I Thought I Was a Good Leader, Until I Learned These 6 Hard Lessons
What I Got Wrong About Leadership, and What You Can Learn Faster Than I Did
When I got my first leadership role, I felt “ready”.
As a computer scientist, I had delivered strong results for years. I was reliable and could solve hard problems. I was the person people went to when something complex needed fixing.
When I moved into a manager role, I believed I was doing well: My team was shipping key capabilities, our stakeholders were satisfied, and the team seemed content.
On the surface, everything looked fine.
But something wasn’t right. I could sense a lack of energy in discussions, and the ownership felt inconsistent. I noticed that decisions kept flowing back to me, even when I tried to delegate.
For a long time, I blamed external factors such as workload, pressure, and deadlines.
But then one day, it hit me. I asked myself the honest question: “What if the issue was me?”
That question hurt, but it also helped, because once I was willing to look at myself honestly, I began to see what I had been missing.
Here are the six lessons I had to learn, often the hard way. 👇
1. Doing the Work Is Easier Than Letting Go
Early in my leadership journey, I often stepped in to “help.”
If a presentation wasn’t sharp, I rewrote it. If a design had gaps, I fixed them. If a deadline was at risk, I took over part of the work.
On the surface, this looked like “high standards”. And sometimes it was.
But over time, I noticed a pattern. The more I jumped in, the more my team waited for me to jump in.
Letting go wasn’t easy and felt risky. I asked myself: What if the work wasn’t perfect? What if stakeholders were disappointed?
Here’s the tough lessonI learned: When you step in too often, you unintentionally signal that you don’t fully trust your team.
I had to learn to tolerate imperfection. I had to allow people to solve problems in ways that were not identical to mine.
It wasn’t easy, but was necessary.
👉🏼 Leadership is not about proving you can still do the work. It is about building others who can.
2. Clarity Beats Motivation
For a long time, I believed my role was to “inspire”.
I spent time crafting vision slides. I talked about impact, and tried to energize the team around the “bigger picture”.
But I noticed something uncomfortable. Even when my team seemed motivated in meetings, execution still drifted. They worked hard, but not always on the right things.
Here’s the tough lesson I learned: Most performance problems are not effort problems. They are clarity problems.
I had not been clear enough about what “good” looked like. I had not defined what “done” meant. I had not made trade-offs explicit.
Once I started focusing on clarity over motivation, my team’s overall performance started improving. They finally knew where to focus.
👉🏼 In leadership, clarity is kindness.
3. Feedback Delayed Is Trust Damaged
I used to delay hard conversations.
If someone underperformed, I told myself I would wait for the “right time”. If behavior was off, I hoped it would self-correct.
I thought I was being “nice” - I didn’t want to discourage people.
But here’s the hard lesson I learned: Silence does not create safety. It creates confusion.
When feedback is delayed, people sense something is wrong but don’t know what. They start guessing, and that takes away from their focus on what really matters.
I learned that when feedback is delivered timely, calmly, and is actionable, it builds trust. It shows you care enough to address the issue. It prevents small problems from turning into big setbacks.
👉🏼 The discomfort of giving feedback is short. The cost of avoiding it is long.
4. Your Mood Is the Culture
I once thought culture was about “values statements” and team events.
Over time, I realized that culture is shaped in small, daily moments. It is shaped by how you respond when a deadline slips. It is shaped by your tone when someone brings bad news.
There were days when I walked into meetings already frustrated from something else. I thought I was hiding it well. But I was not.
Leaders underestimate how closely they are observed.
Research from MIT Sloan highlights that leader behavior under stress strongly influences team climate. Your team watches how you react, and they calibrate their own behavior accordingly.
👉🏼 If you want a calm team, you must model calm. If you want accountability, you must show accountability.
5. High Standards Without Support Create Fear
I have always believed in high standards, and still do.
But early on, I confused “pressure” with leadership. If the bar was not met, I raised expectations again. I assumed the gap was effort.
What I realized was that, sometimes, it was not.
Your team often needs context, coaching, and feedback to reach a higher level. Pressure without guidance creates anxiety. It may drive short-term results, but it rarely builds long-term success.
I had to learn to pair expectations with support. That meant being there with the team when they needed it most. It meant explaining why something needed to change, not just that it needed to.
👉🏼 High standards are necessary. Support makes them sustainable.
6. Not Everyone Is Motivated by the Same Things
The final lesson took me the longest to understand.
Early in my career, I was ambitious. I wanted growth, a larger scope, and high visibility.
I assumed everyone on my team wanted the same.
Turned out, that assumption wasn’t true.
Some team members valued depth over a promotion. Some cared about stability. Some were navigating life stages that shifted their priorities that I wasn’t aware of.
When I projected my ambition onto others, I unintentionally judged them by the wrong yardstick.
The shift happened when I started asking one simple question during one-on-ones: “What does a good year look like for you?”
Every single one of my team members had a different answer to that question.
👉🏼 Leadership is not about building replicas of yourself. It is about understanding what matters to each person and aligning work accordingly.
Looking back, I realize something simple.
The skills that made me a strong individual contributor did not automatically make me a strong leader.
If you are in that uncomfortable stage where leadership feels harder than you expected, you are not alone.
💬 What was the moment you realized you still had a lot to learn? Share it in the comments.
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This resonates deeply, Gaurav. Leadership isn’t just about doing the work well, it’s about letting others grow, being clear about expectations, giving timely feedback, and understanding that each team member has unique motivations. The hardest lessons often teach us that influence comes from awareness and presence, not just skill or authority.
I really enjoyed this post. It reminded me of a number of things in my own experience.
The first being a series of corporate training videos that Peter Director did in conjunction with his textbook that my professor had us watch throughout “the Principles of Organization and Management Course”.
The videos are usually about 15-20 minutes long always a single topic about management.
Drucker was a brilliant communicator. And I think your post accentuates that in many ways because in order to be a good communicator, you have to really know what you’re talking about first of all. Secondly, you have to have clarity about that knowledge in order to communicate it well.
So it kind of interacts completely with what you wrote and it reminds me of so many mistakes I’ve made in the past as a manager.
It was never on a corporate level. It was mostly on a small business level, brick and mortar, in entities I owned.
However, my very first management job I kind of got by accident. I ended up managing warehouse and logistics for the initial Perrier marketing launch in San Francisco with no prior management experience.
At the time I was enrolled in my last year of management school at a private university in San Francisco.
I went into it figuring this is easy we can handle this, it’s just boxes and trucks.
The mechanical side was easy, but I found out very soon, people are not mechanical.
I guess I was tyrannical to some degree. But my management style kind of reflected my attitude about life, which is something else you talk about slightly differently, but similar concept.
I always figured if I needed something done right I’d do it myself - until I had a task bigger than I could handle by myself.
I remember very distinctly talking to one of the guys in the warehouse that I had hired. I had a conversation with him and it went like this.
“I’ve told you and shown you how to do this at least six times I’m not gonna tell you again.”
At the time that made total sense to me. I mean, when you load a truck for deliveries, you put the last deliveries on first in reverse order.
So that your first deliveries are at the tail end of the truck.
To me that was total common sense but not everybody. The big dilemma that got created by not following that order was that the driver would get to a location and the product that needed to be delivered was not at the back of the truck.
I realize I’m getting sidetracked so I’m gonna get back to my point.
It took me about six months to figure out how to talk to different people about the same items.
When you talk to six different people, there are often six different ways of hearing what you said. I didn’t realize in the beginning.
It took years of marinating my ego and learning that people hear things differently than you say them.
I’ll stop now.
Really like how you communicate.
I’m in the planning stages of a project and I’m trying to figure out how to design a system to grow effective leaders through education and hands-on experience.
I think management responsibilities and aptitudes in the future are gonna be a lot different than they are today.
Maybe I’m wrong about that but I think our culture is getting very complicated.
I enjoyed your article. I’ll keep reading your stuff.