People who don’t know Harry tend to underestimate him. They cast a skeptical eye on his typical outfit: ragged jeans and shirts that bear evidence of his most recent meal. And his most frequently uttered expression, “Waaaal, I just don’t know,” can make him sound less than bright. So, some enter a negotiating session with Harry relaxed and confident that their side will prevail and that Harry will gain no concessions for his group. That assumption is one that Harry cultivates, and it is a big, big mistake.

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In this passage, it describes how people tend to underestimate Harry due to his unkempt appearance and his habit of saying "Waaaal, I just don't know." As a result, when entering into negotiations with Harry, they think they have the upper hand and that Harry won't be able to secure any concessions for his group. However, the passage also suggests that this assumption is a big mistake and that Harry actually has a way of turning the tables in his favor.

To understand why this assumption is indeed a mistake, we can examine the context and perhaps consider some strategies that Harry might employ during negotiations. It can be helpful to analyze his behavior, tactics, and mindset.

Firstly, Harry's choice of clothing and unkempt appearance could be seen as intentional. By presenting himself in a ragged manner, he creates a certain perception that he is not serious, organized, or intelligent. This causes the other party to let their guard down and underestimate his abilities.

Secondly, Harry's frequent expression of "Waaaal, I just don't know" might be a strategic way for him to create doubt and confusion in the minds of the other participants. By appearing unsure or indecisive, Harry can make others question their own positions and potentially be more open to compromise.

Thirdly, it is mentioned that Harry cultivates this underestimation as an advantage. This implies that he is aware of how others perceive him and intentionally takes advantage of their preconceived notions. He may use this underestimation to gather information, identify weaknesses in the opposing party's arguments, and exploit their overconfidence.

Therefore, it is crucial to not judge people solely based on their appearance or initial impression. When negotiating with someone like Harry, it is important to approach the situation with an open mind and not underestimate their capabilities. One should consider their tactics, strategies, and past experiences that might give insights into their true abilities.

In summary, underestimating Harry due to his appearance and mannerisms can be a big mistake. By intentionally projecting an image of incompetence, Harry can actually gain an advantage in negotiations. It is important to approach such situations with caution, carefully analyze the other party's behavior and tactics, and avoid making hasty assumptions based on initial impressions.