356. The Leadership Skill Nobody Trains You For
Most leaders think they struggle with risk. They don’t. They struggle with uncertainty.
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Most leaders think they struggle with risk.
They don’t.
They struggle with uncertainty.
There’s a difference - and it’s an important one.
The Difference Between Risk And Uncertainty
Think about why you got promoted.
Maybe you were an exceptional worker.
You delivered results.
You made smart, defensible decisions.
Maybe you even worked on a team with clear goals, measurable outcomes and feedback loops you could trust.
That’s a risk-related environment.
Risk is comfortable because it’s something you can quantify. You can spreadsheet it and defend it.
Uncertainty is different.
Uncertainty means you can’t reliably predict outcomes at all.
It involves moving targets, new technology, and decisions that won’t make any sense until well after you’ve made them. Sometimes long after.
And here’s the nutso part of this:
The most important leadership decisions are rarely risk decisions.
They’re mostly uncertainty decisions.
Your Fear Is Camouflaged As Confidence
When leaders say things like “I just need more data” or “We’re not ready to decide yet,” it sounds strategic.
It isn’t.
It’s fear, camouflaged in a costume of confidence.
I know, because I was that leader for a long time. Too long. So long that I’m embarrassed to tell you how long it was.
I wasn’t bad at risk-based decisions - I could assess the probabilities just fine. But uncertainty? I was kinda like a plane idling on the runway. The engines were on, the passengers were restless to move, and I convinced myself I was being careful by going absolutely nowhere.
Join me on Substack Live this Thursday to discuss risk and uncertainty
Click here
Why Uncertainty Freaks Leaders Out
If uncertainty scares you, you’re not alone. It’s scary for a lot of leaders - not because of what might happen, but because of what it reveals about you.
That’s right.
Risk tests your intelligence.
Uncertainty tests your ego.
Here’s what I mean:
Uncertainty could threaten your identity as a knowledgeable leader
(“I’m supposed to know the answers, but I don’t.”)Uncertainty could expose your need for control
(“I can’t control what I can’t predict.”)
That’s exactly the reason why uncertainty feels personal. Because it is.
And that’s why so many leaders respond to uncertainty by avoiding it instead of learning how to navigate it.
The ability to navigate uncertainty is a critical element in becoming a successful leader.
So we’re going to talk about that for a wee bit.
When Waiting Feels Safe
I have a client, the CEO of a $50m non-profit. He’s great at risk-related decisions. If there’s a better option, he’ll choose it quickly.
But when it comes to uncertainty, he freezes.
So he waits. Because waiting feels safe to him.
But waiting doesn’t reduce uncertainty. It just postpones accountability.
Remember, not deciding about uncertain situations is still a decision. It’s just a really bad one.
How AI Increased Uncertainty
AI was supposed to help leaders feel more confident. That’s what they told us. It was supposed to give us the answers we need to help us make more informed decisions.
In some ways it does. It puts more information at our fingertips. It gives us faster analysis, better pattern recognition. I’ll give it all that. But there’s a catch:
AI reduces the effort, but it increases the uncertainty.
Because of AI, the pace of change has accelerated like an F1 car on race day. And when the world is flying by that quickly, your competitive advantage can disappear before you even realize you had one.
Here’s the problem: No one actually knows where AI adoption is headed.
Sure there are theories and forecasts and a whole lot of opinions from people on LinkedIn. But certainty? Hell no.
What we do know is that every company will need to embrace AI at some point, in some form. Everything beyond that is a foggy fen of uncertainty.
When do you need it?
Why do you need it?
Where does it actually help?
How will you integrate it?
And what will you sacrifice if you guess wrong?
Those aren’t technical questions. They’re leadership questions.
And they’ll force you into the uncomfortable position of making decisions without knowing the true risks.
That’s uncertainty.
The leaders who are struggling right now aren’t struggling because they lack data or intelligence. They’re struggling because uncertainty doesn’t give the emotional security that risk does.
You can’t sleep as soundly at night with uncertainty as you can with risk. It’s all about the discomfort.
What Great Leaders Do With Discomfort
The leaders who handle uncertainty well don’t have more answers, they just have a higher tolerance for discomfort.
Risk is about decision-making.
Uncertainty is about ego.
Your tolerance for discomfort is directly related to your ego’s need to be right.
Here’s how the great leaders make decisions in a world of uncertainty.
They decide with incomplete information
They stop waiting for clarity because they know it isn’t coming.
They make smaller, reversible bets
Taking small steps instead of power punches allows you to learn fast and be much more agile in decision-making.
They shorten feedback loops
They’re less focused on perfection and more on the speed in which they can learn what works and what doesn’t.
They communicate direction, not certainty
They say things like:
“Here’s what we know and here’s what we don’t”
“Here’s what we’ll adjust as we learn”
That type of talking builds trust.
But pretending you have certainty will destroy it.
Join me on Substack Live this Thursday to discuss Risk and Uncertainty
Click here
A Simple Reframe
If you’re stuck in decision-making purgatory, here’s a simple reframe.
Stop asking yourself “What’s the safest decision?”
Start asking yourself “What decision helps us learn the fastest?”
When it comes to uncertainty, progress is better than perfection every single day.
Why This Matters More Than Ever
This matters more than ever now because we’re living in a moment where technology is transforming jobs, companies and communication. Employees are anxious. Leaders are increasingly lost and exposed.
The future isn’t going to give you enough information to feel safe. That’s not the way this works.
If you’re waiting to feel ready, you’re going to be too late.
The leaders who win won’t be the ones who waited for certainty. They’ll be the ones who admit they don’t know what’s going to happen, but move forward anyway.
That’s leadership.
Be that leader.
Are you ready to understand why parts of leadership still feel too hard? You need to join the diagnostic workshop to learn the patterns holding you back.
Sign up on the waitlist for discounts and updates on the next session (February).
I like the approach you suggest. Cutting the elephant down by taking micro decisions and focussing on how we can learn fast. A really interesting framework. Thanks.
This lands. It’s something that I think intuitively I felt but never actually gave it much thought.
Discomfort tolerance is an underrated leadership capability. The best leaders I’ve seen and worked with don’t actually eliminate uncertainty, they operate inside it without needing to protect their ego.
Small bets, fast feedback, and honest language create their momentum.
Certainty always feels comforting, but learning is what actually scales.
Thanks for the insights!