curtis fisher.

questions for understanding and connection

- 3 Minute Read

During my role as a leader in a 100+ person organization (TAMID), I've mentored many individuals. The goal of TAMID is to help students become the best version of themselves. Part of helping individuals become their best, is understanding where they are at. I've come up with a list of questions that I'll use from time to time to better understand where people are starting from. Here are those questions:

Small Talk

Great for starting and ending conversations.

  • How was your day so far?
  • How was your week?
  • Any fun weekend plans?
  • What do you like to do for fun?
  • What do you have for the rest of the day? (great way to initiate the end of a conversation)

Medium Talk

Great for creating the space to talk about more meaningful things.

  • How are you really?
  • What are you most passionate about?
  • What are your friends like?
  • What's the earliest memory you have?
  • If you were a type of bread, which bread would you be?

Deep Talk

Great for getting to the root of who the human you're speaking with truly is.

  • Imagine you're on your deathbed looking back at your life. What kind of life did you ideally live?
    • Follow up: why?
    • Second follow up: why?
    • (and so on until you get to what truly drives someone)
  • What do you value most?
  • What holds you back from doing what you truly want to do?
  • Do you think you are on the right path?
  • What was it like growing up for you?
  • Are you happy?
  • What would you do if you weren't afraid?
  • Do you love yourself?
    • If no, why not?
  • What keeps you up at night?
  • Do you have any regrets?
  • What's the hardest thing you've gone through? (this is a really tough one to ask without building the right space of vulnerability for it)

These questions are merely for guidance to start a meaningful conversation. Please do not go into a conversation and expect to run down the list of deep questions. That is the quickest way to turn someone off to speaking with you.

The goal of a good conversation is to learn something about your conversational partner. Ask lots of questions! Lean into your curiosity! In general, provide a good listening ear, and people will be more than willing to share who they are.

Conversations are not one-way streets either. Don't ask a question that you're not willing to answer. If you expect vulnerability from others, be prepared to get vulnerable yourself.