WEBVTT 1 00:00:00.100 --> 00:00:16.640 [gentle music] Both the what, the why, and the how. Yeah. Hmm. I'm still thinking about the vibes at the dinner party. [laughs] Hey, friend. It's David Nebinsky, the community lead at the Chief of Staff Network. 2 00:00:16.680 --> 00:00:27.070 We help chiefs of staff through the three Cs, cohorts, curriculum, and community, via Slack with over 900 people in it. Learn more about our membership events and programs at chiefofstaff.network. 3 00:00:27.640 --> 00:00:37.780 You can also subscribe to our newsletter there to stay in touch as well. This episode of the Chief of Staff podcast is with Dara Chen. Dara is currently the chief of staff at Rad AI. 4 00:00:38.300 --> 00:00:40.080 She has prior chief of staff experience as well. 5 00:00:40.340 --> 00:00:54.660 In this episode, you'll learn about her chief of staff experiences, how she got her current role through networking, the importance of thinking about where you spike as a chief of staff, how a chief of staff helps shape a product, and the product being the company, and so much more. 6 00:00:55.000 --> 00:01:05.310 Excited for you to level up as a chief of staff. Here we go with Dara. Uh, Dara, welcome to the podcast. Thanks, David. Um, it's great to keep the conversation going from Chief of Staff Connect- Yes... 7 00:01:05.360 --> 00:01:14.610 just a couple of weeks ago to here in New York. I know you're visiting from Austin. Um, this is a part of, uh, just glad you're here. I know you used to live here in New York. Um, 8 00:01:15.600 --> 00:01:20.080 so yeah, uh- And thanks for having me at Chief of Staff Connect. I mean, it was so, 9 00:01:21.000 --> 00:01:36.090 so great to, you know, get the frameworks, also, like, learn, um, from some really senior executives and chiefs of staffs, you know, who were panelists, and it did workshops, and it was also just great to connect with people- Yeah... 10 00:01:36.130 --> 00:01:45.450 in person. Yeah. What do you think? Did anything, like, particularly really stand out? Uh, is there any, like, thing you really brought back to Rad or- Yeah, definitely. 11 00:01:45.540 --> 00:01:53.460 I mean, uh, the fact that it was so well organized, and you sent across all the slides and materials afterwards. I, I was really impressed. 12 00:01:53.980 --> 00:02:00.760 Um, I was also impressed by other chiefs of staffs who were attending, and they crowdsourced notes- [laughs]... [laughs] for everyone. 13 00:02:01.660 --> 00:02:14.720 And I was like, man, these chiefs of staffs really are the backbone and run a lot of organizations. And it's an honor to be part of- [laughs]... a community of these individuals who are just so on top of things. 14 00:02:14.880 --> 00:02:21.940 [laughs] Yeah. And yeah, and I got to meet with people and continue the conversation after, you know, the, the conference. 15 00:02:22.520 --> 00:02:30.140 Um, met up with some people over dinner and met up with some people- you know, they shared resources with me afterwards, and it's been, it's been great. 16 00:02:30.680 --> 00:02:45.250 I'm not gonna get, um, upset that I didn't get invited to that a- [laughs]... that other hangout, but, uh, we'll talk about that offline. [laughs] Um, no, just amazing to see. Um, uh, so you're at Rad AI. Mm-hmm. 17 00:02:45.380 --> 00:02:51.180 Um, and you've had another chief of staff role. Um, how did you get your current chief of staff role at Rad? Yeah. 18 00:02:51.340 --> 00:03:02.000 So, um, I think I get this question a little bit, uh, you know, pretty often of, like, how do we, how do I or someone else, um, get the chief of staff role? 19 00:03:02.080 --> 00:03:13.280 And, you know, I had the chief of staff role before, and the connection to Rad AI was actually through my network- Hmm... at Austin, through my, um, MBA Wharton alumni network. 20 00:03:13.540 --> 00:03:29.170 I, you know, kind of serendipitously met someone [laughs] in, at a networking event through Wharton at, in Austin. And it's those types of events also that just bring me s- like joy and serendipity- Mm-hmm... 21 00:03:29.170 --> 00:03:49.020 um, of what I really enjoy about, like, a big city, like a New York, SF, or Austin, is that there are events like this that bring together like-minded people that are hungry and ambitious and also just eager to learn and, and create, um, value for, for companies, communities, um, a- other people. 22 00:03:49.860 --> 00:04:02.640 And so I got this role because I had had the chief of staff role before, but also, um, funny enough, like before my first ever chief of staff role, it was really working as a chief of staff to the chief of staff to the CEO. 23 00:04:02.960 --> 00:04:12.620 [laughs] So I think there's many avenues to the chief of staff role. Yeah. You know? Yeah. And before that, it was a biz ops role, which is- Okay... very similar, if not adjacent. And this was at Dot? 24 00:04:13.260 --> 00:04:19.100 Um, this was at Dot Lab. Yeah. Yes. A 10-person biotech startup in- Yeah... women's healthcare. 25 00:04:19.220 --> 00:04:28.100 And, you know, I think it's funny that you guys have the Chief of Staff Network and the Biz Ops Network because they are very, I think- Hmm... 26 00:04:28.110 --> 00:04:39.400 um, you know, they probably build upon each other and complement each other- Yeah... if not, like, have a lot of overlapping similarities. Yeah. So at that networking event, like, what, like, did you... 27 00:04:39.460 --> 00:04:51.330 Like, how did it go down? Like, was it just, like, an off-the-cuff comment? Did someone say, like, "Hey, um, I know this company that's hiring"? Like, how... So- Well, that's the funny thing- Yeah... 28 00:04:51.430 --> 00:05:07.400 because they weren't hiring for a chief of staff at that time, and I, um, my friend who had connected me with Rad AI was already working at Rad AI, had come f- um, he was the class after me at, uh, Wharton, and he just, you know... 29 00:05:07.440 --> 00:05:15.830 We were talking about, like, what we were doing in, in Austin, what brought us here, and the fact that, um, he really loved the work that he was doing at Rad AI- Hmm... 30 00:05:15.840 --> 00:05:32.100 leading product, um, for this company that was really kind of building a, um, a very niche u- use case within Rad AI, but it was getting... uh, within radiology, and it was getting a lot of traction from customers. 31 00:05:32.870 --> 00:05:47.600 And then I was, um, already chief of staff at this restaurant SaaS company called Par, working for the GM of Punch, and I was kind of, like, itching for my next thing, um, and a little bit interested in something that was a little bit more fast-paced. 32 00:05:47.720 --> 00:05:54.480 I was, you know, chatting with him about, uh, I had done a startup before. I was kind of curious if I wanted to go back into startups- Mm-hmm... 33 00:05:54.510 --> 00:06:06.184 or go into something that was, you know, maybe a little bit larger and more mature. And then eventually we just kept in contact and theyI saw on LinkedIn that they were hiring for a chief of staff, and I called him up. 34 00:06:06.264 --> 00:06:17.604 I, I think I texted him and was like, "Hey, I noticed this LinkedIn post, and I'd love to chat with you about it." And he was like, "Yeah, send me your resume. Let's chat about it." Cool, cool, cool. 35 00:06:17.634 --> 00:06:32.124 And that was a year- That was almost two years ago. Yeah. Um, a year and a half ago. Yeah. Cool. Yeah. Um, obviously, AI's in the news a lot. Um, like, what's it like working at an AI company? 36 00:06:32.184 --> 00:06:42.764 Like, is there different skills, or, like, d- would you say, like, you're... Like, when you compare this chief of staff role versus your other ones, like, is there anything, like, different because it's an AI company? 37 00:06:42.844 --> 00:06:55.954 Yeah. So, I mean, this company is- We just crossed 100 people. I started when it was closer to, like, 70 people. Um, and the size of the company is very different from the- Yeah... 38 00:06:56.004 --> 00:07:00.444 the restaurant SaaS company I was at, which was th- in the thousands already. Oh, wow. 39 00:07:00.564 --> 00:07:14.914 Um, but it was similar in that the restaurant SaaS company was acquiring startups in the space, and, um, I had, my actually first f- couple of roles out of undergrad were related to data analytics. Yeah. 40 00:07:14.944 --> 00:07:27.614 So I was, uh, in data analytics consulting with Ernst & Young in New York for five years, roughly. Yeah. And so it was almost kind of full circle to be able to go back into AI- Mm... 41 00:07:27.844 --> 00:07:38.904 um, from a SaaS perspective, because I really wanted to move into SaaS, which I was able to do, um, after the biotech startup and move into restaurant SaaS. 42 00:07:39.424 --> 00:07:50.924 And then it was nice to go back into AI and healthcare because way back, uh, I, I think probably similarly as every Asian American probably goes through, I, I used to be pre-med back in undergrad. 43 00:07:51.264 --> 00:08:07.024 [laughs] You know, I, uh, yeah, I, I, I almost did, essentially, two years of that all the way to org chem, and then I kind of realized I wanna do business and think, um, think there's an opportunity to move to New York if I studied- Yeah... 44 00:08:07.044 --> 00:08:10.264 you know, business, uh- Was that something your parents wanted you to do, or? 45 00:08:10.584 --> 00:08:27.134 It was more of kind of, um, an interest area, because also I saw my friends' parents, who were in a better socioeconomic class, have that, you know, profession, and I was like, "Wow, that, maybe that would be, you know- Yeah... 46 00:08:27.144 --> 00:08:32.744 a great opportunity for me to, um, up-level, you know, my family's life." 47 00:08:33.844 --> 00:08:43.024 I think I'm glad that I am working in healthcare again because, you know, the skillsets you asked me, like, are, are they similar, are they- Yeah... different. 48 00:08:43.384 --> 00:08:55.914 I think the main thing for me is there's more alignment in terms of my passion and, um, and the experiences I've had. I've, you know, I've helped women give birth in Peru, um [laughs] Wow... 49 00:08:55.924 --> 00:09:03.854 when, when I used to be pre-med. I've volunteered in ER. And, and our AI product, AI product within, um, 50 00:09:04.784 --> 00:09:18.614 Rad AI is really focused on enabling physicians and radiologists currently be more productive, to be able to, um, have less burnout. Mm. Um, if you think about ER, especially ER trauma radiologists, 51 00:09:19.924 --> 00:09:31.974 they're going through hundreds of cases typically on a, a day, and our AI products help alleviate, if not make them more efficient and accurate, and it's personalized to their exact language- Mm... 52 00:09:32.044 --> 00:09:47.764 um, for the reports that they produce. And it helps them have less cognitive load and, and burnout. Um, it actually, our first product saves them an hour on an average nine-hour shift. So it's really meaningful to me. 53 00:09:47.864 --> 00:09:58.244 Um, and, and for me, that makes it, that makes it more enjoyable to get my day-to-day done. Yeah. And it also helps me relate to other people that I work with. 54 00:09:58.284 --> 00:10:14.194 S- we have, you know, some of the most incredible radiologist executives at our company. Um, these radiologists have started companies before that have successfully exited to getting acquired by Microsoft, um- Wow... 55 00:10:14.264 --> 00:10:22.404 essentially. Um, our co-founder's also the youngest radiologist in US history. [laughs] He, um, is just 56 00:10:23.724 --> 00:10:40.114 not only incredibly smart and, um, and inspiring, but also a very humble human who is- has the most generous heart. Yeah. And, um, and, and I really resonate with that, you know, type of culture a- and, um, 57 00:10:41.084 --> 00:10:54.294 an environment where it's really h- hungry, hardworking people who also want to help other people and collaborate and, um, bring up the best ideas. And for me, a lot of the chief of staff role is about- Mm... 58 00:10:54.294 --> 00:11:06.054 building relationships. Mm. Um, because, you know, as a chief of staff, you often don't have direct reports. Mm. And so it really is about helping augment the team- Yeah... 59 00:11:06.054 --> 00:11:15.344 the leadership team to kind of play at their best, um, play in their strengths, and also be the glue, kind of like be the assistant coach or coach- Mm... 60 00:11:15.424 --> 00:11:21.784 to the entire team and helping them get stuff, um, done so we all focus on, like, the right priorities. 61 00:11:21.904 --> 00:11:34.824 And, uh, a lot of that, like, a lot of the, um, ability for me to be effective is, is reliant on having and developing relationships with people. And is that, uh, or how do, how do you do that? 62 00:11:35.544 --> 00:11:43.184 Yeah, that's, that's the hard part, right? [laughs] That is, es- especially in a fully remote environment- Mm... which is, like, Rad AI. 63 00:11:43.724 --> 00:11:56.984 Um, and, you know, don't get me wrong, I love, I love the, the flexibility that a, um, a remote environment can bring, but at the same time, it becomes harder to develop those- Mm... 64 00:11:57.024 --> 00:12:10.626 long-lasting relationships because there's so much additional context that you can gather from people's body language, but also, like, getting to meet other people in person, um, I think-Creates bonds that are- Yeah... 65 00:12:10.676 --> 00:12:18.696 you know, very helpful for, like, a, a virtual setting. Are you reading my body language right now? [laughs] Okay, he's about to ask me this question. 66 00:12:18.956 --> 00:12:27.696 [laughs] And it, but it's, it's really like, oh, how engaged are they in these meetings? Mm. Right? And, like, if they're not engaged, uh, uh, I can pick that up easier- Mm... 67 00:12:28.576 --> 00:12:37.276 in, um, in meetings, and then I can have, like, one-on-one follow-up calls with them, you know, side c- well, not so much side conversations, but hallway conversations. Mm. I'm like, "Hey, you know, 68 00:12:38.496 --> 00:12:45.876 kinda got a sense that you weren't super engaged or you disagreed but you didn't wanna voice that in the meeting. Like, why is that?" You know? Oh, you say that kind of stuff? 69 00:12:45.886 --> 00:13:01.176 [laughs] Well, I, I try to, uh, bring that out because- Nice... I think eventually, you know, it, the, I see the, the role as only being effective if I can get buy-in from stakeholders- Mm... 70 00:13:01.186 --> 00:13:14.496 um, if I want to make a change in our planning process, if I want to make a change in, um, in our recruiting process, it is a lot about getting others to buy in to that process of, like... 71 00:13:14.536 --> 00:13:19.916 and also understanding, like, is this the right process? Um, because oftentimes I'm not an expert. 72 00:13:19.976 --> 00:13:30.926 For example, I took over the recruiting team for, you know, three months roughly, and, um, yeah, I'm not, I'm not a, you know- [laughs]... expert in recruiting. However, I am really good at 73 00:13:32.056 --> 00:13:43.756 structure and, and creating playbooks from scratch- Mm... for people, um, so that we can all play off the same sheet of music and we're not, like, this- Yeah... 74 00:13:43.776 --> 00:13:53.626 disjointed orchestra that, you know, the left side doesn't know what the right side is doing kind of a situation. I, I'd rather... you know, I'm trying to be the conductor. Mm. Um, and 75 00:13:54.756 --> 00:14:13.046 so with, you know, the recruiting process, it's, it's also about, since engineering and, and the product, uh, org is 60% of our organization, it was also about understanding where the pain points were for our engineering org and how I could be that person- Yeah... 76 00:14:13.096 --> 00:14:26.456 to really streamline it, make it more effective for everyone, and help the recruiting team also not be bottlenecked by having to think about that structure. 77 00:14:26.576 --> 00:14:46.676 Um, and instead, they could really, like, bring out the best ideas, and I could go and, um, create that and at the same time bring everyone on board, um, with this new process and streamline it using technology ideally to streamline it as well, um, and not just, like, throwing more bodies at problems. 78 00:14:48.476 --> 00:14:58.476 So when you took over the recruiting function, um, was that something that, like, an opportunity you saw, or did someone get buy... 79 00:14:58.496 --> 00:15:08.996 like, or did your principal or somebody else say, like, "Hey, Dara, we need you to take this over." Like, what, what was that like? Yeah. It was, um, it was a little bit of both. I could sense it, and then my CEO 80 00:15:10.656 --> 00:15:27.296 decided that it was neces- needed. Like, it was the right time for me to, um, start to kind of, like, not only dip my toes, but really take it over. Um, and also I think, too, like, I think some of the best, um, 81 00:15:28.576 --> 00:15:34.396 you know, ways to be a chief of staff is to also kind of spike in certain areas. Mm. 82 00:15:34.476 --> 00:15:44.576 Um, well, I think one of the things that I spike in is, is people and, um, and not only, like, developing those relationships, but also, like, caring about the culture and the people, 83 00:15:45.616 --> 00:16:03.256 getting a sense of, like, what are their, um, what are they working on and how can I ensure that the office of the CEO, the chief of staff also enables them to do their best work, and then also that we collectively help do Rad AI, uh, or help Rad AI do its best work. 84 00:16:03.296 --> 00:16:18.836 And so, um, people and culture and, like, you know, inspiring people to want to, uh, do stuff that is often behind the scenes, it is often unglamorous sometimes. [laughs] And, you know, it often is, um, 85 00:16:19.796 --> 00:16:35.546 stuff that is necessary, um, but it may not be their highest priority, right? Um, is it's hard work, it's a h- it's a lot of relationship and, um, and soft influence and inspiration. Mm. 86 00:16:35.556 --> 00:16:45.236 And I think because I had some of those qualities already and I, I think, you know, uh, my CEO, or mainly my principal, who's the CEO, 87 00:16:46.156 --> 00:16:55.636 saw that in me, also realized that I could be a good person to fill that gap in the, in the- Yeah... interim until, you know, I hired for that particular role. 88 00:16:56.136 --> 00:17:06.706 Um, he also recognized that I am quite tech savvy, and so they were going through this large back-end system of changing software, um, essentially their [clears throat] 89 00:17:07.156 --> 00:17:21.355 CRM, but for, um, for recruiting candidates, which is an ATS, applicant tracking system. So, you know, there was a, a huge transition. We were also hire... we had very aggressive hiring goals, the most aggressive ones. 90 00:17:21.886 --> 00:17:30.165 [laughs] Let's get Dara in here. We gotta hire. Let's go. [laughs] And, and it's not just about quantity, right? Mm. It's, it's quality too, and how do you measure quality? 91 00:17:30.276 --> 00:17:37.956 And w- in many ways, at a start of 70 people, we didn't have formal rubrics at that time to really assess that. 92 00:17:37.966 --> 00:17:49.396 And so creating that structure of like, okay, h- here's the ways that we are going to formally assess and create, um, rubrics or every single type of engineering hire that we were hiring for. 93 00:17:49.556 --> 00:17:57.976 It's, it's a lot of work, um, behind the scenes that to create and, and get the right hire for our team. Um, and, 94 00:17:58.896 --> 00:18:12.896 and not only, like, get the right hire, but also how do we, um, how do we ensure that they're successful f- in their first 60 to 90 days, right? Yeah. Like, the most crucial part, um, and creating the onboarding m-... 95 00:18:12.956 --> 00:18:26.556 pieces of, uh, of the workflow and, and making that playbook. So yeah, I, I think to your point, it was, it was definitely needed, um, because we were growing. 96 00:18:27.296 --> 00:18:40.756 And similarly, I think I, like, spiked in certain areas that my CEO knew I was, um, c- or had a sense of like, a gut feeling that I would be successful in that role. Um, and I think to your point about like how do you 97 00:18:41.796 --> 00:18:52.116 become a chief of staff? I, I think relationships and networking and then, and then, like, talking to other chiefs of staffs- Mm... about their role is very helpful. 98 00:18:52.196 --> 00:18:58.296 Um, to, to be honest, every chief of staff role is different at every single company, and even within companies. 99 00:18:58.316 --> 00:19:12.576 And so, like, the networks that, um, the chief of staff network brings, as well as the content that you help publish and, and bring to life is very helpful. Like this podcast episode. [laughs] Yeah, exactly. 100 00:19:12.586 --> 00:19:24.976 [laughs] It, it's really helpful probably for people because, you know, everyone has a different idea of the role and, and, um, and that can be challenging, n- you know- Mm... to navigate because the role evolves. 101 00:19:25.036 --> 00:19:35.906 It constantly evolves. Um, did I know I was going to be taking over the recruiting team when I took on the chief of staff role? No. [laughs] I had no idea. [laughs] Had no idea. Right? Like- No. Yeah. Yeah. 102 00:19:35.936 --> 00:19:40.616 I mean, when I was hi- I was hired, at that point I was, like, six months into the role. Okay. 103 00:19:41.156 --> 00:19:51.796 Did not know I was gonna take on the recruiting team, but I did because, like, I already naturally spiked in a couple areas that made it a good fit and the right, the right timing. Um, and so... 104 00:19:51.816 --> 00:20:06.686 And then afterwards, when new team members are coming on board, um, it's also useful at, like, every quarter, uh, um, or so often to refresh everyone on, like, the priorities for the chief of staff. 105 00:20:06.746 --> 00:20:19.926 And now, now for example, I'm, I'm working on strategic planning for the leadership team as well as, like, the entire, you know, company for 2025. Um, that to me is more, like, biz ops. Mm. Like, typical biz ops. 106 00:20:19.976 --> 00:20:24.196 Like, um, quarterly annual planning, KPIs, board decks. 107 00:20:24.396 --> 00:20:34.836 That stuff is, like, almost, you know, pretty much generally you will always own as a chief of staff in my, in my mind, unless you have a dedicated biz ops person- Mm... which is a little bit rare. 108 00:20:35.536 --> 00:20:48.296 Um, but that stuff is, like, pretty standard or c- like, more, um, more common. The other, like, special projects is stuff that will evolve over time. Yeah. 109 00:20:50.176 --> 00:21:06.656 So what I'm also kinda hearing here is, like, this kind of, like, powerful skill set related to, like, people and getting buy-in, but also being very tech savvy. Uh- Yeah, yeah. Um, tech savvy. I'm also... 110 00:21:07.246 --> 00:21:22.176 It's funny 'cause the, um... You know, when you were kind of, like... We've been on a couple of meetings together and, and, um, there's been, you know, uh, some... 111 00:21:22.216 --> 00:21:35.506 And, and I've mentioned this on other, um, other panels as well is, like, it's helpful if you do spike in certain things. And I think because you're often a generalist, and, like, as a generalist, that's useful. 112 00:21:35.565 --> 00:21:47.866 Like, it's useful to be able to dive into s- a certain area and, um, be the, you know, the person who learns really quickly and ramps up and then, like, delivers it in a nice package for some, for someone- Yeah... 113 00:21:47.896 --> 00:22:01.116 more longer term to carry on. But also ideally identifying and knowing, like, what you spike in is helpful because that gives people a framework of, like, um, knowing other projects that you'll be successful in. 114 00:22:01.556 --> 00:22:12.836 And so it's, for me I think it's, you know, people. I think the other piece of it is, like, using technology to i- ideally be more efficient. Um, and it's not only using technology. 115 00:22:12.896 --> 00:22:29.276 It's really about, uh, in my mind, like, technology and information because information- Mm... is often the, the currency and the, like, um... It's how we create alignment across the company, which- Mm... 116 00:22:29.336 --> 00:22:37.656 means if we can create better alignment, then we are tackling the right problems with the right team and resources, um, to achieve our goals. 117 00:22:37.856 --> 00:22:52.006 And that makes us, that's, that's, like, our, you know, part of our secret sauce. Um, I think the other aspect of, like, things that I'm, like, good at or great at, um, it's- Yeah, great. Yeah. [laughs] Yeah, yeah, yeah. 118 00:22:52.006 --> 00:22:59.166 Yeah, let's... Yeah, exactly. Let's, let's- Great at... own that. Yeah. Yeah. It's- Let's celebrate that. So at two companies- Yeah... 119 00:22:59.166 --> 00:23:09.216 in, in both the chief of staff roles, I've been called, uh, the most organized person in the, in the entire company. Wow, okay. And this is sometimes thousands of people. [laughs] Wow. And I... 120 00:23:09.276 --> 00:23:20.576 Like, that is mind-boggling to me because, [laughs] 'cause my husband, it's so funny, my husband at home is like, "I can't believe that because you are not [laughs] at home." Like, it's, it's a bit... 121 00:23:20.696 --> 00:23:32.556 Sometimes I'm like, "Yeah, we need to get a cleaner." [laughs] Like, you know? Like, I, I just don't have time. [laughs] Um, and so it's funny to be called the most organized person at a company because I, like... 122 00:23:32.596 --> 00:23:46.946 And even in consulting, I know that I'm, like, I... Organization is a little bit of my love language. And I, I struggle with that, um, compliment a bit because- Mm... twofold, right? 123 00:23:47.116 --> 00:24:02.816 I think there's this conception that people who are organized and detail-oriented don't make big-picture strategic thinkers. Mm. And I would say to some extent, yes, I prefer more the details. 124 00:24:02.916 --> 00:24:19.950 However, at the same time, I think-I'm, m- you know, the strategic arm, the, the, the, um, the focus on outcomes versus process, to me, is also very important, and I'm, I'm learning to be better, um, and more outcome-oriented. 125 00:24:20.020 --> 00:24:34.060 However, the organization piece is, is still really important to me because oftentimes, like the big strategic thinkers, um, are usually, right, in the CEO, like, um, C-suite arena. 126 00:24:34.090 --> 00:24:42.190 And oftentimes you need them to play in that space. You need them to play and focus on, like, why are we doing things? Um, what are the outcomes and the objectives? 127 00:24:42.260 --> 00:24:51.250 And then ideally you need a strong how person- Mm-hmm... like a process-oriented, detailed person to complement that, um, big strategic thinker. 128 00:24:51.700 --> 00:24:57.690 And that's, that's like the best kind of duo to tackle and, and elevate the entire company, right? 129 00:24:58.110 --> 00:25:10.080 And so oftentimes I do see like the chief of staff role, and oftentimes the chief of staff role, like one of the requirements to be a, a great chief of staff, um, can be, you know, the organization piece. 130 00:25:10.440 --> 00:25:31.680 But ideally, I think over time you are delegating more of that to other people on the team, whether that is executive administrators, whether that is, um, more senior, uh, you know, or slightly like junior strategy and ops professionals that can support the chief of staff and the office of the CEO. 131 00:25:31.700 --> 00:25:43.060 Like oftentimes at these large, um, corporations with the chief of staff structure, these chiefs of staffs have mini chiefs of staffs, right? [laughs] I was one of them. Yeah. I was one of them, [laughs] right? Yeah. 132 00:25:44.080 --> 00:25:57.700 Yeah. Um, and that is the way that, you know, the chief of staff can often elevate themselves into more of the big picture thought partner, uh, strategic advisor to the CEO. 133 00:25:58.000 --> 00:26:11.530 Um, that, that's oftentimes how I see it play out. And I also think there's a misconception of like, oh, well, why, you know, why are we, you know... Is it useful for, for, um, someone to be organized? 134 00:26:11.580 --> 00:26:21.080 And then, you know, well, like, oh, it creates a lot of work for people, you know, 'cause they have to like ha- make sure information is stored in the right places- Yeah... and make it accessible. Yeah. 135 00:26:21.109 --> 00:26:32.360 Like, why do we have to do that? It's, like inefficient to be so organized. Yeah. Yeah. Right. Um, and I, I would say ideally at some point AI automates that. I would love that. [laughs] Right? 136 00:26:32.460 --> 00:26:35.580 So I- I wonder who's thinking about that. [laughs] I would love that. 137 00:26:35.720 --> 00:26:53.900 Um, I think that's also why some of the AI companies, um, not that this is meant to like sponsor them, but, you know, so there are often, you know, AI companies that are coming on board that can create those connections between Slack, G Suite, and Notion, and elevate, you know, access to those documents. 138 00:26:54.080 --> 00:27:00.859 Um, but first of all, they have to be written down. So who's writing them down, right? [laughs] The documentation piece. 139 00:27:01.540 --> 00:27:11.079 [laughs] Uh, but, but, you know, hopefully at some point we'll all just be connected to, uh, to computer chips, and then our thoughts will be seamlessly integrated [laughs] into- That's what you want? 140 00:27:11.100 --> 00:27:22.280 [laughs] I mean, that would, that... Eventually, I think we will get there. Yeah. Mm. Um, I mean, you know, Elon Musk's Neuralink company is one that is working on that. I, I think- Would that make your role easier? 141 00:27:25.780 --> 00:27:39.020 I, I definitely think it would help. Um, it would be interesting to know what gets sent to the computer and what doesn't- [laughs]... and how you would, uh, control for that. [laughs] Um, [clears throat] 142 00:27:39.080 --> 00:27:47.900 but, you know, uh, that's a problem for, for Neuralink and Elon to ta- tackle. I think, um, I think though in the meantime, you know, while we're not con- 143 00:27:48.820 --> 00:28:02.740 connected to, to computers, yeah, it is, it is work, but it's also, it's culture. Um, and, and it's... Like, is culture strategic is then like the next question. Mm. 144 00:28:02.750 --> 00:28:12.300 Um, is culture a strategic investment of the company and the leadership team? Because, you know, for me, organization and q- organization, like, is- Strategic... 145 00:28:12.380 --> 00:28:28.820 it's, it's strategic, but it's strategic because it's about culture, and culture is like the type of, uh, it's like the type of people you want to have at a, um, at a, you know, a dinner party. 146 00:28:28.880 --> 00:28:41.460 It's, it's like the vibes that you're trying to- Yeah... um, cultivate at your home, right? And, um, and or at this dinner party. And let's just like play this thought experiment out loud a little bit. 147 00:28:41.540 --> 00:28:55.060 Like [clears throat] is your home, um, you know, and is your dinner party more of this like modern, sleek, kind of like, you know, minimalist, uh, type of vibe, 148 00:28:55.980 --> 00:29:11.400 uh, where things are, you know, organized and neatly put away and, um, and you're inviting people to come participate in, you know, like a, a, a beautiful kind of like sh- charcuterie board that you've put together? 149 00:29:11.420 --> 00:29:22.900 But, but all of that takes time, right? Or is it more of like a last-minute house party at a college dorm? Yeah. Right? [laughs] Um- And it has that frenetic energy. Yeah. Like, yeah, yeah. Yeah. Uh, right? 150 00:29:23.030 --> 00:29:35.280 And, and those are two very different vibes and two very different cultures and, and both are, um, both are not better than the other. Yeah. They're just, they're just different. 151 00:29:35.290 --> 00:29:44.200 [clears throat] And one could be better for a certain stage of a company than the other. Um, right? And, and you can have so many different... 152 00:29:44.260 --> 00:29:59.400 Like you could have, um, you know, uh, uh, so many different types of houses and- Yeah... or dinner parties, right? A- and they can be at old Victorian homes, right? Mm. Um, with a lot of trinkets and knick-knacks. 153 00:29:59.540 --> 00:30:12.040 Um, and, and, and they're like fully displayed, right? Um, or they could be at, you know, uh, like a warehouse. Yeah. Um, [laughs] right? Yeah. Uh, w- with, you know, maybe you're just moving in. 154 00:30:12.080 --> 00:30:16.328 Anyways, so-I, I think culture is, um, 155 00:30:17.408 --> 00:30:33.268 strategic, especially in the earlier stages of a company because the f- the culture that you build at a ten-person company is going to help attract and bring on board the next a hundred people. 156 00:30:33.298 --> 00:30:47.448 And then the culture that [clears throat] you r- um, you know, you cultivate at that hundred-person startup is then going to bring on the next thousand, two thousand, so on and so forth, right? And, um, and 157 00:30:48.648 --> 00:30:56.328 ideally there is, you know, naturally, I think, more process and structure in, in place- Yeah... um, the bigger you, you grow, right? 158 00:30:56.468 --> 00:31:07.808 Like for example, a college dorm party, uh, or [chuckles] dinner party, there's only one bathroom. But when you get to like a thousand people and, um, you know, you're at a warehouse, 159 00:31:08.748 --> 00:31:21.488 y- you ideally have a map so people know where [chuckles] - Yeah... where the bathrooms are, or you make it a- accessible, right? So that they can't miss it. Um, and, and that is also how I kind of see information. 160 00:31:21.548 --> 00:31:33.468 Information is about how do you get people to go to the right places that you need them to be in, um, at a particular point in the company's trajectory. 161 00:31:34.548 --> 00:31:45.828 Um, and that could be we need to really focus on, um, rebuilding the roof over in this part of the, you know, the house, and we have to all get people aligned there. 162 00:31:45.848 --> 00:31:57.708 But we also need to make sure like the garage and the cars work, right? Yeah. And that our, our kids are taken care of. Um, and so we, we still need people in those areas as well. 163 00:31:57.918 --> 00:32:10.328 [clears throat] And anyways, I, I like being and playing at, at that, um, level of like trying to think of the organization. Yeah. Um, and I think I was on a panel, 164 00:32:11.568 --> 00:32:25.948 um, for SF Tech Week, and someone in the audience asked a great question, which was, you know, "Oh, the, you know, I, I see a lot of similarities between product management and the chief of staff role, because, and as a product manager you often don't have direct reports. 165 00:32:25.958 --> 00:32:36.228 So what's the difference between like product management- Mm... and the chief of staff role?" And, uh, my answer to that was the, the product that the chief of staff is working on is oftentimes... 166 00:32:36.268 --> 00:32:48.668 And it- it's not just the chief of staff, it's oftentimes the office of the CEO. The product that the CEO, the chief of staff, you know, the office of the CEO is working on is the company. It's thinking about- Mm... 167 00:32:50.368 --> 00:32:54.668 do we have the right people working on the right things at the right time? 168 00:32:54.828 --> 00:33:08.488 And, um, you know, fe- our feature sets are like the people, the culture, the, uh, the priorities that we're trying to, to plan out for the next year. And, and then it's also like, how are we doing that? 169 00:33:08.948 --> 00:33:16.448 Um, it's like both the what, the why and the how. Yeah. Hmm. I'm still thinking about the vibes of the dinner party. 170 00:33:18.387 --> 00:33:33.088 [laughs] Uh, hopefully the vibes of this podcast are, are on, uh, are good for people that are listening. Um, if you've got feedback on the vibes of the podcast, let us know. Um, okay, so wow, that's fascinating. 171 00:33:33.288 --> 00:33:41.788 And how do you think about, or like what, are there any other chief of staff hot takes or, you know, obviously you've been in this role for a little while. 172 00:33:42.168 --> 00:33:55.728 Um, yeah, anything else that you really wanna share to kind of current or aspiring chiefs of staff? I mean, I guess, um, more like tips [clears throat] and probably not hot takes. 173 00:33:55.988 --> 00:34:06.768 Um, but yeah, my, I mean, to summarize, right? Like my first hot take is like organization and detail isn't strategic. I think it actually is strategic from a culture spe- perspective. 174 00:34:06.888 --> 00:34:15.688 Um, and that trickles down a lot from the top. The other, I think, tip and/or hot take maybe, um, is 175 00:34:17.308 --> 00:34:32.547 it's oftentimes necessary to have someone focused on the why, and usually that's the principle, right? Like the big strategic thinking is oftentimes in like the, the CEO's brain and, and, uh, vision. 176 00:34:32.607 --> 00:34:44.248 And that needs to be, um, both communicated well and also needs to stem from like the, the top. Um, but then also the how. 177 00:34:44.288 --> 00:34:56.918 We ne- you need someone to really focus on, on, uh, being the detailed person and focused on like bringing it to life [clears throat] in a way that elevates everyone else and also inspires- [laughs]... 178 00:34:56.918 --> 00:35:06.708 and is enjoyable, which is [laughs] often harder to do- Yeah... than like, you know, um, just winging it. And then I guess my other tip is it's, it's a whole team. 179 00:35:06.968 --> 00:35:20.348 Um, it's not, it's very rarely, unless you're like small Series A, Series B. But like, I would say once you get to that a hundred person stage where we are, it's often like 180 00:35:22.088 --> 00:35:36.638 three or more people in this office of the CEO type of function. Um, [clears throat] and even before then, you know, I think some of the most successful startups, and oftentimes why VCs, um, invest in, um, 181 00:35:37.668 --> 00:35:46.388 startups that have more than one founder is because the founder role, the CEO role is, is really hard. It's really hard to do it- Mm... alone. And, and you need a whole team. 182 00:35:46.468 --> 00:35:57.138 And, um, I would say invest in the relationships within the leadership team, but also the EA relationship. Mm. The executive administrator, like those EAs are also leaders in their own rights- Mm... 183 00:35:57.148 --> 00:36:09.708 because they see so much behind the scenes. And I, I would highly recommend like people invest in those relationships, um, because it really is a team sport. Anything else you wanna share? That, that's about it. 184 00:36:09.858 --> 00:36:16.928 [laughs] And we're gonna have to throw a dinner party [laughs] somehow. I'm in. I'm in. Yeah. We'll see if our friends from Connect are still in as well. 185 00:36:16.968 --> 00:36:27.898 [laughs] Um, speaking of information, um, if people wanna find you, they can find you on LinkedIn? Yeah, definitely. Cool. Uh, well, Dara, thank you so much. This has been so fun. This was really fun, David. Thanks. 186 00:36:27.898 --> 00:36:27.968 Thanks. 187 00:36:30.708 --> 00:36:50.308 [outro music]