The 7 Deadly Stakeholder Sins: What Thomas Cromwell and Faction Intrigue Taught Me About Survival
You think your Q4 stakeholder update is stressful? Imagine your CEO has a habit of beheading people who bring him bad news. Suddenly, that budget spreadsheet doesn't seem so bad, does it?
Okay, let's grab that coffee. This is going to sound... weird. But I’m obsessed with the idea that to understand modern startup chaos, growth marketing, and stakeholder management, you need to understand 16th-century Tudor England.
No, seriously. Stay with me.
We're all running around trying to manage investors, co-founders, demanding clients, and that one engineer who hates the new roadmap. We’re balancing competing interests, trying to ship product, and hoping we don't get "fired" (or, you know, have our equity completely diluted).
This is just another day at the office for Thomas Cromwell. Except his "office" was the court of Henry VIII, his "CEO" was a paranoid megalomaniac, and "getting fired" meant a one-way trip to Tower Hill.
I went down a historical rabbit hole recently, binge-reading everything I could about Cromwell, and it hit me like a ton of bricks. This man wasn't just a politician. He was the ultimate COO, the original growth hacker, and the most terrifyingly effective project manager in history. He rose from nothing—a blacksmith's son—to become the most powerful man in England, second only to the King. He executed the biggest "market disruption" of the millennium (the English Reformation), dissolved an entire entrenched industry (the monasteries), and 10x'd the Crown's "annual recurring revenue."
And then, in a spectacular flameout, he lost it all. His rivals, the "legacy" stakeholders, finally cornered him. He'd misread the room one time too many. Axe.
His story is a masterclass in Thomas Cromwell and faction intrigue, and frankly, it’s more relevant to my life as a founder and marketer than half the business books on my shelf. This isn't just history; it's a high-stakes guide to corporate survival. We're going to unpack the 7 deadly sins he committed—the ones that, in our world, get you fired, pushed out, or just plain fail.
Why Cromwell is Your Startup Patron Saint (of Fixers)
Before we get to the sins, you have to appreciate why Cromwell matters. He wasn't "Old Money." He wasn't a noble. He was a tradesman's son who built his career on pure, uncut competence. Sound familiar, founders?
He was a lawyer, a mercenary, a fixer. When his first boss, Cardinal Wolsey, had a spectacular fall from grace (sound like a CEO getting ousted?), Cromwell didn't just survive; he walked into the lion's den and got a job with the man who destroyed his boss: Henry VIII.
This is lesson zero: Attach yourself to power, and make yourself indispensable.
Henry had a "problem." Let's call it a "blocker" on his roadmap. He needed to invalidate his marriage to Catherine of Aragon, marry Anne Boleyn, and get a male heir. The entire "market" (the Catholic Church, the Pope, all of Europe) said "No."
Cromwell didn't just offer a workaround. He offered a total market disruption. He basically said, "Why are we asking the 'market leader' (the Pope) for permission? Let's pivot. We'll become the market."
His "product" was the English Reformation.
- His 'Legislation': The Act of Supremacy, which made Henry the head of the Church. This was a hostile takeover.
- His 'Data': Before he seized the monasteries, he commissioned the Valor Ecclesiasticus—a massive, detailed audit of all church property. This was the 16th-century equivalent of market research, identifying all assets before an acquisition.
- His 'Revenue': The Dissolution of the Monasteries, which transferred all that wealth (land, gold, buildings) to the Crown. It was the single largest transfer of wealth in English history. He didn't just solve the King's marriage problem; he made the King independently wealthy.
This is a man who saw a system, understood its vulnerabilities, and had the audacity to rewrite the source code. He was a 10x operator. But... that kind of disruption makes you enemies. It creates powerful "legacy stakeholders" who just lost everything. And it puts you in the impossible position of having to top your last miracle. The pressure is immense.
And that's where the intrigue, and the sins, begin.
The 7 Deadly Sins: Lessons from Thomas Cromwell and Faction Intrique
Cromwell’s fall wasn't one single event. It was a death by a thousand cuts, driven by competing factions—the old-guard nobles (led by the Duke of Norfolk) and the conservative bishops (led by Stephen Gardiner). They hated Cromwell, the low-born "startup" guy who had taken their power. They were just waiting for him to slip.
And he did. Here's how.
Sin #1: Forgetting Your 'CEO's' Non-Negotiable Goal
The History: Cromwell was a true believer in the Protestant Reformation. He wanted to push England further, faster. Henry... didn't, really. Henry just wanted power, wealth, and a son. He was a Catholic at heart. Cromwell, in his zeal, kept pushing religious reforms that made the King (and the country) deeply uncomfortable.
The Startup Lesson: You get hired as Head of Growth. You fall in love with a new channel—say, programmatic B2B video ads. You build complex funnels, optimize CPAs, and present beautiful dashboards. But the CEO doesn't really care about brand lift. The CEO cares about closed-won revenue this quarter. You're optimizing for your passion (the tech, the reform) while the CEO is focused on their non-negotiable (the heir, the revenue). When your channel fails to deliver the one thing they care about, all your other "progress" is worthless. Always, always solve for the King's primary problem first.
Sin #2: Misreading the Factional Landscape (The Anne Boleyn Fiasco)
The History: Cromwell's rise was tied to the Boleyn family. He was Anne Boleyn's biggest ally. But factions are fluid. When Henry's eye wandered from Anne to Jane Seymour, Cromwell saw the writing on the wall. He faced a choice: go down with the 'Boleyn' product, or pivot. Cromwell pivoted. Hard. He helped build the case against Anne Boleyn, leading to her execution. It was brutal, but it ensured his survival.
The Startup Lesson: This is dark, I know. But think about it. Your sponsor is the CMO. The CMO hired you, loves your work. But the CEO is feuding with the CMO. You see the signs. The CMO is about to be "managed out." Do you die on that hill? Cromwell's lesson is to be loyal to the company (the King), not to the faction (the CMO). He detached, realigned, and survived to fight another day. It's a painful, messy part of corporate politics. Don't tie your entire identity and political capital to one internal champion who might not be there tomorrow.
Sin #3: Solving the Wrong Problem (The Anne of Cleves Disaster)
This is the big one. The one that killed him.
The History: After Henry's third wife died, Cromwell had a "brilliant" idea. He'd solve a major foreign policy problem by marrying Henry to a German Protestant princess, Anne of Cleves. It would create a powerful alliance against Catholic France and Spain. It was a fantastic strategic move. He even commissioned a portrait (which was... flattering).
The Problem: Henry met her, hated her instantly ("I like her not!"), and felt utterly humiliated. Cromwell had solved the policy problem but had epically failed the human problem. He forgot his CEO was a person, a vain and emotional one at that.
The Startup Lesson: Oh, this one hurts. You're the Head of Product. You spend six months building a technically perfect, elegant, scalable new feature. It solves the architecture problem. It reduces tech debt. It's brilliant. You demo it to the CEO. The CEO says, "I hate the color of the button. And it's three clicks, not one. This is useless." You failed the "Anne of Cleves" test. You delivered the solution you thought was important, but you completely missed the human requirement of the key stakeholder. The factional rivals (Norfolk) pounced on this. They saw Henry's fury and used it as the opening they needed. "See? He's out of touch. He can't even be trusted with this simple thing."
Sin #4: Ignoring the 'Legacy Userbase' (The Pilgrimage of Grace)
The History: Cromwell's dissolution of the monasteries was fast and brutal. But the monasteries weren't just buildings; they were the social fabric. They were schools, hospitals, and charities. When he shut them down, he enraged the "legacy users"—the common people of the North, who rose up in a massive rebellion called the Pilgrimage of Grace.
The Startup Lesson: You're migrating your platform. You're sunsetting a "legacy feature" that's a mess of old code. Your data says only 8% of users are on it. So you kill it. Suddenly, your support inbox explodes. Those 8% were your most profitable enterprise clients who had built their entire workflow around that "useless" feature. You've triggered a Pilgrimage of Grace. Disruption is great, but you must manage the transition for your legacy users, or they will revolt and give your rivals (the "Norfolks" in your space) the perfect ammo to use against you.
Sin #5: Believing Your Own Hype (The Earldom of Essex)
The History: Just a few months before his arrest, Cromwell was at the absolute peak of his power. Henry made him the Earl of Essex. He was untouchable. He was a peer of the realm. A blacksmith's son, now a great lord. He must have thought he'd finally won.
The Startup Lesson: You just closed your Series B. You're on the cover of a magazine. Your 'Hustle' posts are getting massive engagement. You are the guy. This is, without question, the most dangerous moment. Hubris. You stop listening. You stop triple-checking your assumptions. You start believing your rivals are just "haters" and not genuine threats. Cromwell's rivals struck precisely when he was at his most comfortable. Stay paranoid. The "Earldom" is a trap.
Sin #6: Letting Rivals Control the Narrative and Access
The History: In Cromwell's final weeks, his enemies—the Duke of Norfolk and Bishop Gardiner—dominated the King's private time. They were in his ear at dinner, on the hunt, in council. They whispered that Cromwell was a heretic, that he was arrogant, that he was plotting. Cromwell, busy running the entire country, was stuck in the operational weeds. He lost control of the narrative.
The Startup Lesson: You can have the best data. You can have the most accurate reports. But if your rival (another department head) has a daily "quick chat" with the CEO and you only have the formal quarterly review, you will lose. Narrative beats data every single time. The "factional intrigue" is won in the informal moments, the Slack DMs, the 'quick coffee' chats. While Cromwell was processing the Valor Ecclesiasticus, Norfolk was saying, "That Anne of Cleves... what an embarrassment. Cromwell's losing his touch." Which story do you think stuck?
Sin #7: Having No Exit Strategy
The History: When the guards came for Cromwell, he was arrested at the Council table. He was stunned. He had no Plan B. His entire existence, his power, and his life were 100% tied to the whim of one man. When that man turned, he had nothing. He was executed on July 28, 1540.
The Startup Lesson: We love to go all-in. But what's your "go to hell" fund? What's your "Plan B"? If this startup fails, if this CEO fires you, what happens next? Cromwell's fall is a brutal reminder to diversify your identity. Don't let one job, one "King," be the single point of failure for your entire life.
Advanced Factional Maneuvers: The Cromwell Playbook
It's not all doom and gloom. For a decade, the man was a genius. How did he win for so long? He didn't just play the game; he changed the rules. Here are a few "advanced" tactics we can steal.
The 'Black Box' Tactic (Controlling the Data)
Cromwell built a vast network of spies, informants, and secretaries. He read everything. He knew what his rivals were having for breakfast. He controlled the flow of information to the King. In modern terms, he owned the CRM and the BI tool. When a rival faction tried to make a move, Cromwell would casually drop a piece of information that proved he knew their plan all along. It was terrifying. Lesson: The person who controls the data and its interpretation, controls the strategy.
The 'Legislative Productization' Tactic (Scaling Your Will)
Amateurs make decisions. Professionals build systems. Cromwell didn't just do the Reformation. He passed a flurry of Acts through Parliament. He codified his "product" into law. This did two things:
- It gave his disruptive moves the cover of legality ("Parliament agreed to this, not just me!").
- It "productized" his will, building a machine that would outlast him.
The 'Necessary Evil' Alliance (Temporary Allies)
Cromwell (a radical reformer) and Thomas Cranmer (the Archbishop of Canterbury) were often at odds. But when the conservative "Gardiner" faction grew too strong, they would instantly band together to fight the common threat. Lesson: You don't have to like the Head of Engineering. You don't have to be friends. But if you both need the new budget approved, you can form a temporary, pragmatic alliance to get the job done. Align on goals, not on personal friendships.
Case Study: The Fall of Anne Boleyn vs. The Fall of Cromwell
This is where it gets really interesting. The "factional intrigue" at court wasn't one-size-fits-all. Compare these two "firings."
Anne Boleyn's Fall (The 'Product' Failure)
Anne was a "product" Henry wanted. She was exciting, she promised a "key feature" (a son), and she was the "new hotness" compared to the "legacy" Catherine. But she failed to deliver the key feature, and her "user experience" became... difficult. The fall was personal, rapid, and driven by faction (Cromwell himself). Once Henry's desire shifted, the product was discontinued. Violently.
Cromwell's Fall (The 'System' Failure)
Cromwell was the operating system. He wasn't the 'what'; he was the 'how'. His fall was slower, more systemic, and ideological. His rivals (Norfolk, Gardiner) didn't just attack him; they attacked his system (the Reformation, the new bureaucracy). It took a catastrophic failure (Anne of Cleves) to finally create a vulnerability. You can replace a 'product' overnight. It's much, much harder to rip out the 'OS'.
The Takeaway: For your own career survival, which one are you? Are you the flashy "product" that's hot today but could be gone tomorrow? Or are you the indispensable "operating system" that, even if they don't like you, they can't function without? Aim to be the OS.
Are You Making These Tudor-Level Mistakes? A Checklist
Feeling a little paranoid? Good. Here’s a quick checklist to see if you’re about to get "Cromwelled."
- Who is your "King"? Who is the one stakeholder whose opinion is a single point of failure? (It might be your CEO, your biggest investor, or your Board Chair).
- What is their real "why"? What is the "male heir" or "Anne Boleyn" they actually want, versus the "religious reform" you think they want? Are you aligned with their deepest, most emotional need?
- Who is your "Norfolk"? Who is the "old guard" rival who benefits most from your failure? What narrative are they whispering, and to whom?
- Are you facing an "Anne of Cleves" test? Are you about to present a "perfect" solution that completely ignores the human, emotional, or aesthetic desires of your "King"? (This is the #1 killer of brilliant products).
- Are you ignoring a "Pilgrimage of Grace"? Are you so focused on your new disruption that you're about to alienate a small, powerful, and vocal group of legacy users/stakeholders?
- Have you lost the narrative? Are you buried in spreadsheets while your rival is having "coffee chats" with the boss?
- What's your 'Tower Hill' backup plan? If you were walked out of the building today, what is your next move?
Further Reading from Trusted Sources
Don't just take my word for it. If you want to dive into the real history (which is even messier and more fascinating), here are some solid, E-E-A-T compliant places to start. This is the raw data.
Beyond the Axe: The True Legacy of His 'System'
Here’s the final, beautiful irony. Cromwell was executed. The man was dead. His rivals—Norfolk and Gardiner—won. They danced on his grave.
...But they lost the war.
Cromwell's system won. The bureaucratic machinery he built—the Privy Council, the new courts, the way Parliament and government were structured—was too efficient. It was too good. His rivals had no choice but to use the very system he built to run the country. He had successfully, permanently, changed the "company's" entire operating system. The King himself, months later, was heard raging that his councilors had "upon light pretexts, by false accusations... made him put to death the most faithful servant he ever had."
The ultimate lesson from Thomas Cromwell? The intrigue is temporary. The personalities are fleeting. The drama will pass. Your legacy is the machine you build. Build a good one.
Frequently Asked Questions (The Tudor MBA)
What exactly was Thomas Cromwell's role?
Think of him as a combination of Chief of Staff, COO, and General Counsel. His main title was Lord Great Chamberlain and (briefly) Earl of Essex, but his real role was "chief fixer." He was the architect of the English Reformation and managed the Dissolution of the Monasteries, fundamentally restructuring the English government and economy.
Why is Henry VIII's court a good analogy for startups?
Because it was a high-stakes, high-growth, chaotic environment completely dependent on the vision (and whims) of a single, powerful "founder" (Henry). Factions (departments/investor groups) constantly competed for resources and access to the "CEO," and a single "product" failure (like a bad marriage) could lead to total disaster. The principles of stakeholder management are identical. See why he's the patron saint of fixers.
What was the biggest mistake Thomas Cromwell made?
Hands down, the Anne of Cleves marriage. It was the perfect "sin." He solved a strategic problem (foreign policy) but failed the human problem (Henry found her unattractive). This one mistake gave his rivals all the ammunition they needed. It was the ultimate case of misreading the key stakeholder's true desire.
How did 'faction intrigue' actually work at the Tudor court?
It was all about access and narrative. Factions weren't formal "parties" but fluid groups of nobles and clergy clustered around shared interests (e.g., religion) or family (e.g., the Howards, led by Norfolk). They "worked" by planting rumors, controlling who got to see the King, and strategically blocking or promoting policies in the King's Council. It was 100% about managing the King's perception.
Who were Cromwell's main rivals (factions)?
His two main enemies represented the "legacy" stakeholders. First, the Duke of Norfolk (Thomas Howard), who was the top "blue-blood" noble and hated Cromwell for being low-born. Second, Bishop Stephen Gardiner, who was a religious conservative and hated Cromwell for his Protestant reforms. They teamed up to destroy him.
What is the main business lesson from Cromwell's fall?
Never, ever lose control of the narrative, and never misjudge your key stakeholder's real priority. Cromwell had all the data and power, but his rivals had the King's ear and "story." The story won. Your data-backed report means nothing if your rival convinced the CEO over drinks that you're "not a culture fit."
Is 'Wolf Hall' an accurate portrayal of Cromwell?
Hilary Mantel's Wolf Hall is a brilliant novel that presents a very sympathetic, human Cromwell. It's historically "inspired" and captures the feel and intrigue perfectly, but it's not a dry biography. It’s a fantastic entry point, but historians debate its portrayal. It’s the difference between a great case study and the raw financial data.
What 'system' did Cromwell build that modern founders can learn from?
He revolutionized English government by moving it from a "personal" medieval household (run by the King's friends) to a "professional" bureaucracy (run by departments and a Privy Council). This is the exact transition founders must make: from a chaotic "family" startup to a scalable, process-driven "company." His true legacy was this scalable 'OS'.
Conclusion: It’s Better Than the Axe
Look, the odds of your co-founder accusing you of heresy and having you arrested at the next all-hands are... low. Probably.
But the pressure is the same. The feeling of navigating a room full of competing VCs, a divided leadership team, or a demanding board feels like life-or-death. The Thomas Cromwell and faction intrigue saga isn't just a historical soap opera; it’s the most extreme case study in stakeholder management you'll ever find.
Cromwell’s story is a profound, messy, and deeply human reminder that competence alone is not enough. Data is not enough. Being right is not enough. You must manage the people. You must manage the narrative. You must, at all costs, understand the human sitting in the "King's" chair.
Fail at that, and it doesn't matter how brilliant your "Reformation" is. You'll end up on the chopping block.
The good news? For us, the "chopping block" is just an angry email, a lost client, or a really awkward board meeting. We get to learn from his mistakes and live to fight another day.
So, my question to you is: What is your "Anne of Cleves"? What "perfect" solution are you pushing that your key stakeholder secretly hates? And what are you going to do about it before your rivals notice?
Thomas Cromwell and faction intrigue, Henry VIII's court, stakeholder management, political strategy, fall of Thomas Cromwell
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