Insecurity in Disguise

How defensiveness, certainty and control can get in the way of good leadership.

Over the course of a long career, I’ve had the privilege of working with some remarkable leaders. I’ve also worked with a few lousy ones, and learnt from them too. Not many, just a few. With only one exception, all the lousy leaders were men.

Am I saying men are more likely to be lousy leaders than women? Yeah, I am. But maybe not for the reason you might think. There are two reasons for that.

The first is simple demographics. For most of my career, men dominated the leadership landscape. More men at the top meant more chances for lousy ones to rise. And tough-guy behaviour was tolerated, often rewarded. That is changing, though not fast enough.

The second reason is this: men misunderstanding masculinity.

Too many men picked up an unhelpful set of beliefs about what leadership — and manhood — required of them. They had to appear confident, decisive, unshakeable. Doubt equals weakness. Questions signal uncertainty. Changing your mind means you were wrong. And being wrong is dangerous.

So they build psychological armour.

It shows up in predictable ways: refusing to admit uncertainty, humiliating people in briefings, blaming the team when something goes sideways.

And it makes real listening almost impossible. Real listening requires openness — a willingness to be changed by what you hear. To an armoured man, that feels like vulnerability. And vulnerability feels dangerous.

I once had a senior colleague, a finance guy, who made his view of my work very clear: “I don’t see any ROI in this culture-building bullshit. What you’re doing is just a waste of money. If I were in charge, I’d shut you down.”

Fortunately, he wasn’t.

A few years later, curiosity got the better of him and he quietly joined a one-day workshop. Soon after, he enrolled in our three-day leadership programme. At the end he admitted: “Okay, now I get it. I thought you were just entertaining people, but you’re actually adding value.”

What had changed? Not the programmes. Not the evidence. Somewhere along the way he had lowered his defences enough to see what had been there all along.

Oh, and by the way, he then earned a major promotion.

Things like this happen all the time. In the right environment, people set the armour to one side. They learn to listen. They lower their defences. They build stronger, more honest relationships with the people around them.

This isn’t exclusively a male problem. Women hear a different version: don’t show too much emotion, it’ll be used against you. Same message — vulnerability is weakness, and weakness is fatal.

But for many men, the need to appear strong has been too demanding, the fear of appearing uncertain too acute, the weight of armour too much to bear. Some men literally collapse. I’ve seen it happen.

The irony is that the armour was never making them stronger. It was just getting in the way. And the man wearing it is the last person who can see it.

And yet…

The best leader I ever worked with was the complete opposite of all this. He never hid his vulnerability. He wore his heart on his sleeve. If he was having a good day, we felt it. If he was having a bad day, we knew that too — but he never made it our problem.

He sometimes criticised himself for being human. None of us ever did.

His openness — the willingness to be seen, to be uncertain, to genuinely listen — is what made him extraordinary.

True, he was a physically powerful, imposing figure — an acclaimed leader in hospitality. Nobody was going to question his strength. You wouldn’t have wanted to get in a fistfight with him — or any kind of fight, really!

But perhaps because he had nothing to prove, he had no need for armour. Or perhaps he had a different upbringing, one where he was allowed to be both masculine and emotional.

I don’t really know how he became the man he is.

Real strength doesn’t need to advertise itself. Real confidence doesn’t need armour. The leaders who appear the most certain are usually the ones who feel it least.

I explore this in the chapter on vulnerability in A Handbook for Hoteliers. I believe it’s one of the most misunderstood qualities in leadership.

Think back over your career. Think about the leaders who made your working life difficult. The ones who micromanaged, blamed, didn’t listen. The ones who always had to be right.

Were they incompetent? Probably not. Malicious? Occasionally, maybe. But most likely, they were just insecure.

In my experience, poor leadership almost always comes back to insecurity. And it rarely announces itself. It’s often disguised as something admirable. Here’s one to watch out for: the leader who can never let go.

Striving to be indispensable is insecurity disguised as commitment.