How to Avoid the Biggest Pitfalls in Leadership: Lessons from the Worst Bosses I've Had

Leadership is one of the most challenging roles anyone can step into. The expectations are high, and the stakes are often even higher. But here’s the hard truth: Not everyone who leads does it well. I’ve worked with and observed many leaders throughout my career, and unfortunately, the ones who stand out most vividly are not always the best ones.

In fact, some of the worst managers I’ve had taught me the most valuable lessons. Their behaviors, while harmful, became case studies in what not to do as a leader. In this post, I’m sharing the toxic leadership behaviors I encountered and breaking down how you can avoid them to become an uncommonly good leader.

As an executive coach in San Francisco, I’ve worked with leaders from every industry, helping them navigate their professional journeys. One thing I’ve learned is that leadership is a mirror—how we treat others is often a reflection of how we treat ourselves. To become a great leader, you must first look inward.

Here’s what I’ve learned from some of the worst bosses I’ve had:

1. Micromanaging: The Ultimate Confidence Killer

We’ve all been there—the manager who hovers, questions your every move, and feels the need to control every detail of your work. One manager I had was so obsessive about micromanagement that she would insist on trivial decisions, like using specific images from Microsoft Clip Art in presentations (yes, really).

The Problem: Micromanagement often stems from insecurity or a lack of trust. Leaders who micromanage aren’t just annoying; they’re crippling their team’s ability to innovate, take risks, and grow. The result? A disengaged team that feels incompetent and lacks autonomy.

The Fix: Trust your people. Give them the freedom to do their work. If you find yourself micromanaging, take a moment to reflect on where your insecurity is coming from. A great leader knows when to step back and let their team shine. As a leadership coach, I help my clients build that confidence, both in themselves and their teams, through self-awareness and trust-building practices.

2. Patronizing: Making People Feel Small

This one really stings. I once worked for a manager who seemed to delight in patronizing me, belittling my ideas, and making me feel like my contributions didn’t matter. Whenever I showed vulnerability or asked for help, I was met with condescension rather than support.

The Problem: Patronizing behavior stems from a leader’s own self-judgment. They put others down to feel better about their own shortcomings. This toxic behavior kills creativity and drives down morale.

The Fix: Empower your team. Leaders need to lift their people up, not tear them down. If you catch yourself speaking down to others, it’s time to reflect on what’s triggering that behavior. Kindness and humility are not weaknesses—they are superpowers in leadership.

3. Disconnected Leadership: Tuning Out Instead of Tuning In

Imagine sitting in a 1-1 with your manager, sharing ideas and concerns, only to notice them typing away on their laptop, barely acknowledging your existence. That was my reality with one particularly disengaged manager. I’d leave these meetings feeling invisible and wondering why I even bothered.

The Problem: Disconnected leadership happens when a leader is so overwhelmed or checked out that they can’t (or won’t) be present for their team. This behavior sends a clear message: "You don’t matter."

The Fix: Be present. Leadership isn’t just about strategy or operations—it’s about people. If you’re feeling burned out or disconnected, it’s crucial to address it before it affects your team. As an executive coach, I often work with leaders to help them reconnect with their purpose and re-engage with their teams.

4. The Politics of Power: When Integrity Takes a Back Seat

In one of my previous roles, I worked under a leader who was a master at playing company politics. They were confident, charismatic, and strategic—but they sacrificed integrity to climb the corporate ladder. While they rose to power, the team beneath them suffered from a lack of direction and sincerity.

The Problem: Leaders who play political games are often focused on self-preservation rather than team growth. While they may achieve short-term success, the long-term damage to their team’s trust and morale is undeniable.

The Fix: Lead with integrity. True leadership is about doing what’s right, not just what’s easy. Ask yourself: Do I want to be remembered as someone who played the game well or someone who led with honesty and integrity? The choice is yours, but integrity will always win in the long run.

5. Lack of Transparency: Keeping Your Team in the Dark

This one was a company-wide issue. Multiple leaders at this organization were masters of withholding information. They kept their teams in the dark about key decisions, and as a result, mistrust spread like wildfire.

The Problem: Lack of transparency creates an environment of suspicion and disengagement. When leaders aren’t upfront about what’s happening, their teams lose faith in them and the organization.

The Fix: Be transparent. Even when the news isn’t great, sharing information with your team builds trust. People can handle the truth far better than they can handle secrecy. As an executive coach, I encourage leaders to cultivate open, honest communication with their teams.

What’s the Common Thread?

Looking back on these experiences, there’s a clear theme: Self-awareness. The best leaders I’ve worked with are the ones who know themselves deeply. They understand their strengths, their weaknesses, and their blind spots. In contrast, the worst leaders are often those who lack self-awareness, allowing their insecurities, fears, and ego to drive their decisions.

If you’re serious about becoming an exceptional leader, you need to do the inner work first. It’s not just about learning new management techniques; it’s about understanding who you are and how you show up in the world.

As an executive coach in San Francisco, I’ve seen firsthand how transformative this self-awareness can be for leaders. When you operate from a place of grounded self-awareness, you can inspire and lead with integrity, empathy, and confidence.

How to Avoid These Pitfalls in Leadership

• Develop Self-Awareness: Take the time to reflect on your own behaviors and triggers. Consider working with a coach to gain insights into your leadership style and areas for growth.

• Build Trust: Trust your team and empower them to take ownership of their work. Micromanagement only stifles creativity and confidence.

• Lead with Integrity: Always prioritize integrity over short-term gains. Your team will respect you more for it.

• Be Present: Make time to truly connect with your team. Leadership isn’t just about strategy—it’s about relationships.

• Communicate Transparently: Even in tough times, being open with your team builds trust and loyalty.

Final Thoughts: Don’t Be Like Them

The path to becoming an exceptional leader is not always easy, but it is absolutely worth the effort. The worst leaders I’ve encountered weren’t born bad—they became that way through a series of unchecked behaviors and unresolved insecurities. Don’t let that be your story.

If you’re ready to take the next step in your leadership journey, I’m here to help. Get in touch for a free consultation and let’s start the work of becoming an uncommonly great leader.

Book your consultation now and start leading from a place of strength, integrity, and self-awareness.

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