How to Have Conversations that Matter Every Day

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I wonder what would be different if we paid a tax on every word we spoke or wrote. 

Would we comment as much online? 

Would we be more thoughtful about our word choices? 

Would we be willing to pay a price just to have a frivolous conversation that neither deepened connection nor opened new windows of thought or experience? 

After reading Ask Powerful Questions: Create Conversation that Matter by Will Wise and Chad Littlefield, I began to think about the value of each word spoken and even more deeply about questions I ask. After having the opportunity to interview both Will and Chad (separately) on my podcast, I have been considering the following three principles related to creating conversations that matter. 

Principle #1: Be clear about your intention

What is ‘intention?’ We tend to find it much easier and more accessible to talk about a ‘goal or purpose,’ and what is unique or different about an intention? In Ask Powerful Questions, the authors introduce the following dictionary definition:  ‘a determination to act in a certain way’ (Merriam-webster Dictionary). What is beautiful is that this definition draws us back from thinking about what we can affect in another person and instead directs us to be accountable for ourselves: How will I show up to this moment? In conversations that matter and build relationships, we are not trying to drive an outcome, but rather seeking to show up as someone who cares about the other person. How might our conversations be different if we took time to ground into a mindful intention? What are the consequences of our failure to do so? 

Principle #2: Ask questions that reflect a deep appreciation of the sacred human experience

We ask a lot of questions every day that I would say are ‘a dime a dozen.’ In other words, if I had to pay a tax to ask them, I wouldn’t. These are questions like the quick ‘Hi, how are you?’ that aren’t really meant to start a conversation but rather act as a gap filler, placeholder, or extended form of greeting. How about the angry parent questions like: ‘Why didn’t you clean up your room? or ‘Why did you just hit your sister.’ 

And then there are questions that can transform a moment, breakthrough barriers of disconnection, and open doors to grace and miracles. How often do we ask these questions? Most recently a dear friend of mine came to the realization that it was time for her beloved dog and companion to transition; his beautiful soul had reached the end of her life. In her planning for the final moments, my friend paused deeply and asked herself, “What matters most to me at this moment?” In asking and creating space to be with this question, she designed a transition ritual that reflected the deep tenderness that had existed between them for the 9 years of their relationship. There was sadness and there was also grace, love, and divine presence. There was a perfect beauty. 

There are also the questions we ask of others. What if we asked questions that truly conveyed to someone, “I see you in all aspects of your pain, joy, suffering, and gladness and I want to know you better.” They seem scary, perhaps too personal, perhaps ‘rude’ according to the standard we believe we were raised with. And… perhaps they are the questions that enable someone to feel truly seen in a very long time. Perhaps they sound like, “What is causing you to feel a deep sadness right now?” or “When was the last time you felt my love?” or “What is causing you to stay silent when I can see you have something to say?” As we learn from Will and Chad, with ‘genuine intention,’ these questions can open doors of connection and transformation we never imagined. 

Principle #3: Show up with the capacity to reverently hold what someone else might share

Once we ask a question that matters, one we would even be willing to pay for the privilege of asking, then what? Listening, being present and holding space for another’s experience is one of the most generous and caring things we can do. We don’t need to fix all situations. While associating with others’ experiences is nice for us, it is not typically helpful to them. And then there are many ways we inadvertently dismiss someone else’s experiences. But in the end, being able to listen, hear, acknowledge and be with someone’s sharing is one of the most precious gifts we can bring to a relationship. Can we simply hold the space? 

So this is an invitation to pause and reflect. In which relationships in your life would you like to bring more intention and develop deeper connections? And for incredible inspiration, take some time and listen in to conversations that matter with Will Wise and Chad Littlefield.

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