Relationships are the key to success of any venture – especially in a team setting. Developing the trust, respect and confidence necessary for effective relationships takes time – but we can accelerate the process through conversation. Conversation is the medium through which relationships start and grow.  

Here are twenty-one conversation-worthy questions arranged from “easy” to “edgy”.

The “root question” – start here every time:

  • Tell me about yourself.

Talk about life away from work – interests and family:

  • Who are the folks who are most important to you?
  • What’s your favorite way to spend a day off?
  • What’s your favorite book (movie, tv show, etc.) of all time? What’s the last book (movie, tv show, etc.) you’ve read?

Talk about career – its safe and easy:

  • What were you doing before your came to work here?  How is this place different from that place?
  • What was the best job you’ve ever had?  What did you enjoy about it?
  • Who was the best boss you ever had?  What made them so good?

Talk about work – but without complaining:

  • What’s going well lately?  What’s something you’re feeling proud or happy about?
  • What’s the best part of your job?  What makes the hassles worth it?
  • What’s something people need to know about what it’s like to do your job?

Talk about goals and improvement:

  • What’s a goal you’re working towards – something you’re getting better at?
  • What’s an accomplishment you’re proud of?  (Most people will talk about ‘family’ – that’s great… but encourage them to share something about themselves.)
  • Who are your role models?  Who do you admire?  What do you admire about them?

Interesting questions – after folks are warmed up a bit:

  • What’s your ‘superpower’ – the thing you do best? What’s your kryptonite – the thing that makes you crazy or ineffective?
  • Who is your oldest friend?  If I asked them what they admire or appreciate about you, what would they say?
  • If you could change or improve one thing about yourself, what would it be?  Why?
  • What’s been your biggest failure?  How has it affected you?

Off-the-wall questions – when you want people to open up:

  • Tell me a story about a time you “got away with something”.
  • Tell me about your first kiss (your first crush, your first girl- or boy-friend).
  • If I gave you a million dollars to spend a) on yourself, b) by the end of the day what will you do?

The “destination question” – finish here every time.

  • What’s something I can do to help / support you?

Interested in learning more?  Ready to start conversations and build relationship?  We’re ready to help.  

About the author: Andy Erickson is a founder and principal consultant at Humanus Solutions, a consulting firm specializing in people-centric leadership. He can be reached at