191 deep questions

Deep questions with room to think.

Questions about values, growth and what makes work and life meaningful. Deep, but never prying: nothing about health, relationships or anything painful. For offsites, small groups and one-to-ones.

Use them in a meeting Try a live check-in

Short answer

A deep question invites reflection without demanding a confession. Ask about values, lessons and hopes rather than private life, give people a minute to think before anyone speaks, and always let them pass.

1.
What's something you changed your mind about recently?
Work
2.
What's one thing you'd tell yourself on your first day here?
Work
3.
When did you last feel properly proud of your work?
Work
4.
What's a habit that has made your weeks better?
Work
5.
What drains your energy at work, and what gives it back?
Work
6.
What's a mistake you learned the most from?
Work
7.
Who taught you something important without knowing it?
Work
8.
What's a question you wish people asked you more often?
Work
9.
What does a really good day at work look like for you?
Work
10.
What would you do more of if you had an extra hour each day?
Work
11.
What's something you're quietly getting better at?
Work
12.
What's the best feedback you've ever received?
Work
13.
What's one thing you want to learn before the year ends?
Work
14.
When do you do your best thinking?
Work
15.
What's a small risk you're glad you took?
Work
16.
What's something that seemed hard last year and is easy now?
Work
17.
What part of your job would you keep if you could only keep one?
Work
18.
What's one thing that would make this team better at disagreeing?
Work
19.
What's a book, talk or podcast that changed how you work?
Work
20.
What do you want people to come to you for?
Work
21.
What's one thing you'd stop doing tomorrow if you could?
Work
22.
What does being 'done' mean to you on a project?
Work
23.
Which of your strengths is most underused right now?
Work
24.
What helped you get through a tough stretch at work?
Work
25.
What's something you've been putting off, and why?
Work
26.
What would you try if you knew it couldn't fail?
Work
27.
What made the best team you've worked in so good?
Work
28.
What do you need more of from this group?
Work
29.
What's one assumption about our work we should test?
Work
30.
What's a win from the last month that nobody noticed?
Work
31.
What does a well-lived week look like to you?
Any room
32.
What's a value you hold today that you didn't hold ten years ago?
Any room
33.
What do you hope people say about you when you're not in the room?
Any room
34.
What's a question you'd love to know the answer to before the end of your life?
Any room
35.
Which experience taught you the most about patience?
Any room
36.
What does success mean to you, in your own words?
Any room
37.
What's something you've learned the hard way that you'd happily pass on?
Any room
38.
When do you feel most at peace?
Any room
39.
What's a belief you hold that most people around you don't share?
Any room
40.
What does it mean to you to be a good neighbour?
Any room
41.
What's a small daily choice that says a lot about who you are?
Any room
42.
What would you do with an extra year that didn't count towards your age?
Any room
43.
What's one thing you wish you'd started earlier?
Any room
44.
What's a kindness you received that you've never been able to repay?
Any room
45.
What's the most important thing you've changed your mind about?
Any room
46.
What do you want more of in your life, and what's stopping you?
Any room
47.
What's a lesson from a grandparent or elder that stayed with you?
Any room
48.
What kind of courage do you most admire?
Any room
49.
What's a dream you've let go of, and how do you feel about it now?
Any room
50.
What do you think makes a good life?
Any room
51.
If you could send one message to everyone on Earth, what would it say?
Any room
52.
What does it mean to you to be generous?
Any room
53.
What's a tradition you'd like to pass on to the next generation?
Any room
54.
Which moment in your life would you like to understand better?
Any room
55.
What's a fear you've overcome, and how did you do it?
Any room
56.
What do you think people need most from each other right now?
Any room
57.
What does home mean to you?
Any room
58.
When have you felt most proud of someone else?
Any room
59.
What's one thing you're certain of?
Any room
60.
What's something you're still figuring out?
Any room

Deep questions: common questions

What makes a question deep but still appropriate at work?

It asks about values, growth or meaning, not private life. What does success mean to you is deep; anything about health or family isn't for a team meeting.

When should I use deep questions?

At offsites, the start of a new year or project, one-to-ones and small groups that already trust each other. Not in a 15-minute stand-up.

Ask it, and every phone answers.

In Agendiq a question becomes a check-in, a vote or an idea board. Everyone answers on their phone at once and the answers land on the shared screen.

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Deep questions with room to think.

Deep questions: common questions

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