Robby Kwok, Chief of Staff to CEO @ Slack
Robby is the Chief of Staff to the CEO at Slack and was the former SVP of People who led a transition to remote work for the company. Robby’s career has spanned strategy and M&A at some of the biggest names in tech, including Yahoo, LinkedIn, and Twitter.
In this episode, we spoke with Robby about:
Succeeding as a leader who doesn’t like the spotlight
Recovering from an incident that almost derailed his career
The key role relationship building has played in his growth
… and so much more!
You can listen to him below or wherever else you get to your podcasts.
On developing Robby’s early motivation
After immigrating from Hong Kong at 10 and being put into a prestigious high school, Robby found himself in quite a competitive dynamic with his fellow students. “I think in my senior year 10 kids got into Stanford and Harvard. I think 40 or 50 people got into Berkley. Out of 400 total students, that’s a lot. I felt like I was pretty run of the pack. This was one of the factors that motivated me early on. That, and also being made fun of because I was that kid who couldn't speak English well. I had this sort of self-drive to improve and do better to improve myself to prove other people wrong.”
On finding his place at college
“I didn’t fit in too well in high school. Other students would mention pop culture references like Sesame Street or Brady Bunch, and I would have no idea what they meant. When I got to Berkley I fit right in because of the diversity of the school. I made it a point to have a wide variety of friends and not just hang out with the group of Asians that only spent time together. I found that useful because I knew in the real world I would need to connect with people from a diversity of cultures, races, genders, religions, and economic backgrounds. This served me well as I progressed in my life.”
When Robby began to sense the importance of relationships
“I worked for a guy named Andrew Braccia who was my boss at Yahoo for almost six years. He fundamentally changed how I would think about a boss-subordinate relationship. Before Yahoo, I was in investment banking and the Managing Director was treated like God, and then there was everybody else in between. When I started working with Andrew he was very senior at the time, but he treated me like I was really somebody. He got to know me as a person. I looked up to him not only as a boss, but as a leader, and as a human. The way he would make connections, not just with me, but with everybody around him, was the best I've ever seen.
2007 was the last time I worked for him but to this day he still sends me and my family a Christmas gift. Every Christmas. It’s now 14 years after I've worked for him and he’s never missed a year. To me, that's the gold standard. So whenever I work with people after that, I take the time to get to know them personally, check in on them, not just ask generic questions. Andrew was the one I modelled how to behave and build relationships.”
Robby’s reflections on the Yahoo Mafia
“The Yahoo mafia is super strong and I don't think it gets a lot of airtime, but that's okay. You've got folks like Andrew, who's a very successful VC at Accel and has invested in companies like Slack and Cloudera and a bunch of others. You have Jeff Weiner, who was a CEO at LinkedIn. Now Ryan Roslansky who is the current CEO at LinkedIn along with Rob Solomon the CEO of Go Fund Me. There are also executives who run successful Silicon Valley companies that have their roots at Yahoo.
These people are intelligent but carry with them a certain sense of humility. They're not seeking attention for attention's sake but are really trying to do well by others. They really try to be leaders that lift others up. When I talk about compassionate leaders who are also very competent and capable, and I think those are the kinds of people that I worked with at Yahoo.”
On working behind the scenes and not seeking the public spotlight
“I think it works for me, but it may not be the right thing for others. For me, what I've learned is it's more important to be who I am to be authentically. That accrues more success than if I'm doing something I think will just come off as fake. People have really good fake detectors. If I’m trying to say something or get credit, it's just going to come off as phoney. It's just not going to work. So the way I think about it is if I help enough people be successful, I’ll be successful.
The people I serve and help are people that will also look after me. They will also help me rise up and help my career, but I don't need to tell them every single achievement I've made or tell others every single thing I've done because I know that the people I help are the type of people that I want to associate myself with.
Like Jeff Weiner the former CEO of LinkedIn and Stewart who's the CEO at Slack. These are people that I've worked with before that I know are genuinely good people, who with the right moment at the right time, have helped me with my career.”
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Until next time,
Jay and Angie