Maintaining my role as “the cross-generational voice,” my blog this month continuing the spirit of Thanks-giving is about approaches to have meaningful conversations with anyone you’d like to get to know or presents a difficult situation you’d like to turn around. 

New York Times columnist and best-selling author David Brooks put together some lessons he gathered from people he wrote are “wiser than myself.”  I summarized them in my own words below:

• Ask questions that are likely to lead to gaining a wider perspective. Try to learn how people experienced what happened to them – feelings, not just the facts.

• Ask open-ended questions, for example, “What was it like…?” “How did you manage to…?” or “Tell me about a time….”

• Listen with full attention – no distractions.

• Listen through the whole comment, and pause before responding.

• Expect to learn, and for both of you to enjoy the conversation.

• If there is a disagreement, dig down to discover the underlying layers of disagreement. Pursuing your curiosity to learn is more important than being right.

• Look for the “gem comment” that can keep the relationship together.

• Don’t try to solve a person’s problem if that is not solicited. Don’t try to seek control.

• Be aware that many people want to feel they have been heard by you before they will listen to you.

• Finding how you appear in other people’s eyes helps you know yourself better. Ask questions that help both you and the other person from a high level. Some examples of questions you might ask are:

  • What commitments have you made that no longer have value for you?

  • What problem did you have that you have overcome?

  • What would you do if you were not afraid?

  • Who are you most grateful to have in your life now?

  • What challenges are looking forward to conquering?

Using these approaches and becoming a good, curious and empathetic questioner can break down tribal blinders and provide strategies to increase the comfort level when meeting new people or dealing with those you expect might be disagreeable. One of the questions I am often asked is “Who should reach out to begin a cross-generational conversation?” My answer is typically “Why not you?” These approaches and questions are a good tool kit for developing more meaningful and satisfying conversations and better connections.

Call to Action: Try them out, and let me know how it goes. It gets easier with practice. If I can help you further to improve your question asking and connections, contact me for a conversation.

© Phyllis Weiss Haserot 2020