The CTO’s Seven Sins
There’s a pattern among the survivors, the CTOs who make it past the two-year mark and build lasting legacies. They avoid seven specific sins that destroy most of their peers.
In 2024, the average CTO stays in their position for just 1-2 years, barely enough time to see a major architectural overhaul through to completion. Fifty-six percent of technology executives changed employers in 2021 alone, and the numbers haven’t improved. Leadership burnout has surged to 56% of executives in 2024, nearly 10% higher than during the peak of COVID-19.
These aren’t just statistics. They represent thousands of CTOs who walked into their offices with grand visions of technological transformation, only to find themselves clearing out their desks before the second annual planning cycle.
A Korn Ferry survey revealed that CIOs average just 4.3 years in their roles, the second-lowest tenure in the C-suite. But here’s what the surveys don’t capture: most of these departures aren’t about better opportunities or natural career progression. The most common causes of CTO failure include struggling to create strategies that support business needs, requiring all major decisions to go through them, and becoming disconnected from the company’s mission.
The pattern repeats across Silicon Valley to Singapore, from Fortune 500s to Series A startups. A brilliant technologist gets promoted to CTO. Within months, they’re drowning. Within a year, they’re disengaged. By year two, they’re gone.
The Pressure Cooker Reality
CTOs experience stress carved deep across multiple dimensions - from development teams, other CxOs, and customers. Unlike the one-dimensional stress of coding, they’re now responsible for aspects that require them to be focused and proactive 16-20 hours a day. Cyberattacks, tech outages and breaches cause stress-related illnesses and impact the mental well-being of 51% of tech executives, reaching 56% among CTO and CIO roles.
The struggle isn’t just personal. Organizations led by CTOs who lack proper leadership skills test low on work engagement and overall morale. Teams complain that every decision needs to go through the CTO, creating bottlenecks that strangle innovation. When a CTO mismanages technological changes, it leads to significant disruptions, project failures, and ultimately, dismissal.
The research reveals something crucial: Companies consistently pick the best technologist instead of picking the best leader who also happens to know technology well. This fundamental misunderstanding of the CTO role creates a perfect storm where technical brilliance becomes organizational dysfunction.
But there’s a pattern among the survivors, the CTOs who make it past the two-year mark and build lasting legacies. They avoid seven specific sins that destroy most of their peers. Successful technology leaders combine technical acumen with leadership skills, understanding that while these capabilities have very little in common, both are essential.
The Seven Sins That Kill CTO Careers
Sin #1: The Product Stranger
One of the most common reasons CTOs fail is their lack of alignment with the business vision. You can architect the most elegant microservices infrastructure on the planet, but if you don’t understand why customers actually pay for your product, you’re building castles in the clouds.
I’ve watched CTOs proudly present their Datadog migration while being unable to demonstrate the actual user workflow of their product. They can explain every technical decision but can’t articulate the problem their company solves. When product managers describe user needs, these CTOs retreat into technical jargon, using complexity as a shield against their fundamental disconnection from the business.
Here’s the harsh truth: if you can’t use your own product competently, you can’t lead its technical development effectively. You become that general who’s never been to the battlefield, making strategic decisions from maps that don’t match the terrain.
The Antidote: Block two hours weekly to use your product as a real user would. Not a demo account, not a test environment, the actual product your customers experience. Feel the pain points. Experience the workflows. Only then can you make technical decisions that actually matter.
Sin #2: The Phantom Executive
Too much micromanagement is a common failure pattern, but the opposite extreme is equally destructive. Some CTOs, scarred by accusations of micromanagement, swing to the opposite extreme. They disappear into C-suite meetings, board preparations, and strategic planning sessions, becoming ghosts to their own teams.
“I was in a 1:1 with a lead engineers a few weeks back and she said that the team misses my presence. The consistency breeds accountability and trust.”
Your team doesn’t just need your decisions, they need your presence. They need you to unblock that architectural debate that’s been raging for three weeks. They need you to ask the uncomfortable questions that everyone’s thinking but no one’s saying. They need you to spot the pattern that connects three separate team problems into one systemic issue.
Where technical leadership seems to work best is when CTOs understand the product in its entirety but also are empathic and have skills in management and leadership. You can’t be empathic from a distance. You can’t lead people you never see.
The Antidote: Institute “CTO office hours”—scheduled time where any engineer can drop in with questions, concerns, or ideas. Walk the floor. Join random stand-ups. Pair program occasionally. Your genius isn’t in your code anymore; it’s in how you multiply the capability of every engineer on your team.
Sin #3: The Financial Blind Spot
A frequent misstep by CTOs is inadequate budget management, which can lead to overspending on unnecessary technologies or underfunding critical areas. Go read my other articles. I write about this a LOT.
I’ve seen CTOs negotiate aggressively for a $50,000 monitoring tool while being completely unaware their engineering burn rate is $2 million per month.
When you don’t understand the financial mechanics of your company, you become a cost center, not a profit enabler. You make arguments based on technical elegance rather than ROI. You get surprised when your headcount gets frozen. You get blindsided when the CFO questions your infrastructure spend.
Most damaging: When executives don’t demonstrate how technological advancements align with business goals, stakeholder confidence dwindles. Without financial literacy, you literally can’t speak the language of business value.
The Antidote: Learn to read a P&L statement. Understand your company’s unit economics. Calculate the fully-loaded cost of your engineering team (hint: it’s not just salaries). Track your department’s ROI monthly. When you propose a technical initiative, lead with the financial impact, not the technical architecture.
Go check out my CTO Ratio.
Sin #4: The Innovation Graveyard
The most valuable skill of a CTO is making timely decisions, but when you’re drowning in operational minutiae, strategic thinking dies. You become a highly-paid project manager, tracking tickets instead of setting technical vision.
CTOs trapped in operational drudgery stop creating. They stop innovating. They stop inspiring. They become administrators of the status quo, and in technology, the status quo is death. In larger companies, you won’t have time to work on the product directly, but that doesn’t mean you should stop creating entirely.
The Antidote: Audit your calendar ruthlessly. If less than 30% of your time is spent on forward-looking initiatives (new architectures, emerging technologies, strategic partnerships), you’re already in trouble. Delegate operational responsibilities. Build systems and processes that run without you. Your job is to see around corners, not to manage today’s traffic.
Sin #5: The Reactive Spiral
CTOs need to be focused and proactive 16-20 hours a day, but without intentional calendar management, you become purely reactive. Your week becomes a random collection of whatever meetings others scheduled, whatever fires erupted, whatever Slack threads exploded.
When you don’t plan your week, you don’t plan your impact. Monday bleeds into Friday without any coherent arc. You end each week exhausted but unable to articulate what you actually accomplished. Your team sees you as perpetually busy but never available for what matters.
The Antidote: Design your week like you’d design a system architecture. Monday is for momentum—reviewing metrics and setting weekly priorities. Wednesday is for deep work on strategic initiatives. Friday is for reflection and communication. Create themed days that force different types of thinking. Your week should have a beginning, middle, and end, not just be five interchangeable days of chaos.
Go check out my suggestion for the CTO’s Perfect Week.
Sin #6: The Invisible Executive
Not enough communication is a big failure factor that affects all aspects of the CTO role. Your CEO has no idea what you do all day. Your peers think you’re just the “tech person.” The board sees IT as a cost center. Meanwhile, you’re orchestrating digital transformation, but nobody knows it.
When you don’t communicate your wins, challenges, and vision, you become invisible. And invisible executives become expendable executives. The cause of CTO failure is often the result of promoting a person solely upon their technical capabilities without considering communication skills.
The Antidote: Send a weekly “CTO Update” to your C-suite. Include wins, challenges, and strategic initiatives. Translate technical achievements into business impact. Use analogies and stories, not jargon. Make your work visible, tangible, and tied to company objectives. If people don’t understand what you do, that’s your failure, not theirs.
Sin #7: The Expertise Fossil
Perhaps the most insidious sin: stopping your own learning. You’re so busy fighting today’s fires that you stop building tomorrow’s capabilities. You’re not writing, not documenting, not building your own knowledge base. You’ve become a consumer of your past expertise rather than a creator of new understanding.
Technology develops at a pace unmatched by any other construct—what is created one day can be broken, fixed, redesigned and expanded the next. When you stop learning, you start dying professionally. Your advice becomes dated. Your architectures become legacy. Your strategies become obsolete.
The Antidote: Maintain a CTO notebook. Write about your decisions, your learnings, your failures. Document patterns you observe. Build your own knowledge base that transcends any single company or role. Remember: you’re not working for your company—you’re working for yourself, building expertise that compounds over decades, not quarters.
Why These Sins Matter More Than Ever
Technology executives are outpacing their C-suite peers in switching companies, and companies face significant risks as new technologies unfold around them. With AI transformation demanding unprecedented technical leadership, companies can’t afford CTOs who fail. Yet most are setting their CTOs up for exactly that.
If you’re a CTO, there’s a statistical likelihood you won’t make it to your third year. If you’re running a company of 40-100 engineers, you’re managing millions in salary costs while potentially committing one or more of these sins daily. Each sin compounds, creating a cascade of dysfunction that ends with either your resignation letter or your termination notice.
Your 30-Day Redemption Plan
Start with brutal honesty. Which of these sins are you committing right now? Not which ones you might be slightly guilty of—which ones are actively destroying your effectiveness today?
Pick your worst sin. The one that makes you uncomfortable to acknowledge. That’s where you start.
Week 1: Face the Truth
Use your product for 2 hours
Calculate your department’s monthly burn rate
Count how many hours you spent with your team versus in C-suite meetings
Review your calendar for the past month. How much was reactive versus proactive?
Week 2: Break the Silence
Send your first weekly update to the C-suite
Schedule office hours with your team
Start a simple knowledge document. Just one page of learnings from this week
Week 3: Master the Numbers
Meet with your CFO to understand the company’s unit economics
Calculate the ROI of your last three technical initiatives
Create a simple dashboard of your department’s financial metrics
Week 4: Reclaim Your Strategy
Block 4 hours for strategic thinking (no meetings, no Slack)
Design your ideal week with themed days
Document three technical innovations that could transform your business
The Compound Effect of Recovery
The first month will feel uncomfortable. You’ll realize how disconnected you’ve become from your product, your team, or your company’s finances. That discomfort is growth.
By month two, patterns emerge. You’ll spot inefficiencies you were blind to. Your team will start approaching you with bigger ideas, knowing you’re available and interested. Your C-suite peers will begin seeing you differently, not as the “tech person” but as a business leader who happens to run technology.
By month three, the compound effect kicks in. Your strategic initiatives gain momentum. Your team’s morale improves. Your stress decreases even as your impact increases.
The Crossroads Decision
CTOs are switching jobs at unprecedented rates, most believing the grass is greener elsewhere. But they take their sins with them. The same patterns that failed them in one role follow them to the next.
Or you can choose differently. You can recognize these sins not as personal failures but as systemic traps that catch most CTOs. You can build systems and habits that make these sins impossible to commit.
The research is clear: most CTOs fail within two years. The question isn’t whether you’ll face these challenges. You will. The question is whether you’ll recognize them as the seven deadly sins they are and build the discipline to avoid them.
Your team needs you to be better than the statistics. Your company needs you to break the pattern. Most importantly, you need to prove that technical leadership isn’t an oxymoron. Someone can be both a great technologist and a great leader.
The sins are deadly, but they’re not inevitable. The choice, and the work, begins today.
Start with one sin. Build one habit. Send one update. Use your product once.
Small actions compound into transformation. But only if you start.
Don’t be another statistic. Be the CTO who survived their seven sins and built something that lasted.
See you at 7CTOs.
Etienne de Bruin <3
References
Burnout and Executive Stress
“Executive burnout statistics 2025: A look into the leadership crisis.” Superhuman Blog, June 11, 2025. https://blog.superhuman.com/executive-burnout-statistics/
“How To Avoid A CTO Meltdown (Warning Signs).” Codemotion Magazine, January 5, 2022. https://www.codemotion.com/magazine/dev-life/cto/avoid-meltdown/
“Pain points for CTOs: A primer of the most stressful aspects of the job.” Help Net Security, December 4, 2019. https://www.helpnetsecurity.com/2019/11/29/cto-stress/
“What about tech leadership makes burnout more likely?” CTO Craft, October 7, 2024. https://ctocraft.com/blog/what-about-tech-leadership-makes-burnout-more-likely/
CTO Tenure and Turnover Statistics
“Age and Tenure in the C-Suite: Korn Ferry Study Reveals Trends by Title and Industry.” Business Wire, January 21, 2020. https://www.businesswire.com/news/home/20200121005146/en/
“Chief Technology Officer Demographics and Statistics [2025].” Zippia, January 8, 2025. https://www.zippia.com/chief-technology-officer-jobs/demographics/
“CTO roles are the hardest C-suite position to fill—and turnover is high.” Fortune, February 22, 2023. https://fortune.com/2023/02/21/chief-technology-officer-in-demand-retention-job-hop-cto/
“Why is the turnover rate so high for technology leaders?” RetailWire, May 23, 2024. https://retailwire.com/discussion/why-is-the-turnover-rate-so-high-for-technology-leaders/
CTO Failure Patterns and Mistakes
“8 Reasons Why Chief Technology Officers (CTOs) Get Fired [2025].” DigitalDefynd, November 15, 2024. https://digitaldefynd.com/IQ/reasons-why-ctos-get-fired/
“10 Common CTO Mistakes and How to Avoid Them [2025].” DigitalDefynd, November 15, 2024. https://digitaldefynd.com/IQ/mistakes-ctos-must-avoid/
“CTO Failure Stories: How to Learn from the Failed CTOs in Startups.” FasterCapital. https://www.fastercapital.com/content/CTO-Failure-Stories--How-to-Learn-from-the-Failed-CTOs-in-Startups.html
“Dead on Arrival: Today’s CTO & CIO.” LinkedIn article by Marc Moskowitz. https://www.linkedin.com/pulse/dead-arrival-todays-cto-cio-marc-moskowitz
“The Problems of the CTO Role.” HackerNoon, February 10, 2018. https://hackernoon.com/the-problems-of-the-cto-role-c2a143a1cec7
“Why CTOs Fail and What CEOs and CTOs Can Do About It.” AKF Partners. https://akfpartners.com/growth-blog/why-ctos-fail