Women Of The C-Suite: Rosalind Lee of ROLA.ai On The Five Things You Need To Succeed As A Senior Executive
An Interview With Candice Georgiadis
Doing nothing is the hardest yet the most important thing to do. Sometimes we want to accomplish a goal too badly and we push too hard. It almost feels like we have not tried enough. But it turns out, the more we push the more likely it would fail. Once, I wanted to close a deal so much that I kept on pushing both sides. I made sure all details were flawless and made a lot of notes and reports to make sure they got all the information and analysis. It turned out, my supervisor back then thought there must be something fishy as I was pushing too hard, whilst the other side also felt it was too perfectly handled and too good to be true. I learned that just trying your best effort, doing nothing too deliberate, and letting it ride when things are out of your hand will be the smoothest way to achieve your goal.
As a part of our interview series called “Women Of The C-Suite”, we had the pleasure of interviewing Rosalind Lee.
Rosalind Lee is the Chief Product Officer and the creative lead of ROLA.ai. She has designed various products and solutions with top-tier corporations from multiple industries, including blockchain, gaming, algo trading, payment, and card products.
Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
If you meant crypto, I went into crypto because of my dog (he is a Shiba, the mascot of crypto). You heard right.
Back in 2020, after working on some projects on fintech and payments, I realized I have a talent for solution engineering and product design. I decided to venture into payment solutions, just when I invested most of my savings into it, he got Lymphoma again. I was quite in debt from his chemotherapy and needed to get more cash and I remembered my adventure with Bitcoin in 2017.
As the story goes, I kept making the same mistakes and losing money, but I started to become curious about why I have been losing money and kept exploring, reading, and learning about this industry.
But still, I am very grateful that I loselost money, if I hadn’t lost money, I wouldn’t have learned so much about blockchain and crypto.
The whole technology and culture became very interesting to me, I just enjoy so much being in the crypto industry. Then I worked on several in-house blockchain projects at a listed fintech company in Hong Kong and eventually got approached with the idea of ROLA.
In general, I guess I just love adventures and hate the idea of being boring. And that’s why I didn’t pursue a career in traditional banking like most of my classmates did upon graduating from Imperial College.
P.S. My Shiba is now doing well, 2023 marks the 4th year of his first therapy on Lymphoma. He has always reminded me to stay strong.
Can you share the most interesting story that happened to you since you began leading your company?
I started getting a lot more insomnia messages from friends in multiple time zones. My friends would text me in the middle of the night in their time zones and say “I can’t sleep. I know you are always online, and you don’t sleep, so talk to me.” It is true that I have a very quick response time because project and product management are extremely time critical. I am always online, but I do sleep, quite well and a lot.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
I am a direct person who doesn’t like guessing or wasting time beating around the bush. When I first started my career, I worked at a company with a very ambiguous and “dodgy” bonus calculating system. One time I had a connection who could bring in a significant amount of revenue to the company. So, I went into the CEO’s room and asked directly “What is the bonus % going to be for me on this?” At first, he tried to give me an ambiguous answer, but I insisted on confronting him and getting the exact answer. Then he said, “I would rather not do it if the profit margin would be this little after giving you the bonus” I replied, “OK, I rather not do it if I don’t get the bonus”. The next thing I knew, I was picked on by the executives, especially after the CEO spread the rumor about me demanding for “illegal commission”. I have learned that sometimes you must fight smarter and adopt different strategies and approaches for different people.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
My idol, Chen Kun, a famous actor, is also my mentor. He has inspired me to embrace my creativity, follow my heart, and trust my instinct.
Ever since I was a kid, I fell in love with literature and drama by watching his performance, and somehow, we bumped into each other in London. I was asking for an autograph but bothneither of us didn’t havehad a pen with us. So, he invited me over to have breakfast at his hotel the next day (You can’t imagine how starstruck I was). He encouraged me to follow my heart and that was also the first time I truly learned about the philosophy of Buddhism and about compassion, these shaped my own thoughts, and aesthetics. Later, we went on a 10-day trekking trip together to the Tibetan plateau, during which he was making fun with me like how your elder brother would, he was spanking my head, doing pranks, and making jokes with me. He did all these just because he could see that I was a very tense person. I have always tried to climb to the highest point and tried so hard to be the best and perfect…but he told me to stay relaxed, and to embrace my own inner child. He is the first person to have ever noticed my inner child as I have always been hiding it to portray the “professional” me. Embracing and being open with my childish side helps me to unlock all my creativity.
Now I am no longer pretending to be a person that I am not. I can confirm that this helps me to do product design, especially with all the creative features you can see in ROLA.
Learning to trust my instinct helps me to respond fast and stay calm when I need to improvise.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?
I had to decide whether to continue working with a service provider or whether should we cut loss and switch to another. This was an example of being decisive in handling sunk cost fallacy. We spent months and development fees on a vendor who turned out to be not delivering and “blackmailing” for more payments. Our team had divided views, as “money and time were already invested”. I understood fully that there might be a chance that the provider just needed a little push to deliver but on the other hand, it might just be an endless hole. In the end, I decided to move on and replace them with a new service provider who actually delivered far better work within a shorter time period.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
Make decisions spontaneously and without hesitation. I think the main difference lies in decision-making and the pace of it.
What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?
It’s not sitting in a fancy room with a glass of whisky in hand as depicted on TV. It is about constant problem-solving and meditating on new ideas 24/7, there’s no actual office hourhours. You just have to be prepared to do anything and to be able to fill up the responsibilities and work when required, no matter how small and trivial they seem.
In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?
I would like to use my experience in the cigar lounge to demonstrate this. I am a person who loves to enjoy a cigar occasionally to relax, but usually, when I am in a cigar lounge, the men inside would walk away or stare at me with strange gazes. One time I even received comments like” Are you a gold digger just coming to get to a rich man?” It feels the same being a female executive in the crypto industry. In the crypto community, we see a lot of macho male influencers and traders flexing hard with their designer watches and supercars, whilst female influencers are deemed as trolls, incapable, and worse still, being made fun of. I remember one time when I was talking to a business partner and he said “Is there a Mr something who can actually make the decision, that we can talk to?” I think the stereotype of women executives isn’t at the decision-making level, is the same as “women don’t know how to enjoy a cigar”.
What is the most striking difference between your actual job and how you thought the job would be?
I think I kind of expected what I had to do. But the number of spontaneous decisions and instances that required quick problem-solving skills did exceed my imagination. Still, I enjoy all of it.
Is everyone cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?
In my opinion, the most helpful traits will be curiosity, flexibility, and the willingness to learn; whilst if you are a person with an easy faint of heart and hesitant to make a decision, then most probably you should avoid aspiring to be an executive. Curiosity and the willingness to learn will allow you to accept new ideas whilst not being afraid to embrace new approaches. Being flexible allows you to respond to rapid changes with calmness and make the decision to solve the problem with ease. However, if you are a person with awho is faint of heart and hesitant to make a decision, then you may end up stalling and hindering the progress of your team and miss the correct timing.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- Doing nothing is the hardest yet the most important thing to do. Sometimes we want to accomplish a goal too badly and we push too hard. It almost feels like we have not tried enough. But it turns out, the more we push the more likely it would fail. Once, I wanted to close a deal so much that I kept on pushing both sides. I made sure all details were flawless and made a lot of notes and reports to make sure they got all the information and analysis. It turned out, my supervisor back then thought there must be something fishy as I was pushing too hard, whilst the other side also felt it was too perfectly handled and too good to be true. I learned that just trying your best effort, doing nothing too deliberate, and letting it ride when things are out of your hand will be the smoothest way to achieve your goal.
- Don’t ever make your friend your business partner. Several years ago, I referred a friend to be the business partner of the company I worked at. The company ended up not making the committed payment and my friend blamed me for being misleading. On the other hand, I was unhappy about my friend being inconsiderate. Friendship can be quite unexpectedly fragile when it involves money. Unless you are 100% in control, don’t ever make your friend your business partner if you cherish the friendship. I regret making this decision a lot.
- You can’t please everyone. There are always “Karens” in the world and they pick on people for ridiculous reasons or no reason at all. I used to work with an executive, being one of the “Karens”, just kept shouting at people across the office for pleasure. Initially, I got shouted at for simply walking near her. I thought it was my fault and that I should try to play nice, and hopefully, she would stop just yelling at me. In the end, I realized it wasn’t personal. She was just being “Karen” and I don’t have to give a light.
- There are no “enough” passion and knowledge. Being passionate helps me from procrastinating. I procrastinate a lot on tasks that I share no interest or passion in, andin and being able to identify the slightest ounce of passion in tasks enables fun and efficient solutions. Always be ready to learn new knowledge as it improves your conversation with people and helps you to be respected by them.
- Be water. Adapt to changes but don’t lose your own nature. Uncertainty is the only certainty there is. There isn’t real “planning” as the situation develops and changes rapidly. Especially in product design and development, the grand plan may not work out due to sudden changes in regulation or the market response. Being flexible and being able to adapt is key to survival. However, don’t bend your way just to fit it, it doesn’t work as it may not fit the branding. I just had too many incidents where the grand plan didn’t work 100%…
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
Mindfulness, for the workplace and for the crypto industry.
I used to volunteer and teach mindfulness, and I did an academic discussion and experiment to demonstrate how mindfulness has improved people’s financial decisions.
I think the rapid changes and volatility in this market require people to stay calm, not just on loss, but I also see many people get too carried away with gains. During the $LUNA fiasco, I was saddened to see people commit suicide and the “nonsense” people talked about when they made a profit. It was so polarized, and I see the need for a more compassionate and mindful community.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them
Florence Pugh. She is the most inspiring woman in the entertainment industry. Her way of being herself is truly a beacon to me. Whenever I hesitate “Should I wear this? Am I not good enough?” I would just think: If Florence can do it, I can be confident to do and wear whatever I want!
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
Women Of The C-Suite: Rosalind Lee On The Five Things You Need To Succeed As A Senior Exe was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.