Starting Significant Conversations

Starting Significant Conversations

A coaching question can be a great way to take everyday conversations from cursory to compelling. Instead of asking “How are you?” or “What’s new with you these days?” and getting the standard reply, taking a risk and talking about something that really matters can lead to a greater understanding of the current reality and illuminate issues of a presenting problem that were unseen before.


In place of the usual icebreakers, these questions are good for launching a conversation with someone you’ve just met. A great strategy is to take a question that would normally be simple small talk, then ask a follow-up question that delves a bit deeper.

  • After a question like “How are you today?”, come back with, “What makes today a good day?”
  • “What do you do for a living?” can be followed up with, “What’s the most fulfilling part of your work?”

Significant Questions

Significant questions go deeper than casual conversation: They make people think about what actually matters to them, help them connect with their own identity and reality, and/or vocalize their deepest desires. These questions are an excellent way to launch a coaching conversation. They are also a way to deepen your relationships with friends or family members, or to make new connections at networking events. Master the art of asking the right questions and you can have interesting and powerful conversations with anyone you come across. Some great examples include:

  • “What’s the biggest thing that’s happened to you this year?”
  • “Tell me a story from your life that helps me better understand who you are.”
  • What’s your personal dream? If you could do anything with your life, what would you do?”

Significant Conversations in a Group

A great way to practice starting these conversations in a group is give everyone a set of significant questions like the ones we have discussed above. Then have every member of the group stand up and pick a partner. Each person asks their partner a significant question, then after three minutes the two switch and the second person asks the question. Once both partners have gotten a chance to ask and answer a question, switch partners and do another round with a different person. This a great way for a group of people to quickly get to know each other and build rapport with one another.

This post was inspired by material from Coaching Questions: A Coach’s Guide to Powerful Asking Skills by Tony Stoltzfus, which has a lot of additional material to help one start significant conversations with a coachee (or just about anyone).