10 Questions that help you get to know someone

As someone that is very curious about people, I’ve been reading a lot about the best way to get to know people and get below the surface of typical conversations. Whether this be a casual conversation with a work colleague, interview, networking event, or party, I feel like a lot of the questions that we ask are very much surface level and don’t help us actually connect with others. The difference between “what have you been up to recently,” and some of the questions below are crucial in developing deep relationships and trust with people.

With that being said, I’ve been on a journey to figure out what are some good questions that get people to open up and get you to really know them. Because of how uncommon a lot of these are to bring up in a normal conversation, I usually preface them with, “I know this is a bit uncommon, but I like asking questions that are different than the norm,” to provide the safe space to ask them. A lot of times when you ask questions like this, people’s faces will light up because they believe the conversation can actually go somewhere, but one person just needs to take the initiative to make it happen. Below are 10 questions I like to ask to get to know someone better.

  1. What is one thing you thought was true that you no longer believe to be true?
  2. What’s one story from your life that best describes you?
  3. When have you failed?
  4. What is a new skill you have learned in the last few years?
  5. What can you not live without?
  6. What is your morning routine?
  7. If you could make one rule that everyone had to follow, what would it be?
  8. What do you want to be remembered for?
  9. What is the biggest decision you’ve made in your life and why was it such a big deal?

And then one final one that I’ve heard recently that really can change your conversations with co-workers and those people where you always seem to have negative conversations.

10. What’s not wrong with your life?

And then just keep asking it over and over until the person begins to feel grateful for everything they have going on.

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