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[upbeat music] Hey, it's Tristan again. Great to have you here. Just as a quick recap, I'm a new guest host on the pod, so I thought I'd quickly drop you an intro.

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So I was previously the chief of staff at Commsor, a Series B community analytics company.

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These days, I work as a fractional chief of staff and also a coach through my company, Beyond Founders, where I help operators and founders lead with more clarity and purpose.

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I'm part of the Chief of Staff Network community, and I'll be guest hosting a few episodes on the pod this year.

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Currently based between Berlin, Kuala Lumpur, and Singapore, and you're gonna find me bringing on chiefs of staff from Asia and Europe and other parts of the world onto the pod.

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For today's conversation, my guest is Zoe Jakubowicz. Zoe is a fractional chief of staff and also an early-stage consumer investor with VHS Ventures.

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She's worn a ton of hats, from management consulting to strategy, operations, business operations, technical product management, and she's worked across companies like Ernst & Young, Walmart JetBlack, and Tula Skincare.

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Zoe currently runs her own practice, and she's managing five client projects at once. Not sure how. Well, we're gonna find out how together [chuckles] as well as being an early-stage investor.

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So if you're a chief of staff thinking about going fractional or you're a generalist figuring out how to turn your zigzagging career into something that actually works for you, this episode is definitely for you.

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Together, we're gonna be going through the mechanics of how Zoe runs her practice, her guiding principles on building trust, and what it looks like to actually better yourself when you no longer have a company or a title to lean on.

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Zoe I found to be incredibly sharp, self-aware, and refreshingly honest about what it takes to build a career on your own terms. I'm sure you're gonna get a lot off this episode. Let's get into it.

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Zoe, such a pleasure to have you with us today. How are you doing? I'm doing well. Thank you so much for having me. I'm excited to be here. Really appreciate you making the time. Why don't we just get right into it?

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A question I thought to kick us off with is: What is some early context that will help our listeners, everybody listening, give us an understanding of who you are today?

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I think the context that sort of helps shape the career that I found myself in, or we'll call it my villain origin story, is I feel like I've spent about a decade realizing I'm meant to be a forever generalist, and I've learned that through sort of the evolution of different professional experiences that I've had.

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I've taken little tidbits from each one that I've started to shape into what is now a fractional chief of staff career, for however long that makes sense.

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And so some early context, like I started out of college with Ernst & Young in consulting, management consulting.

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Loved the problem-solving, loved how everything changed day to day, but didn't necessarily feel like we were solving the right problems.

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And so I was thinking, "How can I have a little bit more control over the types of work that we're doing?" And so I took that with me, and I found internal strategy and operations teams.

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And so first I joined Nordstrom Trunk Club. I also joined a team later at Walmart JetBlack. At Trunk Club, I learned how wonderful it is to work with really smart, capable people who challenge you.

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It's still one of the most incredible networks I'm a part of today.

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And at JetBlack, I learned about different business models and what it means to scale revenue and top line and what it means to build for sustainability and profit and what that can do to teams and culture.

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And so collected these pieces, kept going, and end up applying to Tula Skincare, which was about twenty-eight people at the time in February twenty twenty and was backed by L Catterton.

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And I'd originally applied for an analytics role and ended up creating a strategy and business ops role reporting to the CEO. So I got very lucky, both in terms of career and timing.

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And Tula taught me that I love context switching. I love learning about international expansion. I love growing sales channels. I like people management.

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I like all of these different aspects that make the value I can deliver better and help me connect dots across companies and explain to people why we're doing what we're doing. But I also learned that I can burn out.

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And so about a year after acquisition, I went to Angie's List, large publicly traded company, because a friend of mine was there, and they were hiring for a product manager, and I said, "Sure."

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And so I got the role, and I learned two things. One, I believe human beings can learn anything, because if I can learn how to be a back-end technical product manager, then anyone can do anything.

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And two, in terms of burnout, I'm the problem. I'm the type of person that I will find things to do. No matter what size company, no matter whether it's the expectation, I will always find something to do.

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And so in collecting these learnings and thinking about I like solving the right problem, I like working with great people, I like building sustainable business models, I like context switching, I like finding things to do, I started to think about, how do I do that in a way that builds the boundaries that I otherwise struggle to find?

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And a friend of mine who I worked with at Tula Skincare reached out. She was the CEO of a data consulting company and asked if I would consult with them to help them get ready to scale. She became my first client.

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Selena Wong is an incredible data leader, and that was sort of the impetus for everything. I was like, "Wow, I can build alongside this team. I can help them put the right process in place.

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I can be valuable, and then I can step back and cheer them on as they continue forward, and I'm done."

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And I think all of these pieces sort of have come together into this collection of contexts that helped me realize, like, I like to do a lot of different types of work.

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I like to learn a lot of different types of things, and I like to work with incredible people. And right now, that's what I get to do. Well [chuckles] thanks for giving us that context.

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I mean, it sounds like, you know, as you swapped for different roles as the career sort of progressed, the titles, you know, you had different sort of titles there and also went through a lot of changes.If you give me like an insight or give us an insight to that experience, like what are some threads that were sort of like being woven over the time to kind of leading us to where we are today?

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You know, I wish I could tell you that at the time I knew what I was doing, but it's more so that looking back I can tell the story in a way that makes sense.

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The titles, I think at different points in your career, it's always valuable to ask yourself how three things stack up.

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All three are important, but how do you feel about whether your work is fulfilling for you, your title, and your compensation? And that can evolve over time at different stages in your life.

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So throughout the career points that I mentioned, those things sort of stack rank in different ways for me, and they continue to.

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But yeah, I went from management consultant to strategy and analytics to customer quality to strategy and special projects to strategy and business operations to technical product manager to group product manager to fractional chief of staff, early-stage consumer investor.

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So the common threads I would say is a bit of a catchall. Like I think it's these roles that are going into smaller companies or scrappier companies and are expected to have a sort of broad job description.

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And when I think about the job descriptions, the sort of commonality is build and maintain a roadmap, whether that's product or that's more process.

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It's we have some exciting amount of growth expected or we need to clean something up.

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So figure out what it looks like, find the right problem to solve to deliver that objective, convince everybody, and then run that through to execution.

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And that's sort of been the common thread I think too is it's these fuzzy, ambiguous roles where someone needs to come in and shape what they're doing and wants to do that, and then it's also not just set the strategy but like do it, try it, break it, try it again, that I think chiefs of staff roles can vary sometimes in terms of are you just setting strategy and consulting roles too.

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Are you setting strategy? Are you actually executing? The common threads I would say is like I'm usually doing both, and I like to do both.

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I like to kind of be like eighty/twenty split, eighty percent execution, twenty percent strategy I would say. That's tricky, right?

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Because the role of a chief of staff is that we- we're filling the gap, and it's about both filling the gap and also understanding like what is the context of this gap relative to the other gaps and relative to the whole organization.

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I'd be also curious about what sort of skills do we need in order to actually fill that gap well and to kind of straddle both of those bits?

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There's three that I always think about, and I think they're consistent in whether you're a full-time chief of staff or if you're interested in fractional. One is organization skills.

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Two is truthfully not just a comfort with ambiguity, like a hunger for ambiguity. And third would be emotional intelligence.

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The organization is because especially if you're a chief of staff at an early-stage company, quite honestly, I think you're probably the only person organized in there because everybody else is flying by the seat of their pants just trying to get their job done, living in the day to day, and it's your role to sort of look, as to your point, like look beyond, connect dots, see opportunities, see ways to take things out of people's mental plates.

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So organization is huge.

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Hunger for ambiguity because I think a human instinct, I believe, is we do not like chaos, but I think the only difference between someone who thrives in a chief of staff role and anyone else is we see it and we go, "Ooh," and then you jump in.

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And like we need to fix it. We need to like get in there. We need to take it apart, figure out which pieces to focus on, which pieces to say not right now, how to set priorities.

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And so if you enjoy managing through chaos, I think that that's something to be celebrated and quite rare. And then the emotional intelligence is high because you are often influencing without authority.

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I have met chiefs of staff who managed and built teams. I have built a team, and I think there's different ways I can look at companies, but usually you're a team of one. You don't have any peers at the company.

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It's a rather lonely job, which is one of the reasons why I love that there's more networks around chiefs of staff now to create that sort of peer community and sounding board across companies, across industries.

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But it's on you. And you start to learn to proxy your stakeholders' decisions. You start to learn to challenge helpfully. You start to learn how to use relationships, I think, quite often to drive that influence.

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But emotional intelligence is a big piece of it, figuring out how to communicate in a way that's effective for those you're speaking to.

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That's one of the most critical skills in this role because otherwise you're gonna spend a lot of time dwelling on things that you said and did, and it will drain you.

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And then when it comes to thinking about how to scale as you start to become more senior chief of staff, I think those things just become even more important and the ability to organize across larger, higher stake projects, the ability to have more of an executive presence, all of those things just continue to compound as you gain experience.

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You know, I think the role is really interesting, right?

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'Cause for the chief of staff role, it can lean on the executive assistant side where you have chiefs of staff that end up doing that role because perhaps the principal doesn't have an EA.

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But of course, every single chief of staff that I've spoken to and that I know want to move to the strategic partner side as fast as possible and as soon as possible.

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You know, it sounds like from the experiences that you've had and from the conversation we had before this as well, your career's moved very fast. It's kind of been back to back.

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You're relentless in ambition, I would say. Sure. Yeah. [laughs] I guess so. I'd really be curious to then understand like what is the counter to that, right?

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So when we go, go, go all the time, what do you do to kind of keep the balance and to, to slow down, especially when we're people that dive into chaos?

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If anyone hears this, has a better answer than me, I hope that they engage and tell me 'cause I think it's a constant learning process.

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Truthfully, I'll say the way that I manage the chaos of being a chief of staff was going fractional.

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It has enabled flexibility and allowed me to leave behind a lot of the stress.It comes with dwelling on one company, one decision, one really bought-in ownership, but allows me to add the value across multiple companies, multiple business models in ways that set me up as a springboard and not a crutch for the business.

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So that was like the biggest sort of change that helped in terms of like the go, go, go and reframing to be less defined by the companies that I work for and more defined by the value that I can add, and the business is me.

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But other things in terms of like tangible pieces of insight I would share that I hope help folks, one of the biggest things that I do that I tell people to do, especially in a role where you're managing so much, or shall we say accountable for so much and responsible for very little, quite often I do an exercise daily where I write down on a piece of paper, left-hand side is what is occupying my mind, what am I stressed about, and right-hand side is one thing I can do to move it forward.

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And so that's one exercise. I probably do it about five times a week. And sometimes it's as simple as this is occupying my mind, I'm just going to set a reminder to work on it tomorrow.

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Or this is occupying my mind, I'm gonna apologize. Or I'm gonna connect these two people. I'm gonna think about that next week. I'm gonna set the reminder for next week.

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So it's just getting things off of your mental plate and some of that organization that I think really helps with the sort of go, go, go mentality.

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I'd also say just finding things that continue to help you find ways to learn that are not tied to your professional career.

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So I have like my scheduled learning time every Friday where I collect all the newsletters that I subscribe to and I sit and I like read them and I take a very academic approach to like what types of AI tools are out there, what's new with performance marketing, what's happening in the VC landscape, and I treat it like I'm in school.

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But I also try to do that with other topics. So right now I'm very into 1800s Russian classics and history because I am learning and pushing my brain in ways that are not tied to professional validation.

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And just learning for the sake of learning is something that I think we don't do as often as we start to get more into a career and that really helps sort of settle my mind. It's a weird one. It makes sense, right?

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Because if we don't block that time, it's just never gonna happen. I know you run a tight ship in terms of your schedule and how you spend your time. Do you wanna share a bit about how do you spend the day?

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How does the day start and how do you go about that? My typical day, so I am a morning person.

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I caveat with that because I actually don't think anyone should try to force their brain or body to operate at a time that does not work for them, but I am glad I'm a morning person.

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I wake up rather early, as you know, which is why I think you asked this question. So I wake up by five typically, and my brain works best at that time.

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So usually, I mean, I always start with like a low stakes Wordle or a crossword, something to sort of really settle into my morning, but I'm usually doing heads down client work between like five thirty and seven.

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And so that's big deliverables, that's my real thinking time. It's a little bit of structuring my day, but that's typically what I handle Monday morning or Sunday night.

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But yeah, first thing in the morning I am getting work done. It could be resume reviews if I'm helping to hire for roles. It could be financial modeling, preparing agendas, anything of that nature.

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Seven to eight I'm outside. I don't care how cold it is. I live in New York City. It is very cold right now. I have to go outside. And so I try to maintain that sort of morning walk.

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Then in the mornings a lot of times I'm out and about at coffees or events and sort of that business development, constant pipeline, constant learning, constant networking. A lot of that happens in the mornings.

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And then I start to get into client calls, business development calls, typically from eleven AM until five. There's not a lot of time where I'm working on client work during the day.

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That's okay because I function much better in the morning anyway. But that's usually what it looks like.

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And then if I have to prepare, typically the only type of work that I'll allow myself to do late, late for me is like after six, is proposals.

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So if I wanna turn something around quickly, if I wanna close an opportunity, if I wanna make sure that I'm giving them a clear picture of what it could look like to work with me, I like to be fast about that.

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Not because from a sales cycle perspective, but more so I'm like, if they're excited I want them to either continue to be excited or know right away that I'm not the right fit and I can introduce them to someone else or just give them that sort of closure.

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So proposals I will do quick turn. But my heads down work and most of my client work is in the morning.

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I try to schedule so that folks don't see too much happening in the morning 'cause I wouldn't want them to wake up to chaos, but that is usually what my day looks like.

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One of the reasons I ask about that, you know, is to give us an insight to I guess how you operate as a fractional chief of staff. And I know you have multiple clients.

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I know you also assess deals at a VC fund right now. How do you manage all these bits, right? How do you manage the client work? How do you manage the blockers for the learning?

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How do you balance these things and how does that system work? I time box is the first and foremost thing. So I mentioned it earlier. I time box in terms of looking one week ahead.

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And so if I have a client that I know I am talking to about recruiting on Tuesday, then Monday I have time blocked where I'm reviewing resumes, preparing their top candidates so that I can have a productive conversation with them on Tuesday.

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If I have back-to-back to back-to-back client meetings that are switching context, I've prepared for each of those prior so that I'm not quite like taking on the burden of context switching right in the meeting, but I have everything prepared to go into that conversation.

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It's similar to being a chief of staff full-time in that way of like you're kind of switching between like marketing and operations and international.

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I also think honestly it's similar to school, like middle school or high school, where you're going from eight different subjects like hour to hour and you kind of just like sit down new folder and you're like now it's history.

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And I like school, so I'm like why wouldn't I wanna do as many things as I can? I don't wanna talk about operations for hours. That sounds awful. No offense to ops people.

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So it's a lot of time boxing and sort of looking ahead.And I think more so than a lot of other fractional folks, whether chiefs of staff or otherwise that I've talked to, I'm very particular about setting expectations up front.

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Like, I wanna set us both up for success.

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So for example, if I'm taking on a client where I'm embedding within their team as, like, an interim COO, I might suggest if they have a bigger team that they have set hours with me, so like Tuesday through Thursday, twelve to five PM.

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They know when they can schedule with me, so I will be very upfront as I create custom proposals and engagements for clients because I want them to feel happy with what they're getting.

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I want them to know when I'm available to them and when I'm delivering value. So I'm very clear on those expectations up front, and then I can manage to them.

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I went very chief of staff into it when I first started doing this, where I was like, I think my perfect balance of a portfolio will be one primary client, like ten to fifteen hours a week, where I'm embedded, and two to three projects where maybe it's, like, a couple deliverables or a little bit more of a shorter term engagement, right?

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And then ten hours of business development a week. That's impractical for this type of work because one of my projects, I'm interim operations for skincare. One of my projects, I'm marketing language for food and bev.

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One of my projects, I'm recruiting for luxury. One of my projects, I'm financial modeling and investor preparation for B2B marketing tech.

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So the way that I do that work, and even considering, like, what I would do in the early mornings versus what I need business hours for, they're different.

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And so I capacity plan based on the types of projects that I'm pitching and what I have in a given month to make sure that I can actually take it on. And so what that looks like right now is five client projects.

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And then to your point, I'm an early stage consumer investor with BHS Ventures, and so I look at about five plus consumer companies a week and chat with founders on that.

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So it's quite a bit of different types of conversations, but there's just this sort of, like, constant learning and constant, like, bringing different points of information.

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And I think also it tricks your brain into creating those patterns that chiefs of staff are really good at creating.

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So if I'm coming from a beauty conversation and I'm going into a food and bev marketing conversation, you know, there are aspects of building a beauty brand and creating an engaged community that you could take and test and see if they work in a food company.

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And because I just came out of one, I'm bringing, like, these thoughts and these ideas and my brain's a little bit more fluid, and it makes it almost easier to see patterns and opportunities across business models.

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It's one of the pros of the wild day. Another person might be super overwhelmed. Like, I can imagine just barely... Maybe use the ship analogy, like we're kind of drowning.

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The ship has holes in it and we're staying afloat, you know, but it's not quite doing that well, especially with that much. So props to you for holding so much context, right?

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I wanna also ask from the perspective of somebody who is currently a chief of staff looking to also build a portfolio career to have, you know, multiple clients be fractional.

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Tell me a bit about the context switching, right?

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Because we're holding so many different contexts with different clients and also your personal context for your own life, as opposed to just having one client where everything is in the context of one organization.

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Now there are multiple. I think you seem to figure out something that, you know, allows you to hold so many contexts. So could you tell us a bit about that?

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I think there are three common paths I believe that a chief of staff can take.

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One is you wanna be a founder, you wanna grow into a C-suite executive, or you wanna be a consultant and you wanna have more of an independent career.

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I'm firmly in the third camp, and I think that more people are landing in that, like wanting to create independent.

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But when I first started doing this, I said what I think a lot of fractional folks say, which is, "I hope that I am working with a client and on a project that I'm so excited that I wanna go full-time with them."

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Now, a year and a half in, I don't say that as much because I'm very happy. Like, I, I'm learning, like to your point, like I have a ship.

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There are a couple holes in it, but like it's a pretty nice ship, and I'm learning so much across all these different businesses. And so I gain the flexibility.

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I can manage across the chaos and the overwhelming, and it helps me balance a lot of the anxiety that came with connecting dots in one company and working full-time. That's what works for me.

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I decide how many clients I take on. I decide what type of work I can absorb. I balance it throughout my day. The real question I'd say to people is just, what kind of person are you?

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What do you enjoy about the chief of staff role? Do you want to be fully bought in? Do you wanna build something from scratch?

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If the answer is yes, you're probably more in the founder or C-suite route, and being fractional might frustrate you 'cause you'll feel pretty removed.

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If you're someone who gets energy from context switching and adding value and then sort of like stepping back and letting the team succeed, then fractional can be great for you and working independently.

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In terms of, like, what I also think for folks who wanna be independent that are coming from a chief of staff role versus a more specialized, like chief tech or a marketing executive, I think it's easier for us because you're already context switching.

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You already don't have one lane, so now just do that. Like, you could do it only for consumer, you could do it only for beauty.

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I'm a bit of an extreme example where I'm consumer and B2B and sort of all different types of projects.

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You could make it as specific as you find value in, but you already have that context switching muscle that you've built from being a chief of staff.

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Whereas I think that is something that other types of people who are specialized and go fractional have to learn when they take that leap. So I think it is easier for chiefs of staff to go independent.

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To manage the context, you know, I mentioned the time boxing thing.

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I also try to give myself grace of, if I'm not actively working on a client today, I'm not actively working on that client today.And that means I don't have a deliverable due for them, my time scheduled to work on them is not today, we are meeting tomorrow, and I have time before that.

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And so it allows me to create the space for what I need to focus on in that moment. If they called me and I had to talk, like, that's where it comes with the context switching. Like, I can pull up the details.

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I have very detailed notes, but I also am fortunate that I have a decent memory, and so far I haven't capped out with what I'm handling, but we'll see.

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So I think some of it is leaning on those organizational skills to give yourself the grace to pick things up and put them down.

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What I'm hearing also from, you know, how you described the journey until now, it sounds like it built up over time.

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With each change of role, regardless of whatever the job description was, like, you figure out how to do it because, you know, as you said earlier, like, you believe humans can learn whatever it is.

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If you can learn how to be [laughs]... What is it? A technical- I owned matching algorithms. Yeah, which isn't really what you studied, I guess. No.

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But, I mean, for what it's worth, I think when you come out of school, for example, like, what you study, what you're usually tested for in interviews is your ability to learn and your critical thinking.

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I don't care how senior someone is, those are the two key things I'm looking for, no matter what role, because I like working with people who can learn and like to think critically.

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So I did undergraduate business school. I've had a very wonderful academic rooting in a lot of the things that I do now, but, like, if you wanna learn something, go do it. It's the best way.

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I also like what you said about, you know, for the chief of staff role. Chief of staff are context switching all the time, and also need to have a bias towards action, right?

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If there's a hole, you need to understand why the hole exists and also, like, what can we do to solve it? Because if no one's gonna do it, and it's gonna be critical for the company, then it's gonna be on you [laughs]

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if something goes wrong. I feel like in, in some ways, that also sets up to go independent, right? Having bias towards action is basically a trait of a founder. Testing things, being experimental. Yeah. It's funny.

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Someone I worked with at Tula, who's now CEO of another company and is one of those people, like, I'd follow her anywhere, when I caught up with her when I decided to be fractional, and I was like, "This is what I'm thinking.

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Like, I'd love your feedback. What do you think? What did you experience from working with me that you think I should lean into or leave behind?" And she was COO/CFO.

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And it was funny 'cause she asked if I procrastinated more, if I found it more difficult to prioritize now that I didn't really have a boss.

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And I, like, laughed 'cause I was like, "Oh, I'm the strictest boss I've ever had." It's my company, it's my name. You're working with me, and if you don't want to, like, respect, [laughs] like, it's a lot.

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But I'm more thoughtful about setting, managing, exceeding expectations than I've ever been because it's my reputation. I'm not hiding behind a team or a business.

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Not that I ever think I was capable of doing that apparently, but I'm very aware of doing the right thing so that I can sleep better at night.

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I would rather say, "No, I don't think this is the right fit," than do something that would compromise my integrity or let something slip. I'd feel awful.

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And so I'm not managed, but I'm the most managed I've ever been in my life, and I think that that's sort of, like, a funny pattern that, yeah, if you're the type of person where you're naturally operating like that, you will find, I think, like, a sense of relief in working independently.

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If you are the type that needs pressure applied, which is fine and good, it's just a different way of working, you might find it a little bit more challenging to go independent.

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[laughs] What happens when you don't have the scaffolding of a company? When there's no longer the title that you can put when it's on you?

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There's no more title that people can associate that you have some sort of credibility or standard because, well, it's you. It's just your name for now, you know?

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And so I liked what you said about stripping things back, and it's just like, "Okay, what value can I actually bring? This is what I have," you know? [laughs] Yeah.

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I've been consistently humbled by the people that want to help me or want to work with me.

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And when I set out to do this too, I felt very strongly that I was building fully through my network, and what that meant is I was just catching up with people who I've had the privilege of working with at the companies that I've mentioned, at the schools that I've gone to, and just chatting with them.

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And, you know, they connect me to other people, I talk to them, I go to events in New York.

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I got connected to the venture capital world completely by chance through a connection I worked with at Nordstrom Trunk Club, and now I get to work with Sumeet Shah at VHS Ventures, who's wonderful.

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He's been in consumer investing for, like, seventeen years. And there's such wonderful people out there doing really cool things.

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I, by nature I suppose, like to ask questions and like to learn about what they're building, why they're excited about it, what they love about it, and what they would give away tomorrow if they could.

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That sort of ends up naturally evolving at times into, like, "Oh, I think I need XYZ. Is that something that you do?" And that's what my, like, sale process looks like.

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Like, I joke because I don't think I hard sell, and yet I'm always... Someone will be like, "Oh, great. Well, then let's write up a contract." I'm like, "Really?"

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Which I hope I never lose, but also I'm like, maybe it's endearing. I don't know. I wanna help people.

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I wanna connect them to others that can be helpful, and if I'm the right person, and I think I can do it, then I will say, "I can do this, and let's talk about it."

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But that's all been just through talking to people about what they're working on and, like, getting excited alongside them about what they wanna do.

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And that's where I think, like, my name has gone f- far, hopefully quietly, is if you wanna work with me, you're working with me.

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And you perhaps heard about me from someone that's worked with me in the past, or we worked together, you know, at two companies, and now you have your own, and I'm coming on board to help with your early stage operations and hiring.

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And so I would never discredit, like, the power of the network for anyone. But especially I'm very grateful for my network, and I very much invest time and energy into my network.

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I lean on them, and I encourage people to lean on me because that's what kinda makes it fun.

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I wouldn't be able to do this if I wasn't enjoying the people aspect of it.And I would say at different points in my career, I have been like, "I don't wanna talk to people. I wanna work on spreadsheets. I'm analytical.

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That's all I wanna do." And there's been two distinct points in my career where I've tried to get away from people. One was when I first applied at Tula, it was for an analytics role. I didn't wanna talk to anybody.

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That wasn't part of the role anyway, but that's what I thought it was. [laughs] And the second was when I went to Angie, I was like, "I will be a technical product manager.

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I will talk to my engineers, my data scientists, and no one else," but I can't help it.

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And so I think that I realize more and more, like, the power of how you make people feel and, like, helping people feel like they can speak confidently about their business, or they understand how things connect, or they see opportunities.

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There's value in that, and the more that I started to put value behind it and realize, like, it could be a skill of mine, it's something that I can use to help people, the more I started leaning into this and stopped trying to be behind a spreadsheet, at least the whole time.

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It's like being the ultimate helper. And I think in the chief of staff role, that's literally what we do. You're just being at of service fully. Yeah.

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Someone said if you like shining the light on others, it's a great role for you, and sometimes people wanna do that, just like we talked about, for a little bit of time, and then they wanna step into the light.

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I'm still very happy shining the light on others. This is me trying to step a little bit more into the light, but I'm working on it. I'm doing things that scare me, but I like cheering people on.

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I like shining the light on others. I like empowering people. That makes me so happy, and that's, I think, a big part of joy you can find in this type of role. You talk about network.

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So network, I also believe, is one of the most important things. You live and die by your network and, you know, the people who know you and are in your circle as well.

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How do we build trust with others in a world where everybody is seeking new opportunities and we're being flooded with different ways and how the best ways to do things and the, the optimal ways to do things?

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So what does trust look like today? I think there's two principles that I come back to.

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As, like, a network-based business that's like, at the end of the day, I need to sell and I need to sell my brain to people, trust is huge, right? Like, that's a crazy concept, and the fact that it works is crazy.

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But two principles that I think of with trust, one is seek to understand before seeking to be understood. I apologize, I don't remember where I got it from, but I certainly did not come up with it.

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In the past, like, six years when I've interviewed, when people ask me things, like, that is my guiding light.

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And where it comes really into play now is I don't come bumbling into networking events with my elevator pitch. I typically will be like, "I'm a fractional operator, and I am an early-stage consumer investor."

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And then I will listen, and I will ask people questions. Like, the way that I find networking and being, like, out and about and, like, the social anxiety, the way that I manage it is facilitating.

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I'll be like, "Oh, you know, I was just talking with Diane about a similar concept. You know, she said she works in retail, and you have an early brand. Do you guys have any similarities there?"

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I like using the connector skill set live because it takes pressure off me. I'm not talking about myself, but I'm showing you what I do. And so by the time someone's like, "Zoe, what do you do?"

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Like, "Tell us more about what you do," you've already gotten sort of a live demo of how I create connections and, like, solicit information and understand about your business.

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And I have more context where it's like, if you wanted to talk more about what type of work I can do, I can give you an example that's more relevant.

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Because in a chief of staff generalist role, like, we've done so many things. Like, I've done some crazy things across, like, the weirdest projects that I've managed, right? Yeah.

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And so there's commonalities across all of that, and the biggest one being, like, I'll get it done, and I'll get it done thoughtfully.

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But if I just start talking about that, that's not helpful to people that I'm talking about. So I think trying to understand where they're coming from, creating connections between others is a big part of building trust.

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And then by the time they hear what I do, it's hopefully just like, "Oh, that makes sense." The second piece is add value.

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So whether I meet somebody, I have an introductory call with someone, they are a first-time chief of staff and they're thinking through what their career trajectory looks like, and they were asked what they want out of their next promotion, and they wanna talk to me about ideas.

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Or I'm talking to someone who's starting an early-stage beauty company, and they're looking for contract manufacturer relationships.

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Or I'm talking to someone who's building a new retail technology, and they're looking for clients, and they wanna talk to different brands. I wanna help. I wanna connect those people.

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If I'm fortunate enough to have a network that I can create value between folks and put them in touch, I'm gonna do that.

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I don't really care if I can monetize that in the short term because I believe that the value over time is stronger, and it's the right thing to do.

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Not to say that I, like, haven't looked at, like, referral agreements and all that for different... Like, I've looked at a few.

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I've signed maybe two, and they're because I would absolutely never sign anything that requires me to only talk about them, and I will always disclose it, and I've told them, like, "If I don't think you're the right fit, I will not connect you."

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So I think there's something just about shine the light on others thing, right? Like, listening to what others are going through and then genuinely trying to put them in touch with people that help them.

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I'm always thinking, like, "How can I help you? What are you looking for? What's one connection you wanna make, and let me see if I have anyone in my network."

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So I try to ask, like, really tangible questions, where it's just like, "How can I help you?"

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And I don't necessarily look for anything out of conversations, and maybe that's why I'm consistently surprised when it turns into work.

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Set the bar low is, uh, perhaps the takeaway, but I think it's just trying to add value, trying to help people, and believing that it all comes back at the end.

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That's what just makes people trust you as, like, someone who wants to help and isn't doing it for their own devices. I think there's also the part of following through, right?

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If you say you're gonna do the thing, do you do the thing? I wanna pull in something that you shared with me, which is a term, Zobot. Oh, yeah. [laughs] What is Zobot? Who is Zobot?

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What is a Zobot?So Zobot is what I, I think affectionately termed as a nickname when I worked at Nordstrom Trunk Club. It's funny when you say if you say you're gonna do something, get it done.

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For me, it's almost to a fault. Like I'll meet someone through a beauty network, we'll connect on like, "Here's the three people that I think will be interesting for you to meet."

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I'll then schedule it on my calendar for me to send thoughtful introductions with details so that you guys have context, and I will introduce you.

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And I'll always check for double opt-ins too, because on the investor side, that can be inundating. So I will do that because like, yeah, to our earlier point, it's trust.

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So if I say I'm gonna do something, I'm gonna do it.

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But I was called Zobot because earlier in my career, and this was maybe like three years into my career in particular, my manager, Josh Beckett, who is the best, so I'm gonna shout him out.

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He gave me feedback that, "If I know I need something done, I know to give it to you. You will get it done.

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But I also worry that if I forget to tell you, 'Hey, we're not going that direction anymore,' you will have marched off the cliff, and you'll just keep going." And I was like, "That is true. Like, I will do that."

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And it was a good sort of like awakening because it's that sort of pivotal point in your career for a lot of people, where you're getting ready to flex into manager.

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You're getting ready to not just take on work and execute, but actually come out of a meeting and be like, "Here's what I heard. Here's what we're gonna do." And set goals and set strategy and delegate.

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And that was sort of like one of those points in my career where I was like, "Oh, I need to challenge what I'm given."

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Like, I need to use critical thinking, not just in terms of how I execute, but also why I'm executing. Whether what I've been directed to do in some cases is the best way to carry forward.

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And as I've gone on through my career, Zobot is still a very real thing, I think, in terms of sometimes how I can present myself. I can be a little bit monotone and a little bit, like, over-polished.

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I think less so anyone who's gotten this far in this podcast will not think that's true, but it can be. But I'm much stronger in terms of, okay, let's break down why we're doing this.

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And then wonderful, so you came at me with, this is what we want to accomplish.

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But I actually think there's a couple different ways that we can address the why that might be more effective or more cost-effective, or just give you more flexibility in terms of what you wanna do with that information.

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And I think that's one of the big values of a chief of staff, that you're constantly learning, is as you work with different teams, as you work with different stakeholders, as your perhaps direct stakeholder evolves and grows, what your role is besides just getting things done is also challenging, and it's healthy and important in a constructive way to grow that muscle.

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I knew I was growing at it because one of my team members at Tula, someone who reported to me, she said, "You're very good at telling people they're wrong without them quite knowing that that's what you're saying."

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And I think that's very important in client work too, is, you know, I wouldn't recommend it. Here's why. Or I think what we're trying to get at is this. What if we explore these other options?

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But the nice thing about client work is it's up to them. Whereas when you're full-time and you're challenging, sometimes you do kind of get swept up in decisions that you don't agree with.

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But the key piece being, especially I think with people who are generalists and, like, are used to just catching all of these different balls in the air, also remember as you grow in your career, one of the exciting points is look at the ball, chuck it back if it doesn't make sense, and be like, "We should use the green one."

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Like, change the perspective, challenge it, because that's the best way to grow in this role.

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Whichever of the paths I mentioned that might be most exciting to you, you will have to take that step into challenging critical thinking, becoming less robotic, less absolute execution focused and obedient and more challenging.

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Yeah, I'm glad we landed on that because it constantly comes up, right? For chiefs of staff that start working the role, okay, I need to prove myself.

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I'm gonna go heads down, execute, think of things three steps ahead, anticipate everything, have plans for those things, you know, overwork, do the crazy hours because I don't want to drop any balls.

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I'm not even looking at what's coming. I'm just making sure that I do everything well, extremely well. It sounds like, you know, you have awareness around that, right?

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Like the critical thinking bit, exercising that, and noticing perhaps the times where some environments don't allow for that, right?

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I've been in certain environments as well where the critical thinking bit is not what is needed from me. Yeah. I think it's hard to gauge that going in. I'm curious if you agree with this.

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I think the chief of staff role is going through a bit of a renaissance.

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Like to your point, sometimes it's more administrative, sometimes it's more strategic, but I've seen more and more people talking about the role, more people wanting to be the role.

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It's more people shouting about how helpful it is for them, but it can look different at every company you're at.

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And it's funny 'cause like five years ago when I was in like a strategy role, one of my like roles that had the word strategy in it, and someone asked me, they're like, "I wanna do like what you do.

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Like how do I find jobs like that?"

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And I said, "You have to read the job descriptions and then find a set of like three to five questions that help you sort of get at the inner workings of the company, help you sort of get at the expectations of your CEO or stakeholder, because it's not the same at every company."

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Product management is like that. Strategy is like that. Chief of staff is like that. Lots of other roles where could mean totally different things depending on the size of company, the type of person you're reporting to.

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And I think the best way to get into a chief of staff role that you are excited about, whether you wanna just be heads down and not challenge, or you wanna step more into sort of that thought partner proxy, but also sort of sounding board for the CEO, I'd say, the best way is networking, because you end up meeting people who maybe don't even realize they need that role, but they need you.

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And I'm biased because it works for me, right? Like so, [chuckles] and then now it's kind of like my sales process.

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But I do think especially when you're coming in where it is so critical that you understand how your stakeholder thinks, you don't have to agree, but you have to understand and then decide if not agreeing works for you guys.

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[chuckles] But that's really hard. I can't imagine applying for a role like that just cold.And people do and it's out there, but, like, that's challenging.

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And so you have to figure out what do you ask to sort of gauge if it's gonna be a fit for you.

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But some of it too, I think, is similar to 10 years ago what it was, was like, "I wanna join a startup because I wanna have a hand in everything."

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Now, that's a possibility or you could say, "I wanna be a chief of staff because I wanna have a hand in everything, or I wanna be close to leadership."

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Either of those types of roles can get you that same sort of exposure. I think the similarity is you wanna be a generalist. You wanna have a hand in everything.

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And there's different ways to get at that, but the best way to know that it's gonna work for you and it's an environment that you want to grow in is to meet the people that have created the environment. Yeah.

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That's perfect. So a question that I've been thinking of was what are you still learning about this role as a fractional chief of staff? Everything. I mean, I'm learning what capacity means.

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I'm constantly learning different Tetris combinations of what my capacity could look like.

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I'm learning what types of work I enjoy and I think, you know, if we go back to, I mentioned, like, a lot of people, myself included, said, "I can't wait till I find a project and a client that I'm so excited about."

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When I'm asked what my favorite project is, I say the combination of all of them. Like, I don't want one of them. I like all of them. There's some that I go into sort of expecting it to not be my favorite.

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Like, I was doing some... I'll out it. [laughs] I was doing some benchmarking, competitive benchmarking to help a company prep to raise a series A.

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And so it was thinking through, like, what are the different sort of tangential categories we can go into, how big could that market size be, and then, like, what does that waterfall chart look like?

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I know myself well enough to know that is not a project that I can do very profitably because I will go down rabbit holes. Like, I will research for days. So I know that about myself. Yeah.

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So the time boxing doesn't work on that one. And it was proven out. Like, it was pretty early on and I was like, "Woo!" [laughs] But I'm learning. Like, I'm learning how much time I spend on things. I'm learning...

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And I've learned over time, I've gotten much better at managing my time, but I think that's where, oh, yeah, I'm learning how to give the most value to my clients, but also, like, remember the value of what I bring and balance that for myself.

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I wish I could tell you I'm learning what I wanna do next, but right now it's, "I wanna keep doing this."

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Like, I wanna do this for as long as it makes sense, and makes sense is I'm learning and I feel like I'm adding value. And as long as those two things are true, I'll keep going.

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And I think it's this constant piece too of, like, I've mentioned, I'm very motivated by learning. And so this allows me to learn so much in one day.

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I can't imagine finding another way to professionally operate where I can get that same sort of output. Last question to wrap things up.

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I'm wondering, is there any interesting book you would recommend or something that you're reading right now?

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I'll put a book out there, but if I may, there's, like, a thought that I would like to leave folks with that I think is interesting from a fractional but, like, generalist perspective.

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The book is Million Dollar Consulting by Alan Weiss. It's currently part of a sisterhood of the traveling book around a couple fractional women in New York City. I've [laughs] lent it out to three people now.

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I wouldn't recommend reading it cover to cover, but it has some excellent guidance on proposal writing, selling, and how to confidently state your value that I found very helpful. So that's a book.

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The idea I'll pose was actually brought to me by another fractional who works in technical product, Anne Warren.

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We were talking about how more and more people seem to wanna go independent, and I take maybe a call a week from someone who just wants to talk about it, and I'm always happy to talk about it.

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And I always say, like, you have to think about what stability means to you and, like, sort of chart out how you feel about the flexibility, but also lack of consistency that can come with this type of career.

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And what she said was, it never has been, but even less so stable at large full-time roles, right? And what actually seems most valuable about independent work or being a generalist is resilience.

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So I've diversified my revenue streams across multiple different clients. I believe in my ability to go sell out and get more work. I'm constantly updating my resume, you could say, or pitching or learning.

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And I'm so grateful for that because I don't fear what's happening in the job market. My ability is to learn.

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My ability to apply that sort of critical thinking and that hunger for learning we talked about that I think is what's most valuable to get hired.

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And so I'd also just leave people with, like, that sort of thought starter of, like, what makes you feel most safe and what does it mean to be stable, what does it mean to be resilient, and how do you want that to look in your career at this point when you're thinking about acquiring new skills, learning new things, being independent, being full-time, building a portfolio career, anything.

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How do you want that to feel for you? I guess a question to that thought is, like, how do we create the space to do that, right?

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If we're heads down all the time and our attention is not doing great as a generation at the moment, how do we create that head space and make time to sit with those questions, to explore them, to take action on them as well?

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It's hard, right? Like, to your point, it is creating a habit. It's the same as I'm gonna go to the gym twice a week. It's I'm gonna set aside an hour.

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Or even, I like the Pomodoro method I think it is, where it's like twenty-five minutes and then you take a five-minute break. Like, set a timer, and for the twenty-five minutes, put your phone away.

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Turn off your email, like Slack, all of it. Get it out of there and, like, focus on learning something.

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Or go find five people from your network that you wanna catch up with and just send them, like, a low stakes, like, "Would love to hear what's going on." Find a Substack that you wanna read.

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Listen to a podcast about a topic that you wanna step more into. Look for job descriptions that are interesting to you.

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Find events around you, whether virtual or in person, that allow you to step more into a space that you want to learn about.

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There's so many different, like, little tasks that you can put into those twenty-five minutes once a week and just create that ritual, but it is unfortunately or fortunately, it is like setting the time to go to the gym, healthy eating.

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It is a habit, but it's doable. And I think some of what helps me is I frame it, this won't work for everybody if you did not like school, but I think of it as I'm like, "I'm going to school."

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Like, I'm kinda like, "You know what? A nice little academic treat." Like, I get to do this thing that's there's no pressure on it. Like, I don't have to perform.

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I'm just learning for the sake of learning or catching up with people with no motive, just to see how they're doing.

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And that pressure that that takes off of me is what makes it really easy to sort of maintain this practice. Thank you so much for sharing, Zoe. Thank you so much for having me.

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