Red Flags in Tech Leadership

Navigating the Minefield of Toxic Work Environments

Over twenty years building and fixing organizations, and I thought I understood the failure modes. Technical incompetence. Political dysfunction. The occasional ethical lapse. Then I encountered something I’d never seen before: a system where the toxicity wasn’t a bug. It was the architecture.

I should have recognized it earlier. The signals were there. I rationalized them because I believed, wrongly, that good process could constrain bad actors. That frameworks could contain malice. That you could debug a system that was designed to be corrupt. You can’t. When the kernel is compromised, everything running on top of it is compromised too.

This is what I learned the hard way.

The Fundamental Mistake

For most of my career, I’ve thought about organizational problems as systems failures. Build better structures, implement better processes, create better incentives. This works when leadership is fundamentally well-intentioned but inexperienced or misguided. The problem is a mismatch between intent and execution. Fix the execution, solve the problem.

But some organizations don’t have a mismatch between intent and execution. The execution perfectly reflects the intent. The toxicity isn’t a failure of the system—it’s the successful operation of a system designed to extract value for leadership at everyone else’s expense. Employees aren’t stakeholders to be developed. They’re resources to be depleted. This is a different kind of problem entirely, and all your frameworks become useless when you encounter it.

I used to think that was hyperbole. It’s not. It’s diagnostic precision.

What a Corrupted System Actually Looks Like

Some patterns took time to recognize because they operated at a level I’d never had to think about before. In healthy organizations, even normatively dysfunctional ones, there’s a baseline assumption that laws are constraints, that employees have rights, that governance structures exist for a reason. Remove those assumptions and you’re operating in different physics entirely.

The inner circle problem was obvious early but I misread its significance. Certain people—founders, childhood friends, whoever had been there longest—operated under different rules. They could be, and were, gloriously incompetent. They could be actively destructive to the business. They could violate policies that would get anyone else terminated. None of it mattered. They were untouchable.

This isn’t just unfair. It’s how you know the organization’s stated values are fiction. When competent people who challenge decisions or advocate for employees get systematically pushed out while incompetent loyalists remain protected, you’re seeing the real incentive structure. Loyalty to leadership trumps everything—competence, ethics, performance, the actual success of the business. Once you understand this, every other dysfunction makes sense. It’s not a broken system trying to function. It’s a functional system serving interests you didn’t realize were primary.

Accountability flowing in only one direction took longer to see as a pattern. Decisions would be made, often over explicit objections, and when they predictably failed, the people who’d objected would be blamed for the failure. Not in a casual “well someone has to take responsibility” way. Systematically. With consequences. Meanwhile, the people who’d made the decisions faced nothing.

This inverts the normal problem-solving process. In healthy organizations, failures generate information. You do post-mortems, identify root causes, fix systems. Here, failures generated scapegoats. The goal wasn’t learning, it was protection. Leadership couldn’t be wrong, so someone else had to be responsible. This makes honest feedback impossible. The moment you identify a problem accurately, you’ve marked yourself as the true problem.

The mercurial decision-making was something else entirely. I’ve worked with indecisive leaders. I’ve worked with leaders who changed their minds as they learned. This was neither. Direction would shift arbitrarily. Commitments made one week would be abandoned the next without explanation or acknowledgment. Goalposts would move mid-flight—not because priorities changed, but because moving the goalposts was itself the point. It kept everyone off-balance, scrambling, unable to build anything stable.

This isn’t is a case of disorganization, but a control mechanism. When nobody can predict what leadership wants or whether today’s mandate will still be valid tomorrow, everyone becomes dependent on leadership’s real-time interpretation of reality. You can’t operate autonomously because the ground is quicksand. Some leaders do this deliberately. Others are just so incompetent that the effect is the same. Either way, teams can’t function.

Then there’s HR. In every organization I’d worked at before, HR had at least tried to mediate between employee welfare and business interests. The competence varied, but the intent was recognizable. Here, HR was intelligence. When they started having conversations like “I know this isn’t what you signed up for, so it’s okay if you want to leave,” they weren’t expressing sympathy. They were delivering a message: comply or be pushed out. Anything you told them would be used to build a case, not to address your concerns.

This transforms HR from a neutral function into an active threat. You can’t report problems through official channels because the channels exist to identify and eliminate people who report problems. Once you realize this, you understand why toxic organizations stay toxic—the mechanisms that should constrain bad behavior have been captured to enable it.

Work-life boundaries became a compliance test. Meetings scheduled during pre-approved vacation. Surveys sent on weekends with next-day deadlines. Expectations of immediate availability regardless of time or circumstance. Some leaders do this because they’re workaholics who don’t know how to separate work from life. That’s bad enough. Worse is when leaders claim they respect boundaries but systematically punish anyone who actually uses them—reduced responsibilities, blocked advancement, manufactured pretexts for termination. The second version is more insidious because it’s duplicitous. At least openly demanding leaders are honest about expectations.

But here’s what broke my model entirely: the relationship to law itself. I’ve worked with leaders who bent rules, who operated in gray areas, who pushed boundaries. This was different. Regulations simply didn’t apply. When you tell someone that something violates federal law and their response is to argue about whether the law is actually relevant to their specific situation (it was)—not as a legal strategy but as a genuine belief—you’re dealing with someone operating under assumptions you didn’t know were possible in professional contexts.

This creates liability for everyone around them. They make decisions that expose the company and its employees to legal risk, and they do it with confidence because they genuinely don’t believe the rules apply. I’m not being hypothetical. I watched this happen. The certainty with which some leaders dismiss legal constraints would be impressive if it weren’t so dangerous.

Governance became performance art. Situations misrepresented to boards and investors. Company funds and personal expenses deliberately blurred. Decisions made that benefited leadership at the company’s expense, presented as sound business judgment. The fact that investors sometimes allow this doesn’t make it okay, it just means you’re operating in an environment where oversight has failed at multiple levels and has, in effect if not intent, become complicit. Everyone who should be providing checks has abdicated responsibility for profits and/or expedience.

But here’s what I’d never encountered before, not in over twenty years: genuine, breathtaking incompetence at the leadership level, paired with an equally breathtaking, absolute conviction of brilliance. The Dunning-Kruger¹ effect is usually a joke. Leaders who couldn’t understand basic business concepts but were utterly certain they were geniuses. Who made obviously irrational decisions and punished anyone who questioned them. Who genuinely lacked the cognitive capacity to recognize their own incompetence.

This is different from arrogance. Arrogant leaders can at least be reasoned with if you present evidence clearly enough. This was cognitive incapacity. You can’t reason with someone who lacks the mental framework to even understand why they’re wrong. Every conversation becomes circular. Every attempt to provide feedback gets reinterpreted through a lens that confirms their brilliance and your obvious disloyalty. It’s like trying to debug code written in a language that doesn’t have logic operators.

I’d worked for bad leaders before. Leaders who were political, inexperienced, occasionally unethical. But they’d all operated within a familiar spectrum of organizational dysfunction and, without exception, within the law. There were still shared assumptions about how businesses work, how people should be treated, what laws mean. This was outside that range entirely. The rules I thought governed professional behavior simply didn’t apply. Laws were optional. Employees were disposable. The business existed to serve leadership’s personal interests, and everything else—product, customers, employees—was instrumental to that purpose.

What I Did Wrong

Due diligence. I did some. Not enough. I researched the company, talked to the team, requested documents. What I got should have been disqualifying. I rationalized it. The opportunity seemed good on paper. My team seemed strong. I thought I could influence the situation from the inside. That was hubris.

The documents were revealing if you knew how to read them. I knew how to read them. I just didn’t want to believe what they were telling me. When you see financial structures that exist primarily to enrich founders regardless of business performance, when you see governance that provides no real oversight, when you see a track record that doesn’t match the narrative—those aren’t yellow flags. Those are air raid sirens.

I talked to people who would report to me. They were smart, aligned with my principles, frustrated with current leadership. I thought: good team, bad CEO, I can be a buffer. What I didn’t understand was that you can’t buffer people from a system that’s toxic by design. You can maybe delay the damage, shield the team from the worst of it. You can’t prevent it. Eventually the corruption reaches everyone, including you.

I had instincts that something was wrong. Multiple conversations where things didn’t add up. Red flags in the interview process. Defensiveness about reasonable questions. I talked myself out of them because I believed, stupidly, that my experience and frameworks would be sufficient. That I’d built enough organizations, fixed enough problems, that I could handle this. I was more wrong than I could possibly have imagined.

The belief that logic and good process can constrain bad actors is a form of professional naivety that gets exposed painfully. Some people can’t be constrained by process because they don’t acknowledge that process applies to them. Some systems can’t be fixed because the dysfunction is intentional. I learned this the expensive way.

What You Should Do Differently

Research leadership not just thoroughly but correctly. Don’t just look at LinkedIn and company materials. Look for their actual track record. If they claim extensive experience but have no verifiable accomplishments, that’s data. If former employees uniformly describe the culture as toxic, believe them. If current employees are carefully evasive when you ask direct questions, that’s signal too.

Request documents and actually read them. For senior roles, cap tables, board decks, financial information matter. Not just to verify the business is sound, but to verify the governance structure isn’t designed for extraction. If they refuse to provide them or give you sanitized versions, don’t join. Companies hiding their governance structures are hiding them for a reason.

Talk to multiple people at different levels. Not just people who report to you—people across the organization. Watch for fear, excessive deference, careful language that suggests people can’t speak freely. Ask about turnover. Ask why people left. Ask how decisions get made. Listen for what’s not being said as much as what is.

But here’s the hard truth: even with perfect due diligence, you can miss things. Toxic leaders are often skilled at impression management. The real dysfunction only becomes visible once you’re inside and see how decisions actually get made, how conflicts actually get resolved, what happens to people who challenge leadership.

Which means you need to know what to do when you realize you’ve made a mistake. Document everything. In single-party consent states, record conversations with HR and leadership. Keep contemporaneous logs of problematic incidents. Don’t conflate this with paranoia. This is protection. When things escalate legally, and they might, documentation is your defense.

Be cautious with HR to the point of paranoia. In toxic environments, HR is a proxy for leadership. Consult an employment attorney before making protected complaints. Understand your legal protections before you trigger them. I learned this early enough to protect myself. Not everyone does.

Build support networks outside the company immediately. Don’t wait until things get bad. You need people you can talk to honestly who aren’t embedded in the system. Start looking for your next role the moment you realize the environment is toxic. Don’t wait for it to get better. When toxicity starts at the top, it doesn’t get better. It metastasizes.

If you’re a manager, protect your team as much as possible. Create a buffer. But recognize the limits. You can’t fix systemic dysfunction from the middle. I tried. The system is stronger than you are. At some point, protecting yourself means leaving. I stayed longer than I should have. That was a mistake. The longer you stay, the more it costs—financially, professionally, psychologically.

What This Actually Cost

Over twenty years in tech. Goldman Sachs, Deutsche Bank, startups, Etsy, Shutterstock, Candid. I thought I understood organizational pathology. I’d seen incompetence, politics, occasional ethical failures. But all within the normal range of organizational dysfunction underscored by basic competence. Everyone was still operating under the same basic assumptions about how businesses work, how people should be treated, what laws mean.

When you encounter a system where those assumptions don’t apply—where laws are optional, employees are pawns, governance is theater—all your frameworks become useless. You can’t process-design your way out of purposeful malice. You can’t create guardrails that constrain someone who doesn’t acknowledge that guardrails apply to them. The belief that you can is professional naivety.

The cost isn’t just the time. It’s the damage to your model of how organizations work. I built a career on the assumption that good systems constrain bad behavior, that frameworks create fairness, that you can architect your way to health. That’s mostly true. But it breaks down completely when leadership is fundamentally corrupt. When the system isn’t failing—it’s succeeding at objectives you didn’t realize were primary.

Some systems can’t be fixed. Some leaders can’t be reasoned with. Some organizations exist to serve interests that are fundamentally at odds with employee welfare or business success. Recognizing this early and leaving isn’t failure. It’s accurate diagnosis. The only winning move is not to play.

That’s the lesson. Everything else is details.

1. Wikipedia, “Dunning–Kruger effect,” July 20, 2025, https://en.wikipedia.org/w/index.php?title=Dunning%E2%80%93Kruger_effect&oldid=1325552154.