The questions that lead to crossfunctional love


I spend just about all of my time thinking about ways humans can work together better and part of what makes my work so satisfying is that there’s an inherent romance in true crossfunctional love. So as Valentine’s Day rolled around, I got to pondering about the reliable ways colleagues could ignite that spark at work, my mind immediately turned The New York Times’ 36 Questions That Lead to Love.


If you’re not familiar, the idea comes from a study that explores whether it’s possible to accelerate intimacy by posing a series of increasingly personal questions to one another and taking turns answering in earnest. 


I thought I might be able to create a modified version of these questions to get the kindling going on an enduring crossfunctional flame. I can’t promise any true love will ignite (though who knows!) but I can offer a path to at least one fun and interesting conversation. 


So grab your closest crossfunctional colleague, however you define it, and get talking.


Set I

  • Given the choice of anyone in the world, who would you invite to edit your next blog post?
  • Would you want to be Twitter famous? For what?
  • What does your calendar look like for a “perfect” week?
  • If your headphones were disconnected, what song would your coworkers be subjected to? (And why don’t you have wireless headphones?)
  • Name three things you and your boss have in common.
  • What was the worst career advice you ever took?
  • What outfit do you feel most yourself in?
  • Share the background image on your computer or phone. What does this image mean to you?
  • If you could wake up tomorrow having gained any one quality or ability, what would it be?
  • You have been granted the power to completely retire the use of one corporate jargon-y statement or term. What is it? Why?
  • Go-to mid-day snack?


Set II

  • If you could ship anything (skills, experience, market is no factor), what would it be? Why?
  • Share your to-do list. What are you most excited to accomplish? What are you dreading?
  • What’s the greatest accomplishment of your career?
  • Whose work do you most admire? Why?
  • What’s the hill you’d repeatedly die on?
  • If you were to get into a scandal, what would it be about?
  • What would your closest colleagues say is your most marked characteristic?
  • What does crossfunctional project bliss look like to you?
  • Crossfunctonal project misery?
  • Sooner or better?
  • What is the skill you most admire in a colleague? Who have you worked with who embodies or exemplifies that skill?
  • What’s the most helpful feedback you’ve ever received? Did it surprise you?
  • If you had to start a company and pick a cofounder from our company today, who would it be? Why?
  • What are you snobby about?
  • What do you miss about your last job?



  • Make three true “we” statements about our company
  • What earlier work are you embarrassed of?
  • If you were to turn into a pumpkin this evening with no opportunity to communicate with anyone, what document or ticket would you most regret not having updated?
  • Your computer, containing every document you own, catches virtual fire. After saving photos of your loved one and pets, you have time to make a dash to safely save one file. What? Why?
  • What, if anything, is too serious to be joked about?
  • What trait would you say is most overvalued?
  • What tables do you want a seat at?
  • Which don’t you?
  • Share a challenge you’re facing at work. What would they do if they were in that situation? Ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.






Thanks to Alia Fite for indulging me one upon a time at an office happy hour and getting a silly idea into actually useful words.