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The Case for Good “Assholes”

Not everything is as it may seem. Sometimes, someone who may be perceived as an asshole, may be your best friend. It may even be someone who considers you to be family.

“Better are the wounds of a friend, then the deceitful kisses of an enemy.”

-Proverbs 27:6

So many companies today have promoted the importance of having a “no assholes” policy for employees. And yet, if you were to ask many of these people how an asshole is defined, I would submit that many people have not thought about this very deeply.

Ironically, some of the greatest creators of all time, such as Steve Jobs, Elon Musk, and – in gaming – folks like Corey Barlog, are generally considered assholes.

Over the past few years, I have had multiple friends who have been fired from their jobs with a common theme: “I had no idea I was going to be fired.”

Let’s consider a manager who invests in an employee and gives critical feedback but gives the employee a chance to improve vs. a manager who smiles and makes an employee “feel” safe but ultimately fires them out of nowhere.

Who truly is the asshole?

A few months ago, I considered these issues deeply while watching a podcast interview with Tony Fadell by Tim Ferriss. Tony (he oversaw iPod at Apple and co-founded Nest Labs) delineated a case for good vs. bad assholes that resonated with my experience. Tony, who worked with Steve Jobs for many years, did a great job characterizing the nuance about assholes in his book Build.

To further sharpen my thinking on this topic, I reached out to one of my favorite people Brett Nowak, CEO of Liquid & Grit. We both agree and disagree on many topics, and I always appreciate his thoughts and wisdom.

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In this conversation, we discuss this notion of good vs. bad assholes and touch upon many related topics, including some that are likely highly controversial, such as the current societal and political environment.

I highly recommend you check out the full discussion, but let me highlight three specific points worth your consideration:

  1. Focus on intent.

Too many people focus on “feelings.” In other words, how does a manager make a direct report feel in the workplace? In some work environments, maybe focusing on feelings is ok. This can be true if you’re working at a profitable, scaled business where performance and results aren’t the highest priority.

However, if the objective of a work environment is to achieve successful outcomes and one in which employee development is a priority, don’t focus on feelings.

Focus instead on intent. What is the manager trying to do or convey? Are they being critical to hurt someone’s feelings, or are they giving critical feedback to improve performance or help employees develop their capabilities?

Also, nobody is perfect. Most managers will not communicate perfectly, and feedback may sometimes be harsh. Don’t conflate imperfect messaging with the feedback. Try to understand the feedback and take what you can to improve.

  1. Engage, don’t attack.

Unfortunately, society and politics today have become increasingly polarized and hateful.

There are too many people today who actively seek to attack others, especially on social media. They look for old tweets or posts that differ from their ideology and then actively attack these people and incite mobs to hurt them.


Many people today are mad at the world. However, anger and hurt from feelings of improper social justice, jealousy, misdirected anger, or moral superiority are not good excuses.

More of us need to engage and try to understand one another. We must stop attacking and trying to hurt others as a first reaction.

In today’s world, many well-intentioned managers who give direct feedback will be attacked with a false narrative of toxicity and poor leadership. I do hope that more people try to engage before they immediately get their knives out and attack.

  1. Don’t expect perfection.

When I was young, I was a complete idiot. This lasted, unfortunately, far into my twenties. My personal development came from making mistakes and by the grace of those around me who allowed me forgiveness. Who knows? Maybe I’m still an idiot.

People improve by making mistakes.

And yet, society today, and especially on social media, expects everyone to be perfect, even while they are far from perfect.

The hatred and desire to witchhunt people for a single, careless remark is seriously getting out of hand.

In our discussion, Brett talks about how a boy in his son’s class called his son a bad name. The boy’s father texted him with an apology for his son. Brett responded that he thought the boy’s son was “a great kid.” He knew that, like all kids, they would make mistakes and need to make mistakes to learn and grow. He also understands that he likely made similar mistakes growing up.

Even good managers will make mistakes. I do hope, at your workplace, you focus on intent and don’t try to crucify a good manager for poor communication with good intent.

We need to remember: Treat others with the same grace as you would like to be treated or that you would like your family to be treated.

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