101 Questions to Ask in One on Ones

So you’re having one on ones with your team. Awesome. It’s an essential element to being a good manager. But are you making the most of them?

Do you come in prepared and ready to make the most of each one or do some go better than others as you wing it half the time? Are you too dependent on them bringing the agenda? Do you ask the same 3-5 questions every time?

This list will help you make the most of each meeting and have a quick reference when you feel your questions may be getting stale or you have a few minutes left in a one on one.

101 Questions to ask in one on ones

One on ones are all about your people and building a strong, trusting relationship with them. Asking questions like the ones below and following through on what you talk about will build a strong, lasting relationship for each member of your team.

Asking 1 or 2 of these questions each one on one will keep things fresh, while ensuring you’re covering important subjects regularly. It also gives you ample time to dive into each question as they often will open up into greater detail as long as you follow up with questions like “Why?” and “Tell me more…”

I’ve organized these questions by the high level categories you’ll commonly touch on in one on ones so you can quickly skim through it for a question in a topic you want to cover that meeting.

Questions to talk about Short Term Goals

Short term goals are things to be done in the current quarter or month. They’re high level projects assigned to that person.

1) How is [project] going? What could we do to make it better?

2) Is there anything blocking you from getting your work done?

3) Are there any projects you’d really like to work on if you were given the opportunity?

4) What parts of your job would you like to deepen your skills in or get additional training in?

5) Is any part of your project unclear or confusing?

These are all about getting feedback so you can improve their day to day and relieve frustrations on their projects. You already spend a lot of time on their day to day job in standups, status reports, etc so this is intentionally a short set of questions relative to other areas you spend a lot less time talking about usually.

Questions to talk about Long Term Goals

Long term goals are all about who they want to become. Everyone is growing in different ways and people are happiest when they feel like they’re making progress on their big life goals. These questions will help you learn what those goals are and see if they feel they’re making progress on them.

6) What do you want to be doing in 5 years? 10 years? 3 years?

7) What are your long term goals? Have you thought about them?

8) Do you feel like you’re making progress on your big goals here? Why or why not?

9) What’s one thing we could do today to help you with your long term goals?

10) Do you feel we’re helping you advance your career at a pace you would like?

11) Who do you really admire? Why? (People often admire those they want to become)

12) If you had millions of dollars, what would you do every day?

13) What are your super powers? What powers would you like to develop?

14) What are your big dreams in life? Are you making progress on them?

15) Could you see yourself making progress on more of your goals here? What would need to change to do so?

16) What work are you doing here that you feel is most in line with your long term goals?

17) As a kid, what did you want to be when you grew up?

These questions will help you make sure your people are progressing in the areas that matter most to them. Realize they will change over time, and it takes time for people to really open up about their dreams, so it helps to revisit them regularly.

Questions to talk about Company Improvement

Company suggestion boxes have a pretty bad reputation for being unread and never acted on. It’s also hard to convey the nuances of a problem or opportunity for a company on a tiny note card or feedback form.

Asking questions about improving the company during one on one time can help uncover what people in the trenches are seeing and get great ideas to improve the company. All of this while having the chance to easily ask follow up questions to better understand them.

18) What is the company not doing today that we should do to better compete in the market?

19) What’s one thing we’d be *crazy* not to do in the next quarter to improve our product?

20) How could we change our team meetings to be more effective?

21) If you were CEO, what’s the first thing you’d change?

22) Do you think our company is loyal to its employees? Why or why not?

23) Are there any aspects of our culture you wish you could change?

24) What are your favorite parts about our culture?

25) Do you feel over-worked, under-worked, or just the right workload?

26) Why do you think [employee who recently quit] left? What did they tell you?

27) What would convince you to leave for a job somewhere else?

28) Which company values do you like the most? Which the least? Why?

29) What is the #1 Problem at our company? Why?

30) Do you feel like you’re on the same page with your team? How often do you think you need meetings to ensure you stay that way?

31) What do you think are the long term prospects of the company?

32) How many hours a day do you feel you’re productive? How could we help you be more productive?

33) How could we be more creative or innovative as a company?

You may not always like the answers you hear when you dig in for feedback like this, but that’s the point. If you take action on the things you can change and help your reports understand why some others are the way they are, you can help relieve a lot of frustration while making people feel heard.

Questions to talk about Self Improvement

Creating a culture of learning and self improvement starts with discussions like one on ones to help people understand what they should do differently. By discussing them in private, you avoid embarrassing them in a more public setting and can coach them through the changes needed.

34) Do you feel challenged at work? Are you learning new things?

35) What area of the company would you like to learn more about?

36) What skills would you like to develop right now?

37) Who in the company would you like to learn from? What do you want to learn?

38) How do you prefer to receive feedback?

39) Do you feel you’re getting enough feedback?

40) What’s a recent situation you wish you handled differently? What would you change?

41) What additional training or education would you like?

42) Are there any roles in the company you’d like to learn more about?

43) What do you think are the key skills for your role? How would you rate yourself for each of them?

44) Is there an aspect of your job you would like more help or coaching?

These questions will all reveal ways you can help people grow and improve them in their job. The key is to realize that the follow up questions need to include action items and advice for helping them make progress on what you just discussed. Doing always trumps just talking about it.

Questions to talk about Manager Improvement

The saying goes, “People don’t leave jobs, they leave managers.” That means receiving and getting feedback from your team members is a crucial part of your job.

Asking your team directly for feedback will help you not only improve, but also build the trust that you’re as open to feedback as you want them to be. Set a good example with questions like these below.

45) What could I do as a manager to make your work easier?

46) What do you like about my management style? What do you dislike?

47) Would you like more or less direction from me on your work?

48) What could I do to make you enjoy your work more?

49) How can I better support you?

50) What would you like to know about me?

51) Is there a situation you’d like my help with?

52) What is something I could do better? What is a criticism you have for me?

When your reports have the courage to give you candid feedback, make sure you fully understand it and thank them. It can be scary to say something negative to their manager. If you don’t follow through on the feedback, you will lose their trust and they may start to resent you.

Questions to talk about Happiness

Whether it’s a work related issue or a personal one, a person’s happiness will have a major impact on their productivity and morale at work. A one on one is the best time to dig into any issues that may be affecting them and do things to help them with it.

53) Are you happy?

54) Are you happy working here?

55) Are you happy with your recent work? Why or why not?

56) What would make you leave this job for another?

57) What’s one thing we do to help you enjoy your job more?

58) Is your job what you expected when you accepted it?

59) What worries you?

60) What’s on your mind?

61) What’s not fun about working here? What do you enjoy most about working here?

62) Who are you friends with at work? (Shown to be a key to enjoying your job)

63) When was the time you enjoyed working here the most?

64) What do you feel is your greatest accomplishment here?

65) What’s something you feel is undervalued that you contribute to the team?

66) What part of your job do you wish you didn’t have to do?

These can be some of the hardest questions to ask. If someone is unhappy, they can be particularly cagey, so do your best to give them space and listen carefully. Helping them based on these answers can save an employee you were on the brink of losing.

Questions to talk about Personal Life

Your employees are one complete person. No matter how much you’d like them to, problems in their personal life will affect them at work. You don’t need to be there therapist, but a little empathy can go a long way with these kinds of questions.

67) How are you? How is life outside of work?

68) How do you feel your work/life balance is right now?

69) How do you feel about your current compensation (salary and benefits)?

70) What’s one thing we could change about work for you that would improve your personal life?

71) If around a holiday: What did you do for [Holiday]? How was it?

72) How are your parents/grandparents? Where do they live?

73) If they have children: How is [name of child] doing? (Ask something related to their age like starting school, playing sports, or other interests.)

74) What do you like to do in your free time? What are your hobbies?

75) What did you do for fun in the past that you haven’t had as much time for lately?

76) What drives you? What motivates you to come to work each day?

These questions can help you much better understand people’s motivations and interests. Empathizing with situations like a divorce, sick parent or grandparent, a death in the family, or positive moments like children, a successful side project, or fun activity can all go a long way towards building great rapport for your team. It can also inspire inexpensive ways to thank a team member.

Questions to talk about Team Relations

Your team spends 8+ hours a day working together. One of the biggest opportunities for improvement in productivity comes from improving the interpersonal relationships among team members. Questions like these help uncover problems and opportunities to help every person become a better team member.

77) Who on the team do you have the most difficulty working with? Why?

78) How would you describe the work environment on the team? Is it more competitive or collaborative?

79) How could we improve the ways our team works together?

80) Who is kicking ass on the team? What have they done?

81) Who do you admire on the team? Why?

82) Do you feel your ideas are heard by the team and I?

83) Who would you like to work more often with? Why?

84) Is everyone pulling their weight on the team?

85) Do you help other members on the team? Do others help you when you need it?

86) What’s one thing we should change about how our team works together?

87) What characteristics make someone a good fit for our team? How would you look for those characteristics in an interview?

88) What’s the biggest thing you’d like to change about our team?

89) What do you like most about working on our team?

90) Has anyone on the team ever made you feel uncomfortable? What happened?

One on ones are a great time to coach people on issues they’re having with coworkers. You can also use it as an opportunity to uncover problems on the team before they blow up into a big deal.

Questions to talk about Work Habits

The more you can learn and understand how each team member operates, the more productive they can become. These questions can help you work with them to learn what their work habits are.

91) What part of the day do you have the most energy and focus? When do you have the least? What changes could we make to your work schedule to accommodate this?

92) What are 3 things would you buy to improve your productivity if money was no object?

93) What is an ideal, productive day at work for you? Walk me through the day…

94) What’s an inexpensive thing we could do to improve our office environment?

95) What are the biggest time wasters for you each week?

96) What makes you excited and motivated to work on a project?

97) When you get stuck on something, what is your process for getting unstuck? Who do you turn to for help?

98) What part of your work routine do you find is working best? What area do you want to improve?

99) Are there any meetings or discussions you feel you should be a part of that you’re not? Are you included in any you don’t want to be a part of?

100) What do you do when you feel low energy or unmotivated?

101) How can I help…? (be more productive/happier at work/enjoy work more/etc)

The best ideas come from people in the trenches. While you may be in meetings, buzzing around the office or traveling, they likely see things in the office that affect their productivity a lot (for better and worse). Making changes can have a huge impact on your team’s output.

…and the 2 questions to ask in *every* one on one:

None of the things you talk about in one on ones matter if you don’t follow through and take action on them. These two questions will ensure you always follow through with the important things you discuss in your one on ones:

1) What can I hold you accountable for next time we talk?

2) What can I be accountable to you for the next time we talk?

Wow. That was *a lot*!

Shout outs to Popforms, Manager Tools, and this Quora thread for help inspiring this list.

Source: https://jasonevanish.com/2014/05/29/101-questions-to-ask-in-1-on-1s/