Communication Lessons from a Con Artist



It is a miracle that I have ventured into entrepreneurship. My 9-year-old self would have never seen it coming.

You have to understand, I was the kid who was never able to sell any of that “World’s Best Chocolate.” I was the only Cub Scout who did not get the badge for sales of the holiday popcorn tins. Rather than go door-to-door, I would just let the catalog molder in my backpack until the very last day. Then, I would beg my mom to buy some crappy nougat so that I did not look like a huge antisocial moron.

I did not know the right things to say that would make someone want to take my advice or give me their money.

I guess you could say I was not adept at communicating.

I always thought that anything remotely connected to sales was grimy subterfuge. I felt bad for what I perceived to be making people buy something they did not want. The problem was that I knew that “World’s Best Chocolate” definitely was not the best in the world. It probably was not even the best in the house. After all, why would I want to “trick” someone into buying an inferior product?

It is not always about what you know.

What I have learned since then is that most of the time people do not buy things because of what they know about a product. People buy things because of what they feel about a product or the person selling it, even if they know there are better things out there. If you can create an environment that allows another person to open up to you, you no longer have to sell them anything. Your values become their values. They feel a strange affiliation with you, almost as if they are buying from themselves; an easy sale for you.

Fast forward 10 years later to the summer of 2009. I am 19 years old and sitting on the loading dock of the warehouse at the factory where I worked, brown short-shorts riding up like they were looking for daylight. It was my lunch break.

Across from me sat a gaunt, yet ruggedly distinguished older man named James. How he was able to smoke half of a pack of cigarettes on his break and still lift heavy boxes for hours afterward will always be a mystery to me. Older guys have interesting perspectives. I liked eating lunch with James very much because he always had a story to tell. They were not just ordinary stories though. James had an exceptionally interesting career history.

He used to be a con artist.

How do I know this? Well, let’s just say that it is probably better that I did not broadcast specifics. We are still friends. His stories, however, were the stuff of legends.

… Sophisticated bank fraud.

… Impersonation of elected officials.

… Racketeering in Vegas.

… Car chases.

That type of stuff.

I often wondered why he would tell me his biggest secrets. I mean, of all people, why me? Why spill his own dirt to a pimple-popping box boy? What did he have to gain? Why was he even still a free man?

Well, that is the other cool thing about older men. They love to take younger men under their proverbial wings. They love to teach lessons. I learned several from James that summer. One of them really stuck.

Although at the time I never thought it would help me in a career outside of extortion or espionage (neither of which I have ever tried), I have found myself using this skill daily in my legitimate business life and my personal interactions.

The big con.

In one of his more long-winded epic retellings, James detailed how he had been able to talk his way into a 5-star hotel penthouse suite for a week free of charge (you know, the kind with the skylight and 24/7 concierge). Mind you, he had actually been homeless at the time. He continually emphasized the conversation structure with the manager that had allowed him to slither in past her defenses and into the penthouse.

At first, I did not think much of it. I thought maybe she had just felt bad for the poor chap. Then, like a ton of bricks, it hit me.

So what was the magic formula to the 5-star con?

Brace yourself. Here it comes:

Smile. And listen.

A little anticlimactic? Not really. This stuff runs deep.

James told me the best way to get people to let you in is not to pry, but to retreat into observation. I was all ears.

What exactly does that mean?

Human psychology 101 confirms that we love talking about ourselves. My guess is that this tendency to jabber on is rooted partly in narcissism and partly in a genuine unawareness of our social surroundings. Sometimes we do not even know that we are hogging the conversation.

As entrepreneurs, we can ethically take advantage of others’ penchant for self love.

Levels of disclosure.

Whenever James wanted to get someone to like him, he simply let them talk about themselves and he would listen intently, showing deep genuine interest through his body language. He adopted a relaxed posture that invited comfort, not project his authority over theirs. Then, he asked pertinent questions at just the right time that allowed for a deepening of the one-sided conversation. Questions like:

“Fascinating, have you ever heard of _______?”

“What do you mean, can you give me some examples?”

“I bet you would know a lot about _______, right? What do you think about ______?”

Any question that requires the speaker to dig deeper than a “yes” or “no” response can work well here.

These types of questions are not randomly selected. They are designed to work like a katana slicing through verbal haze. Specifically, they accomplish 2 tasks:

First, they show the speaker that you have been listening to them. People love when others genuinely listen to what they have to say. Too often we just “hear” somebody, barely able to restrain our interjection, grateful when we can finally say the line we have been planning to blurt out. Stop that — listen and respond to what is actually being said and interact in real time.

Second, these type of complex questions allow the person speaking to continue creating more and more meaning, which creates an unspoken bond between you two. When someone feels like you know a little bit about them, he or she gives a small piece of themselves to you. In communication theory, this is called levels of disclosure.

Now you have them.

The key here is that anybody who wants another person to open up to them has to express genuine interest in what the other person has to say. So learn how to become interested in more than yourself. Ironically, when you become more interested in others, you become more interesting to others.

In a situation that requires you to gain the acceptance and approval of others (as any business situation does), shine the spotlight on the other person and let them do the talking. The conversation will fly by quickly for that person and you might even notice them commenting on how “easy you are to talk to.” When this happens, you know you are in.

Once the other person knows that you genuinely care about the things that they care about, they will automatically care about you. It is impossible not to. People form kinships with those who live near them and form bonds with those with whom they work and go to school. The deepest affections are formed with those whom they share the same thoughts, opinions and values. This type of emotionally-rooted relationship is the foundational crux of some of the most powerful organizations in the world, including religion.

If I had known this back in my Cub Scout days, I would have focused much less on selling the chocolate and much more on selling myself by aligning my values with the values of other people.

As I have had time to reflect upon all of the things James taught me that summer, I came to realize that a skill can be applied maliciously or completely benevolently. It is the individual’s choice whether to use the skill for good or evil. That being said, go forth and conduct ethical communication that helps people and wins them you your side. When your transactions all go according to plan (insert maniacal laughter here), you can smile to yourself because you know the skill came from the most unlikely of sources.



Reprinted by permission.

Image credit: CC by Nick_Webb

About the author: Under30CEO

Under30CEO is the leading media property for entrepreneurs, inspiring the world’s next generation of business leaders. Under30CEO features direct interviews with the most successful young people on the planet, profiles twenty-something startups, provides advice from those who have done it before, and publishes cutting edge news for the young entrepreneur.

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