Make work friends and practice empathy by asking questions

Building a high-performing team starts with practicing empathy. The best source of empathy? Providing team members with tools and time to get to know each other paired with active listening. To help team members create better relationships, Casey Spille, our HR lead, crafted a series of questions based on “The 36 Questions That Lead To Love,” originally published in the New York Times in 2015. The original questions, penned by research psychologist Arthur Aron, et al, are delivered in a specific order from least to most intimate. Our list of questions may not be scientific but it delivers for the workplace.

Of course, workplace and romantic relationships are different but all relationships share things in common such as a need for trust, a level of intimacy, appreciation of positive character attributes, and tolerance of less positive attributes. This process has special relevance for me during this time of social distancing and quarantine. Without a water cooler, lunches out, happy hours, triathlons, or service projects, we are all looking for ways to sustain productivity and improve work relationshipsThe process starts with some basic rules.


  • Break out into groups of two. For remote team building, this can be done using Zoom, Google Hangouts, or other video conferencing software.
  • Agree to mutual transparency. It only works if both parties are mutually vulnerable and transparent.
  • Keep confidence. Ensure that your coworkers know that they are safe sharing with you and that you will hold any sensitive answers in confidence.
  • Take turns talking and listening. No multitasking!
  • Don’t get hung up. It is ok to skip any question.

Empathy-building questions for surviving the COVID-19 crisis, working from home, and staying sane

  1. What helps keep you sane when you feel like you can’t be yourself these days?
  2. What do you miss the most about going out into the world? When will things feel normal to you again?
  3. What has been the hardest part of dealing with the crisis?
  4. If you could give one piece of work-from-home advice to your co-workers, what would it be?
  5. What do you miss the most about going into the office?
  6. What has your favorite thing about staying at home been? What has your least favorite thing been?
  7. What is the best thing that has happened since this began?
  8. How are your parents? How is your family?
  9. If you had a genie in a bottle and could make three wishes related to this current situation, what would you wish for?
  10. What song/movie/hobby has been keeping you company?

Everyday empathy-building questions 

  1. Describe your perfect day.
  2. Given the choice of anyone in the world, whom would you want as a dinner guest?
  3. If you had a theme song, what would it be and why?
  4. If you had the chance to be famous, what would you like to be famous for?
  5. Before having a conversation, do you ever rehearse what you are going to say? Why?
  6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want and why?
  7. Name two things you and a fellow teammate appear to have in common.
  8. For what in your life do you feel most grateful?
  9. If you could change anything about the way you grew up, what would it be?
  10. Who is your favorite superhero?
  11. What do you value most in a co-worker?
  12. Take four minutes and tell your teammate about your career in as much detail as possible.
  13. If you could wake up tomorrow having gained any one quality, skill, or ability, what would it be?
  14. If a crystal ball could tell you the truth about one thing in your life/career, what would you want to know?
  15. What would be your dream job and why?
  16. What is the greatest accomplishment of your work life?
  17. What do you value most in a boss?
  18. What is your most treasured memory of work?
  19. What is your most terrible memory of work?
  20. What does transparency mean to you?
  21. Share with your teammate an embarrassing moment in your life.
  22. What role does teamwork play in your life? Please provide an example.
  23. Make three true “we” statements each based on what you have learned about each other so far.
  24. What, if anything, is too serious to be joked about?
  25. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
  26. Share a current work problem and ask your teammate advice on how he or she might handle it. Also, ask your teammate to reflect back to you how you seem to be feeling about the problem you have chosen.

Give it a try with your team. You won’t be disappointed.

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