The Confidence Man: A Lesson in Social Awareness
- ejorigin

- Jun 8, 2023
- 7 min read
Written by: Rebecca Yap (22-O1)
Designed by: Tan Zhi Shan (23-I1)
The ‘Put Up’ Imagine you’re approached by a man who just has asked for a $500 investment in his up-and-coming game development company.
Any normal person’s reaction would be an immediate “No!”. After all, you barely know the guy.
Again, imagine you’re approached by the same man who just has asked for the same $500 investment in his tech firm. Now the difference is, he’s just helped you pay for your coffee when he noticed you didn’t have change and asked you about your shirt — which just so happens to have a picture of your favourite video game character. Contrastingly, he’s wearing a nice suit and looks like he has important places to be but wow, he stopped to talk to you! You ranted a bit about bugs in the game, he listened. He commented himself on the declining quality of AAA games and you were impressed by his insider knowledge. Then only after that pleasant conversation, he presents the question.
Considering his expertise and his great impression, wouldn’t you feel more inclined or at least obligated to say ‘yes’?
The art of persuasion and gaining trust is a skill that usually takes time and effort to cultivate, yet some people seem to simply bypass this process and create strong connections anyway.
To gain greater insight into this phenomenon, we can look no further than one whose livelihood depends almost entirely on persuasion and trust — The Confidence Man.
The Confidence Man, or conman in slang, is someone who swindles and tricks other people for personal, usually monetary, gain. From the earliest conman in 300BC committing financial fraud to modern online love scammers, leagues of conmen have appeared across history in various shapes and forms. However, the one thing these ‘aristocrats of crime’ have in common is the possession of extraordinary finesse in worming their way into people’s hearts and, eventually, their pockets.
These smooth criminals are in the trade of trust. They don personas of credibility and capability to present a fantasy so real that millions of people willingly open their wallets for it. But don’t get me wrong, the marks of these grifters are in no way naive. In fact, even the smartest and most influential people can find themselves dancing to the tune of these cunning Pied Pipers.
So how do they do it?
Two words: Social Awareness.
By being acutely aware of what happens in their interactions with others, conmen are able to extract and manipulate information to build rapport with their marks. This information can be split into 3 basic things — how you look, what’s being said, and who you’re talking to — all of which can be captured in even one short conversation.
Let’s break down how this comes into play.
It’s All in The Name There’s a reason they’re called Confidence Men.
Whether in the way they speak or in the way they dress, conmen exude a certain confidence that inspires awe, especially on first meetings. These first impressions are crucial in establishing the curated perception of the conman, that of trustworthiness and competence.
When celebrity conman Frank Abagnale was 17, he purchased the uniform of a pilot to impersonate one working at Pan American World Airways. This allowed him to deadhead over 2 million air miles and “recruit” air stewardesses to stage a company-funded “promotional tour” with a handful of girls. Even the simple act of putting on a uniform lends conmen the appearance of credibility that makes marks more inclined to trust them because of the presence of social proof. Think of the tie-wearing counsellors you’ve passed by in school. Can you be sure that each and every one was an official student leader? Credibility feeds into the logic that ‘since they are qualified, they can be trusted’, forming relational highways from conman to trustworthiness.
Even putting aside attire, confident mannerisms alone have also taken conmen far in the play.
Inspiring the biographical drama ‘The Dropout’, Elizabeth Holmes is a modern-day conman who is notorious for her company Theranos, boasting a miraculous blood-testing machine that never existed. Still, she managed to dupe huge corporations into investing in her company and swayed public opinion into rooting for her, even appearing on the revered Times’ “100 Most Influential People’’ list.
And to no one’s surprise, her charisma played a big part.
Holmes was an exceptional public speaker. With her signature baritone voice, Holmes employed clever conversational tactics such as manipulating her voice into sounding deeper to gain a greater air of authority as a woman in a male-dominated sphere. Her charm and strength made people want to put their confidence in her and by extension, her cause. This allowed her company to amass a whopping US$724 million from venture capitalists and private investors alone.
Through manipulation, conmen display their prowess in understanding the intricacies of seemingly straightforward human perception — proving once again that the devil really is in the details.
Simon Says But looking good and speaking boldly is hardly enough to sustain this trust.
Conversational intelligence is paramount in interactions with marks because it not only conveys a sense of sincerity but also allows conmen to attain more information about you. One way in which they go about this is by listening more than they speak. Have you ever had a long rant session with your friend and felt better afterward? Well, you’re not alone. In fact, science shows that talking more about yourself elicits a pleasant biological response in the brain akin to eating or earning money. Not only that, but having someone else affirm your viewpoint can boost your self-esteem, making you feel doubly good about yourself.
In selling the satisfaction of a conversation, conmen are able to quickly build a rapport and establish themselves as friendly and inquisitive, both of which aid in establishing the appearance of trustworthiness.
Take Sylvia Mitchell, a self-proclaimed psychic, for example. She managed to swindle US$138 000 from various clients visiting her by demanding large sums of money for “safe-keeping” or ordering charms that never arrived. Her trade lay in her display of sympathy towards her victims who were in dire need of a listening ear. In a victim’s recount of their interactions with her, Mitchell had reacted with a ‘pained face’ when “uncovering” bad news in their future and showed a sense of seemingly genuine concern. So rather than a grifter looking for an easy victim, Mitchell disguised herself as a sympathetic and understanding friend who really, truly wanted what was best for you.
As in the case with Mitchell, mirroring someone in terms of physical reaction as well as tone subconsciously results in victims being more open and more likely to accept others who share the same values and beliefs as them. Although subtle, mirroring can have huge impacts on one’s impression of reliability and understanding of another — something these observant conmen would exploit at the drop of a hat.
Different Strokes for Different Folks Say you were tasked to interview a high-ranking minister who is coming down to your school for a talk. Naturally, to ensure you maximise your time and the information you receive, you would want to do prior research on him to figure out the best questions to ask.
Well, a conman is no different.
Case in point: Have you ever wondered why so many elderly fall prey to financial scams? Or why more young adults fall for job scams? The answer lies in the demographic.
In any society, people from different walks of life would have different priorities or beliefs. As peddlers of ideals, conmen shape themselves into the bait of different groups to catch the right type of fish.
One of the most skilled conmen in the industry, Victor Lustig was most famously known for being able to sell the Eiffel Tower (that most definitely did not belong to him) not once but twice. In his first sale in 1925, Lustig read extensively on the public’s concerns about the high maintenance costs and favourable sentiments towards scrapping the structure. And using this information, he invited a group of scrap metal dealers to bid for the structure under the assumed identity of the Deputy Director-General of the Ministry of Posts and Telegraphs.
Now, while Lustig’s ability to appeal to the wants of the scrap metal dealers was already impressive, the man took it a step further. He singled out one businessman — André Poisson — whom Lustig sensed ‘desperately wanted to join the ranks of the Parisian business elite’. Lustig then twisted his persona into that of a corrupt official, offering to take a bribe for the tower. Well, as a testament to Lustig’s skill, Poisson eventually forked out US$70 000 which went right into Lustig’s happy pockets.
The specific awareness of the societal context allows conmen to gain all the shrewdness of a snake, bending to people’s whims and fancies with all their whims and fancies.
Conclusion The mind of a conman is constantly observing and adapting in interactions with others, providing them with extraordinary cognisance into the art of persuasion and manipulation of trust.
I am in no way suggesting that being a conman is a good decision nor am I glorifying conmen. Despite the name, the confidence game should never be played. However, there is definitely much to learn from the masters of manipulation. Through confidence, conversational intelligence, and (understanding) contexts, you can most definitely replicate tactics of persuasion to a much more lawful degree. Whether it be going for an interview for a position or making a good impression on a new friend, the soft skill of social awareness can benefit you in so many ways.
With a little style, confidence, and understanding your people, why wait for doors when you can open your own?
References: Capps, R. (2012, November 20). First Impressions: The Science of Meeting People. Wired. Retrieved April 3, 2023, from https://www.wired.com/2012/11/amy-cuddy-first-impressions/ Farnam Street. (2020, March 2). Maria Konnikova on How We Get Conned. Farnam Street. Retrieved April 3, 2023, from https://fs.blog/maria-konnikova-confidence-game/ Mccarthy, J. (2022, December 7). 💸 Victor Lustig: The Con man who "sold" The Eiffel Tower. Law Office of Justin R. McCarthy. Retrieved April 3, 2023, from https://jrmccarthy-law.com/2022/12/06/%F0%9F%92%B8-victor-lustig-the-con-man-who-sold-the-eiffel-tower/Mckinley, J. C. (2013, October 11). Psychic Found Guilty of Stealing $138,000 from Clients. The New York Times. Retrieved April 3, 2023, from https://www.nytimes.com/2013/10/12/nyregion/greenwich-village-psychic-found-guilty-of-stealing-thousands-from-clients.html Tun, Z. T. (2022, July 18). A Timeline of Theranos's Troubles. Investopedia. Retrieved April 3, 2023, from https://www.investopedia.com/articles/investing/020116/theranos-fallen-unicorn.asp#:~:text=Based%20largely%20on%20the%20company%27s,venture%20capitalists%20and%20private%20investors



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