The Pain and Power of Judgment

Justin Streight
Framing
Published in
5 min readFeb 25, 2018

Judgment can bring you wealth, influence, scorn and humiliation. It’s an essential skill that deserves training.

Schlesinger, the man with the glasses and bowtie, faced the ultimate challenge of good judgment — and failed.

The Power of (Good) Judgment

Here are some quickie examples of people who made it big, just by having sound judgment:

  • Barry Cunningham signed J.K. Rowling in 1997 for Bloomsbury Children’s Books and published Harry Potter.
  • Steve Jobs developed an affordable mouse, making his personal computers far more user friendly.
  • Henry Blodget predicted that Amazon stock would hit $400 a share in 1998 when it was only at $240.

The reason I mention these little snippets is not just that these people saw an opportunity and jumped on it. They had to move against the crowd when making the big call.

Cunningham signed Rowling after 12 other publishers had already rejected her manuscript. Jobs found (or arguably stole) the mouse after seeing it just wasting away at Xerox. Blodget predicted Amazon stock would pass $400 when other analysts thought the eCommerce leader, and many tech stocks in general, had hit a wall.

If only Blodget had practiced good judgment before getting charged with securities fraud.

But for every Jobs there are 10 others who put their necks out, and got their heads cut off. And even more who just never tried.

The Pain of (Bad) Judgment

Too often, the pain comes not from picking the wrong things, but from not picking anything at all. Instead, looking to everyone else and nodding along.

In the book Influence: The Pyschology of Persuasion, Robert B. Cialdini cites two situations where people are likely to defer judgment to others:

  • The first is “the rule of social proof” — everyone else is saying/doing it, I should too.
  • The second is “the rule of authority” — that person knows better than I do, I will follow their judgment.

We learn about both of these situations as children, from the Hans Christian Andersen tale: The Emperor’s New Clothes.

Two clothiers arrive at the palace, and tell the emperor they have a great robe for him, but only intelligent, truly kingly, people could see it. The emperor, not wanting to seem like a bumpkin to these medieval fashionistas, pretends to see it — ignoring his own judgment to the point of being naked.

The townspeople fall into the rule of social proof. The clothiers spread lies about the robe, ensuring the crowd pretends to be able to see robe. The more people who pretend, the harder it is for anyone to say anything. It takes a daft little boy to finally end the farce.

To children that story might seem a bit silly. Who wouldn’t call out the naked emperor? But as adults, we see “The Emperor’s New Clothes” stories all around us.

Ever been with a group of friends who love a movie, and you say you love it too — even though you never saw it? Ever come out of a team meeting thinking a plan was full of holes, but you didn’t say anything because — hey, they probably know better?

The movie 12 Angry Men convincingly portrays the emperor’s new clothes problem, and how powerful good judgment can be.

So, how do you cultivate good judgment?

There are good reasons people defer judgment sometimes. If everyone is fleeing in one direction, it’s probably best to just go along with it, rather than getting trampled by the stampede. And sometimes deferring to authority is essential, like when you don’t know anything.

But the mob’s reasoning is often questionable, and even Homer nods. So how do you cultivate good judgment:

-Understand the difference between what’s objective and subjective.

If you like something, you like it. There is no arguing for or against your liking of something, it simply is. It’s a subjective judgment, and it matters, because if you like something, odds are other people will like it too. Would you read it? Use it? Pay money for it? All of that matters — even if your friends think it’s dumb.

If you like something, try and figure out why. Too often people work the other way around, attempting to “quantify” good and doing the math in their heads to determine if they really “like” this or not.

-Expose yourself to as much of something as possible.

Read a lot, and you’ll refine your taste in books. Watch a lot of TV, and you’ll refine your taste for television. Eat a lot, and you will be a fat connoisseur.

You might like something, but not know there’s something similar or better out there (that’s often the case). Your judgment still matters regardless, but being able to compare means a lot too.

Of course, not everyone can be an expert in everything, but knowing enough at least allows you to question the experts intelligently. If their reasoning is unconvincing, then you might as well ignore authority.

-Learn to read between the lines.

Ever give something to a friend for feedback, only to get a “I liked it…” Did that friend really like it? Or are they just protecting your feelings? Or are they not confident in their own judgment? Or do they just not care and “I liked it” is the easiest path to avoid talking further?

If you see that happening to someone else, you might want to go ahead and stick your neck out and say what you really feel. Don’t follow the crowd into into endorsing something no one really believes, be a better friend and tell the truth.

By the way, the opposite happens too. Did he or she really not like it? Or do they just want to take you down a notch? Or do they not believe you would be capable of making something good? Or do they not trust their own judgment, and don’t want to risk being seen backing something unless someone else likes it first?

· Never fear the group meeting.

On April 4th, 1961, John F. Kennedy authorized the final plans for the Bay of Pigs invasion, which would pit some 1,500 counter-revolutionaries against an overwhelming force of Cuban fighters in one of the worst military blunders in U.S. history. In hindsight, it was really bad; but in foresight sight, it was really bad too. Why didn’t anyone speak up?

To maintain harmony in the group.

Presidential advisor Arthur Schlesinger, well aware of the plan’s many flaws, didn’t voice his convictions at the time, but he later said, “I can only explain my failure to do more than raise a few timid questions by reporting that one’s impulse to blow the whistle on this nonsense was simply undone by the circumstances of the discussion.”

Don’t be a Schlesinger, let your voice be heard.

And on the opposite side — don’t ask for opinions in a group.

Easier said than done. Judgment takes courage and practice. Everyone feels the pressure of a group, no one wants to be an unpopular whistleblower.

But your fears might be exaggerated. You’d be surprised how many groups appreciate an honest opinion. Sure, the boss may not be open to criticism. That happens. By all means, tell them what they want to hear, and while the boss’s decisions are tanking the business, start getting those resumes out, until you find the place that appreciates good judgment.

Just be sure to have it when you get there.

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Justin Streight
Framing

I spend too much time in my own head and try to drag others there with me. Email: recklessspeculations@gmail.com Youtube: https://bit.ly/2WjKodY