A Guide to Scaling Yourself

How to keep your head above water

I was having lunch with a friend today, and we were discussing how does someone know when a person is scaling or not. Who will scale as the company grow and what stops someone from scaling further?

Some companies have early members scaling beautifully as the organization grows, while some don’t. A lot of smooth scaling happens typically when the company is growing organically and the growth rate is relatively modest (< 50% YoY). When a company is growing > 50% YoY, and in some cases, doubling or more, it becomes incredibly difficult for people to keep up with the scale of the company, as humans grow linearly, yet companies grow exponentially.

Below are a few questions to ask yourself to check if you are scaling with the growth needed and some tips and strategies to continue on the fast growth trajectory.

1. Am I “going horizontal?”

I came across the concept of “Going Horizontal” during 10xCEO program and we discussed extensively on how to make sure the executive team is continuing to scale at the right capacity level for the growth needs of the company.

The team internally might already be “over capacity” if the company’s growth rate is modest and the team is experienced. But if the needs for the leadership capacity emerging from growth out weigh the current capacity, then it will hurt the growth rate and the potential upside of the company as long as the leadership team is not fully built to handle the needs.

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Family Core Values

The information and knowledge I know today will quickly become obsolete as years go by, so instead of focusing on the transfer of knowledge, I came to believe that providing a useful set of core values and life’s frameworks are more scalable for the generations of family members. So here is the 1st version of family core values.

Purpose

The core value is to help our family live and grow with a purpose and meaning in life. It will help us prioritize, make decisions, stay genuine and consistent, maintain integrity, with a long-term perspective.
This is a living document and we should continue to evolve it throughout the generations.

Theme: Entrepreneurship

The theme of the core values is “Entrepreneurship (企業家精神, 기업가정신)”. Entrepreneurship is a mindset and a way of living as a leader, that involves identifying problems and opportunities, coming up with solutions to those problems, and executing them resourcefully and tenaciously to create significant value to the world.

Our Family’s 4 Core Values

1. Positive Tenacity

Positive tenacity means we’re being tenacious towards positive missions and goals. It means we look at the future with optimism and execute with high energy. We are biased towards action and we believe in positive changes. We get things done by being resourceful. We work smarter and harder to achieve our goals. We are tenacious and pursue our dreams relentlessly.

2. Leadership

We are the leaders and we take responsibility in any situation regardless of the circumstances. We embody first-principle thinking and decision making. We uphold our integrity and always do the right thing. We are able to think both strategically and tactically. We are independent thinkers. We also know the importance of great communication and being positive examples to others. We believe the good in people and focus on their strengths and positives, rather than their shortcomings and negatives. We inspire people to take action and lead towards a positive future.

3. Learn & Adapt

The world and the universe is constantly changing and the only way to survive and grow is to adapt to the changing world rapidly. We continuously learn and adapt to any environment. Adaptation is not a single event, but a continuous and never-ending state of being. It means to learn anything as quickly as possible, stay curious throughout our entire lives, never get complacent, always pursue becoming better than the best.

4. Think Long-term

We are long-term forward thinkers. We aspire to a positive future and make that dream become a reality. We live with a long-term perspective and are patient through our lives, stay generous and resilient, and are able to embrace the challenges with a long-term view.

The Art of Setting Personal Annual Goals

People tend to be a bit skeptical about setting a personal annual goal. Plans often don’t align with your reality and we’ve all experienced the frustration of setting a goal and giving up a few months into the year, unintentionally hurting your self-esteem.

But, if we don’t have a goal and a plan, we don’t really know whether we are headed in the right direction nor whether we’re making a progress towards a goal or not.

I deeply believe one of the core purpose of personal goal setting is not only to achieve them, but to build up your confidence and increase your self-esteem.

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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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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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