How to Be a Great Judge of Character

Throughout childhood and adolescence, we’re told not be judgmental – not to ‘judge’ others. That’s horrible advice, especially in business and entrepreneurship. Working with the wrong people can cost you tens of thousands, if not millions, and tremendous other opportunity. Hell, working with the wrong people as an entrepreneur can cost you your career…

There are great people in this world to work with, but just as many, if not more, self-serving and short-term thinking individuals. Deciphering between the two is paramount to your success as an entrepreneur. This is exactly why I say the most important asset a business has is its management team.

Lucky for us, there are two sure-fire ways to judge a person’s character

Two Ways to Judge Someone’s Character

Their actions

Forget what they say, smooth talkers are everywhere. What have they done? People’s actions tell you a lot about their trustworthiness.

Ask yourself these questions about said person before going into business with them:

  • What does their track record look like?


  • What do they do with their free time? From my experience, real winners like to accomplish something with their free time, or spend it with family and friends. Either way, they never waste it because it’s a treasure to them. People who have too much free time (in other words, those who aren’t ambitious) don’t value it, and that’s a concern.


  • Are they always looking for an excuse to grab a drink at the local watering hole, or do they have a hunger to hustle hard and burn the midnight oil?


  • Do they live like a millionaire on a modest income? These people are dangerous to go into business with, especially for startup scenarios – frugality leads to freedom.


  • Are their favorite things to talk about fantasy football and movies, or what they want to accomplish?


  • In conversation, does it always turn into something about them? Self-absorbed people have an uncanny ability to make every conversation about them.


  • Have they dealt with adversity in their life and made themselves better because of it? This is a big one for me. If I’m going into the trenches with someone (i.e. starting a business), I want to know that they’re fighters, not entitled brats. And to thicken one’s skin, one must be battle-tested. I need to know that said person can take a punch and keep on rolling. When starting a business, you’re guaranteed to take a few, but you have to keep on rolling and learn to fight back.


  • Do they have pets? If so, how do they treat their animal(s)? Don’t laugh. I’m serious. How someone cares for something or someone that can’t take care of themselves says a tremendous amount about that person. It also demonstrates how responsible and committed that person is. Purchasing a puppy or kitten is easy. Caring for and loving that animal throughout its life takes work and commitment.


Their Interests

What people are interested in says a tremendous amount about their internal motives and priorities.

Here are some questions to ponder before jumping into business with someone:

  • Are they well-read? Someone who reads a lot is very interested in gaining knowledge, and open to learning from others. And as a result of the reading, they’re likely to be well-spoken and a good writer (important in business), and have context around a multitude of issues. Someone who doesn’t take the time to read is either not interested in learning or simply boring. Every successful entrepreneur I know loves to read, and views it as a mental exercise on par for importance with staying physically healthy.


  • Do they enjoy physical activities? Unless physically unable, once again almost every successful person I know enjoys the outdoors, be it hiking, golfing, skiing, running, whatever. There’s something cerebral about being in nature and enjoying the great outdoors. Winners have an appreciation for this. Not only that, but taking care of oneself is vitally important for confidence, and is reflected in the boardroom.


  • If involved in a relationship, do they talk more about their significant other or the attractive waitress in the restaurant? This is a dead giveaway from my experience as to what they are like to work with. Granted, I haven’t experienced women behaving like this (although I’m sure there are many that do), a cheater in a relationship is likely a cheater in business. Enough said.


  • Do they talk more about the money they want to make or the impact they want to have? Money is great, but it can never be the prime motivator behind someone’s desire to start a business. It’s dangerous and leads to short-term, and often selfish, decisions. The mission must be more important than the money.


  • Are they workaholics? Workaholics are good to go into business with. No successful entrepreneur I know doesn’t put in long hours, all the time. And I know very few who live the proverbial ‘balanced life.’ The reason they put in the insane hours and are deemed ‘workaholics’ is because they love to work! These are people you want to go to battle with.

“It is the working man who is the happy man. It is the idle man who is the miserable man.”
–    Benjamin Franklin


  • Are they interested in current events? This is important. Entrepreneurs need to be up to speed on what is going on in the community, country and global economy.



Judge the character of a man from his actions and interests. While this list of questions to ponder is not all encompassing, it is meant to give you a great starting point on things to consider before going into business with another entrepreneur. Of course, in order to find the answers to these questions, you need to truly get to know said person. From my experience, there’s no better way to start to get know someone than through sports. It gives you the chance to bond, chat and exposes whether or not they have a competitive streak (which is great to see). The second best way to get to know someone: take them for a few pints and shoot the breeze. A couple brewskies have a way of making people open up and let their guard down.

Be judgmental. Become a great judge of character. It’ll make you more money as an entrepreneur, and improve your overall quality of life.

Stay hungry,
Aaron Hoddinott signature


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