Imagine if you had a limit on the number of words you could speak each day. What would you choose to use them on? What conversations would you want to have, or what questions would you want to ask the people you care about most?
With this perspective, consider that the art to deep conversation comes down to three things:
1. Create a safe enough environment to go deep. Many people struggle because they immediately attempt to ask a question that is well outside the degree of safety that has been established.
Consider this example. When I was introduced to someone at an event, I shook their hand and told them my name. Without skipping a beat they looked at me and asked,“ What would you tell your younger self if you could go back in time?” Although it’ s a great question, the reality is that without a name tag, I couldn’ t even remember this person’ s name. It was a little early for us to be talking about what we’ d tell our younger selves. There was no safety established in our relationship and no reason for me to want to be vulnerable with a stranger.
I’ ve seen a similar phenomenon with people who have been to therapy, briefly picked up a concept there, and then attempted to use it when dating. This can work against them, because most people are repelled by questions that go too deep too fast. Safety comes from small questions that go increasingly deeper each time.
2. Give people time to answer. If you are going to ask a big question, make sure you’ re willing to stick around for the answer. When I played chess regularly, I would sometimes play with players who took a long time to respond. I would move a piece in three seconds, and they would take thirty seconds to move theirs. Every second felt like too long to wait. And yet that’ s the time it took. So, if we’ re going to have a meaningful conversation and we’ re going to ask the question, we need to give space for them to answer. For many people, the answer is going to take time, and that’ s okay. We all have our different rhythms and pace.
3. Find the right time and place. Our goal should be to read the room and identify what is appropriate in the moment. Not every conversation is a place for deep connection. Some relationships are shallow and temporary, and that’ s okay. One of the keys to knowing if you should go deep with someone is knowing if you trust them with your stuff. Are you willing to be vulnerable with them? If not, recognize that while depth might be a future goal, the relationship cannot sustain it today. Sometimes you must craft the message needed in the moment, not the one you most want to give.
When you are speaking with someone, whether you’ re using the LISTEN framework, going deep, or otherwise, the questions to ask yourself are:
1. Do I want this conversation to continue?
2. If I do, am I making it easy for the other person to speak to me?
Number two is key. If you want to talk with someone but you make it difficult for them to speak to you, or are unwilling to be present, they won’ t engage. People have many choices of how to spend their time and many things
61