52 Questions to Get to the Heart of Your Team and Make Meetings Matter

everal years ago at dojo4, it felt like pulling teeth to get everyone in a room once a week to check in with each other. Just the word ‘meeting’ made people avoid eye contact with me; it felt like punishment rather than a way for people to know what everyone else was doing and see how we could best help each other.

So I decided to structure the weekly meetings as simply as possible and promise that they would never take more than 15 minutes once a week. Everyone would stand in a circle and be asked to go around and answer the basic questions: “What are you working on?”, “What do you need help with?”, “What will you be working on next?” But the feeling didn’t change. The punishment theme held steady, and even if it wasn’t that bad, it was definitely dull, tedious, and frankly, useless. We each got a dry overview of what other people around dojo4 were doing, but not particularly any more than we could have figured out by just paying even mild attention to each other throughout the day-to-day. Perhaps more importantly, we weren’t connecting with each other any more than we would just casually around work.

But the need still felt like it was there: how could we connect with one another on a regular basis, providing some cadence and cohesion within the group of us that make up this company?

Then one day, my co-founder Ara came to me with a thought. He had been thinking about how we offer our clients and their projects much more than design and technology services; we offer our clients understanding. We base our relationships on developing sturdy, innovative and satisfying technology and design products. This takes listening and understanding to figure out what is unique about each client and each product, what the nuances are of the market that the product will be entering, and what the particular context requires. We are building technology not for users, but for humans. Since that is one of the main things we offer as a business, the logic follows that we should be cultivating that within the company. With that in mind, Ara suggested and I offered to host a different kind of weekly check-in.

Thus, at dojo4 we have asked each other one question every Friday at noon for the past six years and counting. Here’s the context…We stand in a circle. We bow. We clap. We do a minute of silent meditation. One person asks a question that helps us know and understand each other better. We’ve had easy questions and hard questions, poignant questions and silly questions.

Obviously, there have been many more than the following queries, but here are a selection of 52, just in case you are inspired to do something similar for a year and need some prompts:

1. If you were not bound by the constraints of time and space and could explore anything in the universe, what would you explore?
2. What’s the most surprising thing that nobody knows about you?
3. What is one of your favorite family traditions?
4. If you could only bring one thing with you on a trip, what would it be?
5. What is a skill with your hands that you would like to develop?
6. How do you deal with distraction?
7. What’s the best concert you’ve been to?
8. Who was the first person you kissed?
9. What’s the last thing you did to help a random stranger?
10. What are you grateful for today that you haven’t yet gotten a chance to say thank you for?
11. What’s one of your favorite places in the world?
12. If your life was a hot air balloon and you could throw something overboard to make it float more successfully, what would you jettison?
13. What was the first album you owned?
14. What is one of your favorite pieces of art and why?
15. What’s a habit you have that you’d like to give up or change?
16. What’s the most dangerous thing you do?
17. What helps get you in the flow?
18. What’s your earliest memory?
19. What is your favorite thing about this season?
20. What is something you aspire to do before the end of this year?
21. How do you deal with disappointment?
22. What is an unusual skill or talent that you have?
23. What is something you like to cook and make well?
24. What’s something you’d like to know how to cook?
25. If you weren’t here right now, where would you be instead?
26. What is your most valuable travel advice?
27. What’s one your favorite places in the world?
28. What is one of the most rewarding or challenging things for you about being in community?
29. How do you experience magic in your life?
30. Ignoring all practical restraints, if you could spend a year doing any charitable activity, what would it be?
31. What is the most surprising / unexpected element of your life?
32. Do you have a good bullshit detector, and if so, how does it work?
33. What is a phrase you’d like to hear more? And what is a phrase you’d like to say more?
34. Which of the sense perceptions are you most attached to and why?
35. What’s something you said too late?
36. What did a typical Friday or Saturday night look like for you when you were about 16 years old?
37. Where do you fall in the sibling lineup (oldest, youngest, middle, single, etc.) and how do you think this has affected you as a person?
38. If you were going to give a TED talk, what would it be about?
39. If you could live one year of your life again, what year (age) would that be?
40. What skill, that you don’t currently have, would you want to develop for life after the apocalypse?
41. With the skills that you currently have, what will your career be after the apocalypse?
42. What executive action would you take if you were President of the country?
43. When you are stressed, anxious, depressed, etc., do you divert yourself or does that make it worse? If you divert yourself, what do you do that works?
44. What’s the longest time you’ve ever gone without speaking? What was the context?
45. Do you plan for worst case scenarios? If so, how?
46. What is your favorite surface to walk on barefoot?
47. How do you justify your worst habits?
48. What triggered the last time you had a belly laugh?
49. What’s the closest you’ve ever come to death?
50. What is something you know now that you wish you would have known when you were a teenager?
51. Of all your worldly possessions, what would be the hardest to give up?
52. Who are you named after?

Then, in addition to asking the questions, we use the following guidelines of council as the framework to respond:

• Speak from the heart
• Listen completely
• Be spontaneous
• Be lean
• Everything is confidential
• …and we signal the end with a clap and a bow, and then we all have lunch together.

We do this every week, whether there are two of us or 12 of us. We do it with guests. We do it whether we’re busy or not. It’s part of how we’ve overcome the inevitable seasickness that comes with the swells and dips of being a small business. No doubt, it’s made us a better business.

A version of this originally published on dojo4’s blog.