How Ultra-Wealthy Entrepreneurs Deal with Difficult People

Marina Gallardo
July 7, 2023
Credit: GR Stocks on Unsplash

Because business relationships are so vital to your success as an entrepreneur, you’re almost certainly going to meet and need to work with a lot of people over the years.

Most people you meet in business are hardworking and caring. A few, however, relish schadenfreude — taking pleasure in other people failing. 

According to Frank Carone, chairman of Oaktree Solutions and co-author of Everyone Wins! How You Can Enhance and Optimize Business Relationships Just Like Ultra-Wealthy Entrepreneurs,

“It’s a given that successful entrepreneurs will have to deal with difficult people. As they build their companies, they’re going to have to work with and sometimes work around people who make things unnecessarily hard. The thing is, by artfully dealing with difficult people entrepreneurs can still achieve their goals, but it requires finesse”

It can be quite beneficial to understand difficult people better, know when it does and doesn’t make sense to work with them, and use the right processes to pursue your interests. There are several distinct types of difficult people you’re likely to encounter on your entrepreneurial journey:

  • Fools do not think critically. Logic is not their forte and therefore not a way for you to connect with them. For example, many fools are prone to believe in off-the-charts conspiracy theories, which makes it hard to negotiate or work with them.
  • Narcissists see everything revolving around them. They’re the ones and often the only ones who can make things happen, at least in their minds. They strive to project an image of supreme self-confidence and likely see themselves as hyper-intelligent, attractive, and incredibly capable. Anyone or anything that calls their self-image into question is simply wrong.
  • Subclinical psychopaths present themselves as caring and likable, but their charm is superficial and underpinned by a lack of empathy. They can be callous and will have no problem throwing you under the bus in a business situation. (They might even make sure the bus rolls over you a few times.)
  • Machiavellians are cunning, deceitful, and all-around manipulative. They figure out precisely what you want and create an illusion of delivering on that desire. They are exceptional at “selling” hope and accomplishments, while always failing to deliver. 
  • Zealots are fanatics. They have extreme belief systems that are incontrovertible and unchallengeable. No matter what the situation or circumstance, they adhere to their belief system even when there is strong, solid evidence to the contrary. They find it completely unacceptable if you don’t agree with them.

Difficult people can make it very problematic for you to achieve your self-interests. Their attitude and approaches to negotiating, for example, can make it nearly impossible to get a deal done. For example, if the other side is negotiating an agreement giving you much of what you want but you know they have a history of not following through, you have to take that fact into account. 

We can offer a few pieces of advice that are true regardless of the type of difficult person:

  1. Don’t rely on reason. The idea of reasoning with a difficult person might sound good, but it can easily lead to tremendous frustration and aggravation. Concentrating on logic and the specifics of the issues is not going to get results for you or them. A good fact-filled argument can be useless.
  2. Expect to work hard. Winning when dealing with difficult people is going to take a lot more work than is required when enhancing relationships with others. Recognize that you will need to spend a great deal of time, energy, or both. You will need to decide if it’s worth the effort. Some difficult people want to win at all costs and are very willing to do nearly anything (including pounding you into the ground) to achieve that. It takes a deft hand to avoid being taken down as well as to ensure that both parties can close a deal and walk away satisfied.
  3. Don’t expect a difficult person to change or become less difficult. Difficult people are difficult. It’s their nature, and their nature is not going to change. One of the biggest mistakes you can make is thinking they will change, grow, or evolve. Always remember that difficult people are who they are and will act as they act. The good news is they become quite predictable, which can work in your favor. By understanding their psychology, you’re able to modify how you behave with them.

As an entrepreneur, it’s pretty much impossible to avoid difficult people. Still, there are ways you can make the best of a bad situation.

Russ Alan Prince is the executive director of Private Wealth magazine and chief content officer for High-Net-Worth Genius. He consults with family offices, the wealthy, fast-tracking entrepreneurs, and select professionals.

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