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[upbeat music] Hey friend, it's David Nebinski, the community lead here at the Chief of Staff Network.

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We help chief of staff through the three Cs, cohorts, curriculum, and community via Slack with over 900 people in it. Can learn more about membership, events, and courses at chiefofstaff.network.

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There you can see our upcoming in-person events and our Chief of Staff Connect conferences in New York in October and London in November. This episode of the Chief of Staff Podcast is with Charlene Gariba.

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She's the executive chief of staff at Coverdash. Before Coverdash, she had operating experience and also was an investor at Layer Hippo.

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In this episode, you'll learn about how she got her chief of staff role, tips on navigating conflict, and so much more. Excited for you to level up as a chief of staff. Here we go, Charlene.

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All right, chief of staff role. Mm-hmm. How'd you get it? Yes, great question. So before I was a chief of staff- Yeah... I was an early-stage VC here in New York, and I was an operator before that. Yeah.

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And so I knew I wanted to return back into operating, and I felt like chief of staff would be a good reset 'cause it'd been a few years since I had operated.

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And so I hit up my friends in VC just asking, "Hey, do you have any portfolio companies that you are super high conviction on and are hiring right now?" And so definitely got a slew of job descriptions from them.

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And so my friend Brian at Cameron Ventures, shout out Brian, introduced me to the team at Coverdash, and so the rest is history. And that was a formal... Yeah. Yeah. I went through the interview process.

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I did a case study. Yeah. It was not just nepotism, but yes, it was a great exercise to confirm the type of work I'd wanna do with the company and just being able to collaborate with the founders.

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So on the VC side, 'cause obviously you worked in VC, so you kinda knew what that's like. Mm-hmm.

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Uh, what, what is that like in terms of, like, reaching out to, like, platform or talent teams to say, like, yeah, uh, like, w- if someone thinks that it's a good idea or has heard of that idea of like, "Oh, talk to VCs, like they know what's going on with companies," like what does that, what does that look like, and how could people, um, like, leverage that for potentially getting chief of staff roles?

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Yes. I will say first always check to see if you have a warm connection to the VC, just because we got a ton of emails.

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And so if I don't recognize the name or if there's no connectivity to me, it's hard to prioritize that person's time. And so definitely leverage LinkedIn and then have a targeted list of VCs you wanna reach out to.

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A lot of them are categorized by thesis. Mm-hmm.

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So if it's like, "Oh, I know I wanna do fintech," then okay, look at Nyca, look at QED, because those VCs tend to invest in the space, and then see if you have mutual connections with the VC there.

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And then typically it can just be like, "Hey, I'm interested in becoming chief of staff. This portfolio company that you guys invested in looks really compelling because of X, Y, Z. I think I can add value this way.

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Can you put me in touch with the hiring manager, or is there a general talent person at your VC fund that I can connect to?" Boom. [laughs] Yeah. So that's the quick- That's how-... form- Yeah, that's it... like take.

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Yeah, that's it. It's a little harder just making sure people respond, but I think- Yeah... being very intentional with how you reach out and not just like, "Hey, I'm looking for a job." Yeah.

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Like, it really needs to stand out with a clear call to action. 'Cause they have a pulse as to how of companies are growing and if, if they're getting funding soon too, which probably affects hiring. Exactly.

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And so you just wanna make sure that the startup is going up- Mm-hmm... and that it's not gonna go down anytime soon, um, just because, yeah, it's a risky bet, especially the earlier you go with a company. Yeah.

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Uh, okay. And so then you mentioned this idea, like how you wanted to make sure it was like a good fit. Mm-hmm. Um, what did that look like when you went through the case study- Mm-hmm... and, and interviewing process?

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Like- Mm... how did you kind of understand that, like, you're gonna hit the ground running, you're gonna have quick wins, or that it's gonna go well? Um- Mm-hmm... yeah, how did, how did you kind of figure that out? Yes.

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Well, I think the case study is always a very illuminating part of the process because, one, it'll confirm whether or not it's the type of work you wanna do. Yeah.

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And then, two, usually there is a readout or presentation, which then you can share what your findings are, what your next steps, and then typically you'll collaborate with the co-founders.

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As a chief of staff, your principal typically will be in C-suite.

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And so just seeing if there was chemistry there, if I felt like I could be honest with my opinions and that we could vibe right away was really important and that I felt like my voice was being heard because I was very clear in my process where I really value having an opinion and not just saying yes to whoever I'm reporting to or other leaders.

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Yeah. I think the best companies and startups, you'll have rigorous discourse as to whether or not you're making the right moves.

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I feel like if everyone's just agreeing all the time, you're not really gonna make the strides you need to.

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So I needed to have confirmation of that feeling, which obviously I did, but that's really what I was indexing for as part of, like, the case study and just interview process.

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Again, just being very clear about the type of environment and leaders I wanna work with. Cool. And now we're recently crossed one-year anniversary. One year, yes.

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And it's, um, what would you say is, like, a lot of your role similar now than it was when you started, or has it evolved?

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I think it's evolved to definitely more strategic initiatives, which I've been vocal about as well.

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There is still wearing different hats just because it is a series A company, so you don't necessarily have all the functional leaders, but have definitely made a greater push to being able to lead more things rather than support.

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Obviously, with a year under your belt, you have a better sense of how the business is humming and where you can add value, but you're still doing everything and the kitchen sink until you hire away those functions, which is something I'm very mindful of in terms of I'm working on this now.

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I think if it takes more of my time, it makes sense to hire X, Y, Z.Also, a- and then that's been happening? Like, uh, let's say go to market or operations- Yeah... or like what would you say is...

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Can you share a story about a time where like you started working on something and then eventually like you took it from zero to one, and then you hired someone to like own it afterwards? Yeah, definitely.

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So multiple examples of that, but I'll go with talent.

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And so there definitely was a light playbook when I had joined the company in terms of how we hire sales, which is a role we are always hiring for, and then building out different functions.

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But I think it was basically tidying up the nodes, creating more systems in place, high level.

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I did not have any talent experience [laughs] before this, and so it was basically just like, okay, this is the outline of how I think start- how I think things are gonna work.

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I had mentioned I looked at ATS vendors because I led the charge to switch.

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[laughs] We had one, I can't even remember what it was called, but I was like, "This is not gonna scale well, especially if we are gonna make these continuous sales hires," and then choosing a new vendor and then getting that foundation set up and then being like, okay, we need someone to actually refine this with actual talent experience.

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And then also start to think about, okay, how do we build on top of this? How do you think about culture and the- Mm... employee experience? That's super important. And all things where I'm like, not my expertise.

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So I think it makes sense that we should hire someone else to own this.

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I still help a lot with talent, especially when it comes to hiring the first key hire in a department because obviously it's so instrumental to the startup, especially here in the New York office.

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But largely it is great to know that I trust another leader to lead talent and people ops. How do you compare this, this experience to your operating experience before? Oh my gosh. Uh,

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I will say Series A is not as mature as I thought- [laughs]... it was gonna be, just because as a VC I did a lot of mostly pre-seed seed. Okay.

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And then the previous startup I was at was basically Series D and, you know, that startup had IT, like we had legal counsel.

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There was just more resources in place and more defined swim lanes because I was doing biz ops for a 401[k] product. So for me it was much more clear what my scope of work was versus being Series A.

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Again, it's also a more infinite scope because you're chief of staff, but again, you don't have all those resources at your disposal.

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I think you're still trying to figure out your identity because there is a huge shift between seed and Series A versus- Mm... maybe a s- like Series C to D.

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And so I feel like those things [laughs] are very different and I just feel, uh, that I have to be even more scrappy at this stage because, again, it's just the nature of where the company's at.

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Seems like you like the scrappiness though. I do. I mean, I always am like, "Oh my gosh. Should I do big tech?" And it... I started out my career at Deloitte and the- Yeah...

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bureaucracy and how slow things move kills me. Yeah. So that's why I do love startups. Yeah. The fast pace, where, where does that come from? I think I just thrive in chaos.

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[laughs] Maybe it's like, [laughs] like an extension of my childhood, but I feel like if things are just too stable I get pretty restless. And I've even told my boss that at our startup.

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I'm like, "Oh my God, I kinda need some chaos right now," because I think it like really pushes me to do better, get organized. Like, really push myself into systems thinking.

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I, yeah, I think the stability, I'm just like, are we doing enough? Are we really pushing ourselves? Are we really growing?

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And yeah, I think it's just something innate, but probably something from childhood as it always usually is. What do you mean by that? I'm an immigrant.

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I feel like part of the immigrant experience moving to the US is kind of chaotic in terms of like, okay, I have this new culture, I have this new identity.

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I'm trying to juggle both and like I just feel like I also had a lot of interests growing up- Mm... in like teaching myself n- new things. Like I learned how to code when I was in middle school. I know, maybe...

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That's when the tech interest started to develop. [laughs] But I was like I don't think I wanna be in the computer coding. That just doesn't gel with my personality.

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But I think I just like creating that chaos and like constantly learning.

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Like would definitely say I'm such a curious person, and I think when you are at larger institutions, obviously it can vary, but it just doesn't beat the speed and how you have to be so on top of things at a startup, especially earlier stage.

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Yeah. Okay, so the conversation where you said, "Hey, I need more chaos." [laughs] What was that like? Uh, I think my CEO was like, "Don't worry. It'll come."

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Like, you should definitely just lean into when things are like chill. And this happened to me too as a VC when- Mm... um, one of the partners, I was just like, "Oh my God. I feel like it's just been quiet.

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Like I haven't been able to like push a deal through." And they were like, "You know, just keep grinding. It'll come." And I think that is true. I'd be...

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I will say at a startup there is very limited chill time, but I feel like I'm always like, okay, we gotta go. Like we really gotta throw the accelerant on the fire.

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Um, but you know, I, I don't seek chaos, but I think again, it does, it does drive me. But in moments where there's not chaos, definitely like take the breather because the chaos will come. Yeah. The, um...

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And s- that's really nice that the CEO was like, "It'll come," as opposed to like- He knows... here- [laughs] He knows... here's 10 things. It'll come. Yeah. Yeah. The... Okay, and so now the company's how many people?

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Oh gosh. I think now like 45-ish. Sure. We're still hiring through end of year just because again we're constantly hiring for salespeople. Um, but yeah, I think I was 20-something when I started a little over a year ago.

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Wow. Yeah. So double in size. Yeah, that sounds about- Yeah... right though for a venture-backed startup. Yeah. Cool.So, um, we wanna talk about topic. Yes. Um, and we wanna talk about navigating conflict. Mm.

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When you think about that topic- Mm-hmm... like, what comes to mind? Emotions, data, adapting.

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So I would say those are, like, things to keep in mind when you're navigating through conflict, and I'm happy to double-click into- [laughs]... any of those things. [laughs] Yeah. So I heard emotions- Mm-hmm...

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data, adaptability. Yes. Um, do we have a new framework now? [laughs] This is... I feel like my whole life frameworks is I always think in threes, and then I come up with an acronym.

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So in case I'm like, "Oh my gosh, I'm gonna forget," I'm like, "Okay, no. This is the acronym." This what I obviously just said on the fly. [laughs] But I'm like, I like to cap it at three. That's like as- Yeah...

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much as my brain can, like, limit and then go deeper in. Once we start getting to four, five, six, I'm like, ooh, it's tougher to keep organized. Okay, so let's, let's start off with emotions then. Mm. So what...

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When there's conflict and you're feeling emotions, how do you, like, how do you work through that? Yeah. It's a great question.

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I feel like it's a lot of breathing exercises, I would say, or just even just taking a step back, of identifying what's frustrating me- Mm... why.

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And then if the conflict is obviously happening real time, [laughs] sometimes you just have to, like, disassociate for a second and be like, "Okay, I'm getting worked up. Why is that?

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Let me just do a quick temperature regulation." 'Cause typically if you can feel yourself getting aggravated, you feel warmer. This is something I've learned through therapy. Mm.

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And so just being cognizant of what your physical wellbeing is like so that you can help quell those emotions.

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And then I'd also say, too, it's like if something more incendiary happens, which is normal, like, at a startup, we're growing so fast.

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Again, I think it's really healthy to have rigorous discourse about whether or not we're doing the right thing, quote, unquote. Yeah. But it is important, like, if that happens, to always check in with your colleague.

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I'm always just like, "Okay, how did you feel that go? Like, I just wanna make sure we're on the same page. I know it got a little bit heated, but, you know, let's just make sure we're aligned here."

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And I give that person space to tell me how they were feeling, right? So I think it's also an acknowledgement of other people's emotions as you're navigating through a conflict. Yeah.

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So, um, are you able to, like, talk high level about a recent example or a example- Yeah... and, like, how you thought about it then and maybe how you thought about it now? Mm. Any learnings from that? Yeah.

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I think just high-level example, I feel like if there is some contention with whether or not to move one way or another, I think it goes back to, like, the adaptability of usually different stakeholders have different driving motives- Mm...

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of what's going to inform their decision. Like, the CEO could care about cost. The CTO could care about eng hours and the amount of talent required to complete a project.

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So I feel like it's always important when you're navigating a conflict to understand what is driving people's perspectives and, like, trying to adapt your proposal or whatever you're trying to share with them within, like, that framework that's driving their decisions.

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And I think that's where data can be really helpful to anchor the conversation just because, you know, sometimes I'll give, like, "Oh, we should do X, Y, Z because, like, my intuition says blah, blah, blah."

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But as you continue to grow as a startup, I feel like data becomes, like, a major key. Mm.

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But obviously if that's, like, not working, usually it's like, okay, let's take a step back, like, what is the goal we're trying to achieve? And then getting alignment there.

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And I think just getting the alignment from day one in terms of, like, what we're trying to achieve as a company helps anchor the conversation. I like the, like, the combination... I mean, all three are great. Yeah.

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But I think, like, this data and emotion, it feels like they bound. They're like a yin and yang- Yeah... in a nice way of like, okay, cool, you might be feeling this way, like, and you have, like- [laughs]...

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bad vibes about the thing. Yeah. And, like, negative vibes or, like, upset about it. But, like, what is, like, what does the data- Data say... really say here? Yeah. Um,

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so do you have a, like, approach or thoughts on, like, how to, like, start a conversation when, like, let's say you're feeling,

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uh, like, misaligned or feels like things are heading in a different direction than where things were going before? Like, is there- Mm. Like, how, how do you, like,

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have the conversation when it feels like things are not heading the right direction? Yeah. That is what I call losing the plot. Um- [laughs]... which can happen, but I think it goes back to, like, the goal and purpose.

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Like, what was the purpose of us even pursuing this? Does the decisions that we're talking about roll up into achieving whatever that purpose was?

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And then I think it's also like, okay, what are some other, again, drivers of your decision?

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Like, I can only assume so much about what a person cares about, and sometimes you explicitly have to call out, like, are your hesitations because of the talent we're gonna need?

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Is it because of, like, some technology that's gonna be deployed?

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Like, I need to fully understand why we might be in conflict and really listen to what that other person's saying, but also coming ready for why I disagree.

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And sometimes maybe it is going back to the drawing board and having to re-anchor your, re-anchor yourself around the goal and purpose, but I think you always need to be aligned there because then if you can't tie that decision into how it's going to further that cause, that's when, again, you start losing the plot.

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So I feel like you need to just have-It's like one sentence where it's just like, "We wanna improve the customer experience. We wanna enhance retention."

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Just try to keep it simple in terms of the goal, and then obviously there's a lot you have to layer on to achieve that goal, but I feel like that's always so important. Yeah. And so losing the plot- Yeah...

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is like we're not... It doesn't feel like we're heading in the right direction- Mm-mm... that we thought we were before. Right. We just started drifting? Yeah, started drifting or it's just like I feel maybe

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some function is m- perhaps, like, doing things that we haven't necessarily, like, agreed with. Maybe it's because they're trying to move faster, and so it's always, like, that reorientation of, okay, this is the goal.

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This is why we need to be aligned. This is why we need to do things in a certain order, blah, blah, blah.

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Because I think startups just move so fast, and sometimes you can lose that communication, especially when you start delegating the work, which is why, again, it's just so important to, like, check in, make sure that you're all on the same page.

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Because I think a lot of conflict, obviously, is just due to miscommunication. Mm. And what do your check-ins look like these days? Oh, my God.

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I feel like if it's a large project, there's always at least a weekly sync with the key leadership involved, and then there's a lot of Slack.

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I'm a huge fan of Notion in terms of, like, at the top I'm always like, "This is the goal."

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So when people go back, they can clearly see, okay, this is what we were thinking at the time, which goes back to always being able to orient yourself around something simple. And so I think it's having those check-ins.

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I honestly think it's always better to over-communicate. You can always just be like, "Oh, we don't have to have this standup," or it's like- Yeah... "Okay, we move forward," like, we made this decision.

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But I think, again, when you're moving so fast, you have to communicate with leaders and, again, get a pulse of how people are also just, like, feeling emotionally. Like, are we moving too fast?

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Are we including the right people? Because sometimes, too, it's like, oh yeah, we should have included so-and-so, and you just kind of forget because [laughs] there's, like, so much- Yeah... happening.

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And so that goes back to, like, okay, having the data, having the goal, but also having the emotions aligned. Okay, so weekly syncs. Mm-hmm. Um- Slacks. Slack. Slacks. Notions with goals at the top.

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[laughs] You bring that into your personal life, too? No. I don't have Notions for my personal life. [laughs] Though I do... You could, though. Um, but no, I love Notion. This is not a sponsored Notion hub.

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[laughs] But they're great. Okay. Um, and so what would you say... Is there anything else on this, uh, on the conflict piece? Like, I think we talked about emotions and we talked about the data.

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Is adaptability, is there anything there that we n- should talk about? Yeah, I think it's all, like...

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I think it goes back to the check-in, but I think we also should remember that s- people have stuff going on in their personal lives- Mm... as well. And so obviously if you like...

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Because we're so early stage, you feel so close to your colleagues that it's also just, like, a check-in of, like, "Hey, how's, like, everything going outside of work?" Because obviously- Mm...

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if someone is going through a period of turbulation and you're just not aware, and obviously they don't have to share that at work because it can be difficult, but if it is starting to impact how their decision-making is or how they view things, I do think it's helpful to understand and, like, check in more on, like, a human-to-human level instead of just, like, colleague to colleague.

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Yeah. And you like to do that? Do you have a lot of, like, kind of personal check-ins like that? Yeah, I think it's just like, "Yo, how's the week going?" [laughs] Like, "How are we feeling? Happy Friday."

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Like, it doesn't have to be this whole heavy thing. Sometimes it's just like, "Hey, just wanted to check in on you. I know this week was bananas. Like, how are you feeling?" How are you feeling right now?

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Oh, my God, I'm excited that tomorrow is Saturday. [laughs] Oh, we are so close to the finish line. Ah, Friday afternoon, you know. Yeah. It's like, hey, what, before you, you know, check out- Yeah...

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we still got- Yeah... I still gotta do this. Right. Definitely we'll get things done before the weekend.

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Sometimes you have to do things during the weekend, but again, early stage startup life, you kind of know what's going into the territory- Yeah... that you've entered, so.

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Okay, so, like, a little bit of work on the weekends, but not a ton? Yeah, I mean, I try to. There's obviously certain periods where you have to sprint. Like- Mm...

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just because time is of the essence, especially at a startup.

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Like, you're definitely just moving so much faster than a normal business, but I think it's always communicating, like, what needs to get done, like, who needs to be involved.

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I think we try to have a culture of respecting people's weekends, but it's also, like, you know, this isn't a company f- with just two employees, right?

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Like, that is a different hustle and grind, but as you start to mature as a business, like, you have to think of more systems and scales so that way the business can function even without certain people.

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Like, very, very early days of infancy, you, everyone has to be on deck. But again, once you go Series A, B, C, D, you need to have systems in place. So if, like, someone can't work on the weekend, it should be okay.

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Cool. Um, okay, so there's another topic I was curious about. So is there any, um... One, do you have any chief of staff hot takes? Oh, my gosh, chief of staff hot takes. Let me see my notes that I wrote for this.

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[laughs] Chief of staff hot takes? I don't think this is a hot take actually, but I was at a dinner with some other VCs turned early stage operators, and I think something that doesn't come

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often as a topic is just, like, you have to be willing to tear things down sometimes. And, and this goes back to, like, okay, when you were scrappy pre-seed seed, you s- [laughs] taped and glued things together.

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But when you reach a certain stage, like, you ha- you might have to tear, like, a total process down in order for it to hit-Scale.

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And so I think we ta- we talk a lot about process building, at least in chief of staff conversations, but not process tear downs- Mm... in order to come out better.

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So I thought that was an interesting topic where I'm like, "Yeah, it's painful, but you need to take the time to do it." And so that was an interesting conversation I had recently.

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And so those are VCs turned operators like you? Yeah, some chief of staff, some first business hire, so kind of chief of staff, but title is kind of ambiguous.

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Some that are, like, head of ops, but still, like, very chief of staff-y in terms of the hats that they're putting on. That's cool. So very, like, operational. I feel like- Yeah...

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sometimes people, like, uh, I don't know it as much, but it's kinda like what's the,

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what's the career path of a VC, and it feels like operating is not as common as maybe some of the other- I think it is starting to more and more. Yeah. Yeah.

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Because there was a few of us that were like, "Oh, we could grow this group," but I was like- [laughs]... "Facts." I, this- [laughs]... I've lost track of whose turned back to operating, but yeah, I think...

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And, again, I'd been an operator before, but I think it's definitely been helpful to now have a VC lens as you work at a startup, as you also try to decide what startup you wanna work for. Yeah. Cool. All right.

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And I love seeing the, like, that's such a niche dinner- [laughs]... that I love it. I- [laughs] Yeah. Yeah, I know. I was like, "Oh, this could be a series."

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[laughs] But no, it was a, an awesome, like, just, like, safe space to just, like- Yeah... trade notes about what the transition was like, what we're talking about, like, how we can learn from each other.

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Because o- one person was, like, employee number three, and then another person is like, "Oh, we might gear up to do another raise soon." So. Nice. Yeah.

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Um, is there anything else you wanna share to existing chiefs of staff or aspiring chiefs of staff that you think that we missed? You should listen to the other podcasts in this series.

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[laughs] But for this topic, I think that's all I got for now. Cool. Um, well, Charlene, thank you so much. And people can find you on LinkedIn or- Yes. Uh, yeah, you can find me on LinkedIn.

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My name is spelled with an S, and I think it's just Charlene G. So yeah, I, I think I'm pretty easy to find on LinkedIn. [laughs] Thank you so much, really appreciate it. Yeah, of course. Thank you so much for having me.

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Woo! [outro music]