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Gentlemen Rule The Deal

Updated on January 25, 2016

In modern times we have seen a significant shift towards flat rate product and service pricing offered a la carte on and off line. Whereas in the past we were more likely required to haggle or negotiate with third parties to settle our purchases and business dealings.

The shift is a relatively recent change, which has occurred in concert with the growth of the internet. Leaving a generation of people communicating face to face less and completing transactions remotely more often.


Without ample opportunities to learn how to negotiate and foster the personal characteristics required to be successful across the table from a buyer or seller. It is important that one has a clear understanding of proven frameworks that have served leaders in the past.

The Gentleman’s Guide lays out several of these frameworks: Gentlemen have historically been successful negotiators because of the disciplined and tactful techniques they bring to the table: It can even be argued that some of our greatest leaders have personified the defining attributes.

With impersonal negotiation on the rise, now’s the time to focus on learning how to approach a deal like a gentleman to insure your success in the rare but important moments when you are hashing out terms with a third party.

Learning the ways of a gentleman will help you make the most out of a variety of situations in your personal and professional life.

Here are some of the rules of the deal I’ve learned from gentlemen who made their mark in the world before smartphones and search engines were created:

A Gentleman Does Not Belittle the Beliefs of Others

Gentlemen realize that regardless of where there values are placed -- two ears have a greater responsibility then one mouth. This is especially valuable in professional environments where gaining an understanding of your opposition, while simultaneously not tipping your hand is of the utmost importance. In short, when you afford people you disagree with respect – you earn the right to demand it be reciprocated, and if it is not you position yourself to leverage your oppositions lack of tact against them.

A Gentleman Does Not Make Light of 'The Protected Subjects'

As time progresses less subjects are considered taboo in our society. A gentleman embraces change but realizes that the following subjects should always be avoided in a formal setting:

  • Religion
  • Politics
  • Money

People have always had a deep and personal relationship with the aforementioned subjects, which warrant the respect of a gentleman. Thus, it is generally not suitable to discuss these topics in business or personal situations until you have a strong rapport established.

A Gentleman is Patient and Decisive

“Patience wears away stones.”

People are always watching and a gentleman realizes that it is important to never let them see you sweat. When an individual has the constitution required to wait for a solution to present itself and then responds in a clear and succinct manner. People will see the subtle resolve and in turn some of the doubters will become believers or supporters.

A Gentleman is Always Dressed and Prepped for the Occasion

A gentleman completes his due diligence before entering a situation to insure – to the best of his ability – that he understands what is customary, expected, and required to be successful in a given scenario. Remember, people are always watching and looking the part (or bringing the right tools to the table) may be the difference between success and failure in a wide array of situations.

A Gentleman Admits Fault

People are proud, stubborn, and unforgiving in every culture I have ever encountered. So much so, that several people feud over the same things for months, years, decades, and even centuries! Even more interesting is the fact that – many of our greatest issues are trivial in nature and blocking our ability to perform optimally.

A gentleman put’s the mission before his pride and in turn is willing to admit fault when it advances his agenda. In short, if pride comes before the fall – a gentleman aims to never (or rarely) fall off.

A Gentleman Never has to Get Ready

One who is always prepared never has to get ready. That said, a gentleman does everything within his power to see all of the angles of a situation and prepare contingencies for a variety of outcomes. Remember, people are always watching. Now a days they may even be recording and when we get down to the brass tacks: your composure & ability to pivot quickly maybe the difference between you controlling a situation, opposed to letting the situation control you.


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