Alex Weinstein
On Growth, Product, and Leadership
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.