[upbeat music] Hey friend, it's David Nabinsky, the community lead at the Chief of Staff Network.
We help chiefs of staff through the three Cs: cohorts, curriculum and community via Slack with over 900 people in it. You can learn more about our membership and upcoming events and programs at chiefofstaff.network.
There, you'll also see our upcoming fundamentals course that starts in the end of March, and also our three Chief of Staff Connect conferences, with the first one being in San Francisco on May 15th to the 16th.
In this episode, you'll learn from Lindsay O'Sullivan, the chief of staff at Applecart. Lindsay is a founding advisor to the Chief of Staff Network.
Lindsay was also previously the chief of staff at SailThru, and has leadership roles at Nautilus Labs, just to name a few. She knows her stuff.
In this episode, you'll learn about being a wartime chief of staff, what Lindsay loves about the chief of staff role, some hot takes, how she got her current role, and so much more.
Excited for you to level up as a chief of staff. Here we go with Lindsay. All right, Chief of Staff Podcast. Um, Lindsay, welcome to the show. Hi, David. [laughs] Thanks for having me. It's good to...
I'm just trying to think about how many times we've chatted, but I think in person one-on-one, this might be the first. We've done a couple different events, at least two events that I know of. Um...
I think you're right. Yeah. I'm excited. I think you're right. Yeah. Yeah. Well, because we met during the pandemic. Yeah. So everything was virtual. I'd heard of you. I need...
I feel like this is, this is my- Well, that's terrifying. [laughs] This... No. No, I mean, you'd been, you know, uh, a founding advisor to Chief of Staff Network. Sure. Um, so I think, like, you know,
I nee- I needed to build relationships across the founding advisors. [laughs] Yeah. Yeah. So I ne- and it did take time. Um, and, uh, yeah, it's been beautiful to see, uh, the relationship develop. And here we are.
Um- Yeah, it's been so nice having you in the network. Such a change from 10 people- [laughs]... sitting in a VC office drinking their warm beer- [laughs]...
and trying to figure out what everyone was doing as a chief of staff. [laughs] So much nice to have the structure that you put to it. Oh, thanks. Thanks. Yeah. I'm really curious about that part.
Um, but I'm also- [laughs] We like to start off the show talking about around, like, how do people get their chief of staff roles. This, I think you're on your, your third chief of staff role right now.
Maybe more, um, depending on how you, like, calculate it or- Sure... but maybe, like, the m- most recent one, or the current one, how would you describe, like, how you got this role? Networking, networking, networking.
[laughs] Came off my last role. Well, so I've had two chief of staff roles, and in between I ran operations for a company, operations and human resources.
And so, uh, after I left the previous company, I took the time to think through what I wanted to do. I realized I wanted to go back into this hyper generalist role. Yeah. And
hit the pavement talking to anyone and everyone. And actually, um, Doug from Raise- Yeah... who spon- has always sponsored Chief of Staff Network events,
invited me to a Sequoia FelFell dinner that he was sponsoring. I had done, I don't know, several coffees, dinners and drinks that week. Yeah. It was the last thing I was gonna do before I went on vacation.
I decided I'm not going. I was about to email him and say, you know, "Catch you next time," but New Jersey Transit trains stopped running that day. Okay. They fully canceled.
So I said, "Well, if I'm stuck in the city, I might as well eat dinner."
So I went, and sitting two seats away from me was our VP of talent at Applecart, who had just been looped into a discreet chief of staff search that wasn't public.
I went on vacation for three or four days, and she called me when I got back, and here we are. Wow. Yeah. Yeah. So all networking, all talking out loud about what you want or need in the next role- Mm... it all pays off.
Shout out Doug Regal at- Yeah. [laughs]... Raise, formerly known as Raise, now JLL. JLL. Um, yeah, he's been a, an incredible partner. Um, wow, what a... Wow, I, I don't think I really kn- knew this story. This is good.
I actually don't think I connected it to the Chief of Staff Network until you asked that question. [laughs] Because the, the network, I've told you, has come through for me in a lot of different ways. Mm-hmm.
But that was very impactful personally, for sure. Mostly good ways. [laughs] Mostly good ways. [laughs] I'd struggle to think of a bad way. Mostly good ways. [laughs] Cool. Well, um, you're eating cake.
I di- I didn't deliver. I didn't give you the cake, so. Oh, don't tell everyone that. [laughs] Okay. So, um, in what you said, um, you were really interested in getting back into this. Like, what, I guess, like, why,
why did you wanna have another chief of staff role after you've done it so many times? So I left the first chief of staff role at SailThru after they were acquired.
I stayed on for some period of time and knew I wanted to go into a more focused role, because I had just had a baby, we were moving to the suburbs. Yeah. I didn't wanna be spread so thin across so many things.
And quite honestly, that was the right move. And so this is actually funny. I met Lee, who was chief of staff at Nautilus,
uh, in that VC office at First Round, where everyone was going, "So what do you do all day as chief of staff?" [laughs] 'Cause nobody knew at that point. She was looking to define a maternity leave policy. Mm.
I had just done maternity leave as a chief of staff, so I was like, "Well, I could talk to you about that." Long story short, wind up meeting with her after that.
She says, "I could put you in a people lead role if you canDo my chief of staff role while I'm out on leave. I said, "Sure, what's the big deal?" So I went to Nautilus, did the HR stuff, eventually took on full ops.
The trend you're seeing there is that I could not stay in one lane. Mm. I had to take on more. Like, I am just a generalist at heart, and so I had mostly recognized that about myself coming out of Nautilus.
[laughs] But having the space to think it through a bit further, I like the one-to-one relationship with your principal. Mm. I like the quick run-up to the top and immediate execution, right?
I like building a process to efficiency and passing it off to others to carry forward and iterate on.
I like that I can walk in in the morning and think I'm gonna have one type of day and wind up it being the exact opposite. Mm. I need that variety, and I don't know another role that provides that, right?
So I often joke here that I'm a lifer. I'm not a two-year term [laughs] person- Yeah... in the chief of staff role, but we'll see. Yeah. Um, when you say need, what does, what does that mean? It's just, like, very,
like, thirsty for change or variety, or, like, you get energy off of different ideas? Um- I think it's mentally stimulating- Yeah...
to have to context switch all the time, and I know that goes against everything everybody else will probably say to you, right? I like putting out fires, and obviously fires are of different- Yeah...
degrees, uh, in this role and i- at any company. But that quick solution or stepping in to identify the quickest solution, for me, gives me the same rush as checking off the item on the to-do list.
It's just that my to-do list isn't always very well defined or foreseeable. Yeah. And so I guess to your point, it gives me that energy and keeps me connected and engaged to the work. Have you, over the years...
And I, I do wanna talk about this idea of a wartime chief of staff. [laughs] Um, s- there's, you know, discussions around wartime CEOs and peacetime CEOs, but wartime chief of staff, um,
when you think of that, like, what comes to mind? The different flavors of wartime chief of staff, right? I have certainly been parts of the big wars, right? Mm.
Sometimes there are really big changes and such going on within a business that, um, that puts you into that mode, but those wars can also be smaller battles. Mm.
And you do have to be able to switch between that mentality of, um, peacetime and wartime, and it doesn't always have to be the same time that your CEO is having. Mm. Right? I think, um,
if your principal goes out on a parental leave, in some ways you become a wartime chief of staff. [laughs] Right? Because you are on top of a lot more. Mm.
You've just, like, lost half of the bandwidth in the office of the CEO, uh, or whoever your executive is that you're supporting. And so that's one way I think about it. Uh,
I don't know, what else can I tell you? What, um... When you're in this wartime chief of staff mode, um,
like, I guess, like, what comes to mind is I, I liked how you said about that there's, like, the small moments, and maybe that's, like, a conversation. Um, so maybe there's, like, a hard conversation as kind of like a,
a wartime chief of staff. Um, maybe there's, like, a, a longer range project of like, wow, we got to, you know, adjust staff or- Mm-hmm. Um- Mm-hmm... but it's probably a similar or could be a similar,
like, way of operating and maybe a way of thinking.
Um, do you, have you, do you think you've developed certain approaches to, like, let's just say, like, hard conversations, um, from having a lot of wartime chief of staff experience? So I think it's twofold, right?
Because if you think about the way you have to communicate up to your principal, that certainly changes. Mm.
And depending on, you know, the air quotes war that you're in, it's really about the filter that you put on it, right? In the example where your, your principal is out on a parental leave,
maybe you're keeping a list, maybe you have a regular check-in with them, maybe you order things by priority with which you need them to be aware of in what different timeframes, uh, and you're, you're putting out the fires for them in the background.
In a scenario where you're going through a fundraise or some sort of M&A activity, and you're charged with keeping the lights on while that externally facing team inclusive of your CEO is really in the thick of it,
you're really only running things up to them that are absolutely necessary that their eyeballs- Mm... you know, touch or see. I...
And all of that is, requires the level of trust and understanding between the two of you to know-What those things are, right?
And so maybe there's a very clear conversation you have on the front end, or maybe you've just established such a rhythm, rhythm of business that
the two of you can anticipate where those touch points are going to come up and, and agree to check in with each other on them. As far as, um, communication with the rest of the organization,
I think it depends on what you're communicating- Mm-hmm... and where that difficult information needs to be relayed, and in what group. I'm a big believer in well-documented comms plans. Mm.
Um, who knows what when, to your example of maybe a reduction in force or, or impending fundraise, um, M&A activity, et cetera.
Getting to alignment with the people who need to be aligned to the comms plan as quickly as possible with who says what to who, when, and why- Mm... and what the answers are to our anticipated FAQs are,
I think is the most important part. And as far as how to address those difficult details- Yeah... I'm big on looking at the organizational context, but for the most part, ripping the Band-Aid off, because I don't think
managing information is always the most useful tact when people can start connecting the dots on their own, right? So tight communication loops both up- Mm... and down, and
directness really as a summary. So like, just to kind of put a little bit more, like to zoom in or double-click, whatever people say. [laughs] Um- Love a double-click.
[laughs] I think what I'm hearing is like, instead of, instead of maybe like trying to be more open and versus like, "Oh, we'll share this week one. Week two, we'll share this other part.
Week five, we'll share more," it's like, "No, no, no, like, just give all the information now." I think you might still wind up in a situation where you decide there is some staging to the- Okay...
information that's shared. It's more that your leaders should probably know more information more fully up front. Mm. So that in the instance where,
God forbid, there's a leak of information or somebody just connects some dots on their own and asks a question, those folks aren't blindsided in answering questions incorrectly. Um, but I do think like
sharing information as soon as you have it and as soon as- Mm... you can best anticipate how it will land- Yeah... is important. Yeah. I like that anticipated FAQs. That was interesting.
I'm not sure that I'm like that familiar with that, but I love that. Yeah, I think it became clear to me that you could anticipate where some questions were gonna come from in an organization.
Some parts of the organization wanna know what next steps are. Some maybe squeakier wheels- [laughs]... wanna know how will this impact me, right?
There's I- there's seldom an issue that somebody doesn't think will impact their compensation in some strange- Mm... way, though tenuous the connection.
[chuckles] And so if you can at least tell leaders who to defer to should some bucket of- Mm... questions arise with their team, then they don't feel the need to scramble and say the wrong thing.
So if anybody asks about their compensation, please direct them to Lindsay or whoever, right? Uh, versus them saying, "Oh, well, I'm sure it won't really impact your compensation." Yeah.
And then a week later I'm talking to them about a pay cut or something, right? It's not, uh, it, it arms those leaders with the tools they need to succeed.
And are you thinking or is this, some of these approaches that we've talked about so far, is that mostly like call it like Series A, Series B plus type of companies?
Or how do you think about some of this stuff, wartime communication approaches and company size? That's a good one. I think when you're really small...
So series, I hate talking in series about communications because I think you have to think about it more in terms of headcount. I think- Okay...
if you're sub 50 people, it's pretty easy to grab everyone over the course of a couple days and check in with them and make sure they're not nervous or- Mm...
uh, they've heard bad news, but like how contextualizing it for them in particular. The larger you get, you more so need to equip the layers- Mm...
in between yourself and those ICs or entry level folks who are maybe experiencing the receipt of bad news for the first time. And I would actually say what's more important there is management training throughout, right?
Mm. And having a pulse on how your managers typically communicate the good, bad, and ugly- Yeah... to their teams and, and where the trouble spots are in the organization for how folks receive that information.
That's where a chief of staff's partnership with the human resources organization and the leadership team is, is really important, right? Uh, where are the gaps that you can help fill when communications go out? Okay.
Um, is there anything else about wartime chief of staff that you wanna touch on?I think the most important skill that a, you know, air quotes- [laughs]... wartime chief of staff can have is to exude calm- Mm...
during those periods of time. I would say I probably seem more flap-able during peace time- [laughs]... 'cause I'm, have a little more... You know, it's easier to be a little silly, right? Yeah. And so, and, and
inapproachable. Um, but I think in those wartime scenarios, you, you wanna remain accessible, but you want to, you know, you wanna be the duck or the swan. What is it?
The [laughs] Very calm on the top of the water- Yeah. [laughs]... and the legs swimming. Very, whatever the bird is on the water. Yeah, I think it's a duck. That's what you wanna be. Yeah, yeah, yeah. Okay. Right?
Uh, because folks, whether you think or not, are looking at you. I always... So on an airplane, I don't love flying. Certainly don't love it recently [laughs] as a concept.
But with turbulence or takeoff and landing, I always watch the flight attendants. Mm. Because my theory is always if they're freaking out- [laughs]... I have something to worry about.
But if they're drinking their coffee, acting like nothing's happening, then I'm probably fine. The chief of staff is the flight attendant in that scenario, right? It's wartime. Things are moving quickly.
Change is happening. Maybe something bad happened. If the chief of staff is calm, you're gonna be okay. Mm. All right. Or at least there's a plan underway. [laughs] The u- We're figuring it out. We're alive.
Under- underwater. [laughs] We're underwater. Yeah, we're swimming. [laughs] If people can't see, but both of our hands are just... [laughs] We've got duck f- Yeah... feet going today. [laughs] Um, the...
And so when you joined Applecart, what has been, what would you say is kinda like the state of the business, and how would you kind of describe as to like, why a chief of staff was needed at the time?
You mentioned there was like a discrete or like a, you know, there wasn't, it was like kind of emerging. What, what would you like... How would you describe like what was... 'Cause it's been about a year? It is.
I am coming up on a year on March 18th. Okay. Yeah. Not that anyone's counting, um. [laughs] No. [laughs] Uh, I just remember that I started the day after St. Patrick's Day. Okay. I am Lindsay O'Sullivan, uh.
[laughs] If anybody wants to send Lindsay an email on March 18th, I don't know the exact date that this podcast comes out. Congratulations. Yeah, but just put that in the subject line, "COS pod one-year anniversary.
Congrats." [laughs] Um, if we get 10 of those emails, um, I don't know, we'll do something really cool. We'll do the duck hands for you. [laughs] Yeah. We'll create videos. Mm-hmm. Yeah. We'll, yeah.
Um, yeah, so what was going on about a year ago? What was going on about a year ago? Quite honestly, I was looking for a couple of very specific things in my own job search.
I wanted to be back in an office and seeing people. Mm. Going through the fundraising M&A activity with Nautilus brought me back into the city more regularly. Mm.
And I had been remote for four years, and I had small children at home. Mm. And I was like, "Oh, goodness. I like people and interacting with adults during the day."
So I wanted to be somewhere in person, but that also had flexibility for said children. And Applecart's in the office three days a week, predictably Tuesday, Wednesday, Thursday, with some added flexibility.
I wanted to go somewhere where talent was dense- Mm... and I had that at both Sailthru and Nautilus. There are some amazing people who I have worked with again since and who I would love to work with again- Mm...
from both of those companies. I wanted to go somewhere where that would repeat, and Applecart really signaled that for me with their hiring process. Mm.
They ran it very similar to how I ran things at Nautilus- [laughs]... which was- It's an interesting way to look at it. You know? Yeah. Yeah, yeah. Kinda like, "I see what you're doing here." Yeah. "I like this."
[laughs] Everybody gets a project. [laughs] My, my hiring project was very meta. It was like create my own hiring project. Yeah. Like, what would you tell a chief of staff to do when you came in?
And it was, it was great. I really enjoyed doing it. I wanted to work somewhere where I got along with my principal, which was a, a clear match for me after we had dinner. That was the second step of my hiring process.
Okay. Nice. We went to dinner- Nice... on Super Bowl Sunday- Nice... for three hours. Wow. Answered every question I could possibly think of, uh, and I wanted to go somewhere where the opportunity was big, right? Mm.
And, and that included an assessment on business health and- Mm... success to date, as well as opportunity for my work to be impactful, and we're at a really exciting growth stage at Applecart.
So there, there are vast opportunities around- Yeah... improving process, or, um, we're revisiting our values. We're, we're putting into place a new rhythm of business or improving that at least, right?
And making changes to our OKR pro- like, things that I really enjoy doing that were presented to me upfront as areas I would be able to address. Mm. So the role had existed previously.
The chief of staff who was in my seat before moved into another role in the organization, which is another green flag for me- Mm... for a company where our chiefs of staff can move around, should they want to. And
there was an established chief of staff, still is, hi Kendall, sh- who reports to our other co-founder, co-CEO. So it would be my first time that I had a bit of a partner in crime- Mm...
in sitting in the same role, uh, across the organization, and that was really interesting to me, so. Is Kendall around? Can we bring her in right now?
[laughs] It's funny, Kendall is usually here, I feel like, on Fridays, and I looked for her before. She's not here. Um, but she did come... Oh, no, I haven't brought her yet. I brought somebody else to the last event.
I was thinking of just like all of a sudden- Yeah... now we bring her into the pod, like, "Okay-" Yeah. "... here's the other..." Yeah. Oh, surprise. Yeah. It's a two-for-one.
Um-So yeah, all of those things were really exciting about Apple Cart, and all of those things have led to a great experience over the past year. Yeah. Um, so yeah. So there was like...
And so within these like OKRs, um, I think you said annual planning. Annual planning. W- like did you- Business...
do you have certain like templates or approaches or like, you know, "Hey, this is the Lindsey O'Sullivan way." Like how, yeah. I try never to have the Lindsey O'Sullivan way.
[laughs] I, I, I tr- truly believe that a lot of people know how to do things better than me, and so I prefer to be a sponge and find the correct mix- Mm... with input from stakeholders.
I also, maybe a hot take, I think OKRs should evolve with the business- Mm... even quarterly.
I don't think that you can take the standard OKR process and apply it blankly to any comp- any growth stage company that you walk in the door- Yeah... and hit, right?
I think leadership and management structures look different, communication structures look different, focus areas for the business can look very different, and so, uh, it's iterative, right?
And so usually I just walk in and assess where we are today, and my early wins that I look for are- Mm... increased transparency, alignment, and understanding. So
first of all, are we all in agreement that we're running the business by these OKRs? Mm. Right? It should not feel like an ancillary side project to anyone. It should be the pure focus. And then does everybody know that?
Mm. Have we told everybody that we're using OKRs? Have we explained what OKRs are [laughs] to everyone? [laughs] It sounds so silly, but- Yeah...
you know, I've had some really junior folks in my career say, "What does, what do the O, K, and R stand for?" As I'm already explaining what a department KR- Mm...
is and how that will be impactful, I'm like, "Oh, I need to go five steps back," right? Yeah. So once those things are in place, then you can decide how to iterate
on the classic structure, uh, to create the focus you need depending on what's going on with the business. What other hot takes you got? [laughs] I don't have that many hot takes. We just did this over lunch here, and my
recent hot take was that hotel bars are the best bars in the city. [laughs] Which is completely unrelated to the chief of staff role. Um,
I have a hot take on the chief of staff role that, uh, lands with people differently, but I think for the most part, a chief of staff to a CEO should be able to walk in and out of any meeting that they need to. Mm.
And I don't mean that in a distracting way, but sometimes it's useful to just audit what's going on in team meetings. Um, obviously, you know, you're not jumping into performance reviews unannounced- [laughs]...
but, uh, it's good to be able to join a few product standups and just hear what's going on and how people are interacting with each other. That was actually a really difficult thing for me to adjust to in the pandemic.
Mm. Um, because being in the office, you could see who was maybe having a tense conversation in a conference room- Oh, yeah... or who was not showing up at the office till 11:30- Mm...
and maybe had something going on over a period of a week. And in the pandemic, you were sitting in your house by yourself. [laughs] Uh, so yeah, having that, having that visibility is, is really useful.
How do you kinda like make that happen? Um... It's relationship building, right? I think here it's a little different 'cause I'm not the chief of staff
directly for half of the organization, so by no means do I think I should be able to walk into every- Yeah... meeting company-wide. But I think with the folks who report directly into my current CEO,
I think we've established strong relationships over the past year, and it's more or less an open door policy. Like I, I- Yeah...
my head of, uh, or head of platform had a team meeting going on that I walked by, and I just gave him the finger point through the glass.
[laughs] And he was like, "Come in," and he thought I had a question, and I was like, "No, I just wanna hang." [laughs] And he was like, "Great."
[laughs] And I sat and I listened to the meeting while I did some other stuff. And so- Mm... I think what's important in that sort of...
Like, you have to tell folks like, "Oh, I'm just here 'cause I like to hear what you guys are working on." Yeah. Right? Like, I'm not here because I have bad news for anyone. Um- Yeah...
also diffrec- difficult during the pandemic to just show up to team meetings- Mm... [laughs] 'cause they would assume I was there to give bad news. Mm. 'Cause I was just eavesdropping. But, but not as much now.
No, now it's great. That's... Yeah. 'Cause now they could see me interact, and they know I'm drinking my giant jug of water and I try very hard- Can confirm that. Yeah.
[laughs] Going back to the like visuals- [laughs]... auditory kinda conversation we've been having, there is a big... There's a big jug. That- Yeah. This is my office jug. Mm. I have a bigger jug at home. Wow.
I like to hydrate. Hmm. Mm-hmm. You're like a two gallons a, a day kinda person? Yeah. Otherwise, you know, just feel tired. Wow. Mm-hmm. Love it. [laughs] We got hot takes. We got life hacks. You know, this is just...
You know, we're just getting started here. This is, this is good. This is- I usually have- This is- I also drink like 40 ounces of coffee a day, so. [laughs] So maybe I just- That, that offset- Maybe I do offset drink...
that probably offsets. Yeah, yeah. [laughs] That probably offsets. Um-And the, and so you kinda talked about it, but just to like kinda clarify, the, um, the departments that you kind of work on are?
Yeah, so I always ex- I do a lot of onboarding sessions here. Yeah. And so the way I talk about our org chart is that Matt, who's the co-CEO, I don't report in to, he owns the, the revenue or client life cycle. Yeah.
And Sasha, who I report into, owns both the employee and product life cycle. So we have product and engineering,
uh, and the other sort of ancillary departments under our platform team, and then we also have, uh, talent and, uh, human resources, uh, on our side of the organization. Cool.
Um, you know, you've been a chief of staff for, for many years. Are there certain resources besides this podcast- [laughs]...
um, besides the Chief of Staff Network, is there certain kind of resources or things that you keep going back to? Is there certain tools that you really like? Like how do, how do you think you are so effective?
So part o- I'm oddly one of those people who remembers things. [laughs] You know? When I was a waitress, I didn't have to write down orders. Really makes people very nervous. Huh. But I think that skill has translated. I
also leverage my network. I, I... The Chief of Staff Network is obviously part of that. Mm. The podcast, the Slack works, but you know I love the Slack workspace.
You can drop a question in there and people will respond to you immediately. Uh, and I told you the bank story, right? Yeah. Yeah. You can share it here if you want. [laughs] But... No, I...
The Chief of Staff Network Slack group, I was having trouble getting a hold of a, a banker, uh, at a very early hour for a rather important situation, and I dropped into Chief of Staff Network, like, "Alert, alert.
Please, does anybody know anyone who can help me get in touch with somebody at this bank?"
And somebody, a chief of staff at another bank, started Bloomberging the people, [laughs] the people that I needed to talk to, and he called me an hour later, uh, maybe even less. So...
The banker that you needed to ho- Yeah... got, you heard, talked to in an hour? In under an hour, for sure. Wow. Uh, and it was like probably 8:00 AM at that point. Um, so
the Slack, the Slack group certainly helps, but I like to look for people who have done it before. Mm. And so for me, that's not always a chief of staff, right? Mm-hmm.
'Cause I think a lot of us are trying new things all the time. So I've done my best to build a network of other executives at various stages of growth in companies- Mm...
who can tell me what has worked for them, but also what's not worked. Mm. The love of hearing what hasn't worked and the why and sort of what the variables were that controlled the failure there.
And so I don't have a go-to book or- Mm... tech stack. I'm, I guess, a little old school in that people are, are my leverage in most scenarios. And when you're reaching out to call out like
a COO at another company, are you saying like, "Hey, I'm going through this," like, "can we hop on a phone call?" Um, are you texting? Like, are you like, how do you kind of like leverage the network? So
I got better at this during the pandemic- Mm... and being remote because I realized giving was the way in. Mm.
And so I made myself really available to a lot of different people, and we were all on Slack and Zoom and Google Meet- Yeah... whatever we were doing.
So it was really easy to pop on a call with people and talk through thoughts, ideas.
The giving piece made it easier to ask later, and then when I was looking for my new role, I spent a lot of face-to-face time with folks just sort of talking about- Mm... what I was thinking versus making asks.
And so now in a lot of areas I feel it a lot easier to reach out and make the ask more immediately and more directly. Yeah. Right? It's, uh, it can be a little more transactional- [laughs]...
because I've built that equity with those people- Mm... uh, in that way. And I said as I was hyper-networking into this role that I couldn't wait for it to be over [laughs] 'cause I was so tired.
There's only so many- Tough, yeah... happy hours you can do. Mm. And you do get sick of talking about yourself. Truly, you get sick of talking about yourself. And so
I said I couldn't wait for it to be over, but I haven't really stopped. Um- Mm... because now I can go back into that giving mode versus the taking 80% of the time, right? Yeah.
Where it's now, it's like an 80/20 split, where I need to pull some knowledge out of someone's brain, that's 20. Um, and the rest of the time I'm just being really available to folks. Yeah. I love that.
I like that split. You want another question? Yeah, I do. Yeah. Okay. Um, what other, like, what else would you share to either, like, enrolled chiefs of staff or aspiring chiefs of staff?
I think for enrolled chiefs of staff, zoom out. I think it's so easy to get caught in the weeds every day- Mm... of what needs to be done, and I think especially when you're early in your career,
you can go into, uh, I call it like good little soldier mode, right? [laughs] It's like, "Do this, do that," and you like sprint as hard as you can. Mm.
And you, and you are creating and developing things, and it is invaluable to the business, right?But in some of those scenarios, you should probably ask why
or push back a little and suggest maybe there's another way to do it, or suggest maybe we should talk to somebody else about it. And I think the f- earlier you can develop
those skills and that muscle to zoom out on is this really a problem for the business? Is it the most important problem to zoom- to solve now?
Uh, the more impactful your work is gonna be overall, and the more valuable you're gonna be to your principal and the company at large. I think for folks who are considering a chief of staff role, it's...
I've had so many of these conversations recently. You gotta be a doer, man. [laughs] Mm. You are 99% of the time not going to walk into a role where you're opining on strategy all day- [laughs]...
with your really smart ideas, and that's okay. Uh, I still do things like move furniture around the office. Mm. And I, I don't mean still because I've... I just mean I'm old is when I say still.
I still, like, crawl under desks- [laughs]... and plug in monitors, right? Like- Yeah... help with move, moving into new office spaces. You have to do what needs to get done, and
on the front end, you should clarify with your prospective principal what the doing is, right? Because most CEOs in startup land will tell you about- Mm...
grand plans that they have and ways that you can help on strategy and such, but you should understand what the nitty-gritty details are gonna be day to day.
You should also make sure you clarify what level you're coming in at. Mm. And I just mean there are varied expectations inside an organization as far as how you will or won't contribute to- Mm... big and small projects.
And if you are not a lifer like myself in the role- [laughs] You should clarify up front what the tour of duty is, right? Mm. Are they thinking two years?
Do they have something in mind that you might slot into at the end? Is it aligned with your vision for your career? And if they haven't thought about that, that's okay. It's a good time to set expectations up front.
Yeah. Otherwise, you know, it's... A chief of staff many years ago said to me, "It's really easy to wind up the garbage disposal where things just get dumped- Mm... because they don't have an owner." And
you can be a doer. The dark, the dark side's the garbage disposal, right? [laughs] Like, you can, you can do that. Uh, but if you're expecting an out, that will become very wearing on you
probably around the two-year mark. So you'll, you'll wanna know what your exit is for that. Whew. This, this garbage disposal [laughs] just really kinda got to me.
[laughs] The woman, the woman who said that is gonna cringe when she hears this, but, uh, I'm gonna give her a heads-up after this. Um, yeah, I mean, it's hard. You're- Yeah... you're...
The other way to think about it is, like I said earlier- Maybe you're managing comms, by the way. That was beautiful. That was, like, a classic example of what we were talking about.
You're like, "Okay, I gotta-" [laughs] Yeah, I have to go talk to her before she hears it. No, and I'm not name-dropping. Yeah. So she will not be outed, but, you know, building process- Yeah...
and taking things on short term to then hand off later, that's what I find really exciting in the role, and that's why [laughs] I'm probably gonna be a lifer.
But if it's a stairstep to something else for you, that's where it becomes- Yeah... you start feeling that way, right? You start feeling... Taking advantage of is the wrong word, right?
It's, you know, you're getting a paycheck. You're, you're- Yeah... you're doing the job you were sold, but, uh, it, it's just wearing. Yeah. Right? It's the, the demand is always on you. Mm.
Well, um, this was an incredible conversation. [laughs] Um, I know we're, we're laughing. We're ending on a high note here. Um, and if, um, if people want to reach out, obviously they can connect with you in Slack.
Any other places or any other parting thoughts, Lindsay? I love to connect with people on LinkedIn. If you're in the chief of staff network, 99% sure I dropped my scheduling- Mm... Calendly link back into my profile.
I don't require any notice. Just plot yourself right onto my calendar. Beautiful. Talk to you about anything.
Otherwise, hoping to connect with some folks in person in the New York City area over the next year or so, you know? Love it. Get, get back out there. Let's do it. [laughs] Thank you so much, Lindsay.
Let's bring Doug, let's, let's bring Doug back in. Yeah. I owe him an email. [laughs] Let's, um, let's give him a heads-up. I was talking about him, too. [laughs] Thank you so much, Lindsay. Thanks, David.
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