I got a scare recently because my friend was fired, albeit from a different job. He didn’t see it coming, and when we talked it through I realized I too had a naive mental model of the workplace. I want to share my takeaways here.

My friend Tim’s retelling: he had a disagreement with his CEO on the direction of a project. His CEO asked him to try X, but Tim didn’t think it would work. Tim asked for an explanation but his CEO’s reasoning didn’t make sense to him, so Tim settled on doing his own approach Y while doing daily tasks for X. Tim was fired.

Why was Tim fired?

First off, I think Tim did the right thing “logically”. If he really thought approach X would fail, then he can challenge that idea. Doing so is natural because, for the vast majority of my (Tim’s) life, school has rewarded intellectual curiosity. Question things. Go to office hours and discuss random philosophical issues, sometimes for hours on end. I have no doubt that a bright mind is a curious mind.

But this isn’t the ivory tower, and your boss isn’t your professor. My read is that Tim had the same mindset he had from college. Would it be ideal if you worked somewhere where all the decisions made sense to you? Of course. But consider why the CEO wouldn’t fully explain:

  1. He doesn’t have the time.

    This is the charitable interpretation. The CEO has more pressing work that you’re not aware of, and he needs you to get this done.

  2. He doesn’t care (about you).

    The more likely case. He thinks approach X works and doesn’t want to consider your alternative Y. How would I feel if I worked my ass off for decades, lead a high-profile company, and some new grad tells me my idea is wrong? Who does this kid think he is?

In short: social status matters. And in this case, Tim did not respect the pecking order.

This is a hard pill for me to swallow, especially given the messaging of the times I grew up in. 2010’s The Social Network inspired a feistiness in my generation. Videos of Google made us think ping-pong at the office was the norm. How is pushing back on my boss not a natural thing to do in this era of unbounded creativity?

Make no mistake: social status matters. It’s hard-wired, as The Elephant In the Brain argues. This is a lesson those in software would do well to remember, since the culture may seem like it’s not that on the surface. I can assure you: your boss is very much your boss, whether he wears a t-shirt or dress pants.

From this principle that social status matters, you can derive more concrete lessons like:

  • Pushing back on your boss is partially challenging the social hierarchy, so you must do so very carefully. Don’t just throw an idea out your ass, have data to at least back you up. I.e. do your homework; this is not just you spitballing with someone.
  • Get a second opinion. If the stakes are high, ask a co-worker if pushing back makes sense.

Another corollary that falls out of this is: master your emotions. If you’re challenging your boss, are you doing it in the moment because you want to prove that you’re right, or because you actually want your boss to go with your idea? It probably is more convincing for you to prove yourself first. If I were the boss, why would I listen to this kid who hasn’t proven his worth?

  • Lesson: Prove yourself first. Competency (and compliance) leads to buy in. Show your creativity later.

And if you don’t want to think about how to phrase things delicately or how to convince people: you need to be the one running the show. Don’t expect founder clout if you’re not taking on founder risk.