Laws and rules are not very good tools for judging whether a person, behaviour or situation is considered “wanted” or “unwanted”. Neither is a public display of character when you are not able to see the hidden agendas or what’s going on when no-one is watching. Judgment requires something deeper, something that can’t be learned by reading laws.  Judgment requires wisdom.  It’s what you do when no-one is watching that determines whether you’re considered “good” or “bad”.  Here are 5 essential questions to help improve your judgment.

Who is the better leader?

Although we think we’re good judges of character, most of us are fooled by presentation. Let me illustrate with a well-known example you might have come across before.

Consider the following two real-life historic leaders and judge who you deem the better leader was.

Person A

On the one side, you have a person who regularly suffered from depression and was prone to lashing out in anger.  He publicly derided his opponents in newspapers and imprisoned reporters who didn’t comply with his demands for 3 months.  He also attempted to silence vocal opponents with a duel to the death.

Person B

On the other side, you have a person who worked long, hard hours to rebuild his country’s failing economy.  He adopted the young daughter of his girlfriend and regularly hired orphaned boys into positions of government service and outreach.  He was a well-published writer and advised by experienced counsel.

Who was the better leader?

If you chose person B you would have chosen Adolf Hitler.  The kind, well-presented person seemingly working towards a cause for the common good of humanity.  His covert agenda, born out of a traumatized childhood that he never healed, however, created a person responsible for the death of millions in a cause he truly believed in to be “good”.

Person A was Abraham Lincoln.  Far from perfect – as all people alive today – but a respected leader and known and loved for his decision that effectively ended the ongoing war at the time.  As the 16th American president, he is remembered as one of the great leaders.

Questions to improve your judgment

1. How do you treat people with a different viewpoint as yours?

People fascinate me.  No matter how many diverse people and cultures I come across or study, no two people are the same.  We have a lot in common, but we each have a unique superpower and diverse perspectives based on our unique background and life experiences.

It is not possible for two people to have exactly the same viewpoint on a topic, just like it’s not possible for two people sitting opposite each other looking at the same object and see the exact same thing.  Even though they’re looking at the same thing, their angle and position in relation to the object will result in them seeing slightly different versions.

Opposing views

When you improve your judgment, you realise good judgment comes from the ability to hold two opposing views at the same time.  We live in a paradox.  An organizational leader is also a father, a husband, a sibling, a friend and a child and possibly grandchild.  He can never separate these aspects fully from each other. Like a beautiful tapestry, the different threads – or parts – are woven together to form one whole.  When you look at a tapestry you might focus on one or another part, but you always look at it within the context of the bigger tapestry.

Knowing this, the first essential question to take into consideration when you find yourself judging someone or something and to improve your judgment is to ask yourself how you treat someone who has an opposing perspective than yours on a topic.

Do you shame or scold them? Do you maybe subtly punish them or ostracize them? Or do you try to understand their perspective and find common ground?

When you improve your judgment, it is not about choosing right vs wrong, it is finding resolve.  It requires an understanding of the opposing and mutual goals of each opposing party.

2. How do you treat the most vulnerable and powerless people?

The true character of a person – and with that their ability to judge fairly – shows when they’re among those less fortunate than them rather than those more powerful than them.  In a little leaflet containing a few verses on how to train your mind in order to be happy that I got years ago at a talk by a Buddhist Monk, one of the hardest verses to comprehend but most valuable in judgment reads:

“When in the company of others

I shall consider myself the lowest of all,

And with respect, from the depths of my heart,

I shall hold them to be supreme”

This goes against everything society has told us we need to be happy or how our court system judges.  In western culture, it’s a race to be the most important that results in happiness and the one with the most money will most likely win the court case. Often it’s the most cunning or talented lawyer that wins the case, not the most worthy.  If you can afford a talented lawyer and your opponent can’t, you have a much better chance at winning the case, regardless of how fair that judgment is. It relies mostly on the skill of the lawyer or advocate to judge a case.

How you treat those lesser than you determine your ability to judge fairly.  Do you look deeper than face value or are you easily fooled by charismatic words?

3. Is what you say and do in public the same as what you say and do behind closed doors?

I once worked very closely to the CEO of a non-profit with the vision of helping the homeless.  When I met the CEO, he spent a lot of energy to show me how “good” he is.  He would apologize for being late because he helped a guy in a wheelchair get home along the way.  Or he would hold out his hand respectfully to a beggar at the traffic light and invite him to come to the homeless shelter while sitting next to me in his car.  Or he would share his vision to give these vulnerable people a second chance in life and how he enjoys being paid for the opportunity to help the less fortunate.

 Good intentions

For a while, I truly believed that his intentions were good and pure and that he is making a big difference.  The cracks, however, started showing after only a few weeks as the effort of keeping up a public image outweighed how he truly felt inside.  One day, after a stressful board meeting, he was stopped by two homeless men who were chased out of one of his shelters.  I didn’t hear the whole conversation, but I did hear how he loudly scolded them for being liars and sent them away without help.  They came back again and again, each time being sent away cold-heartedly to sleep on the street.  The video footage containing their claimed assault at the shelter mysteriously disappeared and no-one bothered looking for it, harshly judging them as lying based on an expectation that addicts and homeless people all lie.

The facade of truly caring about homelessness evaporated like a cloud in front of the sun.  He didn’t care so much for the homeless as being in a position where society would see him as a good person.

You can’t fake authenticity.

Given enough time, or put under enough pressure, any facade will start crumbling if what you say is not aligned with how you truly feel behind closed doors.

4. What drives your decisions?

Do you consider the impact of your decision?  Or do you only worry about immediate gratification and the immediate relief your decision brings?  Are your decisions inclusive – giving everyone a voice – or are you the sole decider?  Secondly, are your decisions driven by fear or love?  Are you maybe afraid to be seen as not good by other people?  Or maybe you fear losing your job or being seen as incompetent?

You can’t make good judgment calls if you make them from fear or driven by short term gains.  You need clear values and looking at the impact of your decisions to make sustainable and fair judgments.  A good judgment is one that ensures the impact of the judgment doesn’t negatively affect anyone now or in the future.

“You don’t inherit the earth from your parents, you borrow it from your children.” – Unknown

5. Would you do what you ask others to do?

In a controversial psychology experiment with the intent to understand how seemingly good people became killers during the holocaust, people were asked to give electric shocks to victims in an adjacent room.  They could hear the screams and see the pain inflicted each time they pulled the lever with an increasing voltage.  Most people wanted to stop when the screams became unbearable at about halfway through the increasing range of voltage but complied when a supervisor asked them to do it regardless of how they felt.

It turns out we would rather obey authority than use our own judgment to decide whether an action is deemed right or wrong, even if it seriously harms an individual.

To expand on this detrimental force of authority figures removed from the actual task, another study concerned with the ability to fairly judge when under severe pressure involved ways to set off a nuclear bomb.  When the codes to the bomb were locked in a safe accessible only to an assistant or trusted advisor, the authority gave the instruction to set off the bomb with relative ease.  However, when the codes were implanted next to the heart of the assistant and required the authority to kill him in order to access the codes, the authority couldn’t do it.

When you are faced with the impact of your decision you might make a different choice, and improve your judgment,  than simply standing afar and giving an instruction for someone else to act out.  Would you do what you ask others to do?


Most of us are quick to judge.  We want to be right and part of the winning team.  We don’t, however, realize that even though you might not be on the losing team, by virtue of having a loser everyone loses in the end.  Everyone suffered during the wars of the past.  Those who won lost as many loved ones as those who lost.

Judgment is not about being right or wrong.  When you improve your Judgment it is about finding resolve so that everyone walks away a winner.  If everyone doesn’t win, everyone loses.

Image source: Depositphotos

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With more than 20 years experience in the software development industry, Kate specializes in helping teams get unstuck, communicate better and ultimately be more productive. She believes in efficiency through fun implementing lean, agile and playful design as tools for process improvement and organizational change. Her goal is to create more happy, healthy and whole workplaces where each person thrives and productivity soars.