Not All Bosses Are Great—But Every One of These Taught Me to Lead Better

Each boss I’ve had left a mark—not all of them were perfect, but every one of them taught me how to lead better. The influences of our supervisors can shape our own approaches significantly. Throughout my career, I have worked under a diverse group of bosses, each imparting unique lessons that have helped me grow both personally and professionally. Here are some key takeaways from their varied styles of leadership that have made a lasting impact.

The Perfectionist Strategist

My first boss exemplified meticulous attention to detail and rapid cognitive processing. He could absorb an overwhelming amount of information, distill it, and ask the most insightful questions, all in the moment. But it wasn’t just his intellect that left a mark. He struck the perfect balance between being a supportive friend and a respected leader.

One critical takeaway from our time together was his practice of time blocking. His calendar looked like a color-coded war plan, but it worked. I adopted that strategy and found myself exponentially more productive and focused.

His knack for maintaining civility during conflict, being direct yet cordial, was unmatched. He led with precision, inspiring me to engage more intentionally and manage time with discipline.

The Supportive Guide

Another boss' leadership was a blend of autonomy and support. He really believed in empowering his team to take the lead. He gave us very long leashes on what we we should work on. He promoted ownership and accountability. He also taught me the importance of strategic silence. Sometimes, the space to wrestle with a challenge leads to breakthrough thinking. He didn’t solve my problems for me, he equipped me to solve them myself.

However, he also excelled in providing support when you asked for it. From him, I learned the value of self-starting and accountability. But equally important was this lesson: It’s about being present when it counts, not all the time.

The Expert Executor

(This isn't actually my boss)

This boss was a laser-focused operator. He was an undisputed expert who had saved the company millions by identifying core issues others overlooked. He didn't make many friends doing it though.

His style was blunt and unapologetic, he believed in efficiency over diplomacy, and results over comfort. His mantra, ironically, was “don’t try to boil the ocean,” though he regularly tried to do just that.

Working under him taught me the value of directness. You don’t need to sugarcoat the truth or be everyone’s friend. Sometimes leadership means asking the hard questions and holding the line on standards, especially when it's uncomfortable. His rigor helped me elevate my own standards and communicate with clarity and courage.

The Quintessential Leader

This leader had an almost instinctive grasp of emotional intelligence. He knew what to say and when to say it. He actively listened, provided real empowerment, and led by example. Every conversation left me feeling heard and guided.

His principles of maintaining balance and prioritizing tasks left a lasting impression on me. He'd compete in Iron Man races, attend his twin's school activities and be a successful executive at the company. He emphasized balance between urgency and patience, detail and vision. He advised against gossip and advocated for a culture rooted in trust. He also dressed exceptionally well. He was always polished and never flashy. That sense of self-respect extended to everything he touched and became part of his leadership presence.

The Delegator

This leader transformed how I viewed ownership. He showed me that owning a process doesn’t mean doing every part of it yourself. You can oversee and guide without micromanaging. He was a master at delegation and always urged me to "let it go."

During a high-stakes project with a tight deadline, I was carrying nearly the entire workload myself. He called me out on it and I finally let it go and delegated to my team. Not surprisingly, we made the deadline.

But the most unforgettable lesson came unexpectedly. One day, he noticed I looked unwell. He insisted I see a doctor and even offered to drive me. I went. Turns out I had appendicitis and needed emergency surgery. He saw people first, employees second. That moment reminded me that real leadership begins with empathy.

He also believed in doubling down on high performers. A little extra support in the right places can create exponential returns.

Reflecting on the Lessons Learned

Each of these leaders, whether meticulous planner, quiet guide, relentless executor, balanced communicator, or empathetic delegator, left a different imprint. And together, they shaped my own approach to leadership.

There’s no single formula. The best leaders flex. They listen. They challenge. They care.

In the end, leadership is less about what you accomplish and more about the growth you spark in others, the trust you build, and the impact you leave behind. If you're doing that, you're a great leader.