The Hidden Struggles of Leadership: Why CTOs Fail Without the Right Guidance
Levan MamulashviliShare
Introduction: The High-Stakes Game of Leadership
In 2014, Randy Komisar, a seasoned entrepreneur and former partner at Kleiner Perkins, was brought in to help a struggling tech startup. The problem? The company had brilliant engineers and a product with strong market potential—but leadership was in chaos.
The CTO, a technical genius, had no authority. He was undermined by his own team, ignored in executive meetings, and struggling with company politics. Worse, he was caught between trying to be everyone’s friend and making the tough calls necessary for the company’s survival.
By the time Komisar stepped in, the company was bleeding talent. Three senior engineers had quit in frustration, and the CEO was already looking for a replacement CTO.
This isn’t an isolated case. Across the industry, brilliant technologists fail as leaders—not because of technical incompetence, but because they never learned the rules of leadership.
If you’re a CTO, engineering leader, or an aspiring tech executive, your biggest risks aren’t scaling systems or shipping code—they are building credibility, handling internal politics, setting boundaries, and making tough personnel decisions.
Let’s talk about the four silent killers of tech leadership.
1. Building Your Own Authority as a CTO: When No One Listens to You
In 2016, Yahoo’s engineering team was in a downward spiral. The company had been trying to reinvent itself under Marissa Mayer, but internal struggles between leadership and engineers stalled progress.
One of the biggest challenges?
CTOs and tech leaders had no real authority.
- Engineers complained about incoherent leadership directives.
- Executives overruled technical decisions with no engineering input.
- High-performing engineers refused to follow direction, believing leadership was clueless.
Yahoo wasn’t alone. Uber, WeWork, and even Google have faced internal revolts against leadership—not because the leaders were bad at technology, but because they never established authority within their own teams.
Here’s what happens when you lack authority:
🚨 Your team doesn’t respect your decisions—they work around you instead of with you.
🚨 Executives see you as a technical advisor, not a strategic leader.
🚨 Your best engineers leave for companies where leadership is stronger.
If you think technical skills alone will command respect, you’re already at risk.
2. Dealing with Inner Company Politics & Gossip: The Silent Killer of Leadership
In 2019, WeWork was at its peak, valued at $47 billion. But internally, it was a mess.
Executives constantly undermined one another, and middle managers engaged in a toxic culture of gossip and power struggles. Employees watched as top executives made backroom deals, leaving entire teams blindsided by decisions that directly affected them.
🔹 Engineers weren’t sure who actually made the decisions.
🔹 Projects were delayed not because of technical issues, but because of internal politics.
🔹 The most talented employees left, sick of the drama and uncertainty.
Company politics isn’t just about backstabbing and power moves—it’s about who controls the narrative and who gets left out of key decisions.
As a CTO, here’s what company politics can do to you:
🚨 Your ideas get blocked by other departments before they even reach the CEO.
🚨 Your best people quit because they feel unprotected from internal power struggles.
🚨 You waste months fighting battles you didn’t even know existed.
If you think staying neutral will protect you, you’re already losing control.
3. Should You Be Friends with Employees? The Leadership Balancing Act
In 2015, Evan Spiegel, the CEO of Snapchat, faced a mutiny.
The company was growing fast, but internally, engineers were frustrated by a lack of leadership direction. Spiegel had spent the early days of Snapchat building close friendships with his team—but as the company scaled, these same employees resented him when he had to make tough executive decisions.
👥 Employees expected special treatment because of past friendships.
⚔️ Tough calls—like letting people go or shifting priorities—became personal.
💥 Trust eroded between leadership and engineers, leading to internal chaos.
The same issue has played out at Facebook, Google, and Tesla—where once-friendly cultures turned toxic when leaders failed to set clear professional boundaries.
As a tech leader, here’s what happens when you blur the lines between friendship and authority:
🚨 You struggle to hold people accountable—because you don’t want to ruin relationships.
🚨 Your team loses confidence in you—because your decisions feel inconsistent.
🚨 You get burned out from emotional strain, constantly trying to manage both friendship and leadership.
If you think being well-liked is the same as being respected, you’re setting yourself up for betrayal and disappointment.
4. Who to Fire & Who to Keep? The Toughest Decisions in Leadership
In 2022, Twitter’s engineering team faced its most brutal test. After Elon Musk took over, he fired 50% of the company’s workforce overnight.
While the move was extreme, most companies struggle with this decision in slow motion.
💡 Netflix has a policy: "Keep only the best performers, pay them top salaries, and let go of the rest."
💡 Amazon uses "Stack Ranking"—forcing managers to identify and remove the bottom 10% of performers annually.
💡 Google, on the other hand, often holds on to underperformers for too long—causing frustration among top engineers.
Most CTOs and tech leaders fail when it comes to firing decisions because they:
🚨 Wait too long—hoping an underperformer will improve.
🚨 Fear backlash—worrying how the team will react.
🚨 Get emotionally attached—struggling to separate personal relationships from business reality.
But keeping the wrong people kills engineering speed.
❌ A toxic senior engineer can derail an entire team.
❌ An underperforming tech lead can slow projects by months.
❌ A disengaged employee can spread negativity across the entire organization.
If you think avoiding tough firing decisions makes you a good leader, you’re already losing credibility.
The Harsh Truth: Most Tech Leaders Fail Because They Don’t Learn Leadership
The difference between a struggling CTO and a high-impact technology leader isn’t technical skill—it’s leadership mastery.
🚨 If you don’t build authority, your team won’t respect you.
🚨 If you ignore company politics, you’ll get blocked at every turn.
🚨 If you blur friendships with leadership, you’ll lose control.
🚨 If you avoid firing tough calls, you’ll drag your team down.
💡 The world’s best tech leaders didn’t figure this out on their own. They learned it.
If any of these challenges sound familiar, you have a choice:
⚡ Keep struggling through leadership mistakes, costing your company months or years of lost progress.
⚡ Or invest in learning leadership—so you can lead with confidence, authority, and clarity.
Because in the high-stakes world of tech leadership, the cost of not learning is failure.
🚀 Are you ready to become the leader your team needs?
👉 Enroll in my course now and take control of your leadership journey.