Skip to content
Resources

Going Deep: 3 Keys to Having Meaningful Conversations

By Jason VanRuler

Going Deep: 3 Keys to Having Meaningful Conversations
Used by Permission

“Friends, do I have permission to go deep with you?” 

This is how I start many of my keynote talks, because I’ve learned over time that if you give people a choice to go somewhere meaningful with you, most will.

Most people love to talk with people who go deep. You know, those people who, instead of asking you about the weather, end up talking with you about that dream you have but are afraid to go after. Because when you have these types of conversations, you share what matters most—and, if the other person receives those things well, intimacy is formed and relationships are built. If you have never had this type of relationship, the first time can be eye-opening.

Thankfully, I have many therapist friends and thinkers who also value going deep and are willing to do so often. I cannot tell you how many times I have met someone at a conference or event and ended up talking for a long time for this reason. Once you know the value of going deep, you realize it’s where all the best relationship things happen. I think this was a gift that Jesus had. There is no place in the Bible that mentions Jesus speaking to someone about the weather, sports, or anything else that was shallow. Instead, Jesus made his words count.

RELATED “WHAT IS A ‘FRIENDLY’ CHURCH?”

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.

Jason VanRuler

Jason VanRuler, MA, CSAT, is a psychotherapist, author, and nationally recognized speaker specializing in communication, attachment, and relationships. He’s the author of Discovering Your Communication Type and Get Past Your Past and founder of a thriving private practice. Known for blending insight, story, and strategy, Jason leads workshops, retreats, and intensives that explore the patterns shaping how we connect, lead, and thrive. His work creates space for clarity, growth, and lasting change. He lives with his wife and three children and enjoys travel, cycling, and fly fishing.

Secret Link