The CTO’s Necessary Friction
When being “difficult” is exactly what your C-suite needs from you
It’s 2009. I’m sitting across from my co-founder and CEO in our cramped office, reviewing our quarterly financials. Our SaaS company is barely three years old, pulling in about $1.8M in revenue with a team of 12. It is a very hot summer’s day in Old Town, San Diego. The air conditioning broke again last week, and I can feel sweat pooling at the small of my back.
My CEO is excited. He just closed a deal with a mid-market client who wants us to build a custom reporting dashboard. “Six figures,” he says, grinning. “And they’re willing to pay upfront.”
I should be celebrating. Instead, I’m calculating. The custom work will take my two best engineers off the product roadmap for at least three months. Our deployment pipeline is already fragile. We’re still manually testing major releases. And this “custom” work will create technical debt that will haunt us for years.
“We can’t do this,” I say.
The grin fades. “What do you mean we can’t do this? It’s $150,000.”
“It’s $150,000 that will cost us $300,000 in opportunity cost and another $200,000 in maintenance over the next two years.”
The meeting that was supposed to take 15 minutes stretches to two hours. I pull up spreadsheets. I draw architecture diagrams on our whiteboard. I explain why this deal, however attractive, will derail everything we’ve been building. My co-founder’s frustration is palpable.
“You’re being difficult,” he finally says. “You’re always being difficult.”
I go home that night convinced I’m the problem. Too technical. Too rigid. Too high maintenance. Maybe I should just shut up and let the business people run the business.
But something nags at me. If I stay silent, who’s going to protect the engineering capacity that actually builds the business?
When Low Maintenance Means Low Impact
Nobody tells you about being a CTO in the C-suite: the pressure to be “easy to work with” is enormous. Your CEO is juggling investor expectations, cash flow crises, and sales targets. Your COO is fighting fires in operations. Your Head of Sales is trying to hit quota. The last thing anyone wants is their CTO pushing back on deals, questioning product decisions, or demanding resources for “technical improvements” that don’t show up on the revenue line.
So most CTOs learn to be low maintenance. We become accommodating. We say yes to unrealistic timelines. We accept insufficient budgets. We swallow our concerns about technical debt. We stop asking difficult questions in leadership meetings because we don’t want to be “that person” who always has objections.
In IBM’s 2021 CTO study, Ericsson’s Vice President noted that many CTOs “started on a very technical level and then moved into higher management positions. It has been easy to hide behind deep technical discussions. You now need to have totally different discussions with the business. And you need to have the confidence to question the business.”
Being low maintenance doesn’t make you a better executive. It makes you invisible.
The Cost of Your Silence
Let me put this in terms that matter: money. In a company with $10M in revenue and a 40-person engineering team, what does “low maintenance CTO syndrome” actually cost?
McKinsey research shows that technical debt accounts for about 40% of IT balance sheets, and companies pay an additional 10-20% to address tech debt on top of project costs. For a $3M engineering budget, that’s potentially $600,000-$900,000 annually in extra costs from accumulated technical debt.
Stripe’s research found that engineers spend 33% of their time dealing with technical debt. That’s roughly $1M in wasted engineering capacity for our example company, engineers firefighting problems instead of building features that drive revenue.
Studies show that on average, 25% of development effort is wasted on technical debt-caused issues. When you’re the agreeable CTO who never pushes back, you’re not being a team player. You’re bleeding the company of $1.5M-$2M annually in lost productivity.
That’s the price of being agreeable. That’s what being “low maintenance” actually costs your company.
What High Maintenance Actually Means
Let’s reframe this entirely. When I say a CTO needs to be high maintenance, I don’t mean being unreasonable, throwing tantrums, or refusing to collaborate. I mean:
Demanding Clarity: When your CEO proposes a new strategic direction, you don’t nod along. You ask the hard questions. “What does success look like? What are we willing to sacrifice to get there? What happens if this doesn’t work?” These aren’t obstructions; they’re the questions that prevent expensive mistakes.
Leaning Into Difficult Conversations: When Sales promises a feature that doesn’t exist, you don’t quietly tell engineering to “make it work.” You escalate immediately. You have the uncomfortable conversation about commitments, timelines, and what’s actually possible. Yes, people will be annoyed. That’s the job.
Trusting Your Spidey Sense: You’ve been building technology for years. When something feels wrong like a vendor choice, an architectural decision, or a hiring plan you say something. Loudly. Even when you can’t fully articulate why. Especially then.
Being Present and Vocal: In C-suite meetings, you don’t sit quietly while others debate strategy. You inject technical reality into every conversation. “That timeline assumes we have infinite engineering capacity.” “That growth target requires infrastructure we don’t have.” “That partnership creates dependencies we can’t afford.”
This behavior will make you seem high maintenance. People will roll their eyes when you speak up. Your CEO might pull you aside and ask you to be “more collaborative.”
Good. You’re doing your job.
The Executive Presence Paradox
There’s a concept in leadership development called executive presence. It’s usually described as confidence, gravitas, and the ability to command a room. But what the leadership consultants miss is this: real executive presence often looks like being difficult.
When the CFO pushes back on the sales forecast, that’s executive presence. When the COO refuses to commit to an impossible delivery timeline, that’s executive presence. When the CTO questions whether the business strategy is technically feasible, that’s executive presence.
The C-suite isn’t a democracy. It’s not a place where everyone gets a gold star for participation. It’s a place where each executive is supposed to be the loud, uncompromising advocate for their domain. The CFO protects the financial health of the company. The CTO protects the technical health of the company.
You can’t protect something while being agreeable all the time.
Your job isn’t to be liked. Your job is to make sure the company builds technology that works, scales, and doesn’t collapse under its own complexity.
The Questions That Signal High Maintenance
When you’re properly high maintenance like when you’re actually doing the job of CTO, certain questions become your constant refrain in leadership meetings:
“What’s the actual cost of this decision?” Not the obvious cost. The hidden cost. The opportunity cost. The technical debt cost. The maintenance cost three years from now.
“What assumptions are we making?” Every strategy relies on assumptions. Your job is to surface them, question them, and force everyone to confront what happens if they’re wrong.
“Who on my team has capacity for this?” Not theoretical capacity. Actual capacity. Engineers aren’t interchangeable resources. This matters when your CEO wants to “just add” one more initiative.
“What are we NOT going to do?” Everything has a trade-off. When the company commits to something new, you’re the person asking what existing work gets deprioritized or canceled.
“What happens if this fails?” Not pessimism. Risk management. What’s the blast radius of this decision? What’s our rollback plan? What’s the worst-case scenario, and can we survive it?
These questions will make meetings longer. They’ll make decisions slower. They’ll make you seem like an obstacle.
They’ll also save your company from catastrophic mistakes.
The Season of Strategic Noise
There’s a season in every CTO’s career usually when the company is between 40-120 engineers, where being high maintenance isn’t optional. It’s survival.
This is when complexity starts to overwhelm intuition. When the CEO can’t simply “know” what’s happening in engineering anymore. When architectural decisions have multi-million dollar implications. When technical debt becomes existential.
During this season, you need to be loud. Not obnoxious, but loud. Your voice needs to be heard in every strategic conversation because technology isn’t a support function anymore. It’s the business.
This is when people should be asking “What does the CTO think?” before making major decisions. Not out of politeness, but because ignoring your perspective is expensive and dangerous.
This is when your opinion should carry weight not because of your title, but because you’ve established a pattern of being right about technical implications. Sometimes annoyingly right.
This is your season of necessary friction.
What Success Looks Like
Back to that meeting in 2009. We didn’t take that custom development deal. My co-founder was furious with me for a week. But we used those engineering resources to finally fix our deployment pipeline and build the analytics dashboard that 80% of our customers had been requesting.
Six months later, that analytics feature helped us close deals worth $2.3M in new ARR. The client who wanted custom development? They signed anyway, because the product we built was better than what they originally asked for.
More importantly, something shifted in how the C-suite worked together. My co-founder started asking “What does Et think?” before committing to major deals. Our head of sales learned to check technical feasibility before making promises. Our board meetings started including honest assessments of engineering capacity and technical risk.
I was still high maintenance. But now that friction was valued, not tolerated.
The Numbers Tell the Story
Korn Ferry’s analysis of the top 1,000 U.S. companies found that CTO/CIO tenure averages around 4.3-4.9 years. A 2021 survey showed that 56% of technology executives changed employers that year, with nearly 40% reporting burnout.
Think about that. If you’re a CTO, you’ll most likely stay in your job for less than five years. That’s barely enough time to execute meaningful technical transformation.
How many of those departed CTOs were “technically correct” in their assessments of business goals, technology strategies, and product-market fit? I bet most of them were. But how many were actually heard? How many were able to have real impact? How many helped steer the ship before it hit the iceberg?
The low-maintenance CTOs are the ones who get fired when technical disasters happen. The high-maintenance CTOs are the ones who prevented those disasters in the first place.
Your Turn to Be Difficult
You don’t need permission to be high maintenance. You need to stop apologizing for it. The next time you’re in a C-suite meeting and someone proposes something that makes your technical instincts scream, speak up. Loudly.
Calculate the real cost and share it. “This feature will take 3 engineers for 4 months. That’s $240,000 in engineering time, plus another $100,000 annually in maintenance. What revenue does this generate?”
Challenge the assumptions. “We’re assuming our infrastructure can handle 10x growth. Have we actually tested that? What’s our plan when we’re wrong?”
Demand clarity on trade-offs. “If we commit to this partnership integration, we’re pushing the mobile app redesign to next year. Is everyone comfortable with that?”
Yes, people will find you difficult. Yes, you might get feedback that you need to be “more collaborative.” Yes, some executives will wish you were easier to work with.
But six months from now, when the company avoids a $2M mistake because you asked an uncomfortable question, no one will remember that you were difficult. They’ll remember that you were right.
Your C-suite doesn’t need another agreeable executive. They need someone who will protect the technical foundation of the business, even when—especially when—that protection is uncomfortable.
Be high maintenance. Be demanding. Be the friction that prevents expensive mistakes.
That’s not a personality flaw. That’s executive presence.
Etienne
P.S. Here are the references:
IBM Institute for Business Value (2021) “2021 CTO Study: The CTO Revelation” https://www.ibm.com/thought-leadership/institute-business-value/en-us/report/2021-cto
McKinsey & Company (2023) “Breaking technical debt’s vicious cycle to modernize your business” https://www.mckinsey.com/capabilities/mckinsey-digital/our-insights/breaking-technical-debts-vicious-cycle-to-modernize-your-business
Stripe (2018) “The Developer Coefficient” - Research on engineering time spent on technical debt Referenced in: https://www.stepsize.com/blog/cost-of-technical-debt
Academic Research on Technical Debt Besker, T., et al. (2019). “Software developer productivity loss due to technical debt—A replication and extension study examining developers’ development work.” Journal of Systems and Software. https://www.sciencedirect.com/science/article/abs/pii/S0164121219301335
Korn Ferry (2020) “Age and Tenure in the C-Suite: Korn Ferry Study Reveals Trends by Title and Industry” https://www.businesswire.com/news/home/20200121005146/en/Age-and-Tenure-in-the-C-Suite-Korn-Ferry-Study-Reveals-Trends-by-Title-and-Industry
Russell Reynolds Associates (2021) Technology Executive Survey - Referenced in Fortune article https://fortune.com/2023/02/21/chief-technology-officer-in-demand-retention-job-hop-cto/