Leadership: Five Lessons in Five Months

I spent the first five years of my professional career working as a software developer and deriving great joy from it. Sometimes I worked on my own, sometimes I worked in teams, but I had never considered moving into a leadership position. In my mind, a leader was someone who delegated work to others while reaping the benefits.

This was until I led a development team, along other leaders who had been at it much longer than me. When I realized what a capable leader can do with a capable team, I was stoked. I wasn’t sure whether I wanted to keep doing it, but at the very least I wanted to give it a shot and make sure that I wasn’t missing out.

In the five months that elapsed, I have been hired as CTO of my current company and managed to launch our MVP. To be fair, this is not my first time managing people: I’ve led a couple of development teams before, but this is definitely the first time I’m more focused on the leadership rather than the technical aspect of the job.

In this time I’ve had my share of successes, which I’m very proud of, and of failures, which I used to be terribly embarrassed of. Following one of those failures, I decided to make a roundup of all the lessons I have learned so far, so that others can benefit from them.

Before you read on, it is important that you understand this: there is no book that will teach you how to be a good leader. There are techniques, approaches and paradigms, but eventually you’ll have to develop your own style and — most importantly — be able to change that style to fit the people you’re going to lead.

1. You Have to Let People Grow

I think this is especially a challenge if you’re moving from a fully technical role to one that has both a technical and a leadership aspect to it, as is the case with me.

It is very hard to ask someone to perform a task, when explaining it takes 20 minutes and doing it yourself would take 10. The purpose of a leader should be to deliver better and better results through the people they lead, but in this situation you are actually hurting the project by wasting time, so why bother?

The thing is, this paradigm (which I’m still guilty of every once in a while) is a very short-term one and it will set your team up for failure.

The most important responsibility of a leader is to allow people to grow, and you can’t forgo it. If people do not grow under your leadership, they will look for an environment where they can. If you do not want people to grow under your leadership, perhaps you shouldn’t be in a leadership position in the first place.

2. Every Failure Is a Leadership Failure

When you’re a leader, there is no failure that is not your failure.

Think about it this way. There are only three ways people can make a mistake:

  1. They screwed up because they’re human. This happens all the time, to everyone. Make sure they own their mistakes, learn from them, and move on. Also consider what systems you can put in place to make sure this doesn’t happen again.
  2. You are constantly mismanaging them, which prevents them from performing at their full potential. In this case, you should re-evaluate yourself and figure out what you’re doing wrong.
  3. You have hired the wrong people. Guess whose fault this was?

Yes, it sucks. It sucks that you used to be in total control of yourself, while now so many people can make you fail without you even realizing it.

Unfortunately, this is the nature of leadership, so be prepared for it: you’ll often feel like you don’t control things, when in reality you are able to control them, but in a much different way. You can’t just fix things by doing them yourself anymore — you’ll need to make sure everyone is accountable for doing their own part, which is a much bigger challenge (and a more interesting one).

3. Talk the Talk, Walk the Walk

This one is particularly important to me because I just failed at it myself. Here’s how.

Ours is a very complex business, where different types of users, each with different backgrounds, goals and expectations, interact with each other. This kind of complexity is difficult to understand, and we’ve been trying really hard to get everyone in the company to understand the full impact of their actions on all of our users.

As part of this struggle, I mentioned on a meeting lately that everyone should spend a day with a user, so that they would fully understand how it all fits together. The suggestion was welcomed with enthusiasm, but I could sense something was off, like I was forgetting a very important piece of the puzzle. Eventually, the proposal just died, with no one following up.

I was talking about this with my CEO last day, when he interrupted me.

“But did you do it?” he asked.

“What do you mean?” I replied.

“I mean, did you spend a day with the users yourself, either before or after suggesting that everyone in the company should do it?”

Seconds of embarrassed silence followed.

I could have come up with a million different excuses for why I didn’t do it: I was too busy, I had other priorities, I have a good understanding of the business already, and many others. However, I couldn’t escape the fact that I had given eveyrone the speech without following up on it myself.

By acting this way, I have not only hurt my credibility as a leader, but also set a very bad example for all those that look at me as someone to follow.

The takeaway from this story is that you should never ask or suggest something if you aren’t willing to do it yourself. You should lead by example, not by authority, and pave the way for the change you want to introduce.

4. You Use Authority, You Lose Credibility

Keep this in mind, and convince yourself that there’s no exception to it: every time you have to say “Because I said so”, you have failed.

When you rely on your authority or your position to force people to do something, you are hurting your credibility, you are hurting your teammates and you are failing to learn very valuable lessons.

Relying on authority is what people do when there is no transparency. When you cannot explain why something has to be done, the only solution you have left is to use brute force.

It’s easy to get frustrated because an employee doesn’t understand the importance or the need for a particular task, but the next time this happens, try to approach the situation from their point of view, and ask yourself these questions:

  • Does this person have all the information they need to evaluate the importance of this task?
  • Does this person come from my same background? Do they share my values? What about the company values?
  • What kind of relationship do I have with this person? Are we close? Maybe they don’t know how I tackle problems?
  • What feedback can I gather from this person’s objections? What can I learn? What can they learn?

When you do this, you are putting yourself in the employee’s shoes and understanding that certain things might not be so obvious to them or to you: maybe they think the task is not important or urgent, maybe they do not have all the information on the task, maybe they feel they are not the right person for the task, maybe they are frustrated because they’re always doing the same thing…

Or maybe they’re right, and the task is actually not a priority — this will happen more often than you think, so be prepared to admit it!

This doesn’t mean that everyone should be happy about every single thing they do. Every job has its boring, soul-consuming parts. What’s important is that everyone understands the importance to carry out those tasks and that everyone is willing to do their part for the well-being of the team.

5. Set Your Own Standards

As a leader, no one will set standards for you — you will have to set your own. You will have to be your fiercest judge. You will need to try new things, crazy things, because they might or might not work, and you’ll have to be ready to fail. If you only do what others expect you to do, you won’t be able to innovate or make a difference in the team.

This entails that you’ll screw up a lot more than others, and that’s good: you have a license to screw up as much as you want, because no one really figured this out yet. It also means that you’ll be constantly questioning yourself and your abilities, which will keep you moving forward.

Remember that everyone feels like they could be doing a better job, especially leaders, and that your team does not expect you to be perfect. They know you’re human, bound by human limitations. They know you’re doing your very best (and if they don’t, it’s your job to make that known). Just keep pushing and questioning yourself — you’ll be alright.




Technology leader and strategic advisor. I work at the intersection of people, software and words.

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Alessandro Desantis

Alessandro Desantis

Technology leader and strategic advisor. I work at the intersection of people, software and words.

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