Counterintuitive Lessons for Becoming a Great Manager

This article “Counterintuitive Lessons for Becoming a Great Manager” originally appeared in Spanish on Forbes by Daniel Bilbao, CEO at Truora.

I’ll start by digressing– I hate the word boss and I won’t use it ever again going forward –in my dictionary, it has a negative connotation: I imagine a person that takes pride in feeling better than the rest, that tries to dominate, and wants to order people around.

I’m not sure when I developed this ‘distaste’, but personally, I never let anyone call me boss– or even worse –jefecito. I prefer to use the word manager since I define my work as managing limited resources (capital and human) to obtain certain results.

I’ve had the privilege of working with very good (and very bad) managers in my career. Working for corporations in Latin America, an investment bank in the US, and afterward in three different startups. This has taught me that there are four lessons that make someone a great manager that, especially in startups, are completely counterintuitive and very little understood. 

Having developed the basic skills needed to manage a team successfully, such as establishing clear goals, focusing on results, promoting mental wellbeing, and providing clear and constructive feedback, the best managers develop other unusual behaviors.

In fact, these new behaviors at a glance resemble those of a crook. If you take a closer look, even the greatest managers cheat. How do they cheat? They steal ideas, outsource their work, or worse –don’t do any work.

I’m using ‘negative’ language because I want to demystify the role of a manager as a superman or a wonder woman that does it all without moving a hair, and without whom the company would fall to pieces. On the contrary, I think good managers look more like charlatans than superheroes. 

Great managers steal ideas

There’s a Mark Twain phrase that I really like that says “there’s no such thing as an original thought”. Of course, there is one original idea for every billion or trillion ideas.

When they are creating teams, the best managers aren’t original, they steal ideas. There are more than 50 recommended books on how to be a good manager. One need only read a couple of them to understand that none of this is rocket science, and to be a decent manager it’s enough to put in a little effort and understand which are the best practices. 

How to best execute these practices brings us to the second lesson. Learning how to cheat.

The best managers know how to cheat

The greatest mistake that managers and founders make in their first company is that when they don’t know how to do something, instead of asking someone who would know, they try to solve it by themselves.

I don’t have any quantitative data, but I see this behavior more in men than in women. It must have to do with their upbringing: boys are taught to ‘fend for themselves’ because ‘no one is going to rescue them’, so when confronted with new problems as adults, they think ‘I can do this by myself’, or worse, ‘I can’t do it but if I ask they’ll realize that ‘I’m not good’. 

Wrong, wrong, wrong, wrong. When a good manager faces new and unfamiliar problems, there’s no better option than to cheat.

Here’s an analogy: being a manager faced with a new problem is like being in 8th grade in an elite school studying algebra when one barely knows how to add and shouldn’t even be in that school.

If you’re lucky enough to have an older sister that studied algebra the previous year and passes you her notes, homework, and exams, well then congratulations and welcome to 9th grade with honors. 

Parenthesis: a personal story to illustrate this point

My first job as a manager was as regional manager in Bucaramanga, Colombia with Mitsubishi Electric. Due to a series of unfortunate events, the person that used to manage the office left and nobody wanted to go to Bucaramanga to take over. 

The position included sales, customer service, accounts receivable, finance, etc. As a naive and arrogant 23-year old kid, I raised my hand and volunteered. I was motivated believing that the best way to grow professionally was managing people, the more, the better. I persisted until they finally sent me.

That’s the behavior of a typical guy that is so blinded by ignorance, confidence, and arrogance that he doesn’t understand that what he’s doing is crazy so he jumps to opportunities that he’s not qualified for. 

Mitsubishi Electric sent me because they needed someone temporary while they found a real manager, and also probably to avoid dealing with the little kid that kept asking when he would get promoted. 

After a week of training, I started at Bucaramanga and I realized that I was in a deep pool and didn’t know how to swim– I was going to drown. I had a team of 12 people in charge, experienced technicians with over 10 years working for the company, very territorial commercial agents (yes, you Margie, you), annoyed clients by the dozen, and numbers that didn’t add up. 

I had no idea how to do anything, not even how to write a check. Since I had endlessly nagged HR about how great I was and that I wanted to be titled ‘Regional Manager’, as well as have a salary raise, flybacks, and several other silly requests, my pride didn’t allow me to call to ask to be transferred back.

Out of desperation, I cheated

Every night, (I don’t exaggerate when I say every night), for weeks I would call my dad telling him everything that had happened during the day and seeking his advice on what to do. 

My dad, Humberto Bilbao, for many years managed a chemical production plant with Pfizer, Warner Lambert. 

He explained everything: what questions to ask, how to manage confrontations with difficult clients, how to treat the team, ask them for support and help instead of trying to control, dozens of strategies and tips to not mess up.

Thanks to his help, I did pretty well in that position. I know what you’re thinking, “ahhh no, that’s cheating, anybody can do that, they should have hired his dad”,– of course.

In almost 15 years of working, I’ve never learned more than I did in those six months that I was in Bucaramanga. Not in the investment bank, not in the MBA, not even founding startups, maybe at YCombinator, but I don’t think so. That’s why it’s so important to have mentors that know what you’re going through, it’s the best shortcut I know.

This is the type of cheating a manager should do. If someone has already done it, ask them for advice, do what they tell you and you’re set.

The following shortcut is a tough one for managers that are in their prime. To outsource their work. Be careful, this isn’t just ‘delegating’, it goes beyond that, it’s literally giving 100% of your role to somebody else. 

The best managers outsource their work

I’ll explain through an example from my cofounder Maite and her role as Product Manager.

Product Management in Truora “should” be my role in theory. That’s what was recommended by various investment funds because it’s closely linked to business strategy. More so, I would love for it to be my role. But I’m a bit unorganized, and I follow many “shiny objects” instead of being a task manager (if you don’t believe me, ask my wife.) 

I’m a lot better suited for other things (sales, conflict resolution, and overall business development) than for the product.

My cofounder Maite, on the other hand, like a good ex-consultant is super organized, an excellent task manager, knows how to prioritize and has a strength (which is also a weakness): she needs to know everything that’s happening all the time. It’s not that she wants to know, she needs to know, otherwise, she does not sleep at night.

In our company’s current state, we have six countries, a series of features and regulations that make our product quite complex that need a lot of attention. I must confess that as the ‘leader’ of our business, I don’t know how our product works in Costa Rica, but I’m not worried about it.

I know that Maite and her team are going to make sure that we deliver what the client seeks and more and that each time it will be more robust.

That role in the product that ‘should be mine’ I delegated to Maite. She gives me the freedom and time to focus on other areas, like searching for our second, third, and fourth product that we are going to launch, as well as recruit, develop business and sales, and write articles. 

According to experts, one cannot effectively manage more than eight people, ideally five. When you have a team of 50, 100, 200 people, how do you do it? Does it mean you have to put layers upon layers of management? Not necessarily. You can build teams that self-regulate where the ‘leader’ or ‘manager’ role takes on more of a facilitator or coordinator role.

Maite now has to go through the boring transition from being a manager to a manager of managers. She needs the job to be done by others and have the most free time, instead of being indispensable. 

As we have discussed on various occasions, her next objective will be to follow through with our roadmap and become an expert in the third lesson of being an excellent manager – not do work.

The best managers don’t work

This skill is the most counterintuitive. So that you’ll believe it, you should know that I’m not the one that said it, Bill Gates did.

He once wrote that one of his biggest lessons in leadership was with Warren Buffett.

He saw how Buffett used an agenda for all of his meetings. Said agenda, instead of being full, had entire days with not a single meeting scheduled. 

For Gates, whose time was always on demand, this was unimaginable. 

Here, we are neither Warren Buffett nor Bill Gates, but the lesson still applies.  A manager that ‘doesn’t do anything’ on many occasions is looked down on and many times we say ‘that man only reports the results of my work and that’s it’.

It is true that the stereotypical boss that hogs results exists. However, it shouldn’t be mistaken with a manager that has overseen the completion of his work with a team.

A final story to emphasize this point: 

In January 2019 when Frubana was going through YCombinator, I spent some time with its CEO, Fabián Gómez. We were hanging out for five days. During 4 or 5 hour periods we talked about business, his personal life, we had lunch and prepared his fundraising pitch – important work but completely unproductive for his business. 

If I hadn’t known about his business, I would have confused him for one of my university friends from the coast that goes to the islands to spend their parents’ money and doesn’t have a job. The most impressive part is that he’s a solofounder, he doesn’t have any cofounders, while I have three.

I called my brother to enviously complain about how this fancy barranquillero can spend a week in San Francisco as if he were on spring break when he has an extremely difficult to operate startup, and Andrés explained to me, “The thing is Fabián knows how to recruit and build KPIs, he’s a better manager than you”.

In his previous work experience at Rappi, Fabián was a launcher. He would arrive in a city, build a team, set objectives, and a couple of weeks or months later would move on to the next. He must have done this ten times.

That’s an impressive skill. To see a problem (launch a city/build a feature/build a company), define a team, create clear objectives, and then do follow-ups.

Not doing work is a key skill, because he becomes a ‘back up’ and when there’s a key problem to solve, he can dedicate himself to that. In a fast-growing startup, this ability to have ‘free time’ is critical for its success, it’s also inevitable when it comes to fundraising.

Every 12-18 months there needs to be an investment round, a process that can take several months and requires 100% focus. If the team can’t function by itself and it falls to pieces, you can’t raise capital, and if you do the process carelessly and don’t focus on fundraising, you also can’t raise. In both situations, ‘working’ comes with a high risk.

Frubana’s management team must be very proud. They have a highly complex business that grows dramatically and efficiently, and in the eyes of those who don’t understand scaling in startups, the team has managed to have Fabián come off as a fancy barranquillero jet setter. It’s as much merit to them as it is to the founder. Congratulations on supporting the best manager of us all.

To conclude, being a good manager is the lowest bar that all of us that manage people and processes should aspire to be.

To be a great manager it’s necessary to develop cheating (efficiency, if we want to use positive language) skills until we become completely unnecessary and can focus on where the company is headed and what future problems lay ahead.

Daniel Bilbao is the co-founder and CEO of Truora, a startup that combats fraud in Latin America through instant background checks. He worked in the investment bank in Wall Street, is a mentor and partner for various startups, and is also an active angel investor. 

If you’d like to learn more about Daniel Bilbao’s story, check out Episode 80 of the Crossing Borders podcast.