A Guide to Conversational Intimacy

I want to discuss conversational intimacy.

Now, I’m not referring to the type of intimacy you may have with a significant other. Instead, I’m talking about meaningful depth in conversation and its power to build trust. The kind of conversation you would have with someone you have known for decades. And how to create fluidity between business and personal conversation.

An analogy is writing in the passive versus active voice. Grammarly often tells me that I’m prone to the passive voice, which I acknowledge is a lazy form of writing. The same is true in conversation.

We can be lazy (passive) in our questions, answers, and listening, or more intimate (active). And I believe the more natural the conversation, the more trust, which is the foundation for healthy relationships. And relationships are a crucial puzzle piece for business success.

Here are some techniques I’m working on to inject intimacy into conversations.

• Ask Active Questions — When I’m first talking with someone new, I don’t ask them, “what do you do?” or “where are you from?”. Why do I need to ask if I can learn it from a glance at LinkedIn? So instead, I will ask questions like “What projects are you working on?” or “Are you watching any good series?” or, if I know they have young kids, “How’s your camp game?”. Dig deeper with your questions.
• Lead with vulnerability — I will tell people I barely know about my insecurities, struggles, kids, parenting mishaps, professional disappointments, business ideas, successes, favorite taco places, etc. Both positive and negative, because I want the other person to know I’m human, and they can be human back. This approach says I trust you. You don’t need to earn my trust. Once trust reciprocates, a meaningful relationship takes shape. I’ve let go of my former beliefs, “trust but verify,” and “earn my trust,” because life is too short.
• No walls between personal and business — I bounce back and forth between personal and business topics. I’m indifferent to whether the conversation’s outcome is personal or business. Maybe we learn our kids are the same age and set a play date. Or decide to play a round of golf. Or perhaps we will arrange to meet to discuss a project. Building a relationship is what matters. Be Stoic to the outcome.
• Active Listening — I am terrible at listening. And I have to work on it daily. But it is essential to build on the flow of a conversation and engage appropriately. If a relationship forms, there will be plenty of opportunities to address your topics. So be patient and let conversations develop.
• Authenticity — I try to talk to folks like I’ve known them my whole life. I visualize that we go way back. I prefer someone to meet an authentic version of me and abort quickly than like a business actor playing me. I’ve often attempted to adapt my style to better align with another individual. It backfires.

Some of these ideas may run counter to your comfort zone. And intuition is fundamental. I will exit with gratitude if I start having a conversation and feel like something is off. But before I go, I ask myself if there are any conscience biases at work. However, there are times when the connections between two individuals are not there; it is better to learn quickly and not force it.

My thinking on this subject formed over time, but its genesis was working with a fantastic sales team earlier in my career. These pros could talk to any customer or prospect. And by the end of the conversation, someone invited the other to a BBQ. And they were successful.

I’ve found the sooner you can build trust, the sooner a relationship takes root. The importance of relationships in business is timeless.

Good luck exploring your conversational intimacy. Thoughts?