A learning journey of being a leader — Part 2

small2kuo
8 min readJul 25, 2021

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This is a series of stories talking about my journey in Shopee as a software engineer leader. For more details and motivation, you can check here.

This article is part two of the “A learning journey of being a leader” series. In the previous story, I talked about my struggle and depression from being a leader.

In this article, I will explain how my mindset changes along with a series of life-changing events, and you will also get what kind of leader I want to be.

Turning Points

Learning from my homogeneous colleagues

In December 2020, I arranged a meeting with my tech lead colleague to get some insight. This talk was a flashpoint for me to do a series of changes. My colleague spent 1.5 hours sharing his experience setting goals with his members and help them to track during 1–1 meetings. Previously, I only had 1–1s with the senior members, and I did not think it would be useful for having 1–1s with my members. The reasons were: I did not know what to talk about, and I did not think it was my responsibility. Nevertheless, after adopting his suggestion, I found having 1–1 brought huge benefits to me. I started to get closer to the people, observe the subtle issues they faced, and most importantly, find lots of TODO for me, so I didn’t struggle on initiating things myself, haha.

Photo by Markus Winkler on Unsplash

One of the surprising lessons I learned from doing 1–1s was that: I found I enjoyed observing the message people wanted to convey from their sentences. Most of the time, people talk descriptively because they do not spend time organizing their thoughts (and I have the same problem, haha.) On the other hand, when I was an observer, I would keep thinking about organizing their idea and what that implied. This was quite interesting to me. Because I am analyzing people’s behavior, just like debugging a system from symptoms, practicing this skill was quite attractive to me.

Learning from my heterogeneous colleagues

A few weeks later, after I did a few runs 1–1s with all of my members, I came up with few questions: How to set the goal for soft skills, which is hard to quantize? How should I ask the correct question to stimulate people to think? For people who did not pursue a career, how to define the goal for them? What happened if their goal has nothing to do with the company goal?

To search the solution, I did 2 things: (1) I scheduled a meeting with my PM colleague who leads 10+ people. (2) I started to find more books/articles to read.

Photo by LinkedIn Sales Solutions on Unsplash

Few takeaways from the discussion with the PM was that:

  1. Setting goals for the PMs are hard. In most situations, their contribution cannot be quantized. Instead of struggling with setting a KPI-style goal, she would ask more questions about their feelings: which area you have not done great was in the past few months(e.g., stakeholder management, data analysis, etc.). And how could they try to improve it in the following months? A few weeks later, they could check again and again whether they had the same feelings to measure their growth in this area. In summary, the approach for setting soft skill goals can be based on people’s feelings rather than quantized numbers.
  2. What is your value in being a team lead? Being a good friend with them is not enough. You can still support people regardless we are their leader or not. However, when you are a leader, you have the power to determine their works, you have the power to push them, and you have the power to make a change to make their life better. This is the thing only you can do while other people cannot. You need to leverage this privilege and make an impact on the people. That will be your value to this role.

The second idea woke me up dramatically. I never thought about the impact I could bring to the people. I put myself in the position to get things done and make everybody happy. But empowering them and inspiring them were never my plans. I finally realized that I was dealing with a human being, not developing task machines. Instead of assisting people in finishing the work perfectly, empowering people is more important in this role.

Photo by Jeffrey F Lin on Unsplash

Learning from books

I read a book: Coaching for performance[1], which really touched my heart — followed by the questions on how to ask the correct questions to guide people. It perfectly manifested a type of leading style I would like to pursuit. Here, I would simply list down few key points I have learned from the book.

A coaching style of leadership requires that you connect at the human level, beyond the task — being before doing — and stop thinking that the boss is “the expert” who has to tell everyone else the best way to do things. Coaching is based on trust, belief, and non-judgment.

We struggled that people kept doing things as we were unexpected. This implied that we believed our experience was correct and they were wrong. We believe our way is the best way due to the past successful experience. However, the truth is that we do not have a correct answer either. Maybe their solution is better, or maybe their solution is less ideal, but it can also achieve the same goal. Rather than forcing people to follow your instruction, all you should do is understand their thoughts, respect their idea, and point out some blind spots. If their conclusion is not the same as yours, free your hand and let people try. If they can achieve the same goal, that’s great. If they mess up, you can work out together to learn a lesson from the failure.

Coaching ethos is a belief in the capability, resourcefulness, and potential of yourself and others which allows you to focus on strengths, solutions, and future success, not weakness, problems, or past performance.

Photo by Cytonn Photography on Unsplash

You need to consider people’s potential instead of just measuring their performance, and this implies that you need to believe people have potential XD. This sounds super super hard as an ego individual contributor like me. Therefore, I tried to change my aspect to think about this. A person may not have the potential to be the one you want at your expected speed, but they can always grow in some way at their speed. We respect everybody as an individual. People have different motivations and various ways of thinking. Once we can find the correct way to communicate with a person, pushing them to grow might not be a dream. This doesn’t work if you do not have good faith in people. That is why trust is crucial in a coaching relationship.

High performance is all about self-awareness and responsibility.

We all encountered a situation that we guided a junior to do a task; he made a mistake and corrected him. A few weeks later, a similar (but not the same) task came; he did again and had a mistake again. You might feel he is dumb and disappointed in him.

The problem here might be: they did not think in deep about your instruction. They just blindly followed without thinking. (Of course, it might be another problem but it was not what I wanted to say.) So the better way to push them to consider is to make them aware of what the issue is and the objective we want to achieve. And then we let them take responsibility for the consequence. Once they have an awareness of the root cause and understand that they need to take the risk themselves, they will figure out a proper solution themselves. This is also a long-lasting solution comparing with just telling them how to do it.

There were still tons of learning points from this book, and you may also have many questions about what I just said above. But all I wanted to explain here was that this was the most influential book for me in the past few years. It completely changed my mindset towards leadership and also inspired me to step on the leadership path. If you want to know more detail, I would highly suggest you read this book.

Photo by Peter Conlan on Unsplash

After the mindset changes

I finally found motivation and purpose for being a leader after struggling for 1.5 years. It did not mean I have already known how to deal with people or became happily ever after. I still felt frustrated, disappointed, upset from time to time. I was also not a good leader or coach. Most of the time, I was still unsure how to deal with people, manage my expectations, or communicate with people. But now, at least I know where my self-achievement comes from, understand what value my work is, and have a clear idea of what kind of leader I want to be.

There was a fun fact that I told my manager that “I don’t want to go with the manager role, and I am keener to move towards the technical path.” in October 2020, when the time I felt extremely depressed. Just a few months later, I found I was kind of more suitable for being a manager. At the end of the day, influencing people seemed more attractive to me rather than technology.

Lesson learned

Look back to my entire journey to learn how to be a good leader. It is also a journey for me to understand myself. I questioned myself, reflected on my behaviors, and considered how I treated people, etc. I would say the struggle for a long period was inevitable. All the pain I suffered make me become better myself. Knowing yourself is a process, and it is not just a spark. Also, my growth came with my member’s growth. All of the changes I got have the credits on my members’ trust, my senior members’ help, and my manager’s support. I could not develop myself without their involvement. I sincerely appreciate it.

The other important lesson from the story is that when you feel your life is stuck, one way is to seek external resources. It may not be easy to find out a solution by yourself because if you can figure it out, you should solve the problem already. Talk to people, read more books, watch some speeches, and probably you will get inspiration or creative ideas. This methodology is remarkably useful for me, not for the first time, and I believe it will not be the last time either.

Being a leader is a lonely journey. I hope these stories will help junior leaders who faced the same struggles as me. My learning journey will continue. Although I will not be in such a leadership role in a short period of time, the learning journey and mindset changes will last affecting me and make me a better human being.

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small2kuo

曾經以為自己是技術人,但後來發現幫助人才是自己的天職的碼農,深信用愛可以改變世界。曾待過新加坡電商,目前旅居愛爾蘭。兼職Life Coach與Career Mentor。