Because business relationships are vital to your success as an entrepreneur, you’re almost certainly going to meet and need to work with many people over the years. Most people you meet in business are hardworking and caring. Few 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 will have to work with and sometimes work around people who make things unnecessarily hard. By artfully dealing with difficult people, entrepreneurs can still achieve their goals, but it requires finesse.”

Understanding difficult people better can be beneficial, knowing when it does and doesn’t make sense to work with them and using 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, there is 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 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 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 robust and solid evidence to the contrary. They find it completely unacceptable if you disagree with them.


Difficult people can make it very problematic for you to achieve your self-interests. For example, their attitude and approaches to negotiating can make it nearly impossible to get a deal done. For instance, 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 must consider that fact. 


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



  1. Dont rely on reason. 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 will not 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 will 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 willing to do nearly anything (including pounding you into the ground) to achieve that. It takes a deft hand to avoid being taken down and ensure both parties can close a deal and walk away satisfied.

  3. Dont expect a difficult person to change or become less difficult. Difficult people are difficult. It’s their nature, and their character 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 that they become pretty predictable, which can work in your favor. By understanding their psychology, you can 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.