Coaching questions can be a great way of starting significant conversations: taking everyday conversations from surface to significance. Instead of asking, “How are you?” or “What’s new with you these days?” and getting the standard replies, take a risk and ask about something you really care about. You can also use them in group settings in place of trivial icebreakers (like, “What’s your favorite color?”) that don’t move the group toward real transparency. A great strategy for starting significant conversations is to take a common question that people are comfortable with, then ask a follow-up question that makes the conversation a little more intimate.

Hint: When starting significant conversations, make sure and reveal some details about yourself and find places of connection along the way, lest your conversation start to feel like an interrogation!

 “How are you today?” When they answer, “fine” or “Great!” come back with, “What makes today a fine [or great] day?”

 “What do you do for a living?” then “What do you like best about your job?”

 “What’s something memorable about you, that I can remember you by?”

 “Tell me a little about your family.” then “What’s something you love to do with them?”

 “Where are you from?” then, “What’s been your favorite place to live? Why?”

 “What do you think of ______?” [fill in the blank with a current event]

 “What brings you here today? What do you hope to gain from this [trip, event, etc.]?”

 “How’s your day going?” then, “What’s been the high point so far?”

Significant Questions

Significant questions go a little deeper when starting significant conversations: they make people think about something important, draw out identity or touch their deepest desires. These coaching questions are an excellent way for starting significant conversations: launch a coaching conversation, or you can use them with friends, family members, at parties or at networking events. Learn to ask significant coaching questions and you can have memorable, life-changing conversations with just about anyone!

Hint: To keep others from being bowled over by significant questions, try giving your own answer to the question first, then ask the other person to answer.

 “What’s the most significant thing that’s happened in your life in the last month?”

 “What’s the best thing about your life right now? (And what’s one thing you’d love to change?)”

 “What is on your mind this week? What are you thinking about?”

 “What’s the growing edge for you as a leader these days?”

 “Name one great joy and one sorrow that you’ve experienced this year.”

Tony Stoltzfus is a best-selling author, leadership coach, master coach trainer and director of the Leadership Metaformation Institute.