There’s a time when most business leaders start sleeping better.
Less second-guessing, less doubting a big decision, less endlessly running scenarios through their head.
Doesn’t that sound like a sign of success?
Well, I’m not so sure.
Confidence and certainty aren’t the same thing
Experienced business leaders rightly feel more confident.
When you’ve made enough difficult decisions, and been through enough twists and turns, you simply have a better understanding of how to be successful.
The self-assurance that comes with that can be valuable: it’s what allows a leader to make decisions under pressure.
But certainty is a bit different.
Certainty is what confidence becomes when it stops being tested. And it’s dangerous – because nothing is a sure bet in business.
Which is why the leaders I worry about most aren’t the ones who doubt themselves too much, they’re the ones who’ve stopped doubting themselves at all.
Where did the doubt go?
Self-doubt generally doesn’t disappear of its own accord.
In my experience, it’s usually one of three things.
- The people around you stopped pushing back.
Probably not because you got everything right, but because they learned, bit by bit, that pushing back wasn’t worth it. Either disagreement got expensive or the rewards of challenging ideas just didn’t cut it. So they went quiet. - The decisions got bigger. The more senior you become, the less likely people are to want to challenge you in the moment, and the greater the expectation feels to be confidently right all the time. That need to project experience can quickly manifest as an absence of doubt.
- Everyone’s opinions converged. As soon as many senior teams hit on a winning strategy, it’s all too easy for viewpoints to homogenise. Through instinct and natural preference, the team becomes samey, filled with people who get you and move at your pace. Just like a band who’ve been together too long and run out of ideas.
What’s dangerous is that at the time, these trends can feel like progress, with teams becoming more streamlined and decision-making speeding up.
When doubt is key
For a few senior leaders, uncertainty can only grow with their experience. And that’s often not because they’ve become worse at managing it, but because they understand more fully what’s at stake and how much can go wrong.
A healthy amount of that doubt is critical. It’s not a weakness, it’s the thing that keeps you honest: driving you to check your thinking, seek a second opinion, sit with a decision a moment longer rather than jumping to action.
The quality of a leader’s decisions tends to deteriorate not when they lose confidence, but when they stop doing their due diligence, and get too comfortable with silent certainty.
So here’s a question for you:
When did someone last tell you something you didn’t want to hear – and what happened next?
Did you act on it? Did you punish them? Did they seem hesitant to speak out?
Because preserving a healthy feedback loop will only drive your business forward.
While we’re talking about doubt, I’ve just written a brand new guide that looks at what drives business decision-making. It’s called How to Make Better Business Decisions and it’s already helped scores of business leaders like you.
Time to harness doubt
The leaders I’ve seen get into real difficulty aren’t usually the ones who lack ability or commitment. They’re the ones who gradually, imperceptibly, lost access to the kind of honest input that would have kept them sharp.
Keeping that element of doubt in your own decision-making – and doing the due diligence of getting an outside perspective and validating your assumptions – will mean your business stays match fit for years to come.
Kind regards,
Chris