Why I think we should disagree with our bosses

Not long after Ching Ern picked up her phone with a “Hello?”, I went into a passionate argument about why I disagreed with one of the decisions she made at work in Colony.

Ching Ern is one of my colleagues at Colony Coworking Space. Before joining Colony, she was an engineer for a Korean firm in Seoul, having landed the job after she finished her university there in Korea on scholarship. After her many years there, she speaks, reads and writes Korean fluently.

Our heated debate carried on for a while until finally she remained quiet for a while and said she understood. At that point, sensing she wasn’t fully sold on my reasoning I asked her to tell me why she still disagreed with me. I said

“I hate it when people just agree with me because I’m the boss. Agree with me instead because you really think I’m making the right decision”.

I pushed her a few more times until she finally let out a few more points she had inside her until I felt like she was finally fully convinced.

Why did I go to this extent when she seemed to agree with me the first time round?

One of the biggest traps that I’ve seen leaders fall into is the trap of confirmation bias. That we believe in a business decision so passionately that we only want to look at reasoning that supports it, ignoring the reasoning of those that does not.

How often do we see in companies where we think the boss is making a mistake but we keep quiet because we’re afraid to stick our neck out and offend the boss. Worse still, how often do we know he’s making a mistake but continue to openly support his decision because we’re afraid to get scolded for not being a “team player”. That isn’t culture that will lead to a company making lots of good decisions.

How do we prevent this? The answer to me is to have a culture where people are willing to argue against any decisions even by the boss. The tricky part though is forming the culture to do so especially in Asia where people are non-confrontational and in many companies for better or worse, it’s almost seen as disrespectful to argue against the boss.

I disagree with that. At Colony I take great pains to make sure people feel safe enough to voice out their thoughts especially if it’s in contradiction to my own. How do I do that?

  1. Before I make a decision or answer how I would handle a situation, I normally ask my colleague what they think. I hear out their thoughts first before I deliver mine. I do this because it helps them commit to a position without being influenced by my position.
  2. I have never said to anyone in the team “I’m the boss so when I say do it, just do it”. The problem with pulling the Nike (ie Just Do It) is that it imbues a culture where the leader isn’t up for debate anymore. It turns the whole organisation into one that takes orders rather than one that thinks on their feet. So no matter how painful the process, I take it upon myself to convince my colleagues on the merits of my decision or ideas.

But… don’t leaders have to be decisive?

I think being decisive and never changing your opinion once you commit to it is overrated. We must always be open to changing our opinions when there is new information in play and the way to have new information is to create an environment where people aren’t afraid to give their thoughts and opinions. A leader’s role isn’t just to make a decision and stick to it forever. It is to curate an environment where the best ideas win based on merit and not because the boss says so.

A lot of my time as the leader of Colony is spent trying to find the best people and then coaching them to peak performance. What’s the point of having the best people if we’re going to tell them what to do?

I’m going to end this article with a quote from the late Steve Jobs,

“It doesn’t make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do.”

To my team at Colony, we owe it to ourselves to always argue against me if I make a decision that you think is wrong. Always have the courage to convey the merits of your argument and stay true to the commitment to let the best ideas always win. I can tell you often that my ideas, and my decisions… are often not the right ones. Your role is to show me how they aren’t.

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