How To Win The (Conversational) Lottery

May 21, 2023

We have an immense amount of choice in the types of conversations we start and continue. For the last couple of years, I’ve been working with the faculty at WSU Tech to help them create engaging content for their classes. Today, I want to bring you behind the scenes into one of my small group Coaching Labs with faculty and share an idea that I’ve been experimenting with lately: the concept of the conversational lottery.

The Concept of the Conversational Lottery

Imagine a conversation as a scratch-off ticket. When you ask a question, you scratch off the first number and get a response. The more you scratch off, the more you learn and understand. But sometimes, we don’t approach conversations with the same level of addiction as we do scratch-off tickets. We scratch off a few numbers and then put the ticket down. When we stop at small talk, though, it is leaving value on the table. Did you know that every year, $500 million worth of lottery winnings are thrown away because people didn’t realize they won something?

Similarly, we may treat conversations like half-scratched lottery tickets, missing out on something important because we didn’t scratch off enough. But conversations have the power to change our lives, introduce us to new perspectives, and give us energy for the day. Therefore, it’s important to increase our chances of winning the conversational lottery.

Increase Your Chances of Winning the Conversational Lottery

Here are some things you can do to increase your chances of having a great conversation that we generated quickly in our discussion:

Mutual Interest

  • Find common interests to connect with people, but don’t mistake commonality for the only way that you can win the conversational lottery. Most of the value exists in hearing perspectives and experiences that are vastly different from your own.

Ask Powerful Questions

  • Asking powerful questions is the first chapter in any conversation. If you’re willing to know someone else, it can lead to a great conversation.

Focus on the Individual

  • Pay attention to the person you’re talking to. Make eye contact and listen actively to show that you care about what they have to say.

Be Engaging

  • Engage in the conversation and show that you’re willing to participate. A willingness to engage is essential to starting a conversation.

Create Interesting Answers

  • When someone asks you a question, don’t just give a one-word answer. Tell a story that happened in the last 48 hours that will provoke some curiosity and lead to something else.

How to Lose the Conversational Lottery

On the other hand, there are some things you can do to decrease your chances of having a great conversation:

Talking Too Much About Yourself

  • Don’t monopolize the conversation by talking too much about yourself. Ask questions and show that you’re interested in what the other person has to say.

Too Much Self-Disclosure

  • Avoid oversharing personal information. It’s okay to share some details about yourself, but don’t make it the focus of the conversation.

Body Language and Focus

  • Your body language and focus on the individual are crucial. If you’re looking at your phone or looking away, you’re not interested in the conversation.

Not Being Authentic

  • Be true to yourself and don’t pretend to be someone you’re not. Authenticity is essential to creating a meaningful conversation.


In summary, conversations have the power to change our lives, introduce us to new perspectives, and give us energy for the day. By increasing our chances of winning the conversational lottery, we can make the most out of every conversation we have. By asking interesting questions, focusing on the individual, and being authentic, we can create meaningful conversations that leave a lasting impact. So, the next time you engage in a conversation, remember to scratch off all the numbers and increase your chances of winning the conversational lottery.