Diplomatic Dispatches
The Confidence Trick of Leadership
In 1849, a well-dressed gentleman approached respectable New Yorkers with a simple request: “Have you confidence in me to trust me with your watch until tomorrow?”
Astonishingly, many did.
They handed over their valuables to a complete stranger who then completely disappeared.
This was William Thompson - the original “confidence man”. And he became famous not for his charm, but for something far more interesting: his understanding that context creates trust faster than character ever could.
He dressed like his marks.
He spoke their social language.
He approached them in settings where refusing him would feel rude.
He engineered trust through environmental cues.
122 years later, Stanford psychologist Philip Zimbardo would accidentally prove the same principle on a much larger - and darker - scale.
In 1971, he put twenty-four ordinary college students into a fake prison. Within days, the “guards” were brutalising the “prisoners.” The experiment was shut down early.
For fifty years, we’ve framed this as proof that people are fundamentally awful.
But that interpretation misses the real insight hiding in plain sight.
Like Thompson’s confidence trick, Zimbardo didn’t uncover some dark truth about human nature. He uncovered something far more powerful:
People become exactly what their environment expects them to become.
And the moment you understand that, leadership changes.
The question stops being: “Why won’t my people behave differently?”
and becomes: “What situation have I created that makes their current behaviour the logical choice?”
What we've misunderstood about the Stanford Prison Experiment
Here’s the overlooked reality: the guards didn’t behave brutally because cruelty was lurking in their personalities.
They behaved brutally because cruelty was situationally appropriate - in the environment Zimbardo designed.
They were reading cues. They were following norms. They were stepping into roles laid out for them.
Just like Thompson’s marks weren’t stupid for trusting a stranger - they were responding rationally to environmental signals that screamed “trustworthy.”
Humans aren’t blank slates, but we are incredibly responsive. We adjust to the atmosphere, the cues, the scripts, and the invisible choreography around us.
Which raises an obvious question that somehow nobody has thought to ask:
If a confidence trickster can engineer trust in minutes, and Zimbardo can design an environment that produces cruelty in six days, what happens when you design an environment that expects people to be excellent?
In 2008, I found myself doing exactly that - quite by accident.
After a terrorist bombing in Pakistan, my boss was medically evacuated and I suddenly inherited a high priority role I was wildly underprepared for: counter-radicalisation strategy, ministerial visits, digital diplomacy before even Facebook was really a thing… and a team who had never once been asked for their views.
They were bright, capable, deeply connected to their country, and had insights I needed desperately - yet the environment treated them as spectators.
So - and I want to be completely honest here - out of pure panic and having no idea what I was doing, I changed the environment.
I physically moved the intimidating glass “boss’s office” - where people had to stand during meetings - and turned it into shared space, not because I had some brilliant strategy, but because I was terrified of making decisions alone.
I broke the team into small units with rotating leadership because I couldn’t handle managing everyone directly.
I invited everyone into strategy discussions - even the most junior colleague - because I desperately needed their insights.
I replaced “Here’s what we’re doing” with “What am I missing?” because I genuinely didn’t know.
The transformation was immediate.
Same people. Same challenges. Entirely different behaviour.
They went from passive order-takers to proactive collaborators.
Six months later, they won a global award for building the UK government’s world wide digital diplomacy architecture.
I hadn’t changed the people. I had changed the situation.
Which is why I now believe: Many leaders are fighting the wrong thing.
The obstacle isn’t character; it’s context.
The Four Environmental Levers Every Leader Controls
What if we started with the assumption that most leadership problems are not behaviour problems - they are context problems?
Here are the four levers any leader can use intentionally:
1. Environment Beats Personality
If your team panics under pressure, it’s likely not because they “lack resilience.” It’s because the situation expects or rewards panic or confusion.
Make calm thinking the default, not the exception. Create contexts where taking a pause is rewarded and expected.
2. Roles Create Behaviour
People behave according to the script they think they’ve been given. If someone’s become a blocker, they often aren’t being intentionally difficult. They’re following the role that the environment assigned them.
Resistance may be the only script that gets them recognition, control, or safety. Re-design roles so collaboration - not resistance - is the only viable path.
3. Norms Are Contagious
Culture isn’t what you write on walls. It’s the micro-behaviours leaders repeat until everyone else copies them.
Cultures don’t drift. Leaders signal. Begin meetings with “What am I missing?” Take notes while others speak. Rotate facilitators. Reward risk-taking instead of perfection.
4. Boundaries Create Performance
When everything feels chaotic, it’s rarely because people are lazy. It’s because the environment is ambiguous.
Ambiguity is the enemy of excellence. Create crisp boundaries, clear accountability for who decides what, and visible priorities.
What Happens When You Forget These Lessons
During the seven years of Brexit, COVID, and constant political churn, I watched deeply competent civil servants become risk-averse, exhausted, and disengaged.
I realise now it was not because they lacked talent, or were intentional sabateurs. But because the environment punished initiative and rewarded self-protection.
When leadership changes weekly, priorities flip monthly, and blame escalates hourly, the smartest survival strategy becomes: Keep your head down. Don’t stick out. Wait for instructions.
It wasn’t laziness. It was logic.
That’s the Zimbardo Effect in professional form: people responding rationally to an irrational environment.
The Real Lesson of the Stanford Prison Experiment
The Stanford Prison Experiment isn’t (just) about human cruelty. It’s about human responsiveness.
Thompson could get strangers to hand him their watches in minutes. Zimbardo accidentally proved that situations shape behaviour faster and more reliably than training, values, or personality.
What Thompson did deliberately and Zimbardo created by accident, leaders can create on purpose.
If a confidence man can engineer trust in minutes and Zimbardo could produce tyranny in six days, you can produce excellence in six months.
Your Move
Most leaders don’t need new people. They need a new environment.
If you’re frustrated by behaviours in your organisation, ask: What context have I designed that makes this behaviour the logical choice?
Context is your most powerful leadership tool. And it works faster than you think.
What's your take on today's article? Did it land? Miss the mark? Change your perspective?
If you enjoyed this read, the best compliment I could receive would be if you shared it.
