The Machiavellian CTO — Evil Path to Glory
A satirical guide to absolute power, meant to highlight toxic, unethical leadership patterns that should be recognized and avoided in real organizations. Any resemblance to actual CTOs, living or dead, is purely coincidental and probably concerning.
Machiavellian CTO
The Prince was written by the Italian diplomat, philosopher, and political theorist Niccolò Machiavelli in the 16th century in the form of a realistic instruction guide for new princes. It takes it for granted that immoral acts are justified if they can help achieve political glory.
A machiavellian CTO can learn from these lessons and apply them to attain and preserve power. It would be wrong not to do so, wouldn’t it?
Leadership
A successful CTO must be feared rather than loved.
The last thing you want is psychological safety. Always shoot the messenger. People will learn not to bring bad news, which is great: bad truths will be covered and people will try to resolve problems on their own.
Ensure your team fears your technical prowess and managerial dominance. Maintain control through rigorous monitoring, making it clear that any deviation from your directives will result in swift consequences.
Repeatedly brag about your unmatched technical skills and always have an excuse for why you cannot demonstrate those skills.
Take credit for others’ accomplishments. When you clearly cannot, explain how your support and coaching contributed to the result.
Attaining Power
Some CTOs rise through engineering, others through business acumen, and some are fortunate enough to be founders. It is easier to maintain power as a technical CTO, for you can mystify your decisions with arcane engineering knowledge. But the craftiest CTOs are those who understand: true power lies not in building technology but in controlling it.
Spread rumors and collect evidence about your potential competitors to power. Make them think you support them and share misinformation about others.
Maintaining Power
Create a culture of competition among your team to prevent alliances that could threaten your position. Reward informants who report subversive activities and discourage camaraderie. Keep everyone slightly on edge, always questioning their standing in your eyes.
Hinting that the lowest performers every quarter have no place in the organization will discourage helping each other and dangerously collaborating.
Managing the CEO
Overpromise and sell dreams to the CEO. Create unreachable goals that look very impressive. Be energetic and optimistic when you describe them. When the inevitable failure arrives, blame the circumstances and the bad planning of your people.
If you set realistic goals or warn that some things are not achievable, you will be seen as an unambitious negative prophet, dragging everyone down. And don’t worry, you can replay this game quarter after quarter.
Keep repeating how engineering is the most important department — they build the product and are irreplaceable, unlike others.
Only present metrics that make you look good. Massage them and make them look better than they really are. For example, measure attendance in training or percentage of filling surveys instead of the actual change after the training or the results of the surveys.
When the CEO or HR starts looking into your abusive behaviors toward the people under you, explain that they make up complaints because they have a hard time performing to the expected high bar you had set, which is the only way to push the company forward, and you need their backs in turning the organization around into excellence. the C level has to be united and not show signs of weakness.
If complaints about being machiavellian come from peers, explain that they are jealous of your success and hard work. Maybe they are not cut out for this level.
Things will be a lot easier if the CEO is machiavellian as well.
Managing the Board of Directors
Blind them with technical brilliance but never educate them. Each board presentation should include at least one incomprehensible architecture diagram. When questioned about expenses, mention blockchain. When pressed about delivery dates, speak of technical debt.
Here again, present vanity metrics that show growth or any esoteric improvement. You must find accomplishments to brag about and take credit for.
If all else fails, whisper “quantum computing.”
Managing VPs and Directors
Keep your leadership team, VPs and Directors, divided and suspicious of each other. Give them overlapping responsibilities. Let them battle over React vs. Vue while you alone hold the full system vision. Remember: directors who fight each other cannot unite against you.
When you see managers treat others badly, celebrate this and do not try to fix it. Let them draw attention to their negative behavior rather than to yours.
Gaslighting is an important tool in your toolbox: ask a VP to work on something and after they invested a month on it, tell them it was just a thought and question their judgment. Surprise a Director in a staff meeting by asking if a task you had never mentioned is finished.
Be usually late for meetings without a real reason to signal you’re always dealing with important topics and everything depends on you. Of course, show anger when others are late. As an additional power move, spice things up by not showing to 1:1s and then demand to have them at a time they already have another meeting.
One of the oldest tricks in the book is to ask for candid feedback about your behavior and effectiveness, explaining how open you are to it. When someone dares to share a negative one, never thank them. Immediately reject it and punish the person by being surprised how they could have gotten it so wrong and publicly sharing negative feedback about them. Never implement any feedback given to you. You’re the CTO for a reason, you know best.
Micromanaging is yet another great practice: give a vague task without reasoning or checking in. When they come with questions do not answer and question their skills. When they are done, tell them that what they did was wrong, redo their work and tell them you cannot trust them, and from now on you will tell them what to do, how to do and when to do.
EMs and ICs
Be intimidating. The goal is for people to hide away when they hear you approaching. People who are afraid will be obedient and will not organize. If they think or say that the CTO is machiavellian, it’s a very good sign!
You can achieve it in various ways: telling stories about previous employees who didn’t achieve the desired results, directly but lightly threatening or asking them questions they don’t know the answer to and making them feel stupid about it. Another way is to fake a video call with an employee, making sure others can hear you scream at them for a mistake.
Occasionally enhance your chats with derogatory remarks about others, on the verge of verbal abuse, so they improve their own performance and will want to prove their loyalty.
Constant criticism and nitpicking even when the result is great will keep their self-esteem low. They won’t have enough confidence to interview and leave or to stay and defy.
From time to time mention how engineers in another country are of higher quality and/or are less expensive. Maybe even open an office in this country.
Keeping Engineering Teams Weak
Strong engineering teams are a threat to CTO power. Keep teams dependent on each other through tangled service dependencies. Encourage the use of different programming languages across teams — Python here, Scala there, perhaps even a strategic sprinkling of Haskell. Unity is the enemy of control.
Overloading the teams with busywork will make sure they cannot learn enough to acquire skills and leave. They will just have enough to keep their heads above the water. When you’re out of ideas, you can revert previous decisions or preach why some new regulation or compliance is necessary.
Architecture
Keep your architecture just complex enough that no single person besides yourself can comprehend it all. Microservices are your allies — create hundreds, each slightly different, each requiring unique expertise. When board members question this complexity, speak of scalability until their eyes glaze over.
Alliances
Form alliances with other powerful figures within the company, but always keep an eye out for opportunities to undermine them. Foster a network of spies among your team to gather intelligence on potential rivals. Use this information to sabotage their initiatives subtly, ensuring your supremacy remains unchallenged.
Decision-Making
When faced with a critical technical decision, prioritize those that solidify your power, even if it means sacrificing the long-term health of the company’s infrastructure. Opt for flashy, short-term projects that garner immediate praise and boost your reputation as CTO, regardless of future ramifications. Your own benefit is the only important thing.
Communication
Maintain a façade of open communication, but ensure real discussions happen only among your inner circle. Use jargon and technical complexity to alienate non-technical stakeholders, preserving your position as the indispensable expert. Misinform and mislead when necessary to keep others in the dark. Make sure to reveal “secret” wrong information to various people to learn who leaks to whom. The uncertainty will create a dependency on a higher authority — you.
It’s important not to be familiar or accessible, the same way rockstars wear sunglasses at night. Besides declaring a “CTO open door policy” but canceling it often or ridiculing any attempt to use it, do not make eye contact or respond to “hi” in the office unless it’s someone you ally with. Silent treatment can go a long way when it comes to punishing.
Keep knowledge silos: documentation is your enemy. Encourage its creation but ensure it’s always outdated. Keep crucial architectural decisions in your head alone. When forced to explain systems, do so in person, never in writing. Remember: written knowledge is transferable knowledge.
Do not communicate anything meaningful for a while and then surprise everyone and make it seem like they should have known things they never heard about. While doing so, communicate tight deadlines to increase pressure and mention that pressure makes diamonds.
Occasionally thank a specific team or individual for their efforts, regardless of the result. This randomness will make them seek your approval, fight for it, and appreciate it when they finally get it, even undeserved.
For external communication, such as panels, podcasts about leadership or conferences, always paint a picture of a hard and smart working environment, a highly collaborative and successful company on its way to ultimate success. To add insult to injury, talk about the importance of psychological safety, diversity and inclusion.
Resource Allocation
Hoard resources to create scarcity. This allows you to distribute them as rewards to loyal subordinates, reinforcing their dependence on your favor. Use budget control as a weapon to punish disobedience and to stifle any projects that threaten your authority.
Control the budget like a miser but spend like a prince. Create numerous cost centers so complex that only you understand the true allocation. Keep a secret fund for “CTO innovations” — useful for emergencies or loyal supporters.
Increase your headcount as much as possible without any real need, even though it goes against the company. Come up with technical initiatives and random work to keep everyone busy. The bigger the headcount the better it will look on your resume and you will get bigger roles at bigger companies with bigger compensation.
When forced to reduce headcount, start with those who question your decisions.
Hiring
Recruit those who show unwavering loyalty over technical competence. It’s easier to mold a loyal subordinate into a competent engineer than to bend a skilled but independent thinker to your will. Ensure that new hires understand their primary allegiance is to you, not the company. New hires go only to your loyal people. Add more tasks and burden to the disloyal ones.
Bring people who were loyal to you in previous companies, bypassing any hiring process you have. You want such people for their loyalty, not for their skills.
If others get scared and demotivated threatening to leave, blame them for being old gatekeepers and you anyway need new blood. If it weren’t for the headcount you were after, it could look good on the budget: fewer people — fewer expenses, but you don’t care about that unless explicitly told by the board.
Innovation
Suppress innovation that doesn’t directly align with your vision. Encourage a culture of dependency where the team relies heavily on your ideas and guidance. Innovation is useful when it increases dependency on your leadership. Embrace bleeding-edge technology only when you can control its implementation. Better to have ten mediocre systems you understand than one excellent system others can maintain.
Forget about meritocracy. It’s about whose idea it is — loyal and obedient to the CTO or not.
When a bad idea comes up, shame the person in public. When a promising innovative idea emerges, take credit for it publicly, demoralizing those who dare to think independently.
Offer a modest learning budget that can hardly have an impact and scold people for not using it. Allow engineers 2 hours or learning time per week for the good feeling, but expect them to do the serious learning on their private time. This is how you got to be CTO.
Use hackathons to present a collaborative, innovative and fun environment, while the real purpose is to make people work really hard, long hours to get things done.
Risk Management
Embrace high-risk projects that can lead to spectacular successes, as failures can always be blamed on your subordinates. Position yourself as the visionary who takes bold steps while scapegoating others for any negative outcomes. This strategy will make you seem daring and forward-thinking.
Perks
Offer superficial perks like table tennis and beers. They allow employees to release energy and vent, and there is no danger that they professionally grow to become a threat. Investing in giving timely feedback and coaching is too dangerous, and people will leave elsewhere anyway at some point, so why bother?
Cheap fruit that are not enough for everyone and a gym membership that people seldom use make an impression you care about their health.
Contribute to retirement plans with the minimum required by law and present it as caring for employees for years to come.
Performance reviews
Make it a yearly process of fear.
Change it every year to cause more uncertainty. Train employees only on using the tool and not on how to give feedback and do the conversation.
Manipulate the reviews in your favor, reward loyal people, and definitely use salary raises as a tool of control.
Make sure your feedback to directs contains surprising information every time, also without examples or explanations, like rating a successful director “needs support”.
Require your directs to create development plans for their directs but don’t bother creating them yourself. Justify it in their high seniority level and ability to grow on their own.
Vendors and Cloud Providers
Sign long-term contracts with multiple cloud providers. Tell AWS you’re considering Azure. Tell Azure you’re considering GCP. Tell your board each is essential for redundancy. In reality, this maze of services ensures only you understand the true cost structure — and only you can untangle it.
Technical Debt and Legacy Systems
Never allow full migration away from legacy systems — they are your fortress. When pressed about modernization, initiate grand rewrite projects destined to fail. A failed rewrite reinforces the necessity of your legacy knowledge. Keep at least three critical systems in a language no one else knows.
Technical debt is always an amazing excuse for failure.
Handling Security and Compliance
Security audits are both a threat and an opportunity. Use them to justify your complex systems. Keep mentioning how important security is without making any real improvement and when breaches occur, blame them on the inadequate budgets provided by the board, the deprioritization by Product and the ignorance of the engineers. Always keep one critical security issue hidden — useful for justifying emergency powers when needed.
Succession
Never train a true successor.
Groom multiple potential heirs for CTO, each specializing in different areas of the system. Keep them competing for your favor. The moment one grows too knowledgeable, promote them to a position far from core systems.
Keep them close and under constant surveillance. Undermine their confidence and capabilities subtly so that they never pose a real threat to your dominion. When the time comes to step down, ensure the transition leaves your legacy untouchable and your influence lingering.
Conclusion
As you see, being a machiavellian CTO takes up a lot of time and attention. You might need to write down your rivals, plans and execution dates for follow-ups. Success doesn’t come overnight.
- Technical excellence is secondary to technical dependence
- Knowledge shared is power diminished
- Complex systems guarantee employment
- The best architecture is the one only you understand
- Keep the board confused and the engineers divided
- Better to be feared for your bad temper and technical wizardry than loved for your leadership and compassion
Everything is a tool for personal gain, mainly other people.
It is better to be the master of a broken system than a servant in a well-functioning one.
