[upbeat music] Hey friend, it's David Nebinsky, the community lead at the Chief of Staff Network.
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Can learn more about the role and apply on our website through our job board, or by going over to the careers page on Flowcode's website at www.flowcode.com, www.flowcode.com.
In this episode, you'll learn from Carly Gilardi, a chief of staff at Zapier, and Brandon Samit, the chief of people officer at Zapier.
Carly and Brandon work together, so in this episode you'll learn about how they started working together, what stood out to Brandon about Carly, how they work together while primarily working remotely, how Carly's role has evolved, and so much more.
So if you're looking to learn more about the chief of staff and principal dynamic, this episode is for you.
Also, Carly and Brandon will be speaking at our Chief of Staff Connect conference in San Francisco on May 15th to May 16th, so we're excited to give you a sneak peek for you to get to know them more, and also hope to see you out there.
I'll be out there, and really looking forward to it. So yeah, let me know if you're going, and I hope to see you there. Uh, really excited for you to level up as a chief of staff. Here we go with Carly and Brandon.
Carly, let's dive into, to the fun stuff. Um, how would you say you got your current chief of staff role, Carly? Yeah.
Well, so I was, uh, I was the chief of staff to, uh, the chief people officer at a previous, um, company, and in that position I had worked, um... It was actually a school, a charter school network.
I'd been there for about eight years, and had been on different, um, in different leadership roles within the department.
And so when that role opened up, um, the head of that department came to me and, and so I interviewed internally. So I would say it was a bit of an internal mobility moment.
Um, but then someone that I worked previously with at that same company reached out, because they now worked at Zapier, and said, "Hey, we have a very similar role open that you currently are in.
Would you be interested?" And, um, I, I was, because it felt like this was the right time. I was excited to kind of potentially explore other industries.
Um, but I had only been in that chief of staff role for about six months, and I was really loving it, so I wasn't ready to, like, change roles, but was excited to kind of take another chance in a new industry and, um, and for a new company.
So that was a little bit how my journey was. Okay. And so then, um, that person just reached out and was like, "Hey..." Like, was it casual, or was it, like, a f- like, more formal?
So she, uh, she works, she still works at, at Zapier, uh, and she was my former boss, um, at, years ago. She hadn't been at, um, the company I was at for a while.
Um, and so we had a good relationship and just was like, "Hey, are you interested in this? This opened." She runs, she does recruitment at Zapier, so she of course had, um, insight into the role.
And then I was like, "Yeah, I'm, I'm open." And, and Zapier definitely gives a bit of a white glove service to referrals.
You know, you get, I think you get an automatic, um, interview with a recruiter, and so it, it made the process really easy. 'Cause at the time I wasn't necessarily looking to, to switch. Cool.
And, and when did, um, and did you and Brandon start working together immediately, or how did that start to go down? Yeah.
So Brandon w- Brandon's always been, uh, the chief of, chief people officer since I've been at, at Zapier. So again, I am the chief of staff to the chief people officer here as well.
Um, and yeah, he was the first, after I had my recruiter interview, he was, uh, he conducted the next interview. So that was about two and a, a little over two and a half years ago.
Um, and Brandon, do you remember, like, what, I guess, like, was there anything in particular that, like, during the interview process that you were...
I think sometimes we get questions around, like, I was talking to a CEO earlier this week who was like, "How should I, like, what's a good way to interview or, like, to understand, um, like, my prospective chief of staff?"
Like, did you have any certain, a certain approach that, uh, was really useful or interesting or... Yeah. Yeah. You know, you know what I would say?
I, I thought about this in part based on past experience, because, uh, I have been a chief of staff before, uh, to the effectively, like, the, the head of talent, uh, in a prior organization.
And you know, I lean on that experience a little bit, but also what we, what we know about hiring in general, which is that, you know, it helps a hiring manager, myself in this case, like, really think about, like, what a great match looks like.
It starts with, like, well, how clear am I about what we need and why we need it? And I think that's especially important for a role like a chief of staff role, because a chief of staff role has so many flavors. Mm-hmm.
Different organizations think about the role very differently. The job descriptions can, like, you almost can barely recognize, like, one from the other, they look so different.
And that's even before you get to the second dimension of difference, what I think is especially, uh, important for chief of staff roles with their leaders that they partner with, which is just, um, kind of where the leader, the CPO in, in my case, is in their leadership journey, and what kind of partner they need outside of the nature of the work.
Mm. So there's the nature of the work, and that's different.
Like, like some chiefs of staff have, like, very concrete portfolios of work, um-Some chiefs of staff are primarily consultative, and they're like almost like, uh, you know, like the chief of staff in, in certain governments, you know, to the, you know, to the president or whatever the case may be.
Like, they're there to like just make sure the stuff gets done. But they may or may not have, like, ownership over specific programs or products.
Other chief of staff roles, including Carly over time, um, you know, has ownership of, like, very specific products or practices.
So that's one, one kind of slider that I see on the chief of shaf- chief of staff job description. The other one is, um, how dynamically those things change, right? Mm-hmm.
Some chief of staff roles, whether it's primarily consultative or primarily program ownership, it stays relatively consistent over a length of time.
But in other roles, uh, Carly's included, uh, it, it changes, and it can change fairly often as well. So that's another slider, uh, that I see on the job description.
And the third dimension, you know, of difference on these specs is just the nature of the leader and what kind of partner they want.
Specifically, do they want someone who takes what the leader says and just goes ahead and execute? Do they want someone that's gonna go toe-to-toe with them? Which is what I'm really counting on. Mm.
Hold up a mirror and say like, "That doesn't make any sense, Brandon," or, "The last time we did this, uh, it went really poorly, and reminder, here are the three reasons why. Let's do it this way instead."
And, you know, and so on. So, um, that's the number one piece of guidance I have to anyone who's, you know, spinning up, um, a process to hire their chief of staff is because there are so many different flavors.
Like, no one can tell you what kind of chief of staff you ought to have, and you can't copy and paste a job description from some other organization or even another leader in your own organization.
You have to have like pretty, pretty good clarity and deep conviction about what you need and why you need it. And then from there, you just do what we do for any hiring, uh, that we do.
It's like, well, what are the skills and experiences that are best matched to, you know, someone being able to succeed within those expectations, and how am I gonna pick up on those qualities when I see them as I get to know them during the interview process?
I was gonna make some kind of ins- some joke around the toe-to-toe part, but I, I don't know if I, I've got it like good yet, so I, I'll probably just like- [laughs]... put a pin on.
Like, there's something there that I wanna say, but I don't wanna mess it up. Um, yeah, I don't know. Uh, but, um, the... In terms of getting to know and like your kind of...
When, when did you, in the interviewing process, how did you start to feel or when did you start to feel like we can really work well together and like that there's like a kind of a, a cultural or relationship like match in addition to like the skills and experiences?
Like, how, how did you test that out? And, um, you know, when did you kinda know, like, okay, she has the background, she has the skills, but also like as you...
You sound like you're, you were interested in the toe-to-toe, but also that you were on kind of a little bit of a journey is what it sounded like you wanted to kind of pursue, uh, in terms of growth.
Like, how did you kind of figure out, like, this was, this was the one? Yeah, you bet.
Well, I, I do think the, the number one differentiator when, when I was interviewing Carly was around just like candor and straight talk and, you know, that came up during references as well.
Um, and I think references are a particularly good way to test for that kind of thing 'cause it can be hard to create an environment where someone can show up, you know, in an interview the way that they just really show up in a job where they've already ramped.
And I'm more interested in like, you know, what the person is really like once they've ramped than what they can or can't show in a, in a fabricated interview environment.
And so that's maybe another big suggestion I have for folks for these roles is, um, references count for a lot. Mm. A lot. Uh, yeah. Carly, what do you, what do you remember from the process?
Did you have like a moment where you felt like, you know, y- you know, every, every, every hire is a two-way... You know, two people have to hit the, the go button, you know, for it to work.
So what, what was that experience like for you? Yeah.
Actually, something I think was unique about the experience, and I know that now knowing this is actually kind of standard at, at Z- as how we do this at Zapier, but, you know, Brandon was...
I actually went through multiple rounds of interviews, and Brandon was the first. After the recruiter interview, Brandon was my first, um, interview.
And then after that, I went through panel interviews with, um, members of his leadership team that I would be, you know...
Part of my role right now is, as the chief of staff to the people department, is coordinating the leaders, um, running planning, running our rituals and reviving them, re- refreshing them. Um, and so...
And then there was another panel interview with people who had my role across Zapier 'cause it was a brand-new role for this department, but there were, that role did exist elsewhere.
So it's funny because looking back on it, those panel interviews stand out a little bit more to me.
But I was, in my past role as a chief of staff, the biggest challenge I ran into was coord- like, my fit with the leadership team and the trust and the credibility and being able to influence. And,
you know, it, it's a funny role you straddle 'cause you are their peers, um, on a leadership team. Like, so Brandon and his direct reports. I'm a direct report. I'm on the leadership team.
And I also hold a role where I am, I- uh, I'm kind of like coordinating constantly and tagging constantly and giving a lot of feedback that may, they may or may not have asked for.
And so I thought it was really cool for me to get, to already feel the connection and like see how I was going to fit and how successful I was ultimately gonna be. Because in speaking with Brandon, I, I sensed...
I knew that was gonna be a big area of opportunity was more on this team coordination piece.
And ultimately, Brandon and I needed to have a strong relationship, and I sensed that was gonna work, but I needed to see also that I was gonna be able to work, um, in a broader context, uh, because that was like, is, was a big need, um, at the time when I got hired.
And what at, um,
the first couple of months or so, like, what was the meeting cadence or, or, or what is it like now in terms of just making sure things are getting done and, but also kind of holistically checking in on things? Yeah.
I... So one thing I love about working with Brandon and I think works really well for us is that we kind of... And actually I would say our leadership team.
We're, we're kind of constantly evolving and-Assessing, being like, does this still work? Does this still, m- you know, satisfy why we, like, started this?
So I would say obviously, you know, I had my onboarding, and Brandon and I, for some of the core work, like leading in semi-annual planning, we kind of co-chaired it.
So that was really great for a developmental perspective.
Um, and I think kind of eased me in to where I'm not just, you know, "Hey, day one, I'm Carly, and you need to submit X, Y, Z documents by tomorrow so I can start driving planning."
Um, but you know, we early on, I would say, had...
We would have a Mon- We- Monday morning we'd sync, and I would kind of review Brandon's calendar and see what was going on and got to, you know, sometimes I would ask, "Can I join that meeting with you?"
So just getting more comfortable with what I was prioritizing for that week and what Brandon was prioritizing for that week.
Flagging things like, "Oh, Brandon, I think, uh, it so looks like you're gonna have to write that memo. Let me take..."
Like, we had to have a lot of open dialogue around what I could take on, what I should be focused on. Yeah, I think, and that has evolved over time.
And then of course that was like our, our sync on Monday morning, and then we also had a, like a, another hour meeting where we'd have more like, "Hey, this is what's come up this week."
So I would say we had more touch points early on to just make sure we were on the same page and, and that we were both really scrubbed in on what we wanted to prioritize. And now I would say that's gotten less.
We don't need as much of that. I think it's more... He, I mean, he knows I still have access to his calendar. I can still check in and be like, "Oh, what's going on here? Do you need me to do anything on this?"
But I also think Brandon now, like we work so well together, also just comes to me saying, "I need... Hey, can you take the first crack at this?" Or, "Hey, actually, like I don't need you driving on this.
Please continue doing this." So I think through the first year or so, we kind of worked through that, and I think more time was hel- really helpful, um, on the front end. Yeah. Totally. That all rings a bell to me.
And you know, um, the other thing you made me think about is that, you know, Zapier has a really neat ritual when folks join the company that helps, um, that person and their manager, but also their peers, like get to know each other at a level that sometimes doesn't happen otherwise, and that tradition's called the Read Me.
You can think about the Read Me like a mini, uh, instruction manual for how each person operates, and they write it themselves in their first, you know, two weeks in the organization, and then it's posted for all to see.
Um, but the first person, or, or the first two people when someone joins, they usually swap those Read Mes are the new hire and their manager. So Carly and myself in this case.
And, you know, in our Read Mes it includes things like, you know, personal values, um, can include things like how you like to give and receive feedback, um, ideas that really like anchor your work or how you go about the work that you do, as well as very practical things like working hours, like other things that are going on in your life that will help someone just have context and empathy for, you know, when you work, how you work, how you show up in the work, that kind of thing.
And, you know, just like it's true I think all over Zapier, I think that, I think that served us well when you were onboarding.
Yeah, and it was unique because we are a fully remote company, so Brandon and I actually don't see each other in person often, um, maybe twice a year, um, for like some annual retreats, um, or summits or, or leadership meetings.
But I think within a month of my onboarding, we had the, there happened to be one, um, an in-person event, and so we actually got to swap, swap our Read Mes, which is kind of Zapier language, um, in, in person.
So that was really, I think, a unique experience. And what did that look like? 'Cause I, I'm familiar with Read Mes and user manuals. So did that like, did you say, "H- here's mine.
Let me get yours," and then like, you know, you asked me a couple questions and I asked you a couple questions? Or how did that kind of, uh, like talking about it in a, a collaborative way, what did that look like?
I think we both swapped ahead of time and kind of took notes and then just came ready to... And I like that. I'm, I'm not...
I think something like a Read Me ritual, you don't need to overly process it or, or like ritual. Like, it just was a free-flowing conversation. And in some ways it was like, "Oh, that's so interesting.
I see you ha- " Like, Brandon's from Michigan originally. My family's from Michigan. So it like also just allowed natural connections to come up, so I don't think we overly orchestrated the conversation. But there was,
I'm, you know, I, I'm big on, you know, like pre-work and like I could tell he had read it and, and, you know, I think there is that like follow through where you're referencing something like that.
Um, so I think we did the work on the front end and then just had a really organic conversation talking through it all. Brandon, I don't know, do, would you add anything to that? Oh, 100%.
I mean, you know, when I'm, when I'm jamming with someone on their Read Me, like I try to think about like what's that next question I could ask that goes even further between the lines on like, you know, if someone's talking about like, I like to receive feedback in writing.
I might ask like, "Hey, tell me more about, you know, um, when you, when you first knew that was true." Hmm.
Do you remember, do you remember when you first really believed like, wow, that really is how I receive feedback the best? And there are just a couple of those questions like you really...
You might learn something practical, and that's fine, but you also inevitably learn something deeper about that person.
Like a moment that mattered in their career or like a formative experience in their life or like, just like a quirk. [laughs] Like we all have quirks. You know, things of that nature.
And that, I think that's part of what we're, what we try to get at with the Read Me.
Again, it can be very practical, but it's also a jumping off point to just like understand someone better at a human level, and that, that pays dividends, you know, when you're doing work together.
S- speaking of quirks, has there been any quirks that, you know, you two have learned about each other that it's been, you know- [laughs]... interesting, relevant, uh, helpful? Like, you know, I, I don't know.
Like, for me- I- Yeah. Yeah. I, well, let me, let me just... It's a long list, but I, I've got to kind of start us off. Um, I was telling Carly this like two weeks ago.
So, you know, when you work as closely together as a, a chief of staff does with their leader, you...
well, it's not uncommon to like kind of like for their different like mannerisms or expressions to like rub off on one another. And, uh, I found myself doing one that is absolutely Carly.
Like you cannot mistake it for anyone else. No one else does this except Carly.Except me now. Uh, and, you know, in a, in a meeting when, um, Carly,
like, is really affiliating with what someone's saying, right, it's like plus-one or like, totally, like I got you, like that's it, like you got it, um, she does this. It's like a little expression.
[laughs] It's like, it's almost like, it's like, it's almost like equivalent to like snaps. It's like a virtual... It's like a, it's like a man- plus-one type mannerisms, like this. She does this. Yeah.
And she's been doing it for years. And then I noticed like the last like four or five months or so, like I caught myself like involuntarily, I'm like up here doing this, right?
And I'm, I'm sure the rest of our team, like, is like totally like, like teases it a lot, and as they should because it's hysterical. But, um,
yeah, you know, in, in terms of like just things you pick up, I mean, that's how closely you work together. Uh, yeah. Yeah.
So, so for people who are listening and not watching, uh, Brandon is literally just like got his index finger and he's just kind of like flicking it in terms of, uh, it's the one finger and just kind of like plus, plussing the one in real time, um, instead of snapping.
Uh, it's... I love that. I don't think I've ever seen that. Uh, and gets me thinking, you know, it's similar to like Brandon's comments earlier of like, when was the first time that you learned t- to do that?
Or what, how did you come up with that? Or Carly, like what, where did that come from? Oh, I think that actually is probably for folks...
In education, I do think maybe during COVID when there was a lot more virtual- Mm... um, learning happening, there was like a bit of a call and response happening with students. Uh, like I agree.
[laughs] And so I think I just have kept that on. And, um, and yes, but it is, it's funny, Ivy very recently was sharing that he started [laughs] doing it.
And honestly I'm not even sure I'm aware I still do it, but yeah. Yes, it is a very... It's funny, you pick up on mannerisms even though we don't work...
Like I said, we see each other maybe twice a year and, but still even Brandon's talking cadence.
And part of it, of course, as a chief of staff, I've needed to learn how he writes and be able to support some of the things, you know, okay, how would Brandon say this? Or how would this need to be represented?
But I, I think there's like, Brandon's a, a, has a very, um, a good pause. He's... I've actually heard him.
He- he'll say something and then kind of pause for a moment, um, 'cause he's obviously speaking often to like our full department, and so I feel like that's something I've noticed.
Even he does more dashes in his writing, and now even when I'm not writing for Brandon, I'm still doing it. So you do pick up on these little things that infiltrate.
I'm sure my husband's like, "Oh, yeah, cool, the pause. Loving that." But yeah, even in your personal life you've started, uh, we call them the, we've been mind-melding, um, in [laughs] in our work together.
I'm gonna really lean into the pause right here. Um, but, um, the... So if you only see each other a couple of times a year in person, how, like what other things do you do to like strengthen the relationship?
Um, yeah, what are like some communication best practices if like something's not, you know, maybe don't see eye to eye immediately or there's like some uncertainties around things? Is it like, you know, quick call?
Like is there... What, what kind of best practices do you have there versus like, you know, sometimes in person you can just like quickly go over to someone's desk.
Like what have you two found to be so effective, um, working remotely? I, I, yeah, I have a few thoughts here. One, I mean, we do have a one-on-one every, every week, uh, for an hour at minimum. Mm.
And I do think there's always... I think from early on, Brandon and I always are...
Or Brandon is very open to feedback, and that again, he's even shared it with somebody that's something he wanted, and I feel like I have no, like I, I'm con- we're constantly sharing feedback to each other.
And sometimes it's really quick, and sometimes it's like, "Oh, hey, we'll talk more about this in our live one-on-one." But I would actually say probably
we typically have a natural, even though Brandon's calendar's pretty full and mine is too, after
like a new ritual we're running or like the quarterly hangout or something, we normally will find a min- a minute, like, "Hey, you got a second?" Like, "Let's do a quick recap."
Um, and so I always appreciate those little kind of one-off unscheduled times that I think allow you to sync more in real time live on like how did you perceive that went? How did I perceive that went?
Do you have any quick feedback for me? Do I have any quick feedback for you? Um, and then I also think, uh, you know, in terms of like building trust and like confidence in your role, you know, Brandon is really good.
You know, he does, you know... When there's news that's gonna come out, like I do find V- Brandon will ensure like I, I heard about it one-on-one and then really make sure that I can support him.
Like if it's a big, you know, something, hey, this is gonna change things or like this is a big shift- Yeah...
he always makes sure that I'm kind of alerted to that ahead of time so we can quickly align on things, and I think that's been really valuable.
I, I know for me that builds a lot of trust in our relationship and how he sees my role within his team, um, is when I get those kind of like heads-up moments. Okay. Um, I love that. A quick, like let's quick recap.
Like I, I think that that's, that's... I mean, it only takes maybe a couple minutes. That, I love that. And also, I think I heard like an hour minimum of, on, uh, each week.
That's like, I think that that's really, uh, special too.
And I think, and again, this is probably the culture of Zapier, but we are big on as- async feed- So Brandon, again, we just re- we just launched a vision for our department and, uh, you know, Brandon is, shares that with me first to give feedback or, you know, it might be me and somebody else, but the, we go through iterations and, you know, Brandon is really good at...
So even, even when we're not live, like there is always correspondence [laughs] and feedback. I mean, he is, he, Brandon is a pinned channel on my Slack channel 'cause we have, I'm in the hundreds of channels.
And, you know, it's, it's a priority channel of course for me, but I, I know Brandon is even in even more Slack channels, and I still, like there's never...
Like I know he prioritizes getting back to certain things of mine 'cause I, I, again, I think that's like the trust we've built and the-Like, the way we see how our- how we work best together is kind of that quick real-time, um,
feedback that we can share with each other. Yeah.
The, the, the, the art of upward management, I, I think is so important for these roles and, and it's something that I was assessing for when I was interviewing candidates for the job, and it's one of the things that stood out when I was getting to know Carly.
It's like, I think Carly's gonna be really good at upward managing to me.
And that takes a couple different forms, and certainly the feedback like Carly talked about earlier, just being able to be like, "Hey, hey," like, you know, "No, no, no," like, "This way, not that way.
[laughs] Maybe this instead," et cetera.
Um, but also, um, you know, Carly will regularly, you know, message me and say like, "Hey," like, "I know we had our one-on-one earlier this week, but based on a bunch of stuff that cropped up over the last 72 hours, like, I need you to do these two things today."
Right? Like, "Don't close your laptop before you do these two things." And she'll, you know, she'll serve it up, like, really clearly, context, like why do I need to do this, why now.
Like, you know, easy button it to the best, best of Carly's ability.
But the most important thing, the thing that I'm counting on for someone in Carly's role is the ability just to be really direct and upward manage in that way.
Like, it's not just okay for someone in a chief of staff role to be directive with their chief. Um, it is, uh, it is, it is needed. Uh, it is, it is expected.
Even if it's not expected, uh, in, in word, uh, practically speaking, that's what, you know, folks in these positions, you know, are really counting on from their chief of staff. Um, I do wanna hear...
It sounds like your role has evolved a lot, Carly, but, um, or has evolved some. Um, as we've been talking about communication and stuff like that, I'm wondering if there's been any other, um,
kind of situation that you needed to, like, work through or, um, anything and, and how you were able to do so.
I think, like, talking about these things is, um, and sharing examples of that could be helpful for other chiefs of staff that are out there that are like, you know, uh, like Brandon, I really like how you're like, I expect, you know, the hard conversation to happen, or I expect the feedback.
I'm wondering if there's been, like, an example in the past where it was like, you know, we were rolling out this new project and yada, yada, yada, and, um, yeah, curious if, like, how, how you're able to work through something like that.
I can share. This is... And Brandon, you might have a different example more on, like, feedback of some, of, of, like, a product or a project. But one, I remember one time having to come to Brandon with some feedback.
And again, I think most chiefs of staff, especially if you're newer and it's maybe newer on a team, like, there is always a mo- moment or there will be many moments, there are still moments where I'm,
again, like I say, like sometimes I'm just, I'm involved in a lot of things, and not everyone understands why I'm there. And I'm like, "No, actually, like, I n- I need you to change that."
Like, a- and, and I think there's, like, a navigating in these roles where it's like I am your peer, and also I know I'm representing Brandon here, and I'm gonna need that t- you know?
So that can be challenging at times. And so like I shared, when I first started, we co-piloted planning, semi-annual planning, and inevitably, Brandon has one-on-ones with his entire lead team.
There's eight, eight individuals. Um, and of course, I have my one-on-ones with them, and I have team meetings with them too. I am, I am on that leadership team.
But inevitably in these one-on-ones, feedback around planning or our rituals come up, and I then, like, would later hear them or be like, "Oh, did we, did we agree to something?"
Like, "Oh, I didn't know that," or like, "Oh, I don't know if I actually agree to that."
And so, you know, kind of during that time where it was still, like, transitioning and gray of, like, now Carly's fully running, I think I had to have a moment where I was like, okay, moving forward, [laughs] like you, you know, if people bring this up to you, I need to trust that you're gonna say, "You need to talk to Carly about that."
If you really want me to drive these rituals and be the decision-maker on these things, I need folks to see me in that way. And if they're sharing feedback with you when I'm not there, or if they're...
Of course, that's appropriate, like, you're their manager, but it needs to come back to me. And so I feel like that was a real moment where I had to be like, "Hey, we need to...
This isn't working potentially, or this is gonna, this is gonna have bigger implications down the road if we don't fix it now." And I, and so that was, like, an op- a really open dialogue we had about, like,
when to include me and when to actually have people go to me directly instead of go through you. That's right. Oh, I remember that.
And it was, it was, um, it inspired, like, a bigger change that I think was really positive for our whole people leadership team in the...
Because part of the root cause there was that, you know, when folks give, you know, feedback in, like, a one-on-one, right? Like, it can create telephone, right? Mm-hmm. What do I do with this now?
And so, you know, that was one manifestation of a broader theme.
And so what I started doing with that feedback is, um, both giving feedback to individuals publicly in our people leadership channel wherever it was reasonable to do so, which is most of the time.
That way everyone gets on the same page immediately.
No one have to, no one has to wonder, like, who knows Brandon, you know, asked so and so to do this or isn't happy with how this is going or, or thinks this thing is going awesome, maybe we should do more of it, whatever the case may be.
Um, but then I also started kind of rerouting my, the other members of our leadership team. So if someone would bring something in a one-on-one, like a piece of feedback or what have you, unless it was...
I'll actually tell you, even if it was feedback expressly about me and how I'm showing up as a leader, even then, like, I would start to just sh- like, ask them to put that in our people leadership team channel just to keep us all on the same page.
'Cause, you know, we can learn from, from each other's feedback. Rarely is a piece of feedback, like, exclusive to a specific person or team because a lot of the work we do- Mm-hmm...
has dependencies, and, um, in many ways doing it, uh, in public or, you know, at least in, in the public of our people leadership team space, uh, saves folks time and makes sure that we, you know, stay aligned like Carly was saying.
Totally. I love that. I feel like I'm almost-S- very public in Slack. Uh, [chuckles] just constantly just, like, sharing stuff. And, you know, I think, like, it's almost...
I see it as, like, little downside and all upside.
Um, and whether that's, like, you know, just the, "Hey, I heard this," like, wanted to shout that person out in public, or, "Hey, this happened," like, and just, like, constantly just airing things out, so to speak, 'cause it feels like it's, again, little downside but a lot of upside.
And also just trying to, like, model the behavior of, like, this is the type of, like, you know, kind of, uh, openness and, and, uh, kind of transparent dialogue that I, I'm curious about and that I would like to see.
So just kinda modeling the behavior I think is, like, what I've been trying to do. But it- in the beginning it's a little bit uncomfortable, though. [laughs] Oh, yeah. I, I agree.
I mean, it's, it's a lot of bit uncomfortable. And, uh, you know, I, I am seeing the benefits of our leadership teams, like, kind of, like, average tenure working together growing as well. Mm. There's part of that too.
But I think the thing, the challenge I have for myself within that is, like, yes, like, as the team, uh, is- becomes more experienced working with each other it, it gets more comfortable to do things like sharing feedback with each other in public rather than, like, on si- like a side chat.
Um, but my challenge to myself within that is, like, you kinda gotta do it anyway even earlier on.
I- in part because, like, it, it definitely can create more creative and interpersonal friction to be doing it while the team is still very much forming and, and kinda new to work together.
But, uh, as long as you have, like, good norms and ground rules and you've hired effectively for folks who, like, you know, have relatively low ego, [chuckles] relatively high EQ, my, my challenge to myself as a leader is I have to be, I have to trust that my team will figure it out.
And in some ways, ironically, sometimes it's the work of doing hard things together, like giving each other feedback in public or working on a really hard project together, that can actually bring the team together faster than trying to, like, engineer, like, a soft, like, climb- Yeah...
you know, based on folks' comfort. And I think if we index for comfort alone, I don't think that... I've done that before as a leader,
and it's, uh, it's a f- it's like a, A, it's a fool's errand because different people are different. [chuckles] So you, like, you can't do that for a team, really. It's like a, a artificial sense of control.
Uh, but the, the more important thing is when I have done that in the past I don't think that's my best way to show respect for my- Mm.
If I think I've hired, you know, A-grade players with low egos and high EQ who can handle their business, you know, even if something pinches in the short term, um, then we just need to go, right?
Like, again, it's like don't be sloppy, right? Set norms, be clear about what you're asking and why you're asking.
If you know in advance as a leader you're asking a team to do something that might have sharp edges, name that so you can normalize the experience they might have.
So, you know, still be thoughtful but at the end of the day, like, do the thing, make sure the team can say the thing. There's no perfect time to wait for when it suddenly gets comfortable.
Something this is making me think about it, and again thinking about other folks in, in s- in this role, is that I think, um, this is, I think this is even a bit of how Brandon and I's working relationship has ev- has evolved even as I'm, I'm having this realization.
I think for me coming in, especially my previous role, it was really important for me and my chief to th- seem like we were always on the same page. Like, that, I felt like that was my duty to be able to...
Like, if you talked to m- you would get... You know, we were of one mind always, and I do think that is important. Like, I need to understand the strategy. I need to represent that.
Um, but I think what that would make me do would be all the back... be- it would be behind the scenes that we had to do all the norming and the- Mm... like, back and forth feedback.
And, and what Brandon is sharing, it's like, so for example, we just launched a team vision, like we shared, and all of that happened transpa- like, anyone coulda seen the v- the version one of it that I shared the feedback on, the version two of it that I shared f- 'cause it was all in a public Slack channel.
Anyone had... So if you wanted to f- or sorry, within our leadership channel. If you had wanted to follow along and see where Brandon and I were disagreeing and agreeing, you could see that.
You could see the, like, kinda how we work together. But I th- I've appreciated that 'cause I think that's a lot of pressure as a chief of staff that you need to... I don't know.
Like, again, you have your peer group, and if they only see you as an extension of your chief, you're only gonna be able to, like, leverage those relationsh- I, I just feel like it's been helpful to be able to be more transparent.
And I share feedback in meetings directly with Brandon or directly with other people that might be, you know, n- a little new, and, and we have that space and trust on our leadership team.
Um, whereas I don't know if I've always felt, um, i- in roles like this that I could, I could kinda, like, challenge my chief more publicly within a leadership team. Nice.
Um, is there anything we j- we should talk about, about the role evolving? I know we're, um, um, we've covered a lot of ground here.
[laughs] Um, but I remember that was in the beginning part you talked about how, like, your role has, has changed and, and how, you know, have a lot more ownership of stuff.
Um, is there anything there that, like, you d- really wanna highlight in terms of, like, it's been a learning, it's been, um, you know,
yeah, how you maybe advocated for where you wanted, like, your growth to be, Carly, and how Brandon supported that. Like, any- anything there that, um...
'Cause sometimes I think ch- the chief of staff role, like, you know, it does seem to, like, evolve, you know, maybe it's every six months or 12 months or anything like that.
S- uh, so curious as to, like, how that's actually been for you, um, with Brandon. Yeah. I sort of have a, an in- like, like Brandon was sharing earlier, right?
Like, every chief of staff is gonna be focused in a different direction.
And in, in my mind I kind of have these buckets where I'm like, I can be, I can be focused internally on our team, like, like, really making sure, like, our, all of our, like, our house is straight and clean and I can, I can really just spend time on this coordination piece.
I could spend a lot of time up-leveling Bran- you know, like, looking at, like, maximizing Brandon's capacity and saying, like, "I'll take that meeting. I'll write that memo.
I'll do that."You know, uh, let me, let me start getting you more time back. I could spend time driving special initiatives that, like, just don't have a clear owner.
Like, so every chief of staff I feel like can spend time in different buckets. Um, and I feel like it's a...
You need to be present in all of those, but the ratio should always be shifting based on the need of the, the team and your chief.
And so I think there are always moments, whether it's quarterly or when we do set goals biannually, where we kind of check in and say, "Hey, looks like, you know, it looks like I'm going to be stepping in.
Like, we have, we have a vacancy on the team. I need to go spend, like, the best thing I could do right now is in, as an interim support there. Like, so that's where I'm gonna be spending about 70% of my time."
The trade-off means I won't be doing... I won't be able to, like, le- you know, maximize your capacity as much or doing these things.
So I feel like we basically, we have kind of an open dialogue pretty regularly of where I'll be focused and what the trade-offs are. Or again, when something pops up, which it always does, I say, "Okay, great, so what...
That means I'm not gonna be able to do this thing. Are you okay with that?" Or Brandon gets tasked to drive a new thing across the company, and him and I will check in.
I'll say, "Hey, at the moment I'm not gonna be able to be your right hand there." And he's like, "Great. Good. You know, I don't need you there." So
I think it's just kind of constantly talking about it and, and norming together so there's no surprises when all of a sudden, you know, I'm not doing, doing something.
So I think every year my role, every quarter my role looks different, and I think that's really by design because every quarter there's a new need for me of where I can have the most impact. Love it. Love it. Love it.
Yeah. That, that checks out.
And it goes back to something that we were all talking about earlier too is that, you know, there, there are different types of chief of staff roles, and some are, are in fact built for more stability.
Like, the work is just as important, but it's more consistent over time.
And, um, I think it's just really important for folks hiring these roles to have a point of view about, you know, whether it's gonna be, you know, the more, more predictable, consistent flavor or much more variable and dynamic, um, so that, you know, when folks are thinking about whether to team up with you, you know, they're accounting for that too.
Um, you know, 'cause the great thing with all these roles, like with so much hiring, is like you just need one great match. Mm. And so even if, you know, as a leader, your particular flavor of chief of staff is not
a great match for nine out of every 10 really otherwise talented chief of staff candidates, it's all good 'cause you just need one, right? You just need one.
And so I think, uh, you know, that I, I would say, you know, for folks hiring for these roles, um, just be clear in, in demanding in what you, what you need because while that can sound selfish, like I'm indexing for what I need to be successful, that clarity is, is what will enable the person you do hire to make a great choice about working with you in exactly that way, which is gonna help them be successful too.
Amazing. Um, a- any other parting thoughts before we head out here, and then I see you two in San Francisco in a little bit. Um, an- an- anything, uh, any other parting thoughts? What do you think, Carly?
No, I was just...
Yeah, I mean, I think the, like, again, and everyone's relationship is different with their chief, but I would really encourage chiefs of staff, I feel like Brandon n- like, Brandon's my manager ultimately, and I, and I really...
and, like, we talk about my career growth. We talk about what I want to focus on. We talk about the longer term, like, trajectory, and we, we graph my impact.
You know, I, I like to get really visual with, with things like that. And I, I have always felt we had a really... I've always appreciated that space Brandon's created, but also I've always made that space.
And so I would really encourage every chief of staff because I think a lot of us get in these roles 'cause they like to take on new things and they like the evolution, or at least that was a big draw for me.
And so I have found that I, you know, I, I do feel like I'm in a driver's seat to have those conversations and, and it is really because, you know, Brandon and I have, have this relationship of trust and we know how we work best together.
Like, that's really enabled my role, like I said, to look different every quarter, and that's kept me really excited and engaged.
Because I know some chiefs of staff, it's like a two-year, two, two-year tenure, and I'm at this place where I could see myself, if, if things continue and they're exciting and every day it's something new, like, that, that's really been motivating for me.
But I think that's b- because we have a very open dialogue about what, what's next, what's more, what, what, what do, what do we say is good enough I can put off my plate so I can take on the next thing.
I think that's the mic drop, Carly. I, I've gotta comment on that. [laughs] You get, you get the last word. See, yep, like a good chief of staff relationship, the last word. [laughs] Love it.
Brandon, Carly, thank you so much. Really appreciate it. [outro music]