Great Conversation

Drink deep, loving friends.

By Matthew Laffer
January 1, 2024

When was the last time you had a great conversation? A conversation that lit you up and made you feel alive.

Great conversation are food and drink for the soul, yet so many conversations today are impoverished and traumatized. In all aspects of life, it seems people are not having *real* conversations. Not with themselves, not with others, and not inside of companies.

Let’s have a look at conversation in these three areas.

1. Self

What’s the conversation you’re having with yourself right now? Does it lift you higher? Does it serve your highest good?

A short story:

A priest is confronted by a soldier in pre-revolutionary Russia. The soldier aiming his rifle at the priest commanded, “Who are you? Where are you going? Why are you going there?” Unfazed, the priest replied, “How much do they pay you?” The soldier replied, “25 kopecks a month.” The priest paused and in a deeply thoughtful manner said, “I have a proposal for you. I’ll pay you 50 kopecks each month if you stop me here every day and challenge me to respond to these same three questions.”

Such questions best not be set aside without answers.

Some more soulful questions for igniting a great conversation with yourself (and with others):

What would it be like to put strategy in the service of your soul?

How do you shine in the world? Where do you shine?

Do you want to be who you are, just a little bit better? Or do you want to be a completely different person?

What have you not learned how to do in your life that your current situation is asking of you?

When was the last time you did something for the first time?

Whether it’s a conversation we’re having with ourselves or with others, vulnerability is required. The conversation stops when vulnerability stops, which is why so many real conversations never begin.

2. Others

Some of my favorite conversations began with a shyness of what I truly desired. Many people become shy when talking about their desires, passions, and talents, and prefer to keep them hidden.

Willie Sutton, bank robber, when asked why he robbed banks, replied, “Because that’s where the money is.” 

If you want to have a great conversation, where you are shy is often where the money is.

 What in your life are you shy about?

I typically adapt this question when working with founders to “What do you know or care about that few other people do?” Generally, founders of companies are not shy people. But they often require outside help when highlighting to the world what is unusual about them.

There’s usually something rewarding for a founder when answering this question with clarity. It frequently leads to a big idea, and is table stakes for securing venture funding.

3. Companies

I have found that people approach a conversation inside of companies with one of two objectives.

1.    To learn, to connect, to build.

2.    To outwit, to control, to destroy.

Unfortunately, most of the conversations inside of companies are of the latter. People are more concerned with winning arguments than they are with solving problems. This is the reason we see so many unnecessary conflicts.

While most companies are focused internally on their disintegration, great companies are focused externally on integrating with their customers and the market.

The next time you leave a company meeting, ask yourself if you feel more or less integrated? Are you more or less motivated? Are you more or less clear on the path forward?

If you’re the leader of the company, ask your team. The answers to the above questions are an excellent indication of where the team is focused.

What we ask, when we ask, and what our attitude is as we ask are all essential when having a conversation and building healthy relationships. And our attitude speaks more truly than our words. People will rarely remember what you say. They will remember how you made them feel.

What if all of life is a conversation?

Sometimes I’ll approach a conversation as if I was in the desert handing a cup of water to the person I’m speaking with. How great is that cup of water? But without a cup, that water is worthless in the desert.

What if a conversation is like that cup? Not a shallow cup, but something deeper. What if a conversation was like drinking from a five-gallon BPA-free water bottle.

Feast on your life and drink deep, loving friends.

Matthew Laffer is a 3x entrepreneur and the Founder and CEO at Goalspriing.