The Organizational Cancer
Dismantling the Echo Chamber: Part 3
This is Part 3 of the Breaking the Echo Chamber series:
Part 1: The Seduction of Yes-Men Culture
Part 2: The Personal Cost of Sycophancy
Part 3: The Organizational Cancer [you are here]
Part 4: Breaking Free
By month twenty-four, the VP had stopped being a victim of the system and had become its engine. The transformation was complete. She wasn’t just enabling bad decisions anymore, she was actively recruiting others to do the same. When a new director of platform engineering started raising concerns about technical debt in his first month, the VP pulled him aside for what she called a “coaching conversation.”
I heard about this conversation afterward from the director, who was shaken by it. The VP’s message was clear: “You’re technically right about the debt, but you need to understand how things work here. The CEO doesn’t want to hear about problems right now. He wants solutions that support the roadmap. If you keep pushing on this, you’ll lose credibility. Better to build relationships first, show you’re a team player, then you can influence these decisions later.”
Everything she said was technically true. And completely corrupting. Because “building relationships” meant not challenging decisions. “Being a team player” meant enabling dysfunction. And “influencing later” was a fantasy; she’d been there two years and hadn’t influenced a single technical decision that mattered. She was teaching him the same rationalizations that had captured her.
This is how yes-men culture perpetuates itself. Not through explicit coercion but through experienced people teaching new people how to survive. Each generation of enablers recruits the next, passing on the same broken patterns while genuinely believing they’re providing valuable guidance.
How Systems Get Captured
The VP’s transformation didn’t just damage her capabilities. It damaged the organization’s immune system. She was supposed to be a check on bad decisions. Someone with the technical expertise and organizational standing to push back when needed. Instead, she’d become a mechanism for making bad decisions look reasonable.
Performance reviews became exercises in documenting alignment rather than impact. The VP rated people highly when they “collaborated effectively with leadership” and “demonstrated cultural fit.” Translation: they didn’t challenge the CEO’s decisions and they helped manage resistance from their teams. Engineers who raised technical concerns found their reviews suddenly full of vague criticisms about “communication style” or “executive presence.”
I watched one senior engineer—legitimately one of the best on the team—get rated as “needs improvement” because she’d pushed back on an architectural decision that was obviously wrong. The VP’s written feedback was a masterpiece of obfuscation: “While she demonstrates strong technical skills, she sometimes struggles to see the broader business context and can be inflexible when her recommendations aren’t immediately adopted.”
What actually happened: the engineer had identified a scalability bottleneck that would have cost the company millions to fix post-launch. The CEO didn’t want to hear it because it would delay his timeline. The engineer kept pushing. So the VP documented it as a performance issue.
This is how organizational immune systems fail. The people who should be identifying problems get classified as the problem themselves. Dissent gets pathologized as poor judgment or bad attitude. And the systems that are supposed to protect the organization—performance reviews, hiring decisions, promotion criteria—get repurposed to protect leadership from accountability.
The Spread of Dysfunction
The most insidious part wasn’t what the VP did directly. It was how her behavior shaped everyone else’s. Other leaders watched her get rewarded for enablement and learned the lesson. New hires watched her model “success” and internalized that model. Within eighteen months, the entire engineering leadership team had adopted similar patterns.
Team meetings became performance art. Everyone knew the technical debt was mounting. Everyone knew the slapdash architecture decisions were creating long-term vulnerabilities. Everyone knew the timelines were unanchored to reality. But nobody said it out loud anymore. Instead, they’d have sidebar conversations after meetings where they’d acknowledge the reality privately while maintaining the fiction publicly.
The director of platform engineering, the one the VP had “coached,” learned quickly. Within three months, he’d stopped raising concerns in meetings. Within six, he was actively helping rationalize bad decisions to his team. By month nine, he was coaching his own reports on “how things work here.” The pattern had replicated perfectly.
This created a cascade effect through the organization. If senior leadership was signaling that alignment mattered more than accuracy, mid-level managers optimized for alignment. If mid-level managers valued compliance over competence, individual contributors learned to stay quiet. Each layer reinforced the pattern in the layer below.
The talented engineers who valued technical integrity started leaving. Not all at once (that would have been obvious), but steadily, one every few months. Exit interviews revealed nothing useful because people had learned not to be honest with HR. They’d cite “new opportunities” or “career growth” while privately telling peers they couldn’t stand watching good engineering be sacrificed to bad leadership.
The engineers who stayed fell into two categories: those who adapted to the dysfunction and those who mentally checked out. The ones who adapted became the next generation of enablers. The ones who checked out did the minimum required to collect their paychecks while investing their actual energy elsewhere. Neither group was solving the technical problems that needed solving.
The Architecture of Institutional Failure
What made this particularly effective as a control system was how it operated through seemingly neutral organizational mechanisms. Performance reviews. Promotion criteria. Compensation decisions. Information access. None of these overtly required enablement, they just consistently rewarded it while punishing dissent.
The VP became the primary gatekeeper for promotion to senior engineering levels. Her criteria were nominally about technical leadership and business acumen, but in practice they measured political alignment. Engineers who “partnered well with leadership” got promoted. Engineers who “sometimes struggle to see broader context” didn’t. The fact that “partnering well” meant not challenging and “seeing broader context” meant understanding that technical concerns were less important than executive preferences—that was never stated explicitly. It didn’t need to be.
Information flow became another control mechanism. The VP held weekly “leadership syncs” where she’d share updates from her conversations with the CEO. Being included in these syncs was a mark of status. The information shared was often trivial, but access to it felt important. What actually mattered was the message: if you’re aligned, you’re in the room. If you challenge too much, you stop getting invited.
This created a powerful incentive structure where the rational move was to maintain access by maintaining alignment. Engineers who pushed back found themselves gradually excluded from information flow. They’d learn about decisions after they were made, get invited to meetings after the real discussions had happened elsewhere, find themselves unable to influence outcomes because they weren’t in the rooms where those outcomes got decided.
The cruelty was that this exclusion was never presented as punishment. It was framed as natural consequences. “We needed to move fast on that decision.” “I didn’t think you’d be interested in that particular project.” “Those meetings are just for the senior technical leads.” But the pattern was clear: challenge leadership and you become organizationally irrelevant.
The Point of No Return
By year three, the organizational culture had calcified around enablement. It wasn’t just that individual people had been captured, the entire system had been redesigned to make capture inevitable. New hires were onboarded into a culture where the rules were never stated explicitly but were absolutely clear: technical excellence matters less than executive alignment, competence is secondary to compliance, and speaking truth to power is career suicide.
The organization maintained elaborate fictions. The values statements still talked about “innovation,” “excellence,” and “honest feedback.” The performance review process still claimed to measure “impact” and “technical leadership.” The job postings still advertised “collaborative culture” and “engineering-driven decision making.” None of it was true, but the gap between stated values and lived reality had become so normalized that people stopped noticing the contradiction.
The VP herself, by this point, probably believed she was an effective leader. She’d successfully navigated a complex political environment. She’d maintained her position and compensation. She’d built a team that consistently delivered against the CEO’s roadmap, even if that roadmap was technically incoherent and long-term unsustainable. By the metrics that mattered to leadership, she was succeeding.
The fact that she’d systematically destroyed the organization’s ability to make good technical decisions, driven out its most capable engineers, and created a culture where honesty was punished and mediocrity was rewarded—that wasn’t visible to her anymore. The perspective necessary to see that had been warped by years of rationalization and reinforcement. She was trapped in the system she’d helped build, and she couldn’t see the bars of her own cage.
This is what yes-men culture costs at the organizational level. Not just bad decisions or political gamesmanship, but the systematic destruction of the organization’s capacity for self-correction. The mechanisms that should identify and fix problems get repurposed to identify and eliminate people who point out problems. And once that transformation is complete, the organization becomes incapable of responding to reality until reality forces the response through catastrophic failure.
Understanding how this system works is essential because it reveals where intervention might be possible. That’s what we’ll examine in Part 4: the strategies for breaking free—both as individuals trying to escape capture and as leaders trying to build organizations resistant to it.
Next in the series: Part 4: Breaking Free