Gentleman Rule the Deal

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.

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:

Gentlemen realize that regardless of where their 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 reciprocated) You have positioned yourself to leverage your oppositions lack of tact against them.

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 rarely suitable to discuss these topics in business or personal situations until you have a strong rapport established.

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 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 (aka — bringing the right tools to the table) may be the difference between success and failure in a wide array of situations.

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.

In short, if pride comes before the fall — a gentleman aims to never (or rarely) fall off.

“Never Falling Down, Only Falling Up.”

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.

Key Takeaway

The platforms change, but the techniques remain the same…

Day One or One Day

Are you ready to invest in your future self?

Gentlemen [women]



If the answer is — “Yes” but you don’t know where to start: Seek help from a pro!


💡 / 💪🏼



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