How to have deeper conversations that foster a real connection with someone

We've all been there: stuck in small talk, discussing the weather or what we did last weekend. But what if I told you there's a way to break through that surface-level chatter and forge real, meaningful connections? Today, I'm going to share some tactics I've learned to have deeper conversations that truly connect you with someone.

Ask open-ended questions: One of the most effective ways to deepen a conversation is to ask questions that can't be answered with a simple "yes" or "no". For example, instead of asking "Did you have a good day?", try "What was the most interesting part of your day?". This gives the other person room to share more and opens up new avenues for discussion.

Show the other person that you're curious about them; that you're interested in getting to know them. I'm always surprised to see how many people in parties don't show interest in the person they're talking to. This is one of the key teachings of "How to win friends and influence people" by Dale Carnegie: ask people questions about themselves, and they'll open up to you.

Something else I realized helps is to really listen to the other person's responses. It's easy to get caught up in thinking about what you're going to say next, but try to focus on truly understanding what they're saying. This will help you ask more meaningful follow-up questions and show the other person that you're genuinely interested in what they have to say.

And the other thing I learned is that we shouldn't be afraid of silence. I know, I know... many of us feel the need to fill every moment with chatter. But sometimes, a brief pause can give both you and the other person time to reflect on what's been said and come up with more thoughtful responses.

Share your own experiences: As you're getting deeper into the conversation, try to open up about your own experiences related to what you're discussing. This vulnerability can encourage the other person to do the same, creating a stronger bond between you. But remember, it's not about one-upping their stories or making the conversation all about you. It's about finding common ground and showing empathy.

Mindset: As you're practicing these deeper conversation skills, try to have a good mindset about it. A lot of people I talk to have resistance to diving deeper because to them, it appears to be uncomfortable or risky. My counter-argument to that is, "surface-level relationships are hard, working to build deeper connections is also hard. Choose your hard". Having deeper conversations gives me a sense of fulfillment. I can't control how the other person will respond, but I can control my own openness and willingness to connect.

Remember, developing the ability to have deeper conversations takes practice. Don't get discouraged if it feels awkward at first. Keep at it, and you'll soon find yourself forming more meaningful connections with the people around you. And trust me, the rewards of these deeper relationships are well worth the effort.