Start with Why: 3 Huge Failures I Had as a Leader and Why They Happened

The reason I became a leader was not a good one. I had experience leading projects, I knew I would grow faster due to skills I had already developed in my career. In addition, I had worked hard as a Software Engineer and lead projects, so I thought I deserved the role. This reason is so self-centered my eyes bleed reading it now–about 20% of the words in the phrase are "I" or "my," oof.

I didn't think much about "Why" I went into the role back then. I could always transition back if I wanted, and if I did a good job, it didn't matter much. Or so I thought. In my first year as a manager, that motivation would drive me to make three serious mistakes, at least 1 with direct connection to employees later leaving the company–and the worst part is I didn't see what I was doing wrong then.

The Tech Lead Engineering Manager

Right after I became a leader it was evident to me I had to be the main person raising the Technical Bar of my team. So I spent a lot of time exploring what we could do to make our product technically better. While the team focused on implementing the features and changing the product, I labored on investigations, adding monitoring, adding observability, thinking of different ways to solve technical problems we had, and suggesting them or, way worse, doing them myself.

Engineering Managers usually come from a maker career. We can think of 99 reasons why we should be doing this technical stuff. The ones that got me were: "I am a shield to the team. My focus is on making them more productive. These tasks will block them from working on the product. Plus, The team only has frontend specialists, and this infrastructure work won't be what they want to do. Finally, the deadline for this is too short for us to add learning how to do this in there." All of those reasons are very bad when I look back at them, but they were enough to me back then. The real motivation here has a lot more to do with me than with the team, and we'll get back to it. For now, let's see why this isn't such a good idea.

Every single piece of technical work I, as the manager, do is a valuable learning opportunity I steal from the team. If I am the only person that can do that–which is seldom true–we have a skill gap in the team. This skill gap is a direct result of bad management. I failed to assemble and develop the team to tackle what they need to. The Skill Gap is something I need to address, and tackling the task myself will rob the team of the opportunity to address that gap.

With time, people will resent us. They will see us constantly taking the "Good work" out from them. What I was doing here was a problem, but it was nowhere near as insidious and damaging as the next one.

The Coward Engineering Manager

My first Performance Review was a big realization for me. I found out I was a coward. I had read High Output Management, and its chapter on Performance Reviews lays it out very clearly:

1. "The Fundamental purpose is to improve the direct's Performance."
2. "Preferably, a review should not contain any surprises, but if you uncover one, swallow hard and bring it up."
3. We need to stop avoiding confrontation. If it's harsh but needs to be said, we need to say it.

Some people had done amazingly well, but some would receive performance reviews that would disappoint them. The mass of feedback that would surprise people I had on this first performance review was devastating. I felt like such a failure—a fraud. I wasn't a leader. Feedback and Coaching was my job, and I wasn't doing it.

I swallowed my pride and wrote what I had to. I had some tough conversations, but I made it very clear that I failed to raise the flags earlier and failed to set clear expectations. As much as that made me feel a bit better, it didn't help. They would still be marked by a bad semester, by feedback that they didn't receive on time. All that because I was a coward that was avoiding difficult conversations.

It's easy to say this means I didn't have the "skill" of feedback back then. But I was pretty confident that I knew how to give feedback. I learned about SBI, and I had given a lot of feedback on their technical output. So my failure here wasn't a skill problem. It was a values problem. We'll get back to that, but first, the last story.

The Fake Delegator

Thanks to some reading, reflection, and harsh feedback, I understood that I should be challenging people's technical skills in my team and that it made no sense to see myself as the most senior Engineer. So I started dedicating more time to addressing context and carving out opportunities for them to grow. This was a considerable improvement. You have to give me that.

I gave one of the engineers the ownership of a technically challenging project and said I would support them and help them succeed in it. The project was challenging. It would stretch their current capabilities. When they started working on the project, however, whenever something wasn't going as fast as I thought it should, I would intervene. It got to the point where I led one of the Architecture Critiques of the project and didn't see a problem with that back then.

All this time, the exact reasons from the first story kept popping up in my head. I would say and think this: "The results and the project come first, so we need to ensure we reach them." Read that again. The results come first. I thought that. But worse, I said that. I didn't say "the team comes first," I didn't say "people come first," I didn't say "YOU come first." And I thought that was okay back then.

Why the Why Matters

The first place I looked to improve when I became a manager was my skills. I felt I lacked critical skills like Job Definition, Feedback, Coaching, Delegating, and many others. So I focused my study on that. I didn't address my values. I didn't address the very reason why I became a manager.

Sure, if I didn't have the skills, some things would be harder to do. But all the stories here and several other missteps and screw-ups I had in my career were primarily caused by the "Why" I chose management and how it misaligned my values with the role I had to and not by skills that I lacked. I understood, rationally, that my work was about others, but I didn't value that work, and I hadn't truly understood the responsibility I had. Instead, I was too much focused on myself, the "reward" I had just received, and on proving I was worthy of it. It was all "me, me, me."

In his book, The Motive, Patrick Lencioni says that there are two kinds of leadership:

1. "Reward-centered leadership: the belief that being a leader is the reward for hard work; therefore, the experience of being a leader should be pleasant and enjoyable, free to choose what they work on and avoid anything mundane, unpleasant, or uncomfortable."
2. "Responsibility-centered leadership: the belief that being a leader is a responsibility; therefore, the experience of leading should be difficult and challenging (though certainly not without elements of personal gratification)."

"No leader is purely reward-centered or responsibility-centered." He goes on to say. "We all struggle at times, and we all rise up to do the right thing at times. But one of these two motives for leadership will be predominant, and that motive will have a profound impact on the success of the leader and the organization he or she serves."

When we're self-centered, we can't be good leaders. When we're motivated by personal rewards, we'll avoid the unpleasant situations and activities that the new role requires.

So, having that realization, quite sometime after I became a manager, I chose the role fully aware of what it meant. I chose it for a good reason this time: I want to serve others. I want to do what's necessary to help people achieve their full potential. I understand the privilege and the responsibility that I have. I understand that sacrifice and suffering are inevitable in this pursuit and that I won't always do what's best for me. I understand that what I have to do will frequently not feel pleasant. But I want to do it anyway because serving others gives me a greater sense of realization than anything else I've done in my life.

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Writing about these stories is a humbling experience and a necessary one. I bring them with an open heart and a heaviness in my chest in the hopes that this will be a public commitment to do better and an invitation for people to pull me back from reward-centered thinking. I understand I can share them and not excessively fear losing my job or others judging me because I'm privileged in so many ways. So I hope this privilege is used for good and:

1. It helps you avoid accepting a job you don't want to do. One that you don't value;
2. It helps you avoid going through the same failures I went;
3. It serves as a conversation starter to support your leader to be more responsibility-centered and less reward-centered.
4. It prevents me from getting blind-sided by these thoughts and feelings again.

Let me know if it did 🤘🏾