How To Have Real Conversations

Knowing how to have real conversations has value beyond the corporate world. While knowing how to have real conversations as a leader is important, you also need to know how to bring this skill to your everyday life. Without the ability to carry on conversations, your world will be a much smaller place.

Man and woman sitting, having a conversation

Photo by Mael Balland

The problem is most people don’t know how to carry on a conversation well. They’ll bring up small talk like the weather or what they do for a living (the boring jist of it).

Small talk can derail conversations real quick.

People use small talk to get the conversation going. Too often, people will get stuck in the small talk and not branch out to more important matters.

If you can get conversations down, you will go far. In leadership… and in life.

How To Have Real Conversations

What does it take to have real conversations? It’s a question you need to ask yourself on the regular. Without focusing on this, you will often drift back to surface level conversations.

I believe real conversations you will have to do a few things. They are:

Real conversations require honesty:

Our world may seem like it has never been more open and transparent. While it appears this way from the outside, more and more people are closed off and unwilling to be truly transparent. They show what they believe the world wants to see.

Take a look at Instagram or Facebook. What do you see? You see pictures of smiling, beautiful people.

Are these images honest and true? Talk to a social media expert. They will tell you they are not.

Many people are taking 5, 10, 15, or more takes of a photo to get it just right. The lives they’re living on social media are not honest lives. They’re images of a life they desire or think people will fawn over.

This extends to our conversations. Because of the false lives people live on social media, they struggle to hold real, meaningful conversations. The lack of honesty is there. And it’s hurting our conversations.

Strive to be open and honest in your conversations. If something is bothering you and the person you’re talking to can help, share with them. Open up about your struggles. Let people truly know who you are.

Real conversations require asking questions:

To get to know someone better, you have to be willing to get to know them. How do you do this? Through meaningful questions.

It’s easy to fall back on the easy questions of:

  • What do you do for a living?
  • Where do you live?
  • How’s work going?

We don’t need more of these questions. These questions won’t get you to know the person answering them. It’ll only give you a surface-level knowledge of who you’re talking to.

Instead, be bold. Be willing to ask deep questions.

These are questions that will politely probe the person you’re conversating with. Your probing questions may look like:

  • Do you mind telling me about your childhood? What was it like?
  • Where do you see yourself in 5 years? Why do you want to get there?
  • If there’s one place you could go in the world, where would you want to go? What’s the reason behind this place?
  • What is something you’ve done that you are extremely proud of? Why is this accomplishment so important to you?

When you ask questions like these, you begin to hear the heart of people. Not the easy answers but the deeper, more personal answers.

Knowing what drives a person and makes them enjoy life will help you understand them better. Get to know the person to have a better conversation!

Real conversations require talking about triumphs and failures:

Triumphs are easy to talk about. They’ll flow off of your lips like a glass of refreshing water being poured out. Everyone loves to talk about the accomplishments they’ve had.

This is good. It allows you to talk about the things you’re passionate about. You can share what you’ve done and how it has impacted your life and the lives of others around you.

Can we say “Saweet!”?

But what about sharing your failures? The moments you’re not proud of? Your failures will say just as much about you as your successes.

Failures tell about things you’ve attempted. They let people know what you’ve done and, maybe, why they didn’t work out.

One of my “failures” is a semi-launched record label that never amounted to much. When I talk to people about this, it lets them know a few things about me:

  • I love music
  • I had the desire to do something outside of my comfort zone
  • I tried, failed, and learned from this experience
  • I am willing to take risks

Use your successes and failures to begin a real conversation. Things will get raw and real really quick when you go this route!

Seeking real conversations will help you succeed in life and business. You’ll discover things about yourself and others that you wouldn’t if you only sat around talking about the weather or how the Detroit Tigers lost last nights game.

Work towards making conversations real on a regular basis. You won’t regret the conversations you have when you do.

Question: How are you creating real conversations in your life? Share your strategies in the comment section below.

Please note: I reserve the right to delete comments that are offensive or off-topic.