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4 Types of Difficult People and How To Win Them Over

By |March 20, 2017

How you handle difficult conversations or manipulative tactics can be a deal maker or deal breaker.  You will face demanding, unclear, frustrating, and manipulative personalities at some point during your negotiations endeavors. You most likely have already.  These 4 specific tactics are used to intimidate you and derail the discussion. A good negotiator is prepared to navigate these personality traits and break down these barriers to effective communications. This article identifies barrier tactics and how to defuse their effects.

4 Most Common Types of Difficult People


1. The “Yes, but…” person

The “Yes, but…” person is one who discounts or rejects just about everything you say. They will appear to be unable to make decisions, making you responsible for the lack of progress in the dialogue. They will acknowledge the validity of the option/decision/action, but there is always a reason why it will not work.

How To Win Them:

One of the most effective ways to deal with this type is by way of the Label and Calibrated Questions. Respond to the “Yes, but” person with calibrated question driving them to provide the solution such as,

“You seem to be having some difficulty accepting what I am proposing. How should we resolve this?


2. The Always Suspicious

The suspicious person is controlled by fear on some level which makes the establishment of rapport difficult.

How To Win Them:

A Paraphrase and Calibrated Questions may be in order. By using these techniques in this fashion, you are identifying the trust issues and refocusing them on the underlying cause of their suspicion.

“You seem to be having a problem trusting me and my company. What can I do to allay some of your concerns?” 

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3. The Hostile 

The hostile or angry person attempts to control you through intimidation. This is the individual who personalizes angry responses and insults you because it is their default coping mechanism. It is also used as a common an avoidance response.

How To Win Them:

Your first response is to control yourself. The only thing you have absolute control over is your response and emotions. If you speak in anger, you will make the best speech you will ever regret. The next step is to use an “I” Message to confront the person without sounding confrontational. “When you ________, I feel ___________ because _________”.

When they challenge you about labeling their hostility, you can respond by saying,

“I didn’t say you were angry. I said you sounded angry. Help me understand how what I am hearing is wrong.”


4. The Challenger

The challenging subject attempts to exert power and a sense of superiority over you. He or she will challenge your experience, knowledge, expertise, ability, or authority. Their focus is on you, not the issue. They are the consummate derailer. You will find them to be calm, composed, and appearing to enjoy the "game."

How To Win Them:

Don’t respond directly to the challenge or the insult. Avoid a power or knowledge struggle. Again, your control is paramount. Show no negativity in tone or response. Ask what they would do if they were in your shoes in the form of a calibrated question.

How would you approach this if you were me? What would you do differently if you were in my shoes? 



Be firm and principled. Don’t back down simply because they are being difficult. Use your Black Swan skills to determine the underlying cause of their behavior to change it and gain the edge. 

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