The Challenge of Leadership - Getting the Basics Right

I’ve had this idea running around my head for a while now: writing about leadership. Not that I consider myself a leadership guru, but I think there’s something worth sharing in my own story about the real challenges of leading. From a programmer at heart with some talent - or so I like to believe - I went on to found and run companies, start ventures, and lead nonprofit organizations. Something unexpected, considering that from a very young age I felt a deep passion for programming, and my career choice was, to put it mildly, extremely simple.

A little under ten years ago I founded a consulting firm with my wife - I should clarify that she has always been the one leading it, and I, as you’d expect, have always gone along with her. With relative success, we managed to work around the fact that neither of us knew the first thing about running a company.

But life doesn’t always go the way we plan it, and after a couple of unexpected blows and some family and personal challenges, we redefined our dynamic. That’s how, a little over 15 months ago, I took on the challenge of helping a British consulting firm land in Colombia.

I have to admit the challenge has been wonderful. Today we’re a bit more than 150 people on the team and, even in a tough year for the tech services industry, the company keeps a firm pace on its growth strategy for the Colombia operation, with a strong presence in Bogotá, Medellín, and Cali. Today we’re deep in the adventure of designing, building, and opening our first own office. There’s nothing but big challenges and expectations about the future ahead. Not bad at all for a programmer at heart who understood little to nothing about starting a business, leading, or the challenges of management.

An Unexpected Path to Leadership

Talking about leadership is complicated, because theory doesn’t work the way it does in the exact sciences - you read about addition and, with a few exercises, you can add. You read about writing and you’re free to write and try out what you’ve learned. But to lead, you need followers. By definition, a leader is someone who has followers. It’s not like going to the supermarket and buying a dozen followers. People follow a leader under particular circumstances that make it possible for that person to lead. It’s like love - you can give it, but you can’t demand it.

From Programmer to General Manager of Operations

I share this idea of writing about leadership and the challenges tied to the leader’s role from my own personal path. In short, I’m a family man, a lover of programming. Even today, whenever the chance comes up - and I can help without getting in the way - I’ll throw in some code, deploy containers to the cloud, and put together a few scripts to automate or simplify operations and monitoring tasks - long live infrastructure as code.

Far from being a computing expert or genius, programming for me is like riding a bike - you never forget it. You just need to practice it every now and then. There are surely newer, more efficient ways to program or solve problems these days. In my case, it was never about the specific language or technology, but about the ability to interpret the need, evaluate the resources available, and put together the puzzle to solve that need or seize the opportunity.

Teaching, and Learning More in Order to Teach

Early in my adult life, with the sole intention of broadening my social horizons, I started working at the university as a teaching assistant, and even taught a few private lessons to other students. Along the way, far from broadening my horizons much or making new friends, I fell in love. I fell deeply and intensely in love - a passionate love, similar to what I feel for programming, but more mature. I fell hopelessly in love with teaching.

Even before finishing my degree, I started teaching classes and some private courses for companies. Today I’ve been teaching for more than 20 years and, as far as I know, I do it pretty well - I’ll leave that to the comments, if anyone reading this has something to share.

That unexpected mix of a very technical programmer profile with my desire to make others understand what I’m trying to explain quickly pushed me, in my professional life, into management and leadership positions. I took on roles as varied as account manager, project manager, program director, portfolio lead, and other similar ones - with names that were maybe more attractive, like Delivery Wizard or Project Magician.

What nobody tells you about leadership is that the better you get at it, the more complex the challenge becomes. What’s the point of bringing in the best surgeon for the simplest procedure? It can happen, but you’re almost always looking for a challenge worthy of the challenger. Someone once told me: this project is like climbing Everest… barefoot.

The Decision to Lead at the Right Moment

Leadership isn’t something you decide, like love - it just happens. When it arrives, each person decides whether to accept it or run from it. They also decide whether to enjoy the process, or suffer through it. With leadership, an opportunity shows up, the space others grant you opens, and then you have to decide whether to step into it or run - remember, a leader only exists because there are people willing to follow them.

And I want to be clear that I’m no miracle worker, and that I’ve never suffered a defeat or accepted a failure. Learning also comes in the form of mistakes and failures. It’s not for nothing that John C. Maxwell titled one of his famous books “Sometimes You Win, Sometimes You Learn .” Accepting the challenge of leadership also exposes us to failure.

Have you ever achieved something, reached a destination, or even failed, and thought you were lucky because of the team or the people who came along with you? And maybe that’s it - something intangible, hard to quantify, and even harder to point to - that has landed me in an unexpected position, far from what I dreamed of back when I was learning to program. Many times, with many people, I can say that the road, walking it alongside them, was wonderful.

Many Challenges for the Leader

Of course, when it comes to the challenges of leadership, you could write about some basic things - the importance of having a vision, how essential it is to know how to communicate, and plenty of other soft, critical skills. But this article is about something simpler that we tend to overlook. So let’s talk about the challenge of leadership through the lens of the followers’ role - in this case, the team of people walking alongside you.

1. The Challenge of Playing as a Team

If you’ve worked with programmers and other very technical profiles, you know we’re not the best team players on the planet. Many of us enjoy working alone, away from others and from the variability of human beings, from their mood swings. I always share, in my sessions, that it must have been a programmer who invented noise-canceling headphones, and that group is surely a big chunk of that industry’s market - right alongside musicians and audiophiles .

So the first big challenge of leadership is accepting that to go far you need to work as a team, and that getting there fast isn’t always the most important thing. I’ll admit it’s still hard for me to balance my inner programmer with my role.

2. The Challenge of the Energy Leadership Consumes

When you’re an engineer, like me, you’re trained to do, to build, to lead by example. But leadership consumes energy. And leading by example is the shortest, most limited form of leadership. For many people, leadership is inspiration and commitment - it’s doing and showing others how to do it - but those aren’t always the same thing. In soccer, for example, the best head coach isn’t necessarily the one who was the best player. A leader doesn’t have to be the best at everything either, but they do need to be good at bringing out and making the most of what’s best in others. Leading by example doesn’t necessarily mean doing it yourself.

I started out saying that leadership is the projection of who you are. The most successful leadership is natural and honest. Successful leadership is when the leader is who they are, and their followers value them for it. That doesn’t mean all leaders are the same, or that there’s a single “right way to be.” You’ll find examples of leaders - and millions of followers - who embarrass us when we read history books. But that doesn’t mean they weren’t leaders, or that their followers didn’t exist.

Leading takes energy. Unlike a title, leadership can be transferred and shared. Learning to share and distribute that energy consumption isn’t simple. Sometimes it competes with ego, and with the idea that leading means directing, commanding, or doing. You need to know yourself and learn what kind of leader you are, or want to be.

3. The Challenge of Accepting That Success Is Only Possible Thanks to Others

A leader is only successful thanks to others. It’s a leader’s followers who build great companies, transform societies, and move the world. Leaders inspire, motivate, and mobilize. But rarely do they also “do.” We love famous leaders, people who show up on magazine covers, and we like to think their success is individual - that they’re the ones who make the difference. Nothing could be further from the truth. Accepting that the real protagonist on the path of leading is always the team is a titanic task for the ego.

Nelson Mandela summed up this challenge well in his famous line:

It is better to lead from behind and to put others in front, especially when you celebrate victory when nice things occur. You take the front line when there is danger. Then people will appreciate your leadership.

Nelson Mandela

The Hardest Part of Leadership

I have no doubt that talking about leadership takes several articles, and surely many books have already been written on it. Should I write one? Is my own path worth writing down and sharing in a book? I don’t know - maybe. I’m already wrapping up and rambling here. But I’ll admit that, even today, I still feel like a programmer, I work as general manager, and I’m passionate about teaching.

Leadership is something that happens through who you are. If you’re a direct, strong-willed person, you’ll be perceived as a commanding leader. If, on the other hand, you’re a warm, approachable person, you’ll be perceived as a kind leader - and, to some people, sometimes a weak one. Both models of leadership have pros and cons. Neither is better than the other. In that sense, we’d be talking about effectiveness: how effective is your leadership style in the particular situation you find yourself in? Could you adjust or adapt it?

That’s where the hardest challenge of leading lies - being a flexible, adaptable leader who understands what role to play at the right moment. Making that flexibility your own without abandoning your own nature, who you are, and what you want for yourself and for others.