Arrogance, a fatal flaw

It’s curious to explore reasons for failure. We often discuss lack of vision, poor execution, wrong team as the killer for technology ventures. Allow me to shed some light on my recent favorite: arrogance.

Our field is full of socially awkward, yet really smart people, and many of them see such drastic intellectual superiority over many of their peers that they catch a fatal disease. At some point in high school, they got an A when everyone failed a test. Or, in their big company, they single-handedly saved the day and saved an entire department from slipping. Or they were a young prodigy in academia and wrote a famous paper.

This is when it hit them – dude, I’m really bright. Moreover, I’m so successful that it must be because I’m so much smarter than folks around me. In everything I do, I can only trust my own judgment – because it’s better than that of others.

And this is when they’re dead. Rand Fishkin, the founder of SEOMoz, calls this “the dangerous hubris of the startup world… the original and most serious of the seven deadly sins.”

They’ll be the ones to build a beautiful new gaming system, only to ship it with a controller that’s too large for half of the world to use. Or they’ll build a gorgeous car, and in their wisdom call it something that sounds great to their own ear – but means “it doesn’t go” in Spanish. All of these are the problems of leaders that think that they have the world in the palm of their hand – and they need no one else’s advice.

I stipulate that the cause of death of countless startups is the stubborn certainty of their founders to keep the original course. The reality is, most successful companies changed course drastically since their inception. You have to be flexible to admit a mistake, make a course correction before it’s too late, and vigorously attack the new path.

I’m a big believer that growth happens through what Einstein called a “school of hard knocks.” Through failure and humility, we see our own imperfection, and strive to improve on it. If we think we’re already perfect, the learning stops. The issue is that the others keep learning – and the world keeps evolving. If we keep using the same hammers for the new tasks, we’ll go extinct.

This issue is exacerbated by our talents. There’s a lot of really brilliant arrogant technologists out there. There ingenuity places them into leadership positions – thus putting not just them, but their followers in jeopardy.

Ask yourself, and be really honest – what were some of the mistakes I made in my professional life? What were some of my judgments that ended up being really false? I’ll point to Eric Sink’s Make More Mistakes article as a fantastic inspiration. The guy pours his soul out for the others to learn – it sure is a painful process, but my god, you get to internalize the lesson from those mistakes so well when you put them on paper.

Here’s a couple of my own dumb mistakes.

1. Do the market research before jumping head-first into a venture.

Cocktail Builder, my first entrepreneurial project. Premise is simple: put in the ingredients you have in your bar, it tells you what drinks you can make. Moreover, it says what stuff you can almost make – so that if you were to buy this one extra ingredient, you’d be able to make this cocktail.

Hey, I thought, when building this – I can sell the missing ingredients online, right on the spot! People are really likely to buy at this point! And so I go on and build the entire site. I market it, get pretty good traffic.. And then I start working on adding the monetization capabilities for selling liquor.

And that’s when I realize: you can’t really sell hard liquor online in the US. Ooooops. There goes that idea… and 8+ months of work with it.

2. There will always be people smarter than me. Find them.

Find Touch, my next entrepreneurial venture. My co-founder and I were convinced that we needed to amass a large client base by luring them with a free product offering, before we can follow on with a jobs marketplace that will leverage that client base.

Our first advisor and lawyer – thank you, David Marks – asked a seemingly obvious question: why aren’t you guys going for the real deal right away? Why not create a jobs marketplace immediately, instead of a silly entry offering that’s impossible to monetize? This question saved us months of work and ultimately made us a viable business.

Our second advisor – thank you, John Kueber – kicked us in the butt when we were obsessed with raising money. We spent 6 months agonizing over decks, financial models, introductions to angels.. All while we had basically no product and little traction on the marketplace. John made us drop this nonsense in favor of making the product sing – and in favor of getting some real customers use this product.

This is just the beginning of my list.. At this point, I know that I probably have more wrong hunches than right ones. That said, I do know one thing for sure – if you listen carefully, someone will quietly whisper a thought that never visited your head. You may just find a missing piece of the puzzle, if only you are willing to listen.


In parting, allow me to offer you a story from a friend. He was recently interviewing in a successful technology company for a senior position; he was speaking directly with a division’s vice president. He asked the VP a simple question: do you see the role of your employees as implementors of your vision, as an extension of your own capabilities?

The VP answered “yes, I simply cannot implement all of my vision myself, so I need my team to follow through on it. I frequently have issues where the team doesn’t quite understand the full scope of my intent, so they have trouble implementing it.”

Is it just me, or does that phrase smell like “I’m the smartest ass in town and I know the solution to every problem. I need cogs for my machine to execute my vision.” No matter how brilliant that guy’s vision is, his team is going nowhere. Innovation comes from diversity and from nay-sayers – from passionate, open, and respectful disagreements. Innovation comes from employees that have autonomy, mastery, and purpose as their motivators.


Interviewing – Challenge Your Assumptions

We’ve all been there. This guy comes in to interview, and three minutes into it you get this feeling. He’s all words and no action. He’s an arrogant bastard. He’s an architecture astronaut.

The interview goes on and on, and with every new topic, you find more and more reasons around why your initial sense is true. Hey, he didn’t give any credit to his peers. He invented it all himself, ha. What an ass!

This is all nice and great, except that you’re really sucking as an interviewer at this point. You had a gut feeling – you made a decision in the first few moments since you met the person – and you’re essentially looking for proof for your already made-up mind.

Since hiring superstars is your #1 priority, this mistake, in my book, is in the category of “lethal” if you’re a founder of a company and you’re bringing in employees #3, 4, and 5.

I’ll go further and stipulate that we’re hard-wired to be making such mistakes. There’s a curious amount of research on first impressions – the amount of judgment people pass on from the first 5 seconds of their interaction. In one leadership training class I took, they brought together a diverse group of people – completely different ages, industries, seniority levels. They had us pair up with a random person in the class, without exchanging a single word with the partner. Then, each of us gave some thoughts about the role, seniority, and industry of the other.

It’s shocking how precise – and how correct! – most of the observations were. The other person didn’t even open their mouth!..

The reason we’re hard-wired to make such a fast, snap call, I believe, is because of the basic fight-or-flight response. You need to judge whether the oncoming object is a danger to us; if we’re bad at it, we’ll get eaten. Thus, natural selection helps advance those that are good at it.

The problem, of course, is that at the workplace, the interactions are much more complex. You WANT to hire people that are radically different from you. You want to hire nay-sayers. You want people with radically different backgrounds, those that approach problems from the other angle. You want the whole of your company to be more than the sum of the individuals. If you fail to challenge your snap judgement, you’ll have a bunch of copies of yourself – creating an environment that magnifies your weaknesses, instead of compensating for them. Like the kings of the medieval times, you’re risking to suffer organizational hemophilia – the disease of “too much blue blood.”

Instead, I invite you to state the assumption that’s popping up in your head, and ask: what could this person say to convince me that they’re NOT what I think they are? If I think they’re not technical enough, can I ask them to code something? If I think they’re too full of themselves, can I ask them about a time when they were wrong? Literally, drop the current conversation topic, and abruptly switch to this new question.

Note that your first impressions, in some cases, will turn out to be exactly true. For example, one gentleman I recently met, I was getting a sense that he’s quite stubborn. I asked him to recall a time when he was convinced by someone else. A time when they thought one way was good and true, but someone jumped in and convinced them of a different approach.

The gentleman thought for a while, and came up with quite a telling example – as a business leader, he saw the technology group gravitate towards a process that he thought was dumb. He didn’t force his opinion down their throats; he let them have it their way. Note a subtle difference: he was NOT convinced himself; he merely allowed his people to make what he considers a mistake. This was quite eye-opening – by focusing on the assumption I made and precisely targeting it, I gave him an honest chance to convince me that my assumption of his stubbornness was wrong; instead, he reinforced it.

I encourage you to do the same the next time you’re interviewing someone for your team. What could this person say to convince me that they’re NOT what I think they are?

What is the single most hurtful way I can interpret this?

Psychology and human relationships are so undervalued in our brainiac, meritocracy culture of technologists. Particularly in software, where there’s a lot of people with vast amounts of intellectual horsepower – and a lot of passion – conflicts arise. Many talented engineers are quite introverted – and socially challenged at the same time; this creates a dangerous mix – we’re often like children playing with weapons at the kitchen table.

No matter how brilliant we are , we spend lots of time making decisions about what to build – versus building it; discussing the variations, instead of trying them; brainstorming instead of implementing. This is good and natural – there has to be a funnel of ideation, where a lot of options are considered, but only few make it through. It makes sense from the cost and efficiency perspective. Here comes the rub, though: generating the ideas and vetting them is a conflict-generating process, by definition; unless we know how to deal with conflict – as mature adults – we’re going to fail as engineers.

I’ve once taken a “soft skills” training that changed my life. A set of CD’s called Crucial Conversations* describes the dynamics of conversations between passionate, invested people discussing matters with high stakes – when opinions differ.

Sometimes, a difference of opinion comes from a asymmetric information – person X knows something that person Y one doesn’t. In this quite typical situation, person Y tends to take the facts that they do have, and combine them in the single most hurtful way they possibly can.

Here are some examples:

1. Hotel Night

A wife finds a single hotel night and a restaurant charge in the husband’s credit card statement. The hotel is down the street. The husband didn’t sleep at home that night, he said he was on business travel.

OK, confession time. What’s on your mind? How do you interpret the situation? OH WHAT A CHEATING BASTARD!

That’s exactly what the wife will think – naturally, that’s what’s hard-wired into us – based on this information, too. The natural reaction would be to confront the husband about infidelity, yelling and screaming and all.

What might this be in reality? The husband might have really been on a business trip. He might have had an office visitor from out of town, and he had to take care of him on a short notice. So he placed the charges on the personal card.

2. Reckless Driver

You’re driving down the street in your quiet neighborhood. Entering an intersection, you see a car that’s RACING towards your, with screeching tires, going easily 30 over the speed limit. He beeps and shouts loudly, swerves around you, almost hits your car, and speeds away.

What’s your natural reaction? FUCKING MANIAC! You almost killed me! I have a little kid here that I’m driving to school, don’t you see my “kid on the back seat” sticker? Your license should be suspended! You should go to jail! What an inconsiderate bastard, putting the lives of everyone around them in danger!..

OK, time for empathy. The guy has his wife next to him, she’s about to give birth. She’s in terrible pain, her pregnancy didn’t go well, and he’s really trying to get her to a hospital.


You’re feeling pretty bad about these snap judgments, aren’t you. I sure was. And yet we’re still making quick-and-dirty calls like this all the time, confronting our coworkers and friends with accusations that damage the sheer foundation of our relationship. How do you think the husband feels when the wife accuses him of cheating? Do you think he’ll feel love and affection and the strong bond they’ve enjoyed so far?..

Let’s try a different approach.

Now that we know that our natural tendency – as humans – is to interpret the lack of information in the most hurtful way possible, we can compensate for it. The question that really helps in such situations is Why would a reasonable and decent person do this?

Why would a husband pay for a hotel + restaurant and not tell his wife, if he’s a reasonable and decent person? Why would someone put the lives of people around them in danger by reckless driving?

With these questions, we’re exercising empathy. We’re placing ourselves in the other person’s shoes. This simple question not only creates a bridge between you and your “opponent” – really, your friend, your loved one, your co-conspirator in your startup. It removes the blindfold of rage.

So next time you find yourself in a conversation where you’re doubting the integrity of your friend, ask yourself: “Why would a reasonable and decent person do this?”

*Microsoft offers the Crucial Conversations curriculum as a 2-day in-person class to employees – I highly recommend attending it. It’ll change your personal life.

Manufactured Happiness and Stockholm Syndrome

A very curious effect happens to people in bad situations. They tend to rationalize that the world around them is actually not bad at all. Moreover, they will honestly, authentically believe that they’re better off because of the adverse position they’re in. There’s a fascinating TED talk about this concept of “manufactured happiness”: a true sense of satisfaction in a situation that any outsider will call straight-up terrible.

For example, someone who’s been on a powerful senator for 30 years, got publicly discredited in a scandal and lost it all, and now lives a quiet life. Or, someone who lost all their limbs in an accident. Someone who spent most of their life in jail unjustly, only to be released in old age with an apology. They all proclaim – in a very honest, deep way – that they’re truly happy that these events happened to them.

You can argue that all of these are examples of nature’s coping mechanisms that are hard-wired into our brains. When we feel that there’s no choice, no exit from a bad position, we give up and start truly believing that it’s all good.

Here’s a problem, though: the world is not black and white. Particularly at the workplace, there is no single situation that is so unchangeable that you have to put up with it. Your brain, however, will be tempted to play that same trick: it’ll try to convince you that it’s all good.

Wait. That person that just yelled at you for an hour – that’s objectively not so good. The fact that your startup sank millions in VC money and still has no idea how to make money – that’s not quite so good. All your coworkers left – hmmm… The product captured 10 times less market share than you expected.

You’ll be tempted to rationalize, every single time. You’ll keep telling yourself that this is just a part of life, and it’ll all get better.


There’s time to press on, and there’s time to step back and think. Ideally, your thinking will be reinforced by an external mentor, someone who isn’t intimately involved in your day-to-day tactics. Evaluate the crap you see at your workplace in objective terms. Not in the context of subjective spin created by “intellectually shallow PowerPoint BS artists” (hat goes off to WhoDaPunk for this expression).

My brilliant friend and mentor once likened the “stuck in a crappy work environment” situation to the Stockholm Syndrome: the victim of a kidnapping falls in love with the kidnappers. You fall in love with the crap that’s falling on you. It’s normal, that’s how it’s supposed to be… And then, three years later, you look back at that mess and think: “why did I put up with all that? Why didn’t I put up a good fight, or find a better place to work?”

Another great mind suggested that it’s very difficult to objectively judge whether the situation you’re in is good – tolerable – and temporary, or not. All you know is where you are now. You also have a few experiences from your prior life. You know that switching to another line of work, another company, whatever – that has cost, too. You start from scratch, and like any optimization algorithm that employs random jumps to get rid of the possible local maximums, you risk to wander forever.

Don’t sacrifice a moment of your life. Take some time to reflect regularly – and do it with an outsider friend.