Interview with Jerry Li, Senior Director at Groupon

Published on Mar 14, 2018

9 min read

image for Interview with Jerry Li, Senior Director at Groupon

Location: San Francisco Bay Area
Current Role: Senior Director at Groupon running orders and payments and common engineering team.

What is your background and how did you get into management?

I started my career as an engineer at Amazon in payments many years ago. After a few years in the role, I started to have more leadership responsibilities. One day my manager pulled me into his office and asked me, “Hey, Jerry, I need your help. I have a team in China whose manager is not performing well. He’s actually going to be transferred out, so can you go back and manage the team for me?” Without even thinking, I said, “No, I don’t want to be a manager. I never thought about that” Then he said, “Well, I understand, but can you do me a favor? Can you run the team for a few months until we hire someone?” I said, “Yeah, I can do that.”

The whole experience of running a small team was all new to me. I was totally independent and away from my manager, and I had the opportunity to collaborate with local teams, such as the country manager, legal team, product management, and business team. Not to mention the different aspects of the team. I had to figure out the strategies and roadmaps while I was leading as a manager and product manager. The team started performing really well. I think we finished in three months what we normally used to finish in a year. It was very impressive and everyone liked that.

That was a totally new thing to me. I realized that as a team you can deliver a lot more than you can deliver individually, which is something that makes me very excited. However, the most exciting thing for me is the opportunity to have a personal impact on my team members. For example; one of the team members back then was going to be managed out because of his performance, but after I started interacting with that person I realized he’s actually really smart and knows a lot about the services and architecture. So, why was this person not performing well?

It turned out there was tension between him and the manager who had different opinions. The developer just happened to have a lot of ideas and was a very independent thinker. That’s the reason it didn’t work out well. After giving that person more responsibility and trust, his performance went up, and I think that’s something that I never experienced before. Being a manager means your job is to deliver something very personal, such as personal impact to the team members.

Vidal: That’s awesome.

Jerry: That’s an important point for me, being a manager.

Vidal: Wow. That’s a great story about the person who was going to be managed out and you were able to turn it around, so that’s really cool.

What are the biggest challenges you face?

My biggest challenge is to teach people self-awareness. It’s really, really hard. I think self-awareness is the foundation for any self-growth. Very often people don’t clearly know their areas of improvement and have a victim mindset. When you sit down with them and tell them they have something to improve, they become defensive and that often leads to a hard conversation.

With almost any feedback you want to give, the recipient can always find excuses. There are always reasons to blame. It’s almost always like that, but that’s not the point. The point is you’re trying to grow. Of course, there are always going to be things that you have no control over. The position is not perfect. The conditions are not perfect. How can you grow, do better, and look inside yourself? There are things that can be done better to strengthen you so that in the future or even in some other business, it will be of you own advantage, and not necessarily for the team alone.

I have the ability to open people up to new perspectives and get them to be aware of how they are being perceived by other people. That’s really hard. Sometimes people just hold onto their ideas thinking that their idea is a fact or a truth, and even if somebody else has the same idea, they are wrong. I think my biggest challenge is opening people up so they have a different perspective and look inside to find areas to improve and prioritize their personal growth. And not really having a victim mindset and then taking your own ownership to grow. I think that’s a big challenge for me.

What is your approach to hiring?

Jerry: It’s related to the first question, actually. Because of the difficulty in opening people up to self-awareness, you need to consider that at the beginning when hiring. What’s the criteria for hiring, so that you can have the right people on your team? To me, the most important aspects are personal characteristics because I want to have my team with that growth mindset. Do you have self-awareness and really embrace growth and changes, so we have an open mind here? We have a need to be humble and don’t just have a fixed mindset where there’s no way to grow or change. I think that’s my number one hiring criteria: Has to have a growth mentality. Actually, there’s a book about it. Mindset: The New Psychology of Success by Carol S. Dweck

Vidal: So, that’s more important for you than, say, technical skills or other things?

Jerry: Yeah, of course. You really need to have some level of technical skills and people skills. We can hire someone as an engineer or manager without those skills, but what is more important is the growth mindset. If someone doesn’t have that, that’s a BIG NO to me.

What is your advice for managers who are just starting out?

When starting out as a manager, I think the biggest challenge is to know what you don’t know. Since you’ve not been in management before, and you’ve probably not had any training or education either, it is important to know what new mindsets and skills you need to have in order to do a good job as a manager.

An effective way is to reach out to people who have gone through that before. New managers should talk to people who have been in a management position for two or three years, but not too long because they may forget the initial challenges they had. They might be taking things for granted just because it’s natural for them. Think about people with two or three years’ experience that are successful, get to know the challenges they faced when they first became managers.

Reach out to multiple people because everyone’s experience is different. Don’t just stick to one set of experiences. I advise you talk to people that are more knowledgeable and ask them questions that you need answers to. Doing this will be tremendously helpful to your career.

What is your work day like, and how do you manage your time, all your emails, and things like that?

My workday starts with half an hour just sitting there with my laptop closed and really thinking about what’s important today that I can do for my team. I’m looking for the highest leverage activities for me to do that nobody else on the team is in a position to do, or wants to do. That will give me a clarity as to what is truly important for the team. I try to avoid starting my day looking at emails or calendars because those are things I don’t have much control over. It’s very easy to get going in those routines, and not step back and look at the bigger picture. I think on a daily basis there are always continuous new ideas. I always look for bigger, and better things for the team, or even for the organization. That’s how I normally start my day.

Then that will lead to actions I can take for the day. Things like putting items on my calendar, starting to read emails, job information, and responding to people, because it’s always like that as a manager. Everyone wants a piece of you, right?

What’s a personal habit that contributes to your success?

I’m not sure I’m that successful in my current role yet. I still have challenges in helping part of my team get to the point where I want them to be. That’s a major goal that I am yet to accomplish.

I can talk about what I found useful to me, in terms of personal habits. It’s a habit I want to form, but I’m not sure it’s fully formed habit yet. I try to get comfortable with being uncomfortable. Basically, I am looking for areas where I am not comfortable enough. Not feeling comfortable is a signal of an area of improvement. I think it’s human nature to stay in the comfort zone, so there needs some level of consciousness to change that and move to an area where you are not very comfortable so you can do something better/different. I think that’s important, but it’s really hard.

Could you share an internet resource or tool that you can’t live without?

I don’t have a single resource where I can pull information from, but in general, I’m more in favor of reading good books than articles, because I think people’s time is very precious. There are tons of really good books written on management. Typical managers, are sort of all over the place, so it’s hard enough to carve out some time for self-improvement, and how to use that time more effectively.

I think reading books is better because typically the authors are experts and they spend a lot of time organizing their thoughts before writing a book. A book is more systematic than an article. It’s easier to remember because it’s a framework; we have the different chapters laid out, so they have a flow of showing the information. That’s my preference. You have to find time for self-improvement, and so I would rather read a book than an article.

If you could recommend one book, or if you want, a few, since you mentioned you like books a lot, to managers, what would the book or books be and why?

There are a lot of good books in different areas that can be useful to people out there, but one I like a lot that I read recently is Conscious Business: How to Build Value through Values by Fred Kofman.

He worked as a consultant and a professor. It goes back to the point I mentioned earlier. It’s really hard to teach self-awareness, and how to have common sense, not as an individual, but also as a team and organization. I think it’s very critical for any organization to be successful.

The reason I like the book is not only for its’ very important information but that it also teaches valuable information about self-awareness and it teaches tactics you can use easily for day to day team management. How do you get a commitment from other people? How do you understand and manage emotions? How do you make a request? How do you resolve conflict? Right away after I read it,  I started using some of the techniques that were taught in the book and it was very effective. Another example is how it teaches business people to perceive and manage emotions at work.

Another one I really like is called Team of Teams: New Rules of Engagement for a Complex World by General Stanley McChrystal and David Silverman. The book is really, really good and it’s especially good for organizations dealing with complicated situations. For example, in software engineering when you are dealing with something like a service-oriented architecture, there are many, many different pieces. A simple, easy task can involve a lot of dependencies and risks, so it requires a very high level of cross-team ability and internal collaboration.

With a traditional command and control style of management, it’s really hard to handle the challenge well, because you need a very high level of ownership from all the individuals involved in your organization to do things well. Traditional command and control relies on someone who has a very good overview of everything and who is anticipating all the different steps and all the risks involved and the dependencies. It’s becoming less and less possible for anyone to convincingly comprehend the entire picture! It doesn’t work like that anymore. The situations in your life or on the go require the need to decentralize, and really good team collaboration is what you need to take on those challenges.

The book uses very successful examples from the battlefield. It has very good stories that transformed the strategy of how we manage new issues on the battlefield because things are changing so quickly. All that can be translated back to our civilian businesses. The book contains very successful examples using those principles in business.

Where can people go to learn more about you?

Jerry: I would recommend a community like the San Francisco Engineering Leadership Community at That leads to our meetup group. From there look and see what we are about, and hopefully join.

Vidal: It’s a fantastic meetup. You’re doing a great job on that. Thank you.

This series asks engineering managers to share their experiences with the intent of helping other engineering managers learn and improve. Have someone you want to see featured or questions you think we should ask? Contact me.

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