Why Are We Such Assholes When We Become Managers?

Why Are We Such Assholes When We Become Managers?
"My boss is inhuman."


Before we were managers, we were all decent people. How come so many of us turned into assholes, once we got promoted?

Before we dive into that, here are 3 random fun things I would like to share with you:

  1. Here is one trick all Dads should know- the ability to fold fancy paper planes. Trust me. Once you know how to fold paper B52s, the kids will love you, the Moms will adore you, and the Dads will envy you.
  2. The Gods of the rational self improvement world love cognitive biases. They swear by it. It's the secrets to rationality, composure, and mental fortitude. But is it?
  3. Do you hoard Apple boxes? If you do, here is why. If you don't, here is why people don't throw away their Apple boxes.


Why Do So Many of Us Become Assholes When We Become Managers?

We all know what a bad boss looks like. We know how not to behave like a bad boss. Yet, so many of us normally kind and good folks continue to turn "bad" when we become bosses. How come?

Here is the inconvenient truth- we become bad bosses because we just want easy choices and an easy life.

When I got promoted, I became an insecure jerk, even though I swore in the name of my mother that I would never be an asshole manager. One of my old peers, David, recalled one interaction he's had with me, after I became his boss.

We had an issue during a weekend and I had to ask him to fix it. The issue was not being turned around quick enough. I began to panic because the situation was about to escalate to my superiors. I became annoyed with his inability to fixing it. I started carpet-bombing him with pressure and strongly worded messages. I challenged his commitment and questioned his abilities. I even threatened to remove him from the solution, deal with it myself, for good. In the end, he resolved the issue, we didn't get into any trouble, but he later told me that he was in tears, because that afternoon, as I was berating him, he was actually trying his best to get the issue resolved while taking care of his sick wife.

I did not like that version of myself. I never imagined myself turning into that kind of bosses. I wanted to be a kind and strong boss, but I ended up being an insecure and panicky boss. What happened to me? What happened to so many of us?

Most of us want an easier life, at work, at home, as a boss, as a parent. You may define "easy" differently, but fundamentally, we want to get tasks completed, feel recognized, feel included, feel purposeful, sooner and faster. This is human nature. This is what millions of years of evolution has ingrained into us.

At the same time, life as a boss is not easy. being a manager is often new and foreign to most of us. Worse, we are under a lot of pressure to perform, the moment we are promoted. The VPs and directors above us expect us to achieve results through others, under tight budgets, while keeping our teams happy, on day 1.

Therefore the desire to have an easier life, coupled with the difficulty and pressure of being a boss, drive us towards choices that prioritize our well being, our own survival. Here are a few examples:

  • Instead of spending the time to try to explain to team members the "why" behind a task, instead of "influencing" them to include that tasks into their own "purpose," we choose the easier option of using our positional power and order them to do what we want them to do
  • Instead of putting in the effort to maintain "trust" and create "safety" with our team members, we pick the simpler option of "this is the office, you are paid to do a job, and please bring your daddy issues elsewhere"
  • Instead of understanding our team members' performance thoroughly, we opt for canned metrics and numbers to adjudicate results
  • Instead of investing the time to develop our team members, we defer to others, such as HR and trainings, to grow others

Worst, being a manager can be a thankless job too. Seldom did I feel my team appreciated my effort and understood my challenges. When I tried to be transparent to them, they felt it was TMI. When I tried to be curated in my messaging, they thought I was being calculated. When I tried to help then solidify a career plan, they felt I was dictating their lives. When I said, "how are you doing?" They felt I was micro-managing.

Whenever we pick up a new hobby, we understand the need to break things down. Let's say you are learning French cooking. We understand and accept that we first need to learn the basics, such as dicing shallots and making mother sauces, instead of trying to conquer a Bavette à l’Échalote at the get go. Similarly, when you first learn swimming, you wouldn't work on all four swimming styles straight away, because we understand it's more effective to work on one style at a time. It makes sense to start with the freestyle, then move onto the backstroke, before we tackle the breast stroke, and maybe take on the butterfly.

With leadership, it's the same. It is more effective to learn leadership in small chunks. However, most of us don't work on our management craft this way. Instead, we try to tackle all of them together, because of the reasons we talked about: the pressure to perform, the desire for the "easier" path, and the difficulty of the job.

This might feel counterintuitive because leadership feels like this one big thing that we are either good at it or suck it at. It seems wrong to be a great at managing vision and purpose but suck at managing and measuring work.

From my experience of being a boss and working with fellow bosses and founders, it is becoming clearer to me that when we narrow our focuses and approach leadership in smaller chunks, not only would we experience success sooner, we will also develop transferrable skills that would benefit other areas of leadership. For example, as you become better at communicating strategies and vision, your ability to anticipate and navigate doubts and confusion will also improve, and these skills are applicable to how you motivate your team to deliver results.

So instead of trying to work on all aspects of leadership, I would suggest you to focus on one or two specific leadership skills. You could pick from these 4 major areas of leadership:

  • Strategizing / prioritizing / planning
  • Informing / relating / influencing
  • Developing others
  • Building effective teams

Start with 1 to 2 skills. Allow yourself to build the scaffolding. Give yourself the opportunities to experience small successes. Soon, you would begin to realize, (work)life is actually easier than you think.


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Thank you for reading this. I think about leadership & psychology in the showers. I know it's odd, but these topics are important and fun. I hope you find them useful too.

Work diligently. You are bound to be successful.