The leader’s anti-asshole list


Part of our responsibilities as leaders, is to put our teammates first.

Dick Costolo, Twitter’s CEO, uses the term “The Leader’s Paradox” – As managers and leaders, we need to care deeply and thoroughly about our people, while not worrying about what they think about us.

We need to figure out a way to push our team towards the right direction. It means we need to be mature enough to contain the pain and disappointment when things aren’t going as expected. We need a way to break emotion from behaviors, so we could judge ourselves based on the outcome we’re looking for.

But before we can act as leaders, we have to understand both the power and risks of putting ourselves in our teammates’ shoes.

Empathy and sympathy

There is an important distinction between these states, one that you should be well-aware of.

Empathy is noticing someone else’s situation or perspective. It means that you get how they analyze the situation. It does not mean you agree with them, or share their feelings. It does not mean you have to solve their problems.

Sympathy is empathy plus feeling the same way as the other person. It’s more than noticing or agreeing with one’s perspective, it’s feeling as if we were that person.

Let’s say one of your teammates is not performing as expected. Empathy will put you in a place where you could analyze the situation from their side: maybe there is a misalignment of expectations; maybe someone or something else was failing them to get the job done on time; maybe they have hard time at home. Sympathy on the other hand, will trigger memories from your own past failures. You will find yourself justifying behaviors you normally wouldn’t, because you remember the pain of your own failures.

Sympathy might lead you to act as if you were the one to fail. This may increase the chances of you judging the situation from a subjective point of view. Your teammates expect you to always act from a place of empathy, not sympathy. To really excel at their work, they need your objective opinion.

The real danger of delaying feedback

We should be fully aware of what it really means every time we say “oh, she’s too busy right now, I’ll talk with her tomorrow” or “he’s having a hard time, it can wait”.

Every time we’re delaying hard calls or honest feedback, we make an active decision that our teammates could see and learn from. Not making a decision is equally important and explicit as making one. The fact that we delayed the conversation doesn’t mean the situation didn’t happen. On the contrary, it means it happened and we decided it wasn’t important enough to take an action.

What started as a “justified” call may become a part of our team’s DNA. Once it’s ingrained, eliminating this behavior will be much harder.

The anti-asshole checklist

In order to judge my own decisions, I had to create a simple way to see if I acted from a place of sympathy or empathy. While I hated the feeling of sharing “bad news”, I reminded myself that my teammates expect me to do my best to push them further.

Here are a few questions I’ve asked myself, after making a hard decision or sharing some harsh feedback:

  • Did I show empathy? The simplest way to do it is to reflect the situation as we see it, e.g. “The feature wasn’t ready on time and we had to delay the entire release. I saw that it was hard for you to get the commitment and cooperation from the Product Team. I also understand that you weren’t the one to set the deadline.”
  • Did I clarify my expectations? e.g. “I expect you to raise a flag earlier, if you believe that you’re not going to meet the deadline. I want to see you more communicative with the Product Team, even if I’m not available to solve it. Earlier sync with them could have reduced the chances of delay on their side. Finally, if you feel the deadlines are wrong, I expect you to ask for help and make sure I am aware of it.”
  • Did I practice what I just preached? It is imperative to demonstrate leadership by practicing it. If we’re constantly late with our own tasks (or meetings), we can’t ask our teammates to keep their deadlines. If we’re bad with communicating dependencies with other teams, we can’t really expect that from them. If they see our own boss chasing after us for status updates, we can’t expect them to be active and create visibility into their own tasks.

If I answered “YES” to each and every one of these questions, then I knew I acted from a place of growth. It didn’t completely eliminate my asshole-like feeling, at least in the beginning, but it helped me to sleep well at night.

When we act based on our deepest beliefs for what’s right for our teammates, when we lead by being forthright and clear, then it’s easier to deal with the rest.

While you may feel as an asshole, judging your actions using these 3 questions will slowly reduce that feeling. You will feel more confident, as these decisions will represent your true self.

Interested in going deep into stuff like this — pragmatic ideas and frameworks to help you systematically get better as a manager — Then you’ll want to sign up to receive a free chapter of my upcoming book, Leading Snowflakes.

photo credit: joelmontes



Oren Ellenbogen

Curate awesomeness @ , Engineer @ Commerce Sciences, Author of , Explorer of Company DNA.