I do a lot of odd things at The Honest Broker. Some days I even give advice.

Today is one of those days.

A few readers will dislike this post—mostly because I’m going to be brutally honest. Even worse, I’m gonna be judgemental. And that’s a big pet peeve among people who judge such things. (Footnote: See point 5 below.)

But if I’m foolhardy enough to call myself the Honest Broker, I do have to tell it straight. And, today, I will give you my 8 best techniques for judging a person’s character.

I made mistakes early in my life by not accurately judging the character and reliability of other people. I was better at evaluating data than individuals.

I took far too much at face value. I believed what people told me. And I paid a price for this, sometimes a high price.

You may have had similar experiences.

Diogenes seeking an honest man (18h century painting by Tischbein)

At least I learned from my mistakes. Over the years, I developed several techniques for assessing character—and a few of them I’d even describe them as secret skills, because such matters are rarely discussed and some of the best evaluation methods aren’t widely known .

The careful application of these techniques has saved me a lot of heartache and agita. My dealings with people tend to be positive nowadays, and mostly because I’ve put a lot of effort into ensuring that they are good, trustworthy people. This is valuable both on the upside and downside.

I wish somebody had told me these things when I was younger. I now practice them when I need to get a fast assessment of people I don’t know well.

This is a sure-fire technique, and it tells you important things about people you can’t learn any other way. A person’s choice of a spouse—or if they aren’t married, their closest lifelong partner—is much more revealing than anything they say or do in public.

This choice tells you about their own innermost longings, expectations, and needs. It tells you what they think of themselves, and what they think they deserve in life (or will settle for). It is, I believe, the clearest indicator of priorities and values you will ever find.

So the next time you’re introduced to strangers at the party, and they start talking business, spend at least a little time sizing up their partners. If you don’t pay attention to this, you will have lost an important source of insights, and may pay a high price as a result.

People reveal their true natures when they deal with others who have no power and can never return a favor. They feel immune and free of all consequences—so they let it rip. Their true self comes to the forefront.

I once had dinner with a CEO who was so abusive that the server left the table in tears and had to be replaced by a coworker in the middle or our meal. In another instance, I dealt with a (different) CEO who, before an important business meeting in a hotel could be heard outside in the hall screaming at one of the service workers.

I learned more about these individuals in those settings than from anything they said or did in a negotiation. In fact, you might not trust anything they say at the negotiating table after you’ve been with them at the dinner table.

In contrast, I’ve seen famous and powerful people who take extraordinary care in their dealings with service workers. This is one of the most reliable indicators of trustworthiness that you will find. 

This is another CEO story, but with a positive lesson in this case. I met this particular corporate power broker when he interviewed me for a project, and we later became quite close.

In the interview, he started by asking me about my earliest experiences—entirely focused on what I did before reaching the age of twenty. I thought this was just small talk, and eventually he would change the subject in order to inquire about my qualifications and plans for the project.

But he never changed the subject. We spoke for more than one hour, and solely about my childhood, my teenage years, and how I grew to adulthood.

Later he explained to me that he lets other people in the organization worry about boring things like credentials. His belief is that people’s character and ability to handle challenges are almost entirely formed during the first two decades of their life. It’s an unusual case, he said, for people to change in any substantive way after that point—not impossible, but very rare. So those early years were always the focal point for his inquiries.

This was one time when my working class origins didn’t hurt me. From his point of view, the distance I traveled before going to college was my most significant attribute.

Perhaps he took this technique too far, and on my first exposure to this approach I was highly dismissive of it. I simply assumed that he wasn’t skilled at interviewing. But I got to know him well, and over time saw he had an impressive track record in assessing people. I now believe he was on to something and practice a similar technique when I need to figure out who people really are and how they might act in difficult situations.

I write articles and books, but the two most revealing documents about me are my calendar and monthly budget. I know some fortune tellers want to look at a person’s palm to read their future, but I’d prefer to take a glimpse at how they spend time and money. Those reveal what a person is really all about.

And that’s true for me and you, and everybody else. It’s so easy to say the right thing, but time and money are far more precious than words. Watch carefully how people allocate those two resources and you will understand them at a very deep level.

This is another instance in which people reveal things about themselves unintentionally. And I’ve seen it so often that it’s uncanny. The flaw people hate most in others is usually their own greatest weakness.

My father smoked cigarettes his entire life (which they shortened appreciably). He was the most forgiving and tolerant of parents, but if I had started smoking, he would have wept. He would have accepted almost anything from me—except imitating the deadly mistake he had made, and kept making.

But this happens everywhere. Cheaters always gripe that others are dishonest. The liar always accuses other people of lying. Parents absolutely lose it when they see their children making the same mistakes they did.

This may seem like pure happenstance, but there’s a good reason for it. When we look in a mirror, we dislike seeing all the flaws in our appearance, and the same thing is true when we examine other people. They, too, are like mirrors. So we are far more likely to forgive a weakness we have never experienced than one we struggle with daily.

When you encounter people in any kind of setting, from professional to social, they can choose to (1) talk, (2) listen, or (3) do neither. I have far more confidence in group 1 than 3, but group 2 is the rarest—I’ve met few great listeners in my entire life. But they are some of the most effective individuals I’ve ever encountered.

There’s often a bias against listening as part of someone’s skill set—that’s why you will never see it on someone resume. I’m sure many of you believe it indicates passivity or laziness or some other character flaw. I think this reaction is a result of mistaking people who do (3) with those who do (2).

Great listeners possess extraordinary skills of awareness and comprehension. They can assess situations with tremendous accuracy, and act in ways that maximize group effectiveness. No organization has enough of them, and if you have one of these great listeners as a friend or colleague, you soon learn that they are an invaluable resource.

I recently heard a man complaining about a bad business deal. His partner had robbed him, and he should have known better.

When they first met, they had played golf. Afterwards his wife told him: “I saw him move the ball when you weren’t looking—don’t get involved with this guy.” He had laughed at this. Why get worked up over a tiny thing like this? It’s just a few inches on the golf course.

But, of course, if someone will break the rules for something as unimportant as a game, what will they do when higher stakes are involved? In this instance, he had a useful warning, but didn’t take it—because he thought it was so small.

Don’t make that mistake. Watch out for the small things, and the big things will take care of themselves.

I heard of a peculiar technique used by a company hiring a senior executive. In the final round of interviews, the candidates are taken to lunch, and during the meal something goes wrong—of course, this is all staged as a kind of test.

Maybe someone walks up to the table and creates a scene, or perhaps the food delivered to the table is completely wrong. The purpose is to see how the candidate handles the situation. You fail the test if you over-react (for example, causing a scene yourself) or under-react (e.g., just letting things get out of control with no response).

My jazz musician friends will immediately understand the value of this kind of test. You can’t tell how a person improvises until they are put into a situation where spontaneous decision-making is required. Some people rise to the occasion, and others lose their cool completely.

Not all of us can stage a restaurant mishap to test somebody. But if you’re around somebody long enough you will see how they deal with unexpected problems. And those situations are precisely when their character and core values come to the forefront.

I should add one last point.

These aren’t just useful in evaluating other people. You can use these same techniques on yourself. Do you treat service people fairly? Can you handle problems and inconveniences without overreacting? Are you trustworthy in small things? Etc.

Perhaps the character you need to assess is your own. I take that idea seriously, although it’s sometimes painful to use these evaluative methods on myself. But that, my friends, might be the most useful piece of advice of them all.

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