Daniel's back with another one of these collision experiments. Last time it was Trump in the chair for an entry-level filing job. This time he wants Winston Churchill applying for an entry-level management consultant role at McKinsey. Same structure: first, what actually defines Churchill's rhetorical style, then how that style would map onto each phase of a first-round interview, and then an actual roleplay dialogue at the end.
I've been waiting for this one. The Trump episode worked because the style was so identifiable and so catastrophically wrong for the setting. Churchill is a different kind of wrong. Trump's style is improvisational, repetitive, dominance-based. Churchill's is architectural. Every sentence is load-bearing.
Right. And the mismatch here isn't that Churchill would be incoherent. It's that he'd be magnificent, and magnificence is not what a forty-five-minute case interview is looking for.
Let's start with what his style actually is, because most people know the greatest hits but not the mechanics. Churchill wrote his own rules of rhetoric in 1897. He was twenty-three. The essay was called The Scaffolding of Rhetoric, and it wasn't published until about seventy years later, two years after he died. But the International Churchill Society makes the point that in sixty years of oratory he never deviated from the principles he set down at twenty-three.
What were the principles?
Four, sometimes listed as five. Correctness of diction. Rhythm. Accumulation of argument. Analogy. Some scholars add wild extravagance of language. The first one, correctness of diction, is the one people miss when they think Churchill was just bombast. He was obsessive about word choice. There's a story of a secretary describing the windings of the Thames as extraordinary, and Churchill corrected him. Not extraordinary. All rivers wind. The word you want is remarkable.
That's a man who treats synonyms as a moral failing.
Yes. And another draft apparently said Germany was isolated and surrounded on all sides, and Churchill struck it and wrote, the word you want is crushed.
The word you want is crushed. That's the whole style in six words. Precision plus force.
The second principle, rhythm, is where the famous long rolling sentences come from. He wrote that the sentences of the orator become long, rolling and sonorous. But here's the thing about his rhythm. The finest hour speech, the June 1940 broadcast, the famous coda is a hundred and eighty words. Three quarters of them are monosyllables. Only twelve are polysyllables.
So the grandeur isn't from fancy vocabulary. It's from old short Anglo-Saxon words arranged in waves.
He favored short old words. The music comes from the arrangement, not the ornament. And the arrangement follows the third principle, accumulation of argument. He described the climax of oratory as a rapid succession of waves of sound and vivid pictures. You hear it in the beaches speech. We shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills. It's anaphora. The repetition of we shall fight. Each clause adds a location, each location narrows the geography, and the pressure builds until the final turn.
And the final turn is the contrast.
The fourth principle, analogy, and the paired contrast. Us versus them. The broad sunlit uplands against the abyss of a new dark age. Max Atkinson's research on audience response identified the list of three, the us and them framing, and contrastive pairs as the devices that most reliably win applause. Churchill used all three constantly.
So the toolkit is: exact words, rolling rhythm built from short words, accumulated clauses that build pressure, and sharp contrasts. What about the delivery?
He had a lisp his whole life. He couldn't pronounce the letter S cleanly. He smoked constantly. He delivered the finest hour broadcast while smoking. And critics at the time called him a word-spinner, a second-rate rhetorician. A Tory MP said that in Parliament in October 1940, while Churchill was holding the country together.
That's the detail that makes the whole thing human. The greatest orator of the century had a speech impediment and a cigar in his mouth.
And he wrote his own material. That's the other thing. He wrote every major speech himself, often dictating to secretaries, pacing the room, trying out phrases aloud. The Scaffolding of Rhetoric says the orator must feel it himself before he can inspire emotion in others. Before he can move their tears his own must flow. To convince them he must himself believe.
So the sincerity is structural. It's not performance. It's conviction.
Which is exactly why the McKinsey interview is such a beautiful collision. Because McKinsey wants something completely different. Let's talk about what an actual first-round looks like.
Two interviews, back to back, forty-five to sixty minutes each. Each one has a case and a personal experience interview, the PEI.
The PEI is a structured behavioral deep dive. Ten to twenty minutes on a single story, with ten to twenty-five follow-up questions. McKinsey renamed its four dimensions last year. Connection, drive, leadership, growth. First round usually focuses on connection and leadership. And the recommended answer structure is what they call SPAR. Summary, problem, action, result. Initial answer three to four minutes. Use I, not we.
Use I, not we.
Yes.
Churchill's most famous speech is built on the word we. We shall fight. We shall never surrender. The royal we, the imperial we, the national we. And McKinsey's rubric says use I.
That's the first structural collision. But it gets worse. The PEI wants a single story with a single clear arc. Churchill's instinct is accumulation. A rapid succession of waves. He can't tell one story. He tells five stories that build to a climax.
And the follow-up questions. McKinsey trains interviewers to probe for specifics. What exactly did you do? What was the number? Churchill would find that insulting.
He'd treat the probing as a failure to grasp the sweep of the thing. The interviewer asks, what was the specific impact of your action, and Churchill says, the impact was that the darkness did not prevail.
And then there's the case interview. Thirty to forty-five minutes. Interviewer-led, unlike BCG or Bain. Math heavy, chart heavy. They want a top-down answer. Lead with the recommendation, then support it.
Churchill would do the opposite. He'd build up. He'd start with the context, the stakes, the landscape of the problem, and only after twenty minutes of accumulation would he deliver the recommendation as a climax. The case interviewer wants the answer in the first sixty seconds.
So he'd fail the rubric.
Spectacularly. But here's the interesting part. Some of his principles would help. Correctness of diction is excellent interview advice. Precision of word choice. No filler. The problem is the scale. If you ask him why McKinsey, he doesn't say, I want to work on hard problems with smart people. He says, I have not become the King's First Minister in order to preside over the liquidation of the British Empire.
Which is a real quote, by the way.
It is. November 1942. The Mansion House speech. He was responding to a toast to the Empire.
So the register is the problem. The content of his mind is not the problem. The calibration is.
Right. And calibration is what consulting interviews are fundamentally testing. Can you read the room, match the register, give the answer at the right altitude. Churchill had one altitude. It was the altitude of a man addressing history.
Let's walk through the phases. Daniel asked for the same touchpoints as the Trump episode. Greeting, pleasantries, then the standard first-interview questions. Previous experience, why you're interested in the job.
The greeting. Churchill walks in. He's seventy-five, but in this scenario he's applying for an entry-level role, so let's imagine him at twenty-three, fresh from Cuba and India, full of the confidence of a young aristocrat who has already been shot at and written a book about it.
The interviewer says, welcome, thanks for coming in, have a seat. Churchill doesn't sit. He stands by the chair, surveys the room, and says something like, I trust this interview shall be conducted with the candor and dispatch that the gravity of the occasion demands.
The interviewer says, absolutely, so tell me a bit about yourself. Churchill says, I was born at Blenheim Palace. My father was Chancellor of the Exchequer. My ancestor the first Duke of Marlborough won the Battle of Blenheim. I have been under fire in Cuba and on the North-West Frontier. I have written a book that was serialized in the newspapers. I am twenty-three years old and I have not yet begun.
And the interviewer is supposed to write down, candidate demonstrates self-awareness and coachability.
The pleasantries phase is where Churchill would actually shine for about ninety seconds. He had genuine charm. The joke he opened his 1941 address to Congress with, about being half-American, if my father had been American and my mother British instead of the other way around, I might have got here on my own. That's disarming. That's self-deprecating. That's exactly what you want in an interview opener.
But then the pleasantries end and the questions begin, and the charm curdles into grandiosity.
The first question is usually tell me about yourself. McKinsey wants sixty to ninety seconds. Not a chronological resume walkthrough. A focused statement of who you are and why you're here.
Churchill would give them his whole biography as an epic. I was born in a palace. I was neglected by my parents. I was educated at Harrow, where I was considered unpromising. I entered the army. I went to war. I wrote about war. I entered politics. I have been called rash, intemperate, and unsound. I intend to be prime minister.
And the interviewer's pen hovers over the scorecard, and the scorecard says, does the candidate answer the question asked.
The previous experience question. McKinsey wants a specific story with a specific role and a specific result. Churchill's previous experience is commanding men in battle and losing an election and writing forty books.
He'd tell the story of the cavalry charge at Omdurman. He was twenty-three. He rode with the Twenty-First Lancers in the last great cavalry charge of the British army. He'd describe it in astonishing detail, the dust, the noise, the horses, the moment of impact. And the interviewer would say, that's very interesting, but what does that tell me about your ability to work in a team.
Churchill would say, I led the charge.
The why are you interested in this job question. McKinsey's guidance is that the quickest way to fail is to describe consulting as a stepping stone with no real interest in the work itself.
Churchill would describe it as a stepping stone to the premiership with no real interest in the work itself.
And he'd do it in a way that sounded like a call to arms. You ask why I seek this position. I seek it because the problems of our age will not solve themselves. Because the great firms of the world are adrift, and someone must chart the course. Because I have looked upon the abyss, and I have resolved that I shall not look away.
The interviewer says, so you're interested in the operations practice or the strategy practice.
Churchill says, I am interested in the fate of nations.
The case interview. This is where it really falls apart. They give him a chart. A declining revenue curve. They say, what would you recommend. Churchill looks at the chart for a long time. Then he says, we shall fight them on the beaches.
He'd treat the case as a war council. He'd reframe the problem. The interviewer says, our client is a regional retailer losing share to online competitors. Churchill says, the question is not one of market share. The question is whether this firm shall endure, or whether it shall be swept into the dustbin of history. I choose endurance.
And then he'd demand more information in a way that sounded like an ultimatum. Bring me the numbers. All of them. I shall not act upon partial intelligence.
The math portion. They ask him to calculate the break-even point. He does the arithmetic correctly, because he was actually good at numbers when he applied himself, and then he says, the arithmetic is sound, but arithmetic will not save this company. Only resolve will save this company.
The recommendation. They want a crisp top-down answer in the final two minutes. Churchill gives a peroration. He stands up. He grips the edge of the table. He says, let us therefore brace ourselves to our duties, and so bear ourselves that if this firm lasts for a thousand years, men will still say, this was their finest quarter.
And the interviewer writes, candidate demonstrates strong communication skills but struggles with concision.
So the analysis is clear. The style is magnificent and it is exactly wrong. But let's do the roleplay. Daniel wants the actual dialogue.
Let's set the scene. McKinsey office, first round. The interviewer is an associate, maybe three years in. Her name is Priya. She's got a scorecard and forty-five minutes. Churchill is twenty-three, already famous, already convinced of his destiny.
I'll be Churchill.
I'll be Priya.
Priya. Welcome. I trust this interview shall be conducted with the candor and dispatch that the gravity of the occasion demands.
Thanks for coming in. Have a seat.
I prefer to stand. The seated posture is the posture of surrender.
Okay. Well, I'll sit. So, let's start simple. Tell me a bit about yourself.
I was born at Blenheim Palace, the seat of my family for generations. My father, Lord Randolph Churchill, was Chancellor of the Exchequer. My ancestor, the first Duke of Marlborough, broke the power of France at the Battle of Blenheim. I have been under fire in Cuba and on the frontier of India. I have written a book, and it has been read. I am twenty-three years of age, and I have not yet begun.
That's quite a background. Can you tell me about a specific time you faced a challenge and how you handled it?
At Omdurman, in the Sudan, I rode with the Twenty-First Lancers in a charge against the Dervish line. The dust rose. The bugles sounded. We rode into the mass of them, and I fired my pistol and cut with my sword, and when it was done I was alive and the day was ours. That was a challenge.
And what did you learn from that experience that would help you in consulting?
I learned that a direct assault, pressed with sufficient vigor, will carry the field. The consultant who hesitates is lost.
That's a very... aggressive approach. Let's shift to a case. Our client is a mid-sized retailer. Revenue has declined twelve percent over three years. Online competitors are undercutting them on price. What would you recommend?
I would recommend that they cease to be a retailer. A retailer sells goods. A nation of shopkeepers cannot compete with the machine. They must become something else. A standard. A symbol. A cause.
Okay, but what specifically would you tell the client to do?
I would tell them the truth. The truth is that their current course leads to ruin. I would tell them that a time of tribulation is before them, but that if they endure, if they adapt, if they fight, they shall emerge on the broad sunlit uplands.
The client is a regional chain of office supply stores. The broad sunlit uplands is maybe a bit much.
The scale of the language must match the scale of the peril. If you would have men follow you into the breach, you do not speak to them of quarterly earnings. You speak to them of honor.
Let me ask a more direct question. Why do you want to work at McKinsey?
I do not wish to work at McKinsey. I wish to lead. McKinsey is the anvil upon which the leaders of the next age shall be forged. I intend to be among them. I intend to be first among them.
So you see this as a stepping stone.
I see this as a campaign. And every campaign has its opening engagement. This interview is mine.
Do you have any questions for me?
Yes. When the history of this firm is written, in the long chronicle of its triumphs and its failures, what shall be said of the associate who sat in this room and failed to recognize the moment when it arrived?
I think that's all the time we have.
Then let us part with this understanding. I have offered you candor. I have offered you vision. I have offered you myself. If you would have me, I shall serve. If you would not, I shall go elsewhere, and the loss shall not be mine alone.
We'll be in touch.
I shall await your summons.
Hilbert: The thing about Churchill is he cost me two hundred pounds once.
What?
Hilbert: I was doing some work for a bookshop in London, must have been around 2015, and they had a first edition of his biography. The one he wrote about his father. I put a bid in at auction, thought I had it, then some collector from Singapore outbid me in the last thirty seconds. Two hundred pounds over my limit. I still think about it.
The biography of Lord Randolph Churchill. Published 1906.
Hilbert: That's the one. Lovely binding. I had a spot picked out for it on the shelf. It's still empty. I put a different book there now, but I know it's the wrong book.
The collector from Singapore probably doesn't even read it.
Hilbert: Doesn't matter. The point is Churchill had a way of making people feel like they were part of something enormous, and that's why the book sold for what it sold for. Same reason a man would follow him into a cavalry charge. You don't get that from a McKinsey scorecard.
That's actually the whole episode in one sentence. The scorecard measures coachability and concision and structured thinking. Churchill measures whether you're willing to die for the cause. The two systems are not just different. They're incompatible.
And yet the precision part. The part where he corrected the secretary. The word you want is crushed. That would score well.
It would. If he could keep the register at the level of the room, the underlying machinery of his rhetoric is excellent. Correctness of diction. Rhythm. Structure. Accumulation. Analogy. These are all things that make for clear communication. The problem is the altitude.
Hilbert: The altitude is the whole thing though, isn't it. You can't separate Churchill from the altitude. You can't have the precision without the grandiosity. They're the same man.
That's right. The man who corrected the secretary's word choice is the same man who stood in Parliament and said he had nothing to offer but blood, toil, tears and sweat. The precision serves the grandeur. You can't extract one and leave the other.
Hilbert: I had a manager once who tried. He wanted us to write reports in what he called Churchillian style. Short words, strong rhythm, no hedging. What he got was a bunch of memos that sounded like declarations of war about inventory discrepancies. The warehouse team stopped reading them.
That's the danger. Churchill's style works because the stakes justify it. When the stakes are an inventory discrepancy, the style becomes parody.
And that's the collision Daniel set up. A first-round McKinsey interview is a low-stakes, high-structure environment. Churchill is a high-stakes, high-structure communicator. The structure overlaps. The stakes don't.
Hilbert: The other thing is, he'd never get past the resume screen now. No MBA. No Excel. The man couldn't use a spreadsheet.
He'd dictate the spreadsheet to a secretary.
Hilbert: And the secretary would quit.
The resume screen point is real though. McKinsey's funnel is brutal. Below one percent acceptance overall. First round pass rate is twenty to forty percent. The PEI carries about half the evaluation. Churchill would be rejected at the resume stage because he doesn't have the credentials, and if he got through, he'd be rejected at the PEI because he can't tell a single story in three minutes.
And yet he led a nation through a war. The mismatch cuts both ways. The rubric that rejects Churchill is the same rubric that would have rejected him in 1940.
Would it have? That's the uncomfortable question. The qualities that made him the right man for 1940 are the qualities that make him wrong for a consulting interview. But the consulting firm isn't trying to find the next prime minister. It's trying to find someone who can build a clean slide deck and not alienate a client.
So the real question is whether the rubric is measuring the right things, or whether it's measuring the things that are easy to measure.
It's measuring the things that are easy to measure. That's what rubrics do. Coachability. Concision. Structured thinking. Those are observable in a forty-five-minute interview. Vision, courage, the ability to make people believe in something larger than themselves. Those are not observable in a forty-five-minute interview.
And they're not what McKinsey is hiring for. McKinsey is hiring for the ability to do the work of consulting. Churchill was not a consultant. He was a leader. The two are not the same job.
Hilbert: I did a consulting project once. For a logistics firm in Birmingham. They wanted to know why their delivery times were slipping. I spent three weeks looking at the data and the answer was that one of their depots had a broken conveyor belt and nobody had reported it. Three weeks. For a broken belt.
That's the consulting job in a nutshell. Uncovering the boring truth that nobody wanted to look at.
Churchill would have reported the broken belt as a symptom of moral decay.
Hilbert: He'd have been right, probably. The depot manager was a coward.
The misconception. What do most people get wrong about Churchill's rhetoric?
That it was bombast. That he was just a loud man with a good vocabulary. The reality is the opposite. He was a precision instrument. He wrote his own rules at twenty-three and followed them for sixty years. Every word was chosen. Every sentence was built. The grandeur was engineered.
The word you want is crushed.
That's not bombast. That's a man who understood that the right word, in the right place, at the right moment, is the difference between a speech and a force of nature.
The open question. If Churchill walked into a McKinsey interview today, and the interviewer recognized who he was, what he would become, would the rubric matter? Or would the interviewer throw away the scorecard and just listen?
I think the interviewer would throw away the scorecard. And then get fired.
Worth it.
We'll never know. But the thought experiment does what Daniel's thought experiments always do. It forces us to ask what we're actually measuring when we measure a candidate. And whether the things that matter most are the things we can't score.
Thanks to Hilbert Flumingtop for producing.
This has been My Weird Prompts.
If you enjoyed this, leave us a review wherever you listen. It helps more than you know.
We'll be back soon.
