How to manage by ethical trolling

“Nice slides Sarah, this pinch of Open Sans Light really makes you forget how bad the numbers are! Maybe add a few buzzwords here to please the investors?”

For my first article here, I’ll try and explain how I’ve learnt to leverage humor, especially trolling, to become a better manager.

Let’s start by defining what trolling is, how it works and why it exists at all.

It all started in a cave

As most of the people my age (30-something), I discovered the art of trolling when I was a teenager, spending too much time on the internet. From the very beginning, the web has been a place of endless debating and arguing. Debates abide by the rules of rhetoric: there are very well documented and finite ways of constructing or destructing arguments, and in some way, manipulate your audience to gain support and help you further your plans, no matter how good or evil they are. Rhetoric has been theorized extensively during antiquity (starting from Mesopotamia and probably even before), and though it is negatively connoted today, it was originally seen as a valuable skill. After all, it is just a theory of speech, which is not inherently good or bad: it depends what you use it for.

Socrates being publicly trolled, triggering a wave of facepalms. He was famous for being a troll hater.

And as with everything, there’s also cheating. You can pick from a wide range of fallacies to demonstrate anything you want, with a flawed argumentation, as long as your auditors don’t realise that these flaws exist. And most of the time, they don’t.

Actually, it’s even worse: we all use and abuse those fallacies, at least to some extent, without even realising ourselves that our own rhetoric has fooled us.

Then came the internet

So what did the internet change about that? Well, instead of arguing with a friend or colleague or even an assembly, where you can also abuse tricks with body language to further guide the audience where you want, you’re now writing or vlogging to hundreds, thousands, millions of people, who can and will analyze what you say and find every little flaw in your argumentation.

With so many eyes watching, you just can’t fool anyone on the internet… or can you? Well, it’s quite the opposite, actually.

What happens when two people argue on the internet is that it propagates, it forks, and it escalates. Controversial arguments or counter arguments generate emotional (and thus less logical and more fallacious) responses, often triggering more emotional reactions and bringing more people into the conversation. Rapidly, the quality of your demonstration doesn’t matter anymore, nobody has time for that. What starts as a little disagreement between two people can turn into a full blown ideological war involving thousands of participants. That’s what we call virality.

Could be useful…

Trolling 101

Trolling is the art of leveraging these principles to bring a debate where you want (though some just do it for the laugh, but they aren’t artists). It’s actually quite easy to use (user friendly?).

You either start, or react to, a conversation, by making a controversial assertion. You can and should use fallacies: they will flaw your argumentation, but that’s not relevant. Your message is not about saying something at this point: it’s just here to light the fire. This initial message is commonly referred to as flame bait.

In most cases, you will upset some people, and they will answer with emotionally tainted messages. Instead of breaking down your argumentation by pure logical reasoning, they’ll begin to tell you what they really feel, the irrational part of them that gives them so much confidence in what they think: their true beliefs. A belief is just something your brain makes up to fill the gaps in what you understand, so that your thoughts make sense, at least to yourself, even though you can’t possibly understand everything.

Now that your sparring partners have exposed the weaknesses in their reasoning, you can use that against them. Or just like in the mine sweeping game: add a flag and continue, you’ll blow everything later on.

Let’s keep digging for now…

About ethics

Trolling is bad, it’s for bad people. Just Google it, you will see: the internet says it’s bad, so it is. Or maybe that’s just fake news. Trolling is a form of rhetoric intended to change the course of a conversation, to start a polemic, etc. That doesn’t make it inherently bad: it all depends on what goal you are pursuing when using it. On the opposite side of the spectrum, I have encountered quite a few people who would go to great lengths to seem like benevolent people, when they were actually very ill-intentioned. You can’t rely on how people speak to judge the nobility of their cause, that’s the basics of rhetoric. And yes, people with bad intentions are the most likely to use these techniques to persuade you of their good will, so if anything, you should be careful with people who seem too nice to be honest.

So trolling is actually just a tool. You can use it in mischievous ways, but you can also use it in good, ethical ways.

How I managed being a manager

Yeah, you thought this paper was about management. Well, it is. So far I’ve taught you how to manipulate people. What’s the difference between manipulation and management? There’s none. Your role, as a manager, is to make people do what you need them to do, even if it’s not what they want to do or what’s ultimately good for them on a personal level (why would you pay them if it was inherently good for them?). That’s commonly called manipulation.

But like with everything, it’s not necessarily a bad thing. You can manipulate people for their own good, you can help them become better selves (not slaves!). You can be a great manager. Or maybe you don’t care and just do it for the money, I’m not here to judge anyone.

Everyone should know and understand how manipulation works, it doesn’t make you a bad person. Thinking that you learn manipulation to become a villain is like thinking that you learn karate to kill people. No: you learn to know yourself and to gain confidence and defensive abilities when confronted to bad people.

Anyway, be it during casual conversations, meetings, after works, whatever: randomly throwing controversial remarks in the conversations you have with your team can give you great insight into their true feelings and motivations, their frustrations, their weaknesses, their fears. It sets them in an emotional state which opens them to being more honest and truthful about what they tell you, which is not a given when you have a hierarchical relationship. Moreover, making them express their feelings is ultimately good, as it helps them release tension.

The main key to being a good manager is to know your people. If you don’t, you’ll fail them. All the information you can gather by provoking reactions can help you a great deal in knowing your team, understanding the ins and outs of it, and thus finding the best solutions to make everyone feel comfortable and give them the sense of purpose they need.

What needs to be fixed in management

What I have often noticed about other managers I have worked with, is that they are not honest with their team, and their team is not honest with them either. So they end up making decisions that do not serve the team, or being oblivious to the true problems that hamper the team, when everyone else on the team seems to know what’s wrong.

This lack of honesty is destructive for the team, and is more common than you think. A lot of managers see their role as serving the company by making people do what needs to be done. The role of a manager is actually to serve the people by making the company give them what they need to do their job (which also benefits the company). A good manager doesn’t listen to stakeholders to convince the team, he/she listens to the team to convince the stakeholders.

To earn people’s trust and deserve their honesty, you have to be a good friend to them. A good friend doesn’t lie to you, a good friend tells you when he/she thinks you’re not doing the right thing, a good friend helps you when you’re not well. And sometimes a good friend makes fun of you, but you know he/she doesn’t mean wrong, he/she only uses humor to make you think about what you’re doing, to check if you’re aware of what you’re doing, or to tell you what people might think of what you’re doing.

Don’t be too evil

So it could be good to be provocative with your team. What could go wrong? Worst case scenario: you get fired. But that’s because you did it wrong.

I’m not, in any case, telling you that you should be aggressive or abuse your colleagues or anything bad like that. Obviously, don’t do that. Just like with everything humor related, you have to be very careful about what you actually say, and who you say it to. Always make sure that everyone ultimately understands that you’re joking.

For example, let’s say you manage a team that works on a project, and the project is behind schedule (so just a regular project). Someone in the team suggests adding a cool feature. You could just reply something like “sounds great, I’ll email the client to tell him to update the release date. We’re already 6 months behind, at this point he won’t care for 8 more weeks”. That should be sufficient to trigger a reaction from the team, and give you insight about how they feel about the delay, and if they really think the feature is important. Maybe they think it’s your fault that the project is behind: you just gave them an opportunity to get back at you. But if they blame you, you need to know it to handle it, so let’s hear it. If this goes bad, just say it was a bad joke and you didn’t mean it (did you?). If you’re scared that you will not be able to handle the situation, just say it was a bad joke right away. Then you’ll still have made your message pass, even though you denied it immediately. It will still grow inside everyone (inception-style), and you’ll be able to collect feedback later on.

Ethical trolling for dummies

There are a few guidelines to being a good and effective managing troll.

Earn people’s trust: be careful with people who don’t trust you, trolling can be a good way to build trust, but you have to do it progressively.

Friendly fire: you don’t want people to think that you like some more than others, so you have to troll everyone, especially yourself.

Contradict yourself: you don’t want people to guess when you’re serious and when you’re not. If you’re a good manager, what you think shouldn’t matter anyway, you’re here to help the team be autonomous, not to tell them what you think they should do.

Leverage existing frustrations: if you already know or have an intuition that there is a problem in the team, just find a funny way to drop the bombshell and see how it goes. Who needs intuitions when you can have facts.

Be respectful: people are not toys for you to play with. That’s true for any management technique (by the way, don’t read management books, you learn management by managing, not by reading stupid things written by whoever). Always be attentive to how people feel, and if you’ve messed them up, you have to fix them.

If you’re not funny, don’t do it: humor is a serious business, your colleagues won’t take you seriously if you’re too serious to be a serious comedian.


Obviously my article is flawed and contradictory, so what? Does that mean that I don’t know what I’m talking about? Maybe… Does it matter? I hope that at this point, you’ve figured out that it doesn’t. That’s just some homemade food for thought, I’ll let you handle the chewing and all.

One more thing: don’t do this at home!


This article is intentionally provocative, and a good chunk of it is not representative at all of what I think (as I said: who cares what I think?). The article is, indeed, a troll: that doesn’t mean that it does not serve a good purpose.

To all the people that I’ve managed through years who might read this article: yes I trolled you a lot, sometimes willingly, but you know it didn’t mean that I was mean, I was actually kind of kind. Love you guys.

Having been a lot of things from developer to CTO, scrum master and designer, I started writing here to share the knowledge I’ve gained so far.