Scaling Leadership through Two Management Frameworks

As an organization reaches certain scale, it is inevitable, at least due to the current limitation set by human interaction mechanisms (e.g. verbal communication, synchronous meetings, groups, hierarchies, physically independent) that there is a certain level of structure that needs to be put in place to manage the organization.

There is a few frameworks that can be useful when scaling the leadership. It’s local applications of the general management frameworks, so let’s explore how they can be relevant to scaling leadership.

1. Convergence <> Divergence framework

This framework demonstrates how to navigate within the horizontal layer (x-axis) of management.

As your organization scales, one thing you constantly run into is the overall increase in diversity within the organization. The proportion of diversity may increase or decrease, but the absolute number of diverse entity (in this case, employees) will simply increase as your headcount grows.

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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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The Adventure of a Fool

Recently, I went on a business trip to South East Asia to meet with some of our customers. There I visited a more developed country like Singapore, and then traveled across a city in one of more developing countries like Indonesia. Jakarta was full of surprises, an eye-opening experience, similar to the feeling I had when I first visited Beijing.

There was an insane number of motorcycles on the road, swerving around a three-column of cars on a two-lane street. They were opportunistic, if not entrepreneurial. It was dizzying, yet mesmerizing to see how so many of them could go past all the cars without scratching a single one.

jakarta.jpg

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On Problem Solving and Not Giving Up

* This is a letter to my family.

I’m not sure if the internet we are using today in 2017 will still be the same by the time you are an adult, but because of the internet, you will be exposed to far more information and stimulants than a single person’s brain can process and handle. (Of course, let’s wait until some AI-leveraging tech for human brains get released!)

What this means is that you can get more distracted than focused, build a habit of consuming more while creating less, and critiquing more and acting less. You can spend your entire day on consuming content and talking about it, without actually making any impact or progress. Of course, a single line of comment on a popular news feed may have an impact — getting a few more likes for ego-boosting — but at the end of the day, the most precious resource you have is your energy, attention, and time, so make sure you save these for the important stuff.

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On Self-Esteem

* This is a letter to my family.

You should take care of your self-esteem. It is different from being merely confident. Self-esteem, backed by strong resilience, can take you far beyond what’s believed to be possible, over come difficult struggles in life, get through deep loneliness, find the right partners for your endeavors, avoid vanity social events, less influenced by external validations, and even rise from the ashes.

When you are running low on self-esteem, you will start acting the opposite of a good leader. You will blame things on other people or the environment. You will avoid conflict. You will seek attention. You will brag more. You will take shortcuts. You will deceive others and bend reality beyond what’s acceptible. You become more authoritative and look down on others. You will ultimately lose the respect of yourself and the others.

When you are yearning for more “Likes” on Facebook, seeking external validation and agreement from others to the extent that you are influenced by it more than it should, unless you are in the business of entertainment, be wary of these symptoms. You will need to replenish your self-esteem.

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On Life’s Framework

pruning

There are a few useful algorithms to help you make life’s decisions, especially around prioritization and pruning, and also the timing of it.

From my childhood days, my tendency was to make decisions quickly. I’ve never really felt much difficulty in picking my choices. It’s not because I was good at it, but probably due to a certain gene characteristics. These days, I try to estimate ‘when is the 30% stage of my information gathering before making the decision and acting on it?’ to use in my business decisions.

This is also a well-known problem in mathematics/computer science as ‘optimal stopping’ problem. A simple version of the answer is 37%. In regards to the number of options, tries, or the length of time, gather information (or explore) up to 37%, then select the best one that appears after that point. Then you will have about 37% chance of picking the best one. Of course, with different conditions (e.g. being able to revisit the choice), the % changes quite a bit, but the moral of the story is that there is only a limited time when you can gather information, and then you have to make a decision to get the highest chance to the optimum.

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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.

boss-vs-leader

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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The Future of Life

I’ve been a strong advocate of the future of VR. Let’s assume we have a device that allows us to wear for a long period of time without motion sickness or sore-eyes, with full peripheral vision and good-enough input device to express ourselves virtually. It doesn’t have to provide full tactile feedback yet.

If we can do just two things: creating/adding value (what people call ‘work’) and having fun (what people call ‘consume’) in such VR-enabled world, it could disrupt a lot of industries and solve many of today’s problems as a side-effect.

Think about some of the high-level problems we face today: energy problems (mostly used by transportation and industrial usages), pollution and climate change, lack of adequate healthcare, unemployment, education inequality, diversity issues (racism, gender, etc.). If VR is done right, we can solve most of these problems pretty efficiently.

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Accelerating Self-growth

Ericsson’s work on deliberate practice has a meaningful implication on self-development. Becoming great at something takes more than mere hours spent on the task itself. Based on the work by Dr. Howard Gardner’s multiple intelligence theory, intrapersonal intelligence helps with structuring one’s own deliberate practice programs.

Looking back at my pro-gaming days, I used to structure my practice into training different aspects of my play in a ‘divide and conquer’ manner — different trainings for each weapon, optimizing plays for a map’s each segments, map-wide navigational movements, vertical aiming, horizontal aiming, mouse analysis (spending over $10k in mouse collection!), system and key configurations, graphic settings, item regeneration timings, and the list goes on.

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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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