Why Training in Philosophy is Vital in Organizational Leadership

A question was raised awhile back about how one can distinguish between a junior and a senior Software Engineer. While many answers can be given, and rightly should, the linchpin eventually boils down to this: how the engineer thinks.

Juniors ask the what. Mid levels ask the how. Seniors ask the why.

The same logic applies for people in positions of leadership. Many think that moving from an individual contributor to an engineering manager is a promotion. I suggest that it should be seen more as a role change rather than a hierarchy change. In any organization, a symbiotic relationship must exist between management and individual contributors. If the manager fails to lead well, not only does he dig his own career grave, he also does so for his team. He who leads without willing followers in the absence of coercion is simply taking a walk.

Interestingly, the same observation applies to managers as with software engineers. A person new to management will ask the what. The more tenured the person is, the more his questions shift to what, to how, to why. Knowing this evolution is important. It is not a judgment of character nor skill. It is rather an indicator of how deep a person is in his experience for the role. Ego is the enemy. So worry not if you find yourself asking a lot of what questions and too little of whys. You’ll get there. (I still ask a lot of what questions myself, probably even more than hows and whys)

By the way, what does Carl Icahn, George Soros, Reid Hoffman, Stewart Butterfield and Peter Thiel have in common?

Answer: they all have a background in philosophy.

In my other blogs, I have always advocated for a philosopher king, that is, in Plato’s perspective, a ruler who asks the whys. Why questions unearth the root cause and knowledge of the root cause is vital to problem solving. He who solves a problem without failing to identify the root cause is simply plugging a leak with his finger.

In other news, a good philosopher is a bad doctor

At BIOLA University where I completed a rather obscure degree called Christian Apologetics, we are trained in matters of philosophy, history, science, and religion. I used to think that the degree is only useful in churches and seminaries. Little did I know that a significant amount of what I learned can be applied elsewhere.

Here are some of them that you should find useful:

As a professional philosopher, you are not allowed to misrepresent your opponent.

In my degree, we are conditioned to be able to repeat and argue exactly for the point of our opponent. Only then can we actually respond. This is important because misrepresentation is very common in the workplace. If you have stayed long enough in an emotionally charged environment, you know this happens a lot, whether consciously, unconsciously, or subconsciously. Yet to a philosopher, this is anathema. Hence, the training helps prevent me from exaggerating my claims or misrepresent those who disagrees with me at work. Sure, sometimes people misrepresent others unintentionally. This usually happens when a person is a bad listener. Bad listeners tend to think of rebuttals while the other person is still speaking, and hence is most prone to misrepresenting arguments.

Here’s a lesson: you will misrepresent people. In order to avoid that, make every effort to understand where the other person is coming from before positing your views. Remember that in a workplace, people are paid to do their work. The psychological phenomenon called the reciprocity bias indicates that people do not want to be indebted. Hence, because the company is paying them money, they generally have good intent to do good work. So listen. Yes. Listen.

A professional listener showing what it’s like to listen

In BIOLA, you are required to exercise maximum respect to people you disagree with.

Here are some tips to shut down opposing ideas.

1. Raise your voice, especially when you’re in a position of power.
2. Interrupt your opponent while he’s speaking.
3. Attack your opponent’s identity, such as his intelligence, his character, his physical appearance, and so forth.

At school, we are not allowed to do any of those. Our course involves A LOT of disagreeing. In fact, I spent about four years in the program showing why I am right and why someone else is wrong. According to the Big Five Personality Test, which is the most researched personality test so far in the field of psychology, I am a very disagreeable person, but this schoolwork helped tamed a lot of how I express my disagreement.

I disagree! Call the manager!

In my first job, I was not well liked by our UI designer (UX was a nascent field back then). There was an incident where I basically tore his entire design to shreds with about a dozen pages of criticisms. To me, it was just me doing my job. To him however, I was one of those software engineers who just don’t know how to work with people. It ended up so bad that my manager took me aside and had a difficult conversation with me. This was not a proud moment for me looking back. While we have since resolved our differences, that didn’t help me change my behavior. What helped me was a forcing function and an example to see how is it like to disagree with other people with diametrically opposing worldview and get the results I want.

Today, here’s what I do when I disagree with my colleagues (although I have to admit, I wish I am better at times. My colleagues are too kind to not point out my quirks for the most part)

1. Instead of saying “you’re wrong,” say “I see it from another perspective.”
2. Instead of saying “we should do x instead,” say “Do you think doing x is better because…?”
3. Instead of saying “I want x to be done this way,” say “Can I suggest we do x this way because…?”

Notice that in all three scenarios, I proposed a different way to do things. However, I propose them in such a way that the other person can keep his dignity. At BIOLA, we are trained to do just that and are penalized otherwise.¹ Now one might think that doing this prolongs the discussion, which is often the case. However, doing this does two things. One, it opens up the topic for further fleshing, which creates collaboration, hence reinforcing long-term benefits by paying short term investments. Second, if successful, it puts the burden or ownership to the other person. When a person obeys you for the sake of obeying, the burden of ownership shifts to you instead of them. Doing this is not scalable because then you have to keep making menial decisions which you should be able to delegate. In general, if someone can do the job at around 70% as effective as you, delegate.

In an exchange of ideas, an assertion is not an argument.

At BIOLA, we are evaluated on the quality of the argument we provide. We are trained to see through assertions without arguments backing them. At work, this is very common, especially in Asia where the culture is very much deferential to people in positions of power.

Here’s an interesting story. Back in 2016, the class was interviewing a certain author which I will leave unnamed. This person basically wrote I think an 800 page book to show why my professor was wrong on a particular subject matter. When it was my turn to ask him a question, I said, “sir, you said such and such… can I understand on what basis do you make these assertions?” His response was, “Intuitions and common sense.” You could hear a collective gasp in the entire roomful of around 30 people. In hindsight, it was a good lesson that intuitions should never serve as a proxy for data when the latter is available. Daniel Kahneman and Amos Taversky has shown in their research how so often we are wrong with our intuitions.²

In order to protect me team from me making assertions without arguments, here’s how I generally do it:

1. Aspire to regularly remind your direct reports that what you want is irrelevant. The best idea needs to win. In Asia, it is very common for people to defer to their boss. It is not enough to tell them once. This principle has to be reiterated over and over again until the team becomes comfortable in contesting my judgment. So when I’m joining in on their discussion, especially when there is a junior engineer, I try to remind myself to say this.
2. Use a lot of belonging cues to surface the best idea. Here’s something to think about: Pavlovian conditioning is generally irresistible. It can therefore be used for good or evil. So here’s what you can do: have fun with them. When people are having fun, they let down their defenses and say what they think. This is proven in a lot of research.³ Next, use an I care tonality.⁴ It is the kind of tonality that establishes subconscious rapport. Here’s how it sounds like. Again, this is very dangerous. People can use it for good or for ill. I’m sharing this to you so that you can think about this when interacting with people, especially those in compliance professions. Finally, thank them often, even for small tasks. Research shows that gratitude improves mental health and productivity of the team by a considerable margin. Using these belonging cues makes it safe for the team to stop you from making assertions without justifications. Because of the rapport that has already been established, they feel a lot safer to share what they really think.
3. Back assertions up with research. Whenever possible, back up what you say with research. This differentiates people simply expressing their opinions from actual data that could be collected with due diligence. Sure, it takes more time to collect them, but one would rather take the longer route and make the right decisions and statements than trust intuitions. To be clear, intuitions can be good when data is insufficient. In this day and age however, data is abundant and those extra hours one spend can help offset days or even years of undoing the mistakes from bad decisions.

Do not sacrifice data on the altar of intuition.

Most people in positions of leadership do not have all the time in the world to study. Yet going through training in philosophy is something I strongly encourage everyone to take. It helps you think methodically, objectively, and hopefully, respectfully. Training in philosophy helps detach one’s identity from his opinions and helps one see through all forms of railroading. It likewise helps protect the leader’s team from his own biases. This is quite helpful if the leader is self aware, which typically helps when one has training in philosophy.

I hope this blog is helpful to you. Happy leading!

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¹ That said, there is always room for me to improve. I still tend to be not sufficiently respectful at times.

² For further reading, you can look at the book Thinking Fast and Slow and The Art of Thinking Clearly.

³ The book entitled Culture Code by Daniel Coyle is a good summation of the research done in this field.

⁴ For more resources on this, the best book I can recommend is Jordan Belfort’s The Way of the Wolf.