. What is taking more of your energy than it should?
  4. Is there a decision you are waiting on from me or anyone else?
  5. What would you like more of, or less of, next week?
  6. Who on the team helped you recently, and do they know?
  7. What is one thing I could take off your plate?
  8. If you had a free day next week, what would you spend it on?

Workload and blockers

  1. On a scale of one to ten, how full is your week, and what number is sustainable?
  2. What did you say yes to that you would now say no to?
  3. Which piece of work keeps slipping, and why do you think it does?
  4. Where are you waiting on another team?
  5. What could we stop doing without anyone noticing?
  6. What are you doing outside work hours that should not need to be?
  7. Which meeting could you skip without missing anything?
  8. If something has to drop this sprint, what should it be?

Career and growth

  1. What do you want to be doing in two years?
  2. Which part of your work would you happily do all week?
  3. What skill would make the biggest difference for you this year?
  4. Is there a project coming up that you would like to be on?
  5. Who in the company would you like to learn from?
  6. What would make your next review an easy one to write?
  7. What is one thing you did this quarter that you are proud of?
  8. Are you being asked to do things below or above your level, and how does that feel?

Feedback, both ways

  1. What is one thing I should start doing as your manager?
  2. What should I stop doing?
  3. What did I do this month that did not help?
  4. Is there feedback you have been holding on to for a teammate?
  5. How did the last decision I made land with you?
  6. Here is something I noticed. How does it look from your side?
  7. What would you change about how we work if it were up to you?
  8. Is there anything you think I am not hearing?

After a hard week

  1. How are you doing, apart from work?
  2. What made this week hard?
  3. What would help right now: time, help, or just someone knowing?
  4. Is there anything you want me to tell the team, or not tell them?
  5. What would a lighter next week look like?
  6. When did you last take a proper day off?
  7. Is this a one-off or has it been building up?
  8. What is one small thing we can change by Friday?

Skip-level meetings

  1. What slows the team down that I might not see?
  2. What would you fix first if you ran the team?
  3. What is working well that we should protect?
  4. Do you know what the company’s priorities are this quarter, and how your work fits?
  5. Is there anything you feel you cannot say in team meetings?
  6. What do you need from leadership that you are not getting?

Questions to ask your manager

  1. What would make you more confident in my work?
  2. What are you hearing about our team that I am not?
  3. What is the most important thing for me to get right this quarter?
  4. Where do you see me in a year, and what would get me there?
  5. What does your week look like, and how can I make it easier?
  6. Is there something you have been meaning to tell me?

Rotate the themes

Asking “what is on your mind?” every week works for a while, then the answers shrink. A simple rotation keeps each theme coming back roughly once a month, with the normal-week questions in between:

A 13-week rotation for one-on-one theme questions over a quarter. Week 1 normal week, week 2 workload, week 3 career, week 4 feedback, week 5 normal week, week 6 workload, week 7 feedback both ways, week 8 career, week 9 normal week, week 10 workload, week 11 feedback, week 12 career, week 13 a look back at the quarter. Hard-week questions replace the theme whenever they are needed. The person's own topics come first every week.

Hard-week questions are not on the schedule. Use them when the week calls for it, and drop the planned theme.

When the work itself is the topic

Workload questions work best with something concrete on the table. If your team uses Jira, our app Burnout Radar builds a private weekly report from a person’s own work: logged time against estimates, overdue items, blocking links and other workload signals. Only that person sees it unless they choose to share it, so it suits a 1:1 the person brings it to, not one where a manager checks on them. When someone is away, OutSync shows who is out on the Jira board, so a 1:1 does not land on a day off.

For the question of how much work is too much, our overwork cost simulator shows what long weeks do to output over time, with the studies behind it.

Sources

Frequently asked questions

What are good questions to ask in a one-on-one?

Ones that open a conversation the status update cannot: "What is taking more of your energy than it should?", "What would you change about how we work if it were up to you?", "What did I do this month that did not help?". Pick by situation; the lists on this page are grouped that way.

What should I talk about in a 1:1 with my manager?

Your agenda first: blockers, decisions you need, feedback you want, and where you want to grow. Questions such as "What would make you more confident in my work?" or "What are you hearing about our team that I am not?" turn the meeting into one for you.

How often should one-on-ones be?

Often enough to be regular. Gallup found that employees whose managers hold regular meetings with them are almost three times as likely to be engaged, and that engagement is highest with some daily communication. Common choices are 30 minutes weekly or 45 minutes every two weeks.

Should a one-on-one be a status update?

No. Status belongs in the board or the stand-up. Keep the 1:1 for what does not fit there: workload, friction, growth, feedback and anything the person does not want to raise in front of the team.

What should I ask in a skip-level meeting?

Questions about the system, not the manager: "What slows the team down that I might not see?", "What would you fix first if you ran the team?", "Is there anything you feel you cannot say in team meetings?". Promise what happens with the answers before you ask.

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