36 questions to fall in love… with your team

36 questions to fall in love… with your team

People often ask me: ‘how can we run more productive team meetings?’ My reply? It depends on your objective, of course. But it also depends on what you mean by productive, and that’s where things get particularly interesting. If, by productive, you mean burning through a to-do list, divvying up tasks or creating work together there are meeting formats like kanbans, standups, ceremonies and Amazon-style no Powerpoint memo meetings. In some cases it’s more productive to cancel the meeting entirely, especially given most of us are now spending 85% of our work week in meetings.

But there’s a different kind of productive which calls for a different kind of meeting, especially now so many of us are finding ourselves on remote or hybrid teams when we didn’t first set out that way. Productive can also mean building deeper relationships and trust. The kind of connections that pay dividends when you need to get into production mode. These are the connections that help us jam in our work by creating a foundation of truth and safety between our team members, which is the number one predictor of high performing teams.

At Brink, when the pandemic first hit and we, too, found ourselves a distributed remote team for the first time, we scheduled a Monday Morning all-hands to stay connected. Our objective was to have a view of all the work going on across the team that week. We even had a spreadsheet of our projects and tasks we would look at together.

But once we’d started the meetings, we noticed something very interesting. The casual ‘how are you?’ we so frequently ask almost as a greeting, became a question people really wanted to answer, truthfully and frankly. And in peak pandemic the answer definitely wasn’t “fine”.

All of us on the team were craving connection, relationships, getting to know each other, and to have a place to Be together, rather than Do.

We stripped everything back to asking just one simple question: “how are you, really?”

This one simple question unlocked so much from the team. Through the biggest crisis section of the pandemic, we heard frank stories of fear and fatigue, about the new challenges and emotional rollercoaster of that time.

Over time, the pandemic evolved and with it, our business and our needs. Our team tripled in size and went global. Our work was growing more complex and there was more of it. We were still fully remote, with new Brinksters joining the team having never met any of us in real life. We all forgot what each others’ legs looked like.

That’s why we began to layer in a second question, inspired by the work of psychologist Arthur Aaron and colleagues who put together 36 questions that lead to love. He shows how, through a series of 36 simple questions, it’s possible to accelerate intimacy between strangers. The idea is that we get closer to one another when there’s sustained, reciprocal personal self-disclosure. It encourages a vulnerability that’s mutual, and unlocks intimacy, respect and trust between you and your counterpart(s).

If we know that collaborative work is relational and that relationships are best built on a foundation of trust, we know that more intimacy, mutual respect and understanding are ways to foster that trust (along with taking more risks together).

My cofounder Lea and I asked ourselves: how we might repurpose this principle and these questions for our team? And so began our Monday morning ritual of the Weekly Question.

By asking the team how are you, really? plus a weekly question, we’ve had laughter, joy, tears, ideas and thought-provoking moments. We’ve heard each others’ stories and dreams, and had a warm start to the week that everyone is keen and enthusiastic to come along to. Most of all we’ve got to know each other on a whole new level.

Productive? Maybe not in the original sense of the metric. But then isn’t building relationships one of the most productive things we could do?

We’re adding to our list of questions every week. You are welcome to borrow and repurpose these for your team, and add your own. We’d love to hear what you end up asking, and what impact these have on your team over time.

Here are 36 of the questions we’ve asked so far, in case you’d like to use with your team:

  1. Thing you’d love to know without having to learn it
  2. Worst job you’ve ever had
  3. Tell us about your best friend
  4. Favourite thing you like to cook / recipe
  5. What did you want to be when you grew up?
  6. Grossest thing you had to eat to be polite?
  7. What’s your dream?
  8. What’s your hidden talent?
  9. What do you prescribe to yourself or friends when in a pandemic funk?
  10. What are you reading / listening to at the moment?
  11. Person you most admire?
  12. What’s the object you lost you wish you still had?
  13. What role does ritual play in your life?
  14. A failure that has changed your perspective or the course of your career (or life!)?
  15. Do you have a mantra?
  16. What’s still on your bucket list for this pandemic year?
  17. What do your friends know you for?
  18. Advice you would give your 15-year old self?
  19. What’s your love language?
  20. Tell us about your dream holiday
  21. What energises you in life?
  22. What’s your morning routine?
  23. What do you do when you have 5 minutes between meetings?
  24. What motivates you?
  25. What’s your best hangover cure?
  26. What’s your favourite stretch and let’s do it right now
  27. What would you like to learn this season?
  28. Who would you like to invite to your dream dinner party?
  29. What’s a life event that changed your perspective drastically?
  30. What do you do to make habits stick?
  31. Show us your workspace!
  32. If you could design a music/food etc festival, what would it be?
  33. Mountains or ocean?
  34. Who was your mentor?
  35. Underrated / overrated (can be anything!)
  36. What’s your favourite holiday or tradition and why?

Update, January 2022: We asked the team what they’d like to know about each other in 2022. Here are the answers, a further 36 questions to fall in love with your team.

Evolving the format for evolving times

So, what’s next? For now, the Monday Morning Meeting format continues and next week we’ll be asking, ‘what are you proudest of from the past week?’ But our business is evolving — since the pandemic began, we now have team in Africa and Europe and are working hybrid in-person/remote — and so is the context we operate within. Hey, we’re not even post-pandemic yet. We are always evolving our practices and making sure they still serve our needs. For this, we’ll be asking ourselves questions like if we keep growing, how many will be too many people for this format to be effective? And do these questions still serve us, what if we stopped now?

Inspo / further reading

For inspiration on rituals and tempos at work, I often turn to First Round, Bracket, Atlassian, and chat with other founders on how they approach this. A bit further afield I turn to psychology, and as it turns out, relationship advice from the likes of the mighty Esther Perel or Arthur Aaron on how to fall in love 😘

We would love to hear from you — what questions would you add to this list? Let us know in the comments below 👇

Interested in this topic, want to know more, or have some thoughts? Drop us a line at [email protected] and let's chat!