The Zone of Sustainable Commitment

I was first recommended the book “Leadership and Self-Deception” from Stewart Butterfield during Y Combinator Growth program late last year. I finally got the chance to open the book recently and the story resonated so much that I recommended this book to our entire company.

A high-level summary might go like this: if you get into self-betrayal, you go “in the box” where your perspective of the world starts to distort in your favor. By self-justifying, you find ways to blame others, while inflating your own virtue.

The result is making your relationship worse and inviting others into the box along the way, starting a vicious cycle. Below diagram shows the inside of Bud’s mind, one of the characters in the book. Bud’s baby son David wakes up in the middle of night. The diagram shows what goes through Bud’s mind as he thinks about whether to get up and tend to David or not, while his wife Nancy is asleep besides him.

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Situational Leadership Matrix (Simplified version)

After managing different teams of various background and scale over the years, I’ve always thought the question “what is your leadership style?” is almost a trick question. An executive from another company once shared with me a framework he learned at one of the leadership classes he took at Harvard.

It seems like the original version of Situational Leadership is a bit more complex, but the simplified version he shared made more sense to me and felt more applicable to everyday managers.

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A Leadership Lesson from Stand-up Comedies

I enjoy watching stand-up comedies. People like Louis C.K., Dave Chappelle, Mike Birbiglia, Trevor Noah, Ryan Hamilton, John Mulaney comes to mind. I’ve been watching the shows to learn English (great teachers, I know) and pick up some useful dialog patterns to use during sales calls.

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I think there’s something magical about stand-up comedies. There’s a great balancing act of psychology how comedians connect with the audience. The comedian captures the audience, puts them in a situation, then does something completely unexpected or extreme that gives catharsis to the audience, letting them play a role that will not likely happen in their own life, things they will not likely do or say. And it creates a seemingly spontaneous reaction in a form of a laughter to so many diverse people in the room, which has been carefully planned and perfected by the comedian.

We all know this, because even though comedies are hard to create, are easy to enjoy.

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The Accountability of a Leader

When I was young, I’ve fantasized about the Wall Street and its masculine bossy cultures. I’m not sure if I admired it, but it was fun to watch in the movies and I felt the catharsis of running a fast-paced organization full of workers doing homogeneous jobs, with the boss being the absolute best at it. Like those Chinese martial art movies where the teacher is the best martial artist in the country.

It became clear to me this was not always the case. In reality, the junior investment bankers stayed up late, crunched numbers, done researches and wrote reports, while their bosses went out to grab drinks and have fun. When the juniors got promoted, they too became like their bosses, reaping on high salary and bonuses while getting the new blood to serve them well. Deep inside, I’ve always felt this wasn’t really the kind of leader I respected nor wanted to become.

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When I worked for a tech company back in my early 20s, our team’s manager was an eccentric guy. He joked a lot, sounded silly from time to time, didn’t seem that intense or focused on work, felt like he was laid back most of the time.

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Order and Chaos in a Company Culture

The society today upholds diversity as an absolute virtue. Diversity across educational backgrounds, race, ethnic group, gender, age is something we all pursue vigorously. It seems almost trivial to choose diversity over conformity or homogeneity in any discussion.

However, to put things into perspective, nature having evolved through millions, if not billions of years, may provide a slightly different view to this pro-diversity world. The balance and the timing of convergence and divergence play important roles in reaching the global optimum in any search space. The selection pressure from the environment acting as a converging force, offset by mutation from perturbation balancing as a diverging force are what make organisms so durable and adaptable to the ever-changing world we’re living in.

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