Laws and rules are not very effective tools for determining 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 your strength of character. It also demonstrates the soundness of your judgment. 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 this with a well-known example you may have encountered before.
Consider the following two real-life historical leaders and judge who you deem the better leader.
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 traumatised childhood that he never healed, however, created a person responsible for the death of millions in a cause he truly believed to be “good”.
Person A was Abraham Lincoln. Far from perfect – like 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 from yours?
People fascinate me. Regardless of the diverse individuals and cultures I encounter or study, no two people are identical. We share much in common, yet each person possesses a unique superpower and diverse perspectives rooted in their backgrounds and experiences.
No two people can have the same viewpoint on a topic. This is similar to how two people looking at the same object from different angles see slightly different versions. Their positions relative to the object cause them to perceive it differently.
Opposing Views
Improving your judgment involves the ability to hold two opposing views simultaneously. We live in a paradox. An organisational leader is also a father, husband, sibling, friend, and possibly a grandchild. These roles intertwine, like threads in a beautiful tapestry, forming one whole. Focusing on one part of the tapestry, you always see it within the context of the bigger picture.
Knowing this, consider the first essential question to improve your judgment when you find yourself judging someone or something. How do you treat someone who has an opposing perspective to yours on a topic?
Do you shame or scold them? Perhaps you subtly punish or ostracise them. Or do you try to understand their perspective and find common ground?
Improving your judgment isn’t about choosing right versus wrong. It’s about finding a resolution. This requires understanding the opposing and mutual goals of each party involved.
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 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, which 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 who 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 determines your ability to judge fairly. Do you look deeper than face value, or do charismatic words easily fool you?
3. Is what you say and do in public the same as what you say and do behind closed doors?
I once worked closely with the CEO of a nonprofit organisation with a vision to help people experiencing homelessness. When I met the CEO, he spent a lot of energy showing me how “good” he is. He would apologise 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 was making a big difference. The cracks, however, began to show after only a few weeks, as the effort of maintaining a public image outweighed how he truly felt inside. One day, after a stressful board meeting, he was stopped by two homeless men who had been 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 people with addictions and homeless people all lie.
The facade of truly caring about homelessness evaporated like a cloud before the sun. He didn’t care so much for them 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 choices inclusive, giving everyone a voice, or are you the sole decider? Secondly, are your decisions driven by fear or love? Are you perhaps afraid of being perceived as not good by others? Or maybe you fear losing your job or being seen as incompetent?
You can’t make good judgment calls if you make them out of fear or driven by short-term gains. You need clear values and to look at the impact of your decisions to make sustainable and fair judgments. Good judgment ensures that the effects 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, about halfway through the growing range of voltage, but complied when a supervisor asked them to do so, regardless of how they felt.
It turns out we would rather obey authority than use our 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 was instructed 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 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?
Conclusion
Most of us are quick to judge. We want to be right and part of the winning team. We don’t, however, realise that even though you might not be on the losing team, having a loser means that everyone loses in the end. Everyone suffered during the past wars. 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 a resolution so that everyone walks away a winner. If everyone doesn’t win, everyone loses.








