Operator Spotlight: Tech Leader Li Fan

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas that may help improve your own operations. This month we spoke with Li Fan, who has led all kinds of engineering and tech organizations—from Pinterest to Google, Lime, and her newest position as CTO at digital currency platform Circle.

Tell us about your road to tech, and how you overcame any bumps along the way.

Li: I grew up in Shanghai, China, and dreamed of being a designer or architect but my mom pressured me to focus on Science and Engineering (as almost every parent in China did at the time). I didn’t learn real programming until college. I chose the major because my teachers told me that computer science was the “future” and I had enough math skills to master it. My first year in college was a disaster. I just didn’t understand what programming was about. If there was an option to change majors at that time, I’m sure I would have taken that.

Unfortunately (or fortunately) the school didn’t allow it so I had to stick with computer science. The second year, I learned assembly language. Many of my classmates disliked the low-level machine language but I somehow clicked by grinding through one instruction at a time. I had a lightbulb moment during one assignment and after that, programming became natural to me.

How has your experience as a first-generation immigrant influenced the way you think about fostering inclusivity and empathy?

Li: When I started my career 22 years ago, my language skills were barely enough for me to get my professional work done. I lacked the cultural background to make deep connections with non-Chinese co-workers. When they talked about an old movie that they grew up watching, or a joke from a famous talk show, I was clueless. I remember feeling lonely at the lunch table, not able to join the lively conversation.

I also remember how grateful I was when my co-workers purposely slowed down their conversation and explained the context to me, knowing I needed this support. Later, when I was in a leadership position and hosted meetings or dinners, I always noticed those “outsiders” who sat quietly in the corner. I understand how one might feel even if he or she looks fine. I try my best to include them in the conversation, and pay special attention to them to let them know they are part of the family.

How has the ongoing era of remote work changed dynamics amongst tech teams? How has this impacted your approach in starting a new leadership role mid-pandemic?

LI: Before COVID, I was not a big fan of remote work. I value in-person interaction and real-time communication very much. After a few months of working remotely, reality sunk in and I had to adjust my work style in order to manage the team effectively over video calls. By the time I joined Circle, a fully remote crypto company, I was completely converted. I enjoy the extra two hours I save from not commuting to work every day (replaced with regular exercise and cooking time).

Nevertheless, not being in the same physical space still presents challenges. For one, over-communication is definitely a must. People rely more on Slack (for real-time interaction) but such tools are not the best for important notices or decision sharing. Some can feel they are “left out” unintentionally, which impacts their work. I now remind both myself and my team to communicate important messages again and again, both in verbal and written format.

Secondly, people need “hallway chats.” When you meet random co-workers at a break room in the physical world, you share unplanned information (both work or non-work-related). Those small talks build trust and connection. In the virtual world, it is hard to re-create this, so we need to be intentional about making connections. I start smaller meetings by asking about weekend activities or family vacation plans or recent books read, purposely diverting from the main topic in order to build those connections.

Finding world-class tech talent is always a struggle. What can early-stage companies do to build a team that matches the caliber of the Googles of the world?

Li: Early startups don’t have the brand or resources big companies have. It is very hard to compete if the candidates were looking for a brand to put on their resume or a low-risk compensation package. However, there are still plenty of talented people who are willing to take risks and work on new areas. The key to recruiting is to explain the risk/benefit of your company.

Tell a convincing story – You have to have the conviction of the company mission and market story before you can sell this to others. 99% of the candidates I talk to ask me “why did you join this company?” I always take 10-15 minutes to explain the research I did, the motivation I had, and the trade-offs I made before I made my choice. I also go further to explain why they should choose this company (or occasionally, why this might not be a good choice for them).

Understand their motivation – Good talent has options, so I never take their interest for granted. Even for those who worked with me before, I try to understand what’s motivating them to move. Comp is a foundation (so you can’t really under-pay and expect talent to jump for mission alone), but most of the time what gets a candidate over is the scope of work, the growth of the product, or an inspirational manager that they can learn from. The best talent wants to grow, so explain what you can offer (bigger platform, chance to build a team from scratch, working on high risk, high potential project, etc).

Female CTOs are hard to find. What advice do you give to female engineers with leadership aspirations?

LI: I always felt I could do more, have a bigger impact, learn new things, and challenge myself to be better. So I looked for those opportunities and focused on opening up more paths for myself. I have had frustrating moments when I realized that I was not in the “club” and was unfairly judged, but I told myself it would be their loss more than mine. My advice is to focus on what you can control and what is ahead of you. Be confident that you will come back from setbacks, accept the harsh reality but do not be defeated by it. Resilience will prevail

We loved your comments about mentorship in the recent Engineering Leadership podcast. What’s one misstep you’d caution new mentors (or mentees) to watch out for?

LI: When people asked me for career advice, my instinct used to be to immediately jump in and start to analyze the change for this person. Subconsciously I thought that they had similar criteria as I had when choosing career paths. It didn’t take long for me to realize that those assumptions were so wrong. 

Everyone’s life experience is different. What I value most might not be the top concern for others. There is no right or wrong when one makes a life choice, only the one that fits best in a situation. I started asking more questions, like: why do you want to change now, what’s your motivation, what do you want to achieve? If things do not happen as you expected, what would you do? Now my mentoring is more like coaching, leading the path by asking questions instead of giving answers. 

In your opinion, what are some ways the tech and venture industries could do a better job of empowering the next generation of diverse leaders?

LI: Interview more diverse leaders, founders, or board members, and give them an opportunity to shine in front of a bigger audience. I’ve met so many impressive women leaders and I sometimes wonder why they haven’t been discovered yet. In my experience, those diverse talents often work harder and smarter when given the opportunity because they don’t take it for granted.

AOC often talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were some of those formative jobs for you?

LI: My first paying job was at Cisco Systems, where I wrote and ran network simulations and analyzed results of different routing algorithms. I developed a specific idea of the scope of work for a software engineer, but then I joined Ingrian networks, a 10-person startup. I was hired to design high-performance web proxies but I soon found myself having to solve all kinds of issues — from compiler performance, release schedules, integration testing, UI bug fixes, network cable issues, hard disk failures, etc. Everything that our storage appliance touched or relied on, I had to understand and be ready to jump in because we were a small team. 

I soon understood that the “job description” doesn’t matter when it comes to getting results. You do what needs to be done. I learned to be adaptive and flexible at Ingrian. I played any role required, data analyst, testing engineer, UI designer, release engineer, or even receptionist or sales rep. I learned to pick up new skills on the job quickly and not be afraid of unknowns. This became one of my strengths that pushed me ahead in my later career.

What’s your secret super power? 

Li: I’m relatable to many people. I love technology and art. I’m a mom of two who volunteers in school while working full time at a FinTech company as an executive. I love spending time with my friends at happy hour or weekend hiking. I grew up in China but have spent half of my life in the US. These diverse life experiences give me the ability to understand and connect with many wonderful people, and learn from their wisdom and insight.

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