WEBVTT

1
00:00:00.100 --> 00:00:13.490
[upbeat music] Hey friend, it's David Nebinsky, the community lead at the Chief of Staff Network.

2
00:00:14.080 --> 00:00:20.760
We help chiefs of staff through the three Cs, cohorts, curriculum, and community via Slack with over 900 people in it.

3
00:00:20.780 --> 00:00:29.510
You can learn more about our membership, events, and upcoming programs at chiefofstaff.network, like our fundamentals course and our AI fellowship.

4
00:00:30.120 --> 00:00:37.640
There you can also learn more about our three Chief of Staff Connect conferences, with the first one being in San Francisco on May 15th to May 16th.

5
00:00:38.160 --> 00:00:45.589
Also, before we dive into this episode, we wanted to let you know that our friends at f- over at Flowcode are hiring a chief of staff that is based in New York.

6
00:00:46.020 --> 00:01:01.440
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.

7
00:01:02.000 --> 00:01:09.980
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.

8
00:01:10.480 --> 00:01:23.300
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.

9
00:01:23.770 --> 00:01:28.100
So if you're looking to learn more about the chief of staff and principal dynamic, this episode is for you.

10
00:01:28.180 --> 00:01:40.440
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.

11
00:01:40.600 --> 00:01:51.480
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.

12
00:01:51.940 --> 00:01:58.280
Carly, let's dive into, to the fun stuff. Um, how would you say you got your current chief of staff role, Carly? Yeah.

13
00:01:58.320 --> 00:02:11.820
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.

14
00:02:12.340 --> 00:02:18.549
I'd been there for about eight years, and had been on different, um, in different leadership roles within the department.

15
00:02:19.010 --> 00:02:28.240
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.

16
00:02:28.520 --> 00:02:41.880
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.

17
00:02:42.480 --> 00:02:52.300
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.

18
00:02:52.960 --> 00:03:05.980
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.

19
00:03:06.280 --> 00:03:16.300
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?

20
00:03:17.160 --> 00:03:27.220
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.

21
00:03:27.920 --> 00:03:37.620
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.

22
00:03:37.660 --> 00:03:43.660
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.

23
00:03:43.720 --> 00:03:54.900
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.

24
00:03:55.160 --> 00:04:02.420
And, and when did, um, and did you and Brandon start working together immediately, or how did that start to go down? Yeah.

25
00:04:02.520 --> 00:04:11.440
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.

26
00:04:12.120 --> 00:04:20.519
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.

27
00:04:21.380 --> 00:04:29.540
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...

28
00:04:29.660 --> 00:04:44.240
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?"

29
00:04:44.300 --> 00:04:53.880
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?

30
00:04:54.000 --> 00:05:06.500
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.

31
00:05:06.600 --> 00:05:18.520
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.

32
00:05:18.580 --> 00:05:29.140
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.

33
00:05:29.680 --> 00:05:36.700
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.

34
00:05:36.740 --> 00:05:55.660
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.

35
00:05:56.380 --> 00:05:58.260
Mm. So there's the nature of the work, and that's different.

36
00:05:58.340 --> 00:06:14.264
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.

37
00:06:14.274 --> 00:06:21.724
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.

38
00:06:22.304 --> 00:06:28.904
Other chief of staff roles, including Carly over time, um, you know, has ownership of, like, very specific products or practices.

39
00:06:28.944 --> 00:06:39.564
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.

40
00:06:39.674 --> 00:06:46.164
Some chief of staff roles, whether it's primarily consultative or primarily program ownership, it stays relatively consistent over a length of time.

41
00:06:46.184 --> 00:06:55.094
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.

42
00:06:55.104 --> 00:07:01.734
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.

43
00:07:01.864 --> 00:07:10.244
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.

44
00:07:11.004 --> 00:07:19.924
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."

45
00:07:20.674 --> 00:07:31.414
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.

46
00:07:31.464 --> 00:07:40.504
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.

47
00:07:40.534 --> 00:07:49.264
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.

48
00:07:49.304 --> 00:08:01.294
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?

49
00:08:02.184 --> 00:08:09.944
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.

50
00:08:10.024 --> 00:08:20.804
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...

51
00:08:20.844 --> 00:08:32.954
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?

52
00:08:33.004 --> 00:08:43.664
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...

53
00:08:43.674 --> 00:08:53.444
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.

54
00:08:53.944 --> 00:08:58.004
Like, how did you kind of figure out, like, this was, this was the one? Yeah, you bet.

55
00:08:58.144 --> 00:09:07.824
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.

56
00:09:09.104 --> 00:09:18.684
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.

57
00:09:18.704 --> 00:09:26.944
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.

58
00:09:26.984 --> 00:09:37.454
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?

59
00:09:37.484 --> 00:09:47.804
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.

60
00:09:47.884 --> 00:09:50.444
So what, what was that experience like for you? Yeah.

61
00:09:50.573 --> 00:09:58.914
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...

62
00:09:58.984 --> 00:10:05.644
I actually went through multiple rounds of interviews, and Brandon was the first. After the recruiter interview, Brandon was my first, um, interview.

63
00:10:06.264 --> 00:10:12.404
And then after that, I went through panel interviews with, um, members of his leadership team that I would be, you know...

64
00:10:12.904 --> 00:10:25.464
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...

65
00:10:25.483 --> 00:10:33.304
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.

66
00:10:33.344 --> 00:10:39.004
So it's funny because looking back on it, those panel interviews stand out a little bit more to me.

67
00:10:39.024 --> 00:10:52.464
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,

68
00:10:53.704 --> 00:11:01.584
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.

69
00:11:02.124 --> 00:11:11.864
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.

70
00:11:11.964 --> 00:11:24.984
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...

71
00:11:25.064 --> 00:11:28.824
I knew that was gonna be a big area of opportunity was more on this team coordination piece.

72
00:11:28.944 --> 00:11:43.484
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.

73
00:11:44.244 --> 00:11:45.244
And what at, um,

74
00:11:46.164 --> 00:12:02.504
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.

75
00:12:02.624 --> 00:12:09.993
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.

76
00:12:10.064 --> 00:12:17.888
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?

77
00:12:18.608 --> 00:12:27.168
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.

78
00:12:27.568 --> 00:12:30.708
So that was really great for a developmental perspective.

79
00:12:31.268 --> 00:12:40.748
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."

80
00:12:41.488 --> 00:12:44.788
Um, but you know, we early on, I would say, had...

81
00:12:45.688 --> 00:12:55.588
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?"

82
00:12:55.728 --> 00:13:01.438
So just getting more comfortable with what I was prioritizing for that week and what Brandon was prioritizing for that week.

83
00:13:02.028 --> 00:13:07.107
Flagging things like, "Oh, Brandon, I think, uh, it so looks like you're gonna have to write that memo. Let me take..."

84
00:13:07.148 --> 00:13:14.968
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.

85
00:13:15.728 --> 00:13:22.948
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."

86
00:13:23.028 --> 00:13:34.348
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.

87
00:13:34.408 --> 00:13:42.888
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?"

88
00:13:43.328 --> 00:13:52.498
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.

89
00:13:52.588 --> 00:14:04.668
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.

90
00:14:04.688 --> 00:14:20.148
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.

91
00:14:20.788 --> 00:14:32.068
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.

92
00:14:32.548 --> 00:14:41.587
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.

93
00:14:41.717 --> 00:15:07.108
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.

94
00:15:07.148 --> 00:15:12.348
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.

95
00:15:13.768 --> 00:15:26.728
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.

96
00:15:26.828 --> 00:15:39.268
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.

97
00:15:39.348 --> 00:15:50.108
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.

98
00:15:50.168 --> 00:16:02.238
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?

99
00:16:03.308 --> 00:16:08.868
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...

100
00:16:09.508 --> 00:16:18.648
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.

101
00:16:18.788 --> 00:16:29.778
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,

102
00:16:30.687 --> 00:16:39.148
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.

103
00:16:39.228 --> 00:16:47.348
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%.

104
00:16:47.388 --> 00:16:59.328
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.

105
00:17:00.328 --> 00:17:05.828
I might ask like, "Hey, tell me more about, you know, um, when you, when you first knew that was true." Hmm.

106
00:17:06.208 --> 00:17:12.948
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...

107
00:17:13.068 --> 00:17:18.848
You might learn something practical, and that's fine, but you also inevitably learn something deeper about that person.

108
00:17:18.908 --> 00:17:28.648
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.

109
00:17:28.697 --> 00:17:32.188
And that, I think that's part of what we're, what we try to get at with the Read Me.

110
00:17:32.248 --> 00:17:40.068
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.

111
00:17:41.568 --> 00:17:52.648
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.

112
00:17:52.688 --> 00:18:01.068
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.

113
00:18:01.168 --> 00:18:06.548
So, you know, when you work as closely together as a, a chief of staff does with their leader, you...

114
00:18:06.588 --> 00:18:16.308
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.

115
00:18:16.448 --> 00:18:27.000
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,

116
00:18:27.960 --> 00:18:37.900
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.

117
00:18:38.060 --> 00:18:45.460
[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.

118
00:18:45.470 --> 00:18:51.520
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?

119
00:18:51.860 --> 00:18:58.500
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,

120
00:18:59.560 --> 00:19:05.400
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.

121
00:19:05.440 --> 00:19:21.960
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.

122
00:19:22.200 --> 00:19:33.820
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?

123
00:19:33.900 --> 00:19:40.920
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...

124
00:19:41.220 --> 00:19:51.980
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.

125
00:19:52.260 --> 00:20:01.760
[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.

126
00:20:01.780 --> 00:20:08.340
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...

127
00:20:08.900 --> 00:20:14.220
Like I said, we see each other maybe twice a year and, but still even Brandon's talking cadence.

128
00:20:14.260 --> 00:20:23.860
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?

129
00:20:23.880 --> 00:20:30.160
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.

130
00:20:30.300 --> 00:20:39.440
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.

131
00:20:40.000 --> 00:20:47.740
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.

132
00:20:47.780 --> 00:20:58.500
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.

133
00:21:00.580 --> 00:21:16.100
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?

134
00:21:16.500 --> 00:21:31.740
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?

135
00:21:31.840 --> 00:21:37.870
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.

136
00:21:37.920 --> 00:21:50.610
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.

137
00:21:50.640 --> 00:21:54.780
And I do think there's always... I think from early on, Brandon and I always are...

138
00:21:55.260 --> 00:22:05.000
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.

139
00:22:05.090 --> 00:22:12.580
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

140
00:22:13.600 --> 00:22:19.000
we typically have a natural, even though Brandon's calendar's pretty full and mine is too, after

141
00:22:19.960 --> 00:22:27.540
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."

142
00:22:28.160 --> 00:22:40.440
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?

143
00:22:40.519 --> 00:22:51.860
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.

144
00:22:51.900 --> 00:23:03.060
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.

145
00:23:03.080 --> 00:23:07.190
Like if it's a big, you know, something, hey, this is gonna change things or like this is a big shift- Yeah...

146
00:23:07.190 --> 00:23:15.220
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.

147
00:23:15.440 --> 00:23:29.460
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.

148
00:23:29.500 --> 00:23:37.360
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.

149
00:23:37.430 --> 00:23:40.700
That's like, I think that that's really, uh, special too.

150
00:23:41.580 --> 00:24:00.960
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...

151
00:24:01.020 --> 00:24:11.040
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.

152
00:24:11.500 --> 00:24:19.680
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...

153
00:24:19.720 --> 00:24:31.660
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,

154
00:24:32.760 --> 00:24:35.520
feedback that we can share with each other. Yeah.

155
00:24:36.160 --> 00:24:49.560
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.

156
00:24:49.580 --> 00:24:54.480
It's like, I think Carly's gonna be really good at upward managing to me.

157
00:24:54.540 --> 00:25:03.540
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.

158
00:25:03.740 --> 00:25:05.960
[laughs] Maybe this instead," et cetera.

159
00:25:06.200 --> 00:25:21.830
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."

160
00:25:22.420 --> 00:25:29.200
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.

161
00:25:29.240 --> 00:25:32.720
Like, you know, easy button it to the best, best of Carly's ability.

162
00:25:32.780 --> 00:25:40.200
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.

163
00:25:40.360 --> 00:25:52.720
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.

164
00:25:52.800 --> 00:26:03.020
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...

165
00:26:03.090 --> 00:26:14.220
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,

166
00:26:15.200 --> 00:26:23.580
kind of situation that you needed to, like, work through or, um, anything and, and how you were able to do so.

167
00:26:23.680 --> 00:26:36.820
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.

168
00:26:36.860 --> 00:26:46.900
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.

169
00:26:47.860 --> 00:26:58.280
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.

170
00:26:58.360 --> 00:27:07.140
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,

171
00:27:08.140 --> 00:27:16.800
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."

172
00:27:16.860 --> 00:27:25.780
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?

173
00:27:25.900 --> 00:27:39.620
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.

174
00:27:39.680 --> 00:27:47.580
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.

175
00:27:48.080 --> 00:27:58.040
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?"

176
00:27:58.120 --> 00:28:01.460
Like, "Oh, I didn't know that," or like, "Oh, I don't know if I actually agree to that."

177
00:28:01.980 --> 00:28:18.320
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."

178
00:28:18.380 --> 00:28:29.220
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...

179
00:28:30.100 --> 00:28:37.220
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...

180
00:28:37.500 --> 00:28:47.439
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,

181
00:28:48.720 --> 00:28:55.440
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.

182
00:28:55.540 --> 00:29:02.180
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...

183
00:29:02.220 --> 00:29:13.400
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?

184
00:29:13.420 --> 00:29:16.600
And so, you know, that was one manifestation of a broader theme.

185
00:29:16.640 --> 00:29:27.160
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.

186
00:29:27.760 --> 00:29:30.240
That way everyone gets on the same page immediately.

187
00:29:30.280 --> 00:29:40.540
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.

188
00:29:41.100 --> 00:29:50.800
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...

189
00:29:51.420 --> 00:30:04.800
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.

190
00:30:04.840 --> 00:30:13.170
'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...

191
00:30:13.170 --> 00:30:25.140
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.

192
00:30:26.580 --> 00:30:41.920
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...

193
00:30:42.080 --> 00:30:44.900
I see it as, like, little downside and all upside.

194
00:30:45.380 --> 00:31:00.440
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.

195
00:31:00.880 --> 00:31:12.700
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.

196
00:31:12.760 --> 00:31:21.500
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.

197
00:31:21.540 --> 00:31:34.260
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.

198
00:31:34.340 --> 00:31:49.440
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.

199
00:31:50.160 --> 00:31:54.920
Um, but my challenge to myself within that is, like, you kinda gotta do it anyway even earlier on.

200
00:31:55.560 --> 00:32:04.100
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.

201
00:32:04.940 --> 00:32:20.080
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.

202
00:32:20.340 --> 00:32:37.020
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...

203
00:32:37.040 --> 00:32:43.780
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,

204
00:32:44.900 --> 00:32:54.880
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.

205
00:32:55.660 --> 00:33:01.860
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.

206
00:33:02.220 --> 00:33:13.480
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?

207
00:33:13.620 --> 00:33:18.800
Like, again, it's like don't be sloppy, right? Set norms, be clear about what you're asking and why you're asking.

208
00:33:19.180 --> 00:33:25.380
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.

209
00:33:25.800 --> 00:33:36.080
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.

210
00:33:36.200 --> 00:33:50.000
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.

211
00:33:50.100 --> 00:34:02.400
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...

212
00:34:02.440 --> 00:34:11.810
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.

213
00:34:11.900 --> 00:34:21.630
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.

214
00:34:21.640 --> 00:34:34.600
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.

215
00:34:34.720 --> 00:34:43.960
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.

216
00:34:44.020 --> 00:34:53.260
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.

217
00:34:53.300 --> 00:35:03.340
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.

218
00:35:03.360 --> 00:35:13.640
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.

219
00:35:13.720 --> 00:35:24.320
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.

220
00:35:24.980 --> 00:35:32.660
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.

221
00:35:33.760 --> 00:35:40.880
[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.

222
00:35:41.460 --> 00:35:49.020
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,

223
00:35:50.140 --> 00:35:57.690
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...

224
00:35:57.690 --> 00:36:05.720
'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.

225
00:36:06.060 --> 00:36:15.820
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?

226
00:36:15.900 --> 00:36:18.690
Like, every chief of staff is gonna be focused in a different direction.

227
00:36:18.720 --> 00:36:33.580
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.

228
00:36:34.320 --> 00:36:41.800
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.

229
00:36:42.000 --> 00:36:50.215
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.

230
00:36:50.236 --> 00:36:58.056
Like, so every chief of staff I feel like can spend time in different buckets. Um, and I feel like it's a...

231
00:36:58.176 --> 00:37:04.776
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.

232
00:37:05.256 --> 00:37:17.076
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.

233
00:37:17.136 --> 00:37:28.356
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."

234
00:37:28.636 --> 00:37:35.396
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.

235
00:37:35.436 --> 00:37:47.116
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...

236
00:37:47.216 --> 00:37:55.476
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.

237
00:37:55.516 --> 00:38:02.376
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

238
00:38:03.356 --> 00:38:12.896
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.

239
00:38:12.996 --> 00:38:23.556
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.

240
00:38:24.356 --> 00:38:25.636
Yeah. That, that checks out.

241
00:38:25.686 --> 00:38:35.766
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.

242
00:38:36.156 --> 00:38:39.516
Like, the work is just as important, but it's more consistent over time.

243
00:38:40.076 --> 00:38:59.076
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.

244
00:38:59.616 --> 00:39:10.916
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

245
00:39:12.056 --> 00:39:21.296
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.

246
00:39:21.376 --> 00:39:44.816
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.

247
00:39:45.456 --> 00:39:59.236
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?

248
00:39:59.296 --> 00:39:59.776
No, I was just...

249
00:39:59.896 --> 00:40:09.926
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...

250
00:40:10.736 --> 00:40:19.716
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.

251
00:40:19.896 --> 00:40:31.716
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.

252
00:40:31.776 --> 00:40:41.476
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.

253
00:40:42.136 --> 00:40:55.476
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.

254
00:40:55.556 --> 00:41:01.276
Like, that's really enabled my role, like I said, to look different every quarter, and that's kept me really excited and engaged.

255
00:41:01.756 --> 00:41:12.956
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.

256
00:41:12.976 --> 00:41:23.616
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.

257
00:41:23.676 --> 00:41:33.616
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.

258
00:41:33.736 --> 00:41:47.935
Brandon, Carly, thank you so much. Really appreciate it. [outro music]