"Knowledge is knowing that a tomato is a fruit.
Wisdom is knowing not to put it in a fruit salad.
– Miles Kington
A few years ago, I met an actual flat-earther.
I was introduced by a friend who wanted to enter into a business venture with her but, for obvious reasons, wasn’t quite sure.
I got excited about our introduction because I always like to meet people with a sense of curiosity rather than judgment.
Also, spending as much time as I do in a place like Bali, you get a little desensitised to wacky folks – mostly other expats – and she sounded next-level.
Besides, believing that we live on a giant spinning disc – despite all the evidence to the contrary – isn’t that big a jump from blaming Mercury in retrograde for every one of your inconveniences or claiming it took seven days to create the universe.
Secretly, I was hoping to meet a charismatic guru who, by slowly planting unreasonable doubts in my mind about entirely reasonable events, would sneakily suck me into her dark web of implausibilities.
Instead, I got a rambling lunatic who, within thirty minutes of sitting down, had already gotten herself lost in a maze of anti-science, Illuminati and, of course, Bill Gates.
Had I been nearer the Earth’s edge, I’d happily have rolled myself over it, avoiding Australia along the way, which, for inexplicable reasons, doesn’t exist according to most flat-earthers.
But the crux of the story is not this person’s outlandish views.
It’s rather that she chose to share them with me so freely and so early upon meeting her.
As a potential business partner, would you put someone in charge who demonstrates such poor judgment in front of a client or a potential investor?
This article covers what good judgment at work actually means, and six practical rules for developing it, drawn from the framework of Sir Andrew Likierman, one of the world’s leading authorities on leadership.
What good judgment at work actually means
You might have come across a loose cannon or two like that too.
Or, perhaps you’ve even been accused of being one.
Truth be told, most of us – myself included – could do with cultivating better judgment.
With unlimited information literally at our fingertips, the world is shifting its focus from knowledge work to wisdom work.
That means discernment and common sense sell at a premium on the job market these days.
Indeed, to create any kind of job security in the age of AI, you need to offer something technology currently can’t and never might: sound judgment.
The question remains: what constitutes such judgment?
Sir Andrew Likierman, one of the world’s authorities on leadership, defines judgment as:
“The ability to combine personal qualities with relevant knowledge and experience to form opinions and make decisions.”
While everyone has the ability to form opinions, what will truly improve your professional and personal standing is getting better at forming good opinions.
Borrowing rather heavily from Likierman’s knowledge on this subject, I’ll briefly summarise what he believes to be the six rules of good judgment and how to apply each of them.
Rule 1: Listen actively and read selectively
The older we get, the more entrenched we are in our beliefs, the less open we become towards new experiences, and the worse we are at listening.
Cultivating better listening skills – indeed, active listening – is the number one requirement for improving the quality of your decisions.
Contrary to popular belief, active listening isn’t about being able to parrot someone’s words back at them.
It’s about getting better at picking out relevant information and conducting a conversation so that you seek to understand rather than be understood.
It requires you to switch off the part of your brain that wants to jump in and, instead, ask further questions that encourage the other person to offer more information than they otherwise might volunteer.
Active listening allows you to get a fuller picture by lifting the curtain just a little more, so you also pick up what is not being said, allowing you to form a better judgment.
When it comes to reading, however, less is often more, so always choose quality over quantity.
As Likierman points out, you’ll likely benefit more from a decent six-page summary than a 300-page document if the latter means you’ll only skim through for information that already confirms your existing opinions.
Rule 2: Seek out people who will challenge your thinking
Overconfidence can be an issue, especially when you’re in a leadership role or if you’re an individual contributor with a lot of experience in your field.
Being decisive is helpful when it comes to solving problems that have clear answers and solutions, but when it comes to high-stakes and more complex decisions, be sceptical of your own opinions and allow yourself to be persuaded by your trusted advisors.
However, be mindful of who you let into your trusted circle because Likierman is clear: if you want to make better decisions, you must increase the number of nay-sayers you surround yourself with.
He refers to Amazon’s Leadership Principles, which state that leaders should always “seek diverse perspectives and work to disconfirm their beliefs.”
Indeed, research shows that homogenous groups, regardless of the commonality that unites them (gender, ethnic background, politics, etc), often make decisions too quickly and don’t question their assumptions enough.
In other words, avoid those who will tell you what they think you want to hear, and when evidence starts piling up against your previously held view, be humble enough to change your mind.
Rule 3: Broaden your experience deliberately
Generally, the more experienced you are in your field, the better your decisions.
Not only does that experience offer plenty more context, but it also expands your toolbox of possible solutions.
But experience is a double-edged sword.
Too much expertise in a narrow field can lead to complacency and a misplaced belief that your expertise transfers into other fields.
In a world with evermore complex problems, we need increasingly sophisticated and interdisciplinary solutions, which in turn requires people willing and able to see connections between their fields and those of others.
This kind of world increasingly favours T-shaped careers where professionals combine deep expertise in one area with a breadth of knowledge across several other domains.
If you want to improve your judgment, start by showing greater curiosity for the work of others, lead with a creative and open mind and be intellectually versatile.
Expose yourself to new developments, situations and people; get postings abroad or seek experience in different areas of your company.
It’s precisely this combination of being excellent at what you do and collaborating well that will allow you to develop sound professional decision-making later on in your career.
Rule 4: Understand your cognitive biases
Ever since our early ancestors decided to crawl out of the ocean, our brains have evolved into seeing patterns everywhere, even when there aren’t any.
These psychological biases are nothing more than mental shortcuts that allow us to make faster decisions and are, therefore, particularly pervasive in times of crisis.
They help our brain get past a couple of major problems, such as having too much information (ex: anchoring, confirmation bias), not fully understanding that information (ex: hindsight bias and negative bias), having to act too fast (ex: sunk-cost fallacy), and not knowing what to remember (ex: unconscious racial bias).
The best decision-makers are those who combine vision and passion with an ability to detach themselves emotionally and logically from those mental shortcuts and whichever solution happens to lie on the table.
They have enough self-awareness to rightly identify their biases and a willingness to look at their options through different lenses, taking various perspectives and playing devil’s advocate.
In other words, people with sound judgment are those who disconnect from their intuitive, automatic and reactive, so-called ‘hot’ thinking by switching to ‘cold’ thinking, which is more reasoned, deliberate and controlled.
Rule 5: Consider more options before deciding
A lousy decision often follows when those who made it didn’t consider enough alternative routes.
Research shows a strong correlation between the success of a decision and the number of options considered.
Indeed, if you’re currently pondering a yes/no decision, it means you’re probably not giving yourself enough alternatives.
Decisions are rarely binary, so you’re better off switching an either/or question into a ‘Which one?’.
Also, be aware of the choice paradox, which states that the more options to choose from, the harder it is to know what’s best, and the more we get stressed about potentially making a ‘wrong’ decision.
Avoid aiming for the ‘best’ solution; instead, have a set of clear criteria to determine any decision that falls on the spectrum of being ‘good enough’.
Remind yourself to look at the big picture and determine how each option aligns with your core values.
Rule 6: Plan for what could go wrong before you commit
Once you’ve settled on a course of action, think through what executing your decision will look like.
Likierman suggests deciding beforehand how you’ll manage the risks involved in executing.
To do so, apply the Stoic principle of ‘Premeditatio Malorum’ by preparing for everything that could go wrong.
One way to do this is through a storytelling technique developed by futurist Peter Schwartz, which involves imagining three future environments: one where things get better as a result of your decision, one where they get worse, and one where things get weird or unexpected.
This is also known as a premortem, where you try to identify every single reason why a particular decision or course of action might fail.
It requires you to develop a habit of running through any bad scenario that could reasonably happen and then deciding beforehand how you will respond if that were indeed to happen.
By making decisions on how you’ll pivot while still in a ‘cold’ state, you’ll avoid making panicked choices when you’re in a future ‘hot’ state.
Better judgment at work: the core point
The ability to make sound decisions is becoming more valuable, not less, as complexity increases and AI takes over more routine tasks.
Good judgment requires excellent listening, intellectual humility, a broad base of experience, awareness of your biases, a genuine consideration of alternatives, and the discipline to think through execution before you commit.
It’s a combination of skills that compounds over time. The earlier you start developing them deliberately, the more reliable your judgment becomes.
And as for my advice to my friend on the flat-earther? I told him I saw no reason not to work with her. Because every so often, entertainment is allowed to take precedence over professional caution.
If you’d like to work on your decision-making or professional judgment as part of your leadership development, the coaching services page has more on how that works.