Dictatorship in pinstripes: lessons from inside a bully's boardroom
AKA... the legacy gift of an absolutely diabolical boss!
By Lucy Hutchings Hunt
When we talk about leadership, we throw around words like vision, innovation, and strategy. But none of that means a thing if a leader does not have honour, clarity, integrity, transparency, fairness, and accountability. Without those, it is not leadership at all. It is just ego in a suit.
I know this because I worked for a man who embodied the opposite. Many moons ago, during the mid-2000s, for a six life-scarring months, I was the Executive Assistant to the CEO of one of the UK’s most important financial institutions. Let’s call him Mr X. On the surface, he was charming, powerful, polished, magnetic. Behind closed doors, he was the most destructive force I have ever worked for.
As his EA, I had a front-row seat to everything. Not one silo of his work, not just a snapshot, but the whole picture. His calendar, his correspondence, his travel, his relationships with colleagues and his personal relationships with friends and family, his public face and his private reality. I saw the contradictions, the half-truths, the sudden shifts from charm to perverse cruelty. And because I was so close, I could not look away.
At first, he dazzled me. Over dinner in Paris, he pitched me a vision of partnership, loyalty, and shared success. He promised, “I really pay.” I was professionally smitten. I believed in him.
Within a few weeks, his mask had slipped.
Dictatorship in Pinstripes
Mr X did not lead, he ruled.
His word, however inaccurate, became law. Disagreement was framed as disloyalty. Facts were dismissed if they did not suit his version of events. He would twist timelines, rewrite history, and expect everyone to nod along.
He demanded not just respect for his position, but blind obedience to his narrative. “You will agree with me. Whatever I say. I am the CEO.” That line wasn’t a one-off, it was his fundamental operating system.
His was not leadership built on trust, clarity, or collaboration. It was dictatorship in pinstripes, fuelled by a spreading paranoia amongst the desk-bound troops and maintained through an atmosphere of blame and fear. People didn’t spend their energy doing their best work, they spent it second-guessing how to avoid becoming his next target. The result was a culture where truth was optional, silence was safety, and everyone walked on eggshells.
Leadership by Humiliation
Fear alone was not enough for Mr X. He preferred to season it with humiliation.
Colleagues were belittled behind their backs and, sometimes, directly to their faces. He took perverse pride in recounting how he managed to reduce senior, mid-life, male managers to tears when firing them (he loved to fire people), as though that was an achievement. He played the firing-long-game, seeding and spreading rumours about staff he had decided to discard. And he enjoyed fueling the fervour of a mounting 'hunt' of an individual, which would inevitably end in the climax of his metaphoric kill. He picked on people to fire because of their colour, size, physical idiosyncrasies or creed, inventing failings where none existed. He encouraged competition between direct reports not to raise standards, but to keep people insecure and dependent on his approval.
This was leadership by humiliation, and it rotted the culture from the inside out. When people are scared of being shamed or scapegoated, they stop taking initiative. They stop telling the truth. They stop trusting each other. The office became a theatre of survival, not a place of excellence.
From Naïve to Awake
Until then, I had been lucky. Before having children, I had worked for a very different kind of boss. He was a thoughtful, family-oriented, imperfect, but fundamentally decent and honourable man. He had integrity. Working for him was a privilege. I am still friends with him and would help him at the drop of a hat now.
So in my mid thirties, to suddenly find myself working for someone like Mr X was terrifying. I had honestly thought that, apart from the obvious villains of history, most people got out of bed in the morning trying to do the right thing. Sure, mistakes happen, feelings get hurt, life deals blows. But to meet someone who seemed to wake up each day actively choosing to manipulate, dominate, and destroy? That was my brutal awakening.
It was soul-crushing at the time. But in hindsight, it was also a gift.
What I Learned From the Worst
Here is the truth no glossy leadership manual will tell you: if leaders are not held accountable to truth, they become tyrants. The only question is whether they run a company into the ground or a country off a cliff.
Working for Mr X taught me:
Honour matters. Without it, every decision is tainted.
Clarity matters. Vagueness is not strategy. It is cover for chaos.
Integrity matters. A lie repeated is still a lie, no matter how loudly it is told.
Transparency matters. Secrets breed fear.
Fairness matters. Respect should not stop at the corner office door.
Accountability matters. True leaders take responsibility, not just credit.
Even inside the organisation, people knew. I still remember a moment with a senior HR professional who looked me in the eye, put her hand over mine, and whispered: “He will get his comeuppance. Maybe not in this life, but in the next.”
Mr X taught me to never confuse charisma with character, confidence with competence, or power with leadership.
The Wider Lesson
Years later, I find myself listening to former U.S. Whitehouse official Miles Taylor describe the corrosion of truth under Trump, and I recognise the same pattern I had lived through in microcosm. Different scale, higher stakes, same disease: unchecked ego, weaponised lies, enablers too scared to resist, profiteers playing a 'winner takes all' game of betting on the devil and selling their souls.
That was when the penny dropped. My six months with Mr X were not just a personal nightmare. They were training. A crash course in spotting the warning signs of toxic leadership.
Why This Matters Now
The world does not need more “strongmen” leaders. It needs leaders who are strong enough to tell the truth, even when it costs them. Leaders who understand that power is borrowed, not owned. Leaders who leave behind not wreckage, but trust.
We have been here before. In the UK and France, the two countries I know best, we have spent the last 85 years rebuilding societies on the foundations of decency. We cared for the less fortunate, created safety nets, and championed capitalism with a conscience. That was the legacy of the post-war years, hard-won from the rubble of destruction.
Do we really need to go down that road again, pandering to strongmen, until millions suffer and die before we remember the truth?
History has already given us the warning. The question is whether we are willing to listen this time.
