Cathy Rong - Chief of Staff for Questlove

Cathy · 0:00

Hi, this is Cathy Rong from New York. I am Questlove's Chief of Staff, and the quote of today is, Leadership is an action, not a position.

Speaker 2 · 0:11

Thank you The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.

Jeremy · 0:25

Thank you Are you tasked with ordering food for your office? Let me tell you about Easy Cater. With over 100,000 restaurants to choose from nationwide and 24-7 customer support, Easy Cater helps assistants like you and me succeed at work and makes our lives easier. Visit easycater.com/leaderassistant to find out more. Hey friends, welcome to The Leader Assistant Podcast. I'm very excited to be speaking again with Cathy Rong. Cathy is in New York City. She's Chief of Staff for Questlove, and we'll hear a little bit more about that here in a minute. But you may recognize the name Cathy Rong, and that's because I spoke with Cathy in episode 117. That was a little while ago. We are now on episode 248, but just so that you can get the background of Cathy and a little bit more of her history, we won't get into as much today. You can check out the first conversation at leaderassistant.com/117, leaderassistant.com/117. Again, that is episode 117, and that was my first conversation with Cathy. Cathy, welcome back to the show.

Cathy · 2:00

Thanks for having me back, Jeremy.

Jeremy · 2:02

Super excited. Last time we spoke, your title was Lead Executive Assistant, and you worked at Complex Network, and now your title is different. It's Chief of Staff and you work for Questlove. For those who don't know, could you just give us a quick summary of who Questlove is?

Cathy · 2:31

Yes. Oh my gosh. I can be trained for this. Questlove is an Oscar Award-winning director last year of Summer of Soul. He is also the frontman and creative musical director of The Roots on The Tonight Show with Jimmy Fallon. Aside from his daytime gig, he also tours with The Roots as well as DJ. He is an author. He is a philanthropist and has a podcast and also does food investments. Really spans the different industries in terms of what he's involved in.

Jeremy · 3:15

Nice, nice. And so tell us a little bit about how you ended up here. So, you know, like I said, in episode 117 we talked and you had a role, a lead executive assistant role. Tell us, catch us up on what's happened over the last, I don't know, what has it been a couple of years now?

Cathy · 3:34

Yeah, I think it's been almost two years. And when I spoke to you last, I think I was in the midst of working on improving kind of operational efficiency within the company. And at that time we were kind of 300 employees. And shortly thereafter, maybe, you know, three months or so we were acquired by BuzzFeed. So a lot of the operations kind of changed the structure and whatnot. But for a long time leading up to that acquisition, I had already been thinking about my next move and switching roles. And I realized that, you know, having worked with brands my entire career so far, I would have really liked to work on the talent side. And so I started considering entertainment a lot more seriously, and specifically a Chief of Staff role within entertainment, which was a very difficult notion because it wasn't really a title that existed within entertainment. Like Chief of Staff is more government or finance or pharma. And so I was perfectly fine with the idea of having to start over again on the internship level because I didn't know anyone in entertainment. But I also really believe in the idea of manifesting. So it took a couple months, but I think it did work out. And for those months, I told everyone that I ran into, that I knew that I was looking for a Chief of Staff position within entertainment. And I think someone just got sick of listening to me and sent my resume out. And turns out that this actor's old assistants started a recruiting agency specifically for Hollywood Entertainment and they had hunted me from Complex. And also really speaks to the value of interviewing for the boss and not the job that I spoke to on the last episode because my boss at Complex was actually the one who calls and made the swaying factor of Questlove hiring me over the one other last candidate. Yeah. So a big shift in title, responsibility, environment, salary. So basically starting over in a whole new industry.

Jeremy · 6:17

That's great. So how long now has it been then since you've been in this role?

Cathy · 6:23

It's been, I think it'll be two years and a month.

Jeremy · 6:27

So, okay, awesome. What's been the craziest thing that's happened during the two years so far?

Cathy · 6:38

Well, I started, I think, last January and immediately it was like all hands on deck into award season and I think two months or so after I started, like he won an Oscar, which I did not think I'd be at the Oscars. I did not think that I would be supporting someone who was at that level so soon. I think I went maybe like zero to 150, like super fast and I was telling my friend the other day, I think the first four months into the job, I think I blacked out. I don't really remember anything. So much going on, but being at the Oscars was pretty cool. Definitely a flashbulb memory for me.

Jeremy · 7:29

That's funny. It's like you say you blacked out. It's like when people ask me, what were the first few months of your son being born? I'm like, I don't know. I don't remember. I don't remember what it was like. My wife and I were zombies. We were just trying to survive, so that's what I thought of when you said. There we are. Yeah. Well, that's awesome. So you shared a few topics that you'd like to chat about today, which is awesome. I know last time we talked about OKRs and you had implemented OKRs at your company and leading a team of assistants. So it's obviously a different environment. So tell us a little bit about the shifts. So for example, how many employees were your last organization versus now and what was it like leaving the corporate environment? What's been maybe the biggest changes?

Cathy · 8:33

Yeah. I mean, it was just a completely different environment that I was coming into that I had no previous experience in. And so the corporate world, although it was on the smaller side with 300 employees, it was still very corporate. And now I not only day-to-day manage Questlove himself, but I also manage his professional and personal staff of 20, as well as some of his business partnerships and things like that. So in that sense, like this role is very solitary in that you're the only, I'm the only one who is doing the same job function and also like managing others and managing up as well. There's not too much of like a traditional HR structure. So a lot of the things, it's like I've had to make operations, processes, and kind of implement them, which already is really hard coming into a new environment and being like, okay, we're going to change everything that we're doing and the way that it's done. So that took a couple of months to get rolling.

Jeremy · 9:54

Yeah. So what's the hardest thing about being in a smaller team and navigating your new role?

Cathy · 10:07

I think it's kind of the lack of support and community. I mean, the team itself, obviously there is community and support, but I think to you as an individual and for your particular job function, I found that it was really hard to make connections in this particular role. Like when I was in corporate, there was the other assistants you could ask, like, hey, how does this expense work? Or if you were in an employee resource. Group, you could talk about maybe the recent world events, but in this role, one, there's not too many boundaries between work and life. I don't have a Slack, it's all text message. So that one is kind of blurry. But two, if you're feeling you need support, community, it's up to you to build that yourself. So one of the ways that I have tried tackling that initially was to network with other celebrity assistants. So being at The Tonight Show with Questlove, a lot of the guests that come in, they'll bring their manager or their assistant, and I'm able to make connections that way. And that was the first year. And now I've started a celebrity assistant group called Assistance Anonymous just to kind of address this community and support issue. So it's a place that we can ask for advice like, hey, I need like a male makeup artist, or even like tips on how to negotiate your salary, because there's not really any salary transparency in this particular industry.

Jeremy · 12:04

Yeah. So you said Assistance Anonymous. So is it like an anonymous group that can share without like they're literally anonymous in the group or does that make sense?

Cathy · 12:18

I think more so anonymous. Well, my fiance came up with the title. So it's kind of like we have monthly dinners and get together. So it's like, oh, we're going to AA.

Jeremy · 12:30

I see. I get you.

Cathy · 12:32

But also anonymous in the way that like, not a lot of people notice us and a lot of decisions that we may kind of like, not like around the world, but like we're anonymous. You don't really know that decisions and what we're doing or like, hey, you hear about this great party in the news where all these celebrities are at. It's like, hey, I planned that, but no one knows, because I'm anonymous.

Jeremy · 13:01

Okay, cool. Love it. Are you literally at the Tonight Show or with Questlove all the time, or do you kind of schedule different meetups and stuff around those shows, or kind of give us a little bit of the day-to-day on what all are you trying to manage?

Cathy · 13:28

I think every role is different, but for me, I've kind of been able to carve out my responsibilities coming in because I am the first Chief of Staff on this particular team. The first six months, I tried to show up and be with Questlove for basically every engagement that he had. That was like being at the show five days a week, Monday through Friday, and traveling with him, and all the different areas of his commitments. Now, I am able to pick and choose when I go into the Tonight Show because he has a very robust support system there, and I have assistance at NBC that I can lean on. Also, he's been doing it for 10 plus years before I even came in the picture, so he's a little autonomous when it comes to over there. It's more so seeing where I'm needed, because I also don't really like to micromanage. Then in all the other areas, I do travel with him as his day-to-day as needed, and that's the majority of his trips that aren't as an active touring musician or DJ, so a lot of his book or speaking or public appearances, for example.

Jeremy · 14:58

Then talk a little bit about, if you wouldn't mind, the difference between an EA and the Chief of Staff. I know there's a lot of talk about being a Chief of Staff and a lot of talk in an EA space about, hey, if you want to level up, Chief of Staff is a natural progression in your career. What would you say are the biggest one or two differences between your prior EA role and your current Chief of Staff role?

Cathy · 15:28

I think it's hard to say outright because it is two different industries. But in corporate, when I was advocating for myself to transition from an EA to Chief of Staff and kind of landed in the middle with like a lead executive assistant position, the main responsibilities that I felt made the biggest difference was leaning more in the realm of operations. So it's beyond expenses, it's beyond calendaring. It's like, hey, I noticed this team is not using its time very well or communicating very well with this other department, and here's what I can do to help alleviate that. And I think specific to the entertainment industry, when you're supporting talent or a principal entrepreneur, for example, it's the difference between running errands and looking after the house and family stuff to like, hey, I'm going to try and negotiate this business deal for you, or I am having oversight into photo approvals of him that outlets are going to use and taking the lead on the different moving parts of like, I can recognize, hey, this is when I need to loop in his publicist or like, the appropriate point of contact for the different things that he's doing.

Jeremy · 17:10

Yeah, that makes a lot of sense. Well, let's talk a little bit about the advocating for yourself in the smaller team. You know, we had talked about that last time when it came to, you know, the more like you said, the more corporate environment. But what would you say would be a good tip for those listening who are trying to advocate for themselves?

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Cathy · 18:22

I feel like people often undervalue how important it is to talk to your peers or reach out to other people, even, and ask for advice or ask for their own experiences. When I was negotiating my salary, for example, I wasn't sure of the range and what was appropriate, and also what more I could ask for. So, like, we're out the gate starting a new job. The most important thing you can do before even starting the job is advocating for yourself in terms of the salary, in terms of signing a document even. So when I spoke to my peers in the industry, one of the best advice I got was if they're not able to match your base salary, you can ask for a guaranteed minimum bonus, ask for a wellness stipend to have your gym or therapy or anything like that paid. That was super helpful because from corporate, I would never be able to get my company to pay for my gym, but it was a completely different realm. So that was super helpful.

Jeremy · 19:39

So specifically on that front then, salary and compensation and all the different levers that you can pull. What are some tips for those that are currently negotiating or have an offer or looking for another role and they're trying to figure out how much they should ask for?

Cathy · 20:02

Well, again, I think that you definitely should talk to your peers and not be afraid to ask because like, you know, what's the harm in asking? You just find out that your friends are girls, girls, and they'll let you know. Otherwise, just find out they're not and you're just going to have to deal with that. But definitely ask and also like definitely counter even like you never want to get a offer and just accept it immediately. Even if it's the number that you ask for, you should always ask for more because it's harder to get your base salary raised during review. It's easier just to go and hire and be happy with that for two years at least.

Jeremy · 20:48

Right. That's good advice. Cool. Well, you know, I actually just had the opportunity to take my family to New York City. And so I wanted to ask kind of a separate, maybe more personal tip question. If someone's visiting New York City, what are the what's the top two things they need to do?

Cathy · 21:12

Top two things. I will. I definitely think Broadway, if you can fit it in. I think like the quality of the shows out here is just amazing. And there's great programming going on this season. And it's very New York. If it's winter, I think you really can't miss all the little winter markets and like the ice skating and Central Park. The art museums. But I definitely do think it's a great experience, for example, to go see The Tonight Show with Jimmy Fallon or any of the show tapings. And those are my top level recommendations.

Jeremy · 21:56

Yeah, that's awesome. I actually, you know, I have a funny quick side story about A Tonight Show. I was actually in LA long, long time ago. And we were like, oh, let's try to let's try to get on one of the let's get in line for one of the, you know, the show tapings. And it was, let's see, Jay Leno, I think, at the time. And we get we get in line and there's this really long line. And I guess they were just giving them out to first come, first serve. And we're in line and it gets to the point where we're like, yeah, there's no way we're going to make it in. There's there's a lot of people in front and whatever. And somebody that works for the show is walking around. They're they're walking down and they kind of it looked like they were about to shut us down and say, yeah, sorry, we don't have any more tickets. And they look at me and I'm decked out. Of course, I'm, you know, a huge Kansas City sports fan. So I've got my Kansas City Royals hat on and my Kansas City Royals shirt on. And the guy looks at me and, you know, he's got his little pass, you know, VIP pass or whatever. And he's like, hey, you guys Royals fans? And like, yeah, he's like, oh, I'm from Kansas City. You know, again, we're in LA. We're waiting for the Jay Leno show or whatever. Because I'm from Kansas City. He's like, how many of our how many are you are with your group? And I was like, oh, there's four of us, you know. He's like, well, come with me. He literally brings us into the show, gives us the last four seats at the very top back row.

Cathy · 23:38

Yeah.

Jeremy · 23:40

And he's like, oh, you know, I just I'm a Royals fan. And I thought, you know, I got to give it to a fellow Royals fan. So anyway, I got into the Jay Leno show because because I was decked out of my Kansas City Royals baseball gear. So anyway, that was fun, though. Yeah. It was like it was it was a cool experience. I mean, it was like, oh, these I think Cheech and Chong or one of them were on the show. And then they had like a live band afterwards. So anyway, it was a fun time. I'm sure you've had to have people ask like, oh, you know, can you get me a ticket to come to see the taping and stuff like that? Do you have to deal with a lot of that with working for some someone like this that's that's well known celebrity? Have you have you had to guard your your social connections a little bit?

Cathy · 24:34

Yeah, definitely. And, you know, not just limited to the show, also like concerts and just general access, really. I think people see things and, you know, their interest is peaked. And so that I think also speaks to a lot of people coming out of COVID and just kind of reassessing their friend circles. And also with, you know, recent events is just reassessing everything, really. And that's one of the areas. But, you know, I feel like I can read people pretty well.

Jeremy · 25:08

Yeah. Yeah, it's definitely a skill that us EAs and, you know, Chiefs of Staff have to really... Well, we figured out pretty quickly. We figured out pretty quickly. No, for sure. Awesome, Cathy. Well, thanks again for being on the show for the second time. What's kind of maybe your parting words that you'd like to share with assistants all over the world, listening, maybe some words of wisdom, maybe a productivity tip, whatever you want. What would you like to say to everyone as we wrap up?

Cathy · 25:48

I would just say, like, don't sleep on the power of manifesting, and you got to believe in yourself first if you want anyone else to believe in you. And also, lay out your gym outfit the night before.

Jeremy · 26:07

That's deep right there. That's deep. That's a good tip. Awesome. Well, where is the best place for people to reach out to you if they want to say hi?

Cathy · 26:17

LinkedIn. You can find me on LinkedIn. And also, you can hit my Instagram DMs, but we will see about that.

Jeremy · 26:29

You're like, you can appropriately hit my Instagram DMs.

Cathy · 26:33

Like professionally.

Jeremy · 26:34

Professionally. Exactly. Exactly. Cool, Cathy. Well, I'll put those links in the show notes at leaderassistant.com/248, leaderassistant.com/248. And thanks again for being on the show. Best of luck to you. I love to follow. I've done this is episode 248, so I've done a lot of interviews, a lot of conversations over the last few years. And it's fun to see the progression of people that I've interviewed like you a couple of years ago, where you've come in your career. And I'm looking forward to maybe doing another round in a couple of years.

Cathy · 27:12

I'll see you then. Thank you, Jeremy.

Speaker 2 · 27:24

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