WEBVTT

1
00:00:00.100 --> 00:00:12.960
[upbeat music] Hey, friend, it's David Nabinsky, the community lead at the Chief of Staff Network.

2
00:00:13.480 --> 00:00:24.360
We help chiefs of staff through the three Cs: cohorts, curriculum, and community, via Slack with over nine hundred people in it. Learn more about our membership, events, and programs at chiefofstaff.network.

3
00:00:24.640 --> 00:00:31.700
You can also subscribe to our newsletter there to learn more as well. This episode of the Chief of Staff Podcast is with Maggie Maloley.

4
00:00:32.060 --> 00:00:41.500
She's a multiple time chief of staff with a particular focus on doing communication type work. She does it all, though, and you'll learn what it's like being a chief of staff in a startup environment too.

5
00:00:41.880 --> 00:00:54.540
Excited for you to level up as a chief of staff. Here we go with Maggie. Maggie, welcome to the show. Thank you, David. Hi. [laughing] Uh, okay. Um, we're gonna talk about chief of staff stuff. Yeah, we are.

6
00:00:54.660 --> 00:01:04.660
Um, and I think a lot of the chiefs of staff have just cool stories about how they got their roles. For sure. Um, I'd love to hear a story about how you got,

7
00:01:05.700 --> 00:01:17.080
um, either in a most recent chief of staff role or one before, um, if you feel comfortable sharing that. Yeah, I'm happy to. And first of all, thank you so much for, um, asking me to come on the podcast.

8
00:01:17.500 --> 00:01:27.980
This is such a moment for me. I've been such a fan of the Chief of Staff Tech Network, um, since your inception. It was one of the very first things I did as a chief of staff was join the network.

9
00:01:28.040 --> 00:01:40.180
So, um, to actually be on the podcast is such a moment for me. So- Aw. Uh, props to you and Scott, and, uh, message to twenty nineteen Maggie, keep pushing. [laughing] Dreams come true. You're on the podcast.

10
00:01:40.820 --> 00:01:49.380
Um, so- All right, we're done recording. This is it. Yeah. That's it. That's all we needed. Yep, just that one little sound bite. Um- Exactly. [laughing] Um, so yeah.

11
00:01:49.400 --> 00:01:59.000
So I'm have kind of an atypical chief of staff path in the sense that I've done the role multiple times, both in a full-time capacity and in a fractional capacity.

12
00:01:59.580 --> 00:02:08.220
So, um, yeah, a couple of different origin stories for the different, um, different times I've, uh, taken up the role. Um, I think the first time...

13
00:02:08.240 --> 00:02:21.060
I'll share, you know, my, my first foray into chief of staffing was, um, I joined, um, a Series B climate tech company, um, in twenty nineteen, and I joined as a special assistant. So- Yeah...

14
00:02:21.100 --> 00:02:31.000
there were some, you know, admin EA duties in there- Yeah... but there were definitely some strategic duties in there too, and I had this really cool hodgepodge role, um, where I was wearing a lot of hats.

15
00:02:31.280 --> 00:02:41.580
Um, and that's when I, I think actually through LinkedIn, discovered what the chief of staff role was- Mm... um, in part due to some of the content that this network was, um- Cool...

16
00:02:41.600 --> 00:02:54.380
putting out, very, very early days stuff. And, um, I pitched myself for the role to my founders at the time, and, um, they were just huge champions of, of me and mentors to me in my career.

17
00:02:54.440 --> 00:03:05.860
And they, you know, told me what I needed to do and in the areas I needed to grow to be able to, you know, take on that role. And, um, took me two years, and I did it. And, um- Took two years to pitch?

18
00:03:06.340 --> 00:03:13.080
Uh, no, it didn't take two years to pitch. Oh, oh. I think, like, the first year, I was just kind of getting my bearings and just trying- Yeah... to, like, create value immediately.

19
00:03:13.140 --> 00:03:19.630
And then I was like, "Hey, you guys, there's this really other- [laughing]... cool role that, like, you should really consider me for." Yeah.

20
00:03:19.700 --> 00:03:23.460
And, uh, they were like, "Yes," like, "What do we have to do to, to make it happen?"

21
00:03:23.560 --> 00:03:35.120
And, um, so there were-- They laid out the areas that I needed to, you know, grow into to take up the role, and I made it, and I got there. And, um, the rest is history, so that was my first chief of staff, um, gig.

22
00:03:35.670 --> 00:03:45.800
And then, um, really through networking, when I did my, you know, fractional chief of staff work is how I kind of met the other founders that I, um, you know, did some consulting for.

23
00:03:45.980 --> 00:03:52.440
So, um, through the network is how I got connected with, um, those awesome clients. Shout out to you guys. You know who you are.

24
00:03:52.480 --> 00:04:04.310
[laughing] And, um, and then most recently, I, uh, joined in a full-time capacity, another really awesome climate tech company, Series B, that, uh, I'm a full-time chief of staff again. So, um- Wow...

25
00:04:04.360 --> 00:04:17.040
a couple of different, uh, you know, a couple different gigs and, uh, different sizes and stages of company, different founders and personality types. Um, so it's been really awesome. Yeah. What did, um,

26
00:04:19.380 --> 00:04:29.550
what did that kinda, like, networking look like? Like, I, you know, I think it runs, like, sometimes people think of, like, the, oh, like, I'm gonna ask someone to pick their brain or like- Yeah...

27
00:04:29.580 --> 00:04:34.580
you know, and then there's, like, you know, drinks or events or...

28
00:04:34.600 --> 00:04:44.520
But, like, what did this-- What kind of networking was effective, or how do you think, like, through networking you got kinda connected to, um, some people that then ended up helping you out?

29
00:04:44.620 --> 00:04:53.200
Um, I think, you know, just candidly, uh, leveraging the networks of the founders that you are already- Mm-hmm... supporting or are close to.

30
00:04:53.400 --> 00:05:07.560
Um, m-maybe that's not, like, [chuckles] such a strategic or novel answer, but, um, yeah, I think if you, um, work for and support really awesome founders that you've, like, created a lot of trust with, um, usually they will be happy to open their networks to you.

31
00:05:08.200 --> 00:05:11.010
And, um, they say great people know great people. Mm-hmm.

32
00:05:11.120 --> 00:05:26.100
And, um, if you're able to, you know, really create value for a person who, who trusts you and has seen, uh, you know, how different, you know, their day-to-day life is because you're in it, they're usually happy to, um, you know, pass your name around to other people in their network that, uh, could use that same type of support.

33
00:05:26.520 --> 00:05:37.660
And what does that look like when you say, like, leverage or, yeah, like, their networks? Is that like, "Hey, I saw on LinkedIn you're connected to this person," or is- are they like...

34
00:05:37.720 --> 00:05:47.480
Or did you reach out and say like, "Hey, if there's any cool, like, dinners that are upcoming, like, I'd love to go," like, yeah, can you share anything about that? Yeah. I think it can look like a couple of things.

35
00:05:47.600 --> 00:05:51.540
I mean, definitely if there's, you know, s- LinkedIn is a great place to start.

36
00:05:51.600 --> 00:06:00.210
If there's someone on LinkedIn that you, you know, follow and, um, you know, wanna make a connection to and your founder is connected to them, absolutely, just make the ask. Um- Yeah... why not?

37
00:06:00.760 --> 00:06:09.469
I think also too, a lot of the people that I've been, you know, lucky to be connected with too, I actually kind of met in some capacity while I was on the job. Mm.

38
00:06:09.480 --> 00:06:17.650
Um, either they were, you know, a partner of, um, the companies or, um, you know, I just met them in the office 'cause they came in for a meeting with my principal.

39
00:06:18.200 --> 00:06:29.340
Um, so I think just, um, by being present, uh, in the role, you will run into people that you, uh, don't even know someday down the line, um- Yeah... you know, what they could do for, for you and your career. Love, love.

40
00:06:29.420 --> 00:06:37.280
So maybe there's, like, a way to, like, start collecting a list or something like that- Yeah... of like, okay, this person's cool. This person's interesting.

41
00:06:37.340 --> 00:06:46.832
I've seen their content on LinkedIn, and now I see them in person. Like, you know, maybe just kinda make a list and, like-Over time, who knows, will it kind of emerge?

42
00:06:46.852 --> 00:06:49.962
But I think like I would like to do more of, of that myself.

43
00:06:49.992 --> 00:07:01.672
I would just make a list of like who's an awesome person that like if something opens up where like sometimes you see s- I see stuff like this on like Twitter, LinkedIn, and it's like, "Hey, I'm in town.

44
00:07:01.712 --> 00:07:10.572
Like I- is anyone free for dinner tomorrow night?" And you're like, "Oh!" [laughs] Like there's like a small window, and you're like, "Uh, like, yeah, yeah."

45
00:07:10.652 --> 00:07:17.692
Or, but I think just like kinda keeping your eyes out for like those opportun- I think whatever that like what you focus on expands.

46
00:07:17.712 --> 00:07:27.252
And I feel like if you kind of think about like who are the people you wanna spend more time with or get to know or learn more from, like if you start to like think about that, then like I think it probably will expand over time.

47
00:07:27.692 --> 00:07:38.592
This is the part of the podcast where we pivot to talk about manifesting for the next hour. [laughs] Yes. Uh, no, just kidding. Um, no, I completely agree. I think you should always have just a call it dream mentor list.

48
00:07:38.682 --> 00:07:47.432
Mm. And like no one is outside the, the realm of possibility, and just always have a, you know, an idea of the people that you would love to emulate or be connected to.

49
00:07:47.512 --> 00:07:57.352
And, um, I think if you focus on it and, you know, work hard and keep expanding your network, um, there's no reason why you can't meet those people and have them be future mentors to you someday. Love, love, love.

50
00:07:58.112 --> 00:08:08.752
Uh, so you talked about kind of pitching the role at the, the first chief of staff role. Um, did like what

51
00:08:09.712 --> 00:08:19.511
those, I gue- I don't wanna say like gaps, but like, uh, it sounded like there was a conversation around like, "Okay, Maggie, here's where you're at. Here's where we kinda need you to be," et cetera.

52
00:08:19.572 --> 00:08:31.182
Like what was-- what did that really look like? Was that like, "Oh, you need to take this course, or you need to be more responsive, or you need to like understand business strategy or financial statements"?

53
00:08:31.252 --> 00:08:38.212
Was there anything like that that was like really specific that you needed to like train to get up to speed, or what did that look like? Yeah.

54
00:08:38.312 --> 00:08:45.122
I think it's a really helpful question 'cause I think there's a lot of people with, um, either admin or like biz ops backgrounds- Yeah...

55
00:08:45.292 --> 00:08:55.821
trying to pivot into, um, chief of staff roles, and I think that was kind of my, my original foray into it was, um, I think that I was just very green and young when I first- Mm...

56
00:08:55.821 --> 00:09:06.692
showed up at this startup and didn't really know what [laughs] Yeah... climate tech decarbonization or electrification was. [laughs] I was completely enamored by it, but I like was in no means a subject matter expert.

57
00:09:06.722 --> 00:09:16.622
And I think when I first showed up, like the feedback was, um, you, you know, "We trust you completely, and you're so great at your job, and you're so reliable, but we just need to get you a little bit closer to the business."

58
00:09:16.661 --> 00:09:25.712
Mm. Like, "You need to start really understanding, like, uh, you need to like get in there in that financial model." [laughs] "And you need to understand like how we make money and what our KPIs are."

59
00:09:25.792 --> 00:09:34.082
And, um, you know, I think my, my greenness, call it, was just, um, my greenness around startups as well as like, "We're a Series B company. What does that even mean?" Mm-hmm.

60
00:09:34.082 --> 00:09:45.842
"What does it mean to raise a Series C and, you know, have an exit someday?" Like, just things I was so excited and willing and eager to learn and to be like living it, um, with two awesome founders.

61
00:09:45.932 --> 00:09:50.872
It was just, for me, like such a exciting journey, so I don't see it as gaps.

62
00:09:50.912 --> 00:10:01.232
And like if you're listening to this and you don't have, you know, maybe the exact background, um, that the, you know, chief of staff JD that you, you want so badly- Yeah... is calling for, um, don't see them as gaps.

63
00:10:01.272 --> 00:10:13.012
See them as opportunities that you, you know, can get paid to learn, um, to get closer to your business, the founders, and also just like the startup ecosystem and cycle- Yeah... which is really cool. So, um, so yeah.

64
00:10:13.072 --> 00:10:22.872
I think that was the kind of initial early conversations of like, "You need to just really understand- Yeah... this, this business and what it means to run a- Mm... run a startup." Um, and I was like, "Hell yeah.

65
00:10:22.912 --> 00:10:32.411
Let's, let's, let's do it." [laughs] So, um, so yeah. That was kind of my, my early days journey into the role. That seems to be maybe a recurring mantra of yours. [laughs] "Hell yeah. Let's do it."

66
00:10:33.392 --> 00:10:48.232
[laughs] It's a great mantra. [laughs] It'll take you far. [laughs] Um, and so when you like kinda compare the different roles and even the fractional stuff, like is there any like

67
00:10:49.532 --> 00:11:03.932
common through lines in terms of like how to position yourself, in terms of getting chief of staff work, um, or yeah, like different skills that are like important or like how to demonstrate value?

68
00:11:04.032 --> 00:11:16.552
Like is there anything that really like stood out that like- Yeah. I think on the, you know, every chief of staff gig will be different because every company is different, and every founder is different. Yeah.

69
00:11:16.562 --> 00:11:19.832
Uh, if your, you know, if your principal is a founder. Every executive, I should say, is different.

70
00:11:20.532 --> 00:11:34.312
Um, and I think there's like a through line that, um, you need to have and, you know, uh, to have and to hold and keep very sacred, um, as a chief of staff is, um, one, discretion. Uh- Mm...

71
00:11:34.352 --> 00:11:44.052
founder mentality in terms of, um, the job's not done till it's do- the job is not done till it's done. Yeah. No task too small. Um, the buck stops here.

72
00:11:44.152 --> 00:11:50.552
Um, so just that, that fortitude and that resilience of, uh, you know, moving forward when the highs are high and the lows are low.

73
00:11:50.652 --> 00:11:59.572
Um, so I think those are, you know, the things that circle around, you know, trust with your principal, that it doesn't matter, um, size, uh, sector.

74
00:11:59.912 --> 00:12:03.132
Um, it'll always, you know, put you in a good position as a chief of staff.

75
00:12:03.612 --> 00:12:15.602
I think something I've learned in doing so many different types of chief of staff gigs is that you, um, you show up really excited to the next one, um, but you don't wanna just, uh,

76
00:12:16.752 --> 00:12:20.122
rush in, problem solve immediately, and kind of like copy- Mm...

77
00:12:20.152 --> 00:12:27.482
paste, I guess, is like, you know, if you're a chief of staff listening to this, like we're, we're framework people who've seen the movie, and you might have- [laughs]...

78
00:12:27.482 --> 00:12:34.572
like tools that you immediately can walk in- Yeah... and draw them on the whiteboard and be like, "I'm gonna fix this issue right now, and we're never gonna worry about it again."

79
00:12:34.672 --> 00:12:45.532
But, um, I think there's definitely situations where you can like show up and create immediate value, and you, you definitely should in your first, you know, 30, 60, 90 days just find a juicy project and create value immediately.

80
00:12:45.572 --> 00:13:00.768
But I think there is, um-I think I wish I had like held more space in some of my gigs to kinda just sit back, listen, and learn, um, and not try and solve immediately because, you know, what works for one startup might not work for another.

81
00:13:01.148 --> 00:13:13.308
Um, and that might seem self-explanatory, but [chuckles] we're, we're doers and problem solvers, so sometimes to like immediately get in there and not problem solve immediately is like a muscle that you have to, to train.

82
00:13:13.528 --> 00:13:26.228
Yeah. Um, what's the muscle like on like speech writing? Um, sounds like you've helped write like 100 speeches- [laughs]... or like what, what does that look like?

83
00:13:26.288 --> 00:13:38.688
What does like that project look like in terms of like coming up with a speech for, let's call it like an all-hands or, um, yeah, some other type of company presentation? Yeah, for sure.

84
00:13:38.808 --> 00:13:45.008
I think, um, you know, internal comms and communications is, uh, my superpower that I bring to the role.

85
00:13:45.148 --> 00:13:52.728
Different chiefs of staff have all kinds of amazing different things and backgrounds that they bring to make them super impactful in their roles, and I think comms has just always been mine.

86
00:13:52.788 --> 00:14:00.738
I don't have any, um, you know, uh, classical comms training. [laughs] I never worked like in-house at like a publishing agency or- Mm-hmm... you know, a PR firm or anything like that.

87
00:14:01.248 --> 00:14:13.668
But, um, I think that, you know, to really, um, create like effective internal or executive comms is, um, to put yourself in the shoes of the person who is receiving the message. Mm-hmm.

88
00:14:13.788 --> 00:14:19.308
And you know, when you're sitting, you know, at the founder's table as a chief of staff, you have perfect information.

89
00:14:19.508 --> 00:14:26.628
Um, you know things that, you know, the rest of the organization doesn't know, or you have like a lens on y- you know, the market or the company- Yeah... that, um,

90
00:14:27.548 --> 00:14:33.847
everybody else who's, you know, just showing up and doing their jobs, um, might not have the same perspective that you do on it.

91
00:14:33.888 --> 00:14:38.778
So just making sure that you are really putting yourself in the shoes of the person who has to receive the message. Mm-hmm.

92
00:14:38.888 --> 00:14:46.868
Both what will excite them about the message, but also what might give them anxiety about the message. Mm-hmm. And just, um, trying to get ahead of that.

93
00:14:47.008 --> 00:14:59.637
So, um, when you're delivering good news, delivering it in a way that, um, the, everyone, no matter who in the company hears it, can understand why this is so impactful for the organization or even for themselves- Yeah...

94
00:14:59.637 --> 00:15:01.857
as you know, in a startup, them as a shareholder.

95
00:15:01.908 --> 00:15:12.948
Or, um, you know, if you're delivering tougher news, um, understanding if, you know, a person in any part of the organization, whichever seat, heard that, what would make them anxious about that- Mm-hmm...

96
00:15:13.008 --> 00:15:20.928
information or why, you know, um, they might not understand or, um, upfront totally agree with a decision that's being made.

97
00:15:21.378 --> 00:15:28.688
And just, uh, kinda getting ahead of those comms and thinking about the message as you're crafting it the way that you would wanna receive it- Yeah... if you were in that seat.

98
00:15:29.328 --> 00:15:38.328
Um, and then I think too just, uh, being authentic and being vulnerable- Yeah... where, where you can and where is appropriate. Love, love, love, love, love. I,

99
00:15:39.688 --> 00:15:50.798
I don't know if I'm like most people, but yeah, there definitely is like when you see a Slack message or you get some type of comms from certain people, you're definitely like, "Oh, shit." Yeah. Like,

100
00:15:51.868 --> 00:16:00.468
"What does this mean for me?" Yeah. "What does this mean?" Yeah. Like, "Am I in trouble?" Like- Yep... "Do I still have my job?" Mm-hmm. Like it feels like just like all these like...

101
00:16:00.528 --> 00:16:12.438
And even I can be super confident about like my role, my impact, like no matter what, just depending on like from certain people, if they say certain things or like the style or like- Mm-hmm...

102
00:16:12.448 --> 00:16:15.348
definitely can feel a little bit uncomfortable. And I feel like,

103
00:16:16.288 --> 00:16:27.368
yeah, I'd like to do a better job of like calling out some of those things and being like, "Hey, I know this might be n- might not be easy to receive," or like, "Here's what this..."

104
00:16:27.428 --> 00:16:38.848
Like, "You might read this this way, but just wanna let you know that like that's not the case, and here's this." Yeah. So hard to do. Definitely. But so important. [laughs] Yeah.

105
00:16:38.917 --> 00:16:48.618
Someone, someone-- I think it's really good to have someone in the organization who is focused on it too. Mm-hmm. Because, I mean, especially in startups, we're moving so fast, and we're all- Mm-hmm...

106
00:16:48.618 --> 00:16:52.637
so very focused on, you know, our functions and what we have to deliver- Yeah...

107
00:16:52.668 --> 00:17:10.408
that, um, having someone, whether it's a chief of staff or someone else, um, an in-house internal comms team that is focused on making sure that we're bringing everyone along and people understand, uh, where we're going and why we're doing certain things, um, it's, it's not just for, you know, the feelings and the, you know, security of the people- Yeah...

108
00:17:10.418 --> 00:17:21.348
in the organization, but it is, you know, for cross-functional alignment as well too, and helping us execute even better because it reduces confusion upfront if you're, if you're good at it. [laughs] Hopefully.

109
00:17:21.368 --> 00:17:29.048
Hopefully, it doesn't create more confusion, but sometimes that happens, so. [chuckles] Yeah. Yeah. Uh, does, um...

110
00:17:30.448 --> 00:17:39.848
Like what, at what stage do you think it's important to bring in internal comms or have someone like oversee internal comms and strategic comms or executive comms? Is it...

111
00:17:41.068 --> 00:17:52.388
Yeah, at what point did any of the companies or any of the roles you've seen in the past been like, "Okay, starting to reach a point where like someone needs to own this"? Mm-hmm. Uh, never too early. Okay.

112
00:17:52.438 --> 00:17:57.968
[laughs] My, to my founders listening- [laughs]... never too, never too early. Um, no, I really don't think it...

113
00:17:58.148 --> 00:18:09.658
It's never too early to have someone at least, you know, part-time focused on, you know, messaging, all-hands global town halls, however your organization, you know, communicates, um, and, and gets everyone together.

114
00:18:10.248 --> 00:18:19.088
Um, but I think, you know, for the early days from like maybe Series A to Series C, it likely, if you have a chief of staff, it will be their job- Mm-hmm...

115
00:18:19.128 --> 00:18:26.998
in partnership and in concert with, you know, the founders, um, 'cause you have to be very closely aligned on those things. And also too, sometimes the marketing team is involved as well. Mm-hmm.

116
00:18:27.048 --> 00:18:34.138
If like, if you have people with, you know, um, branding and comms backgrounds, like that's kind of your, your A team there. But, um, it's,

117
00:18:35.128 --> 00:18:43.498
you know, in the chief of staff roles that I've had, it's been a huge slice of the pie of all the things that, um, you know- Yeah... I've had to own. Um, it's something I enjoy the most too. Mm-hmm.

118
00:18:43.748 --> 00:18:46.028
Um, just comms in general, internal and external.

119
00:18:46.268 --> 00:19:01.296
But, um, yeah, I think it's, um, in partnership with, with the founding team, and the chief of staff is really the people that need to be focused on it the most, especially like Series A to C or pre-A.Does that affect social media stuff too, like content for founders, et cetera?

120
00:19:01.336 --> 00:19:03.436
Is that a part of that, or is that something separate?

121
00:19:03.516 --> 00:19:12.556
Um, there are definitely chiefs of staff that, um, help with, you know, internal executive comms and also, you know, external, uh, call it ghost writing on LinkedIn [laughs] and stuff.

122
00:19:12.566 --> 00:19:23.156
[laughs] There's, you know, um, a, a bunch of people who are doing, you know, fractional chief of staff work, and part of it is, you know, uh, ghost writing externally, um, for, for things like LinkedIn and Twitter and stuff like that.

123
00:19:23.216 --> 00:19:33.016
So, um, yeah, there's definitely demand for that out there with some founders if, you know, their brand is something that they wanna be spending time on and getting out there. Yeah. Okay.

124
00:19:33.156 --> 00:19:46.076
So, you know, s- so in addition to also being focused on exec- like that being kind of your X factor, uh, your sweet spot, your superpowers, comms, um, also spent a lot of time in climate.

125
00:19:46.176 --> 00:19:59.696
Do you think that that has been helpful as you've been kind of in your chief of staff career? Like, kind of s- picking a lane and, uh, kind of focusing time there, or is that-- has that just like been

126
00:20:00.616 --> 00:20:14.606
like, not to say by accident, but just more like random? Yeah, it's a good question. I think I fell into climate by accident, but every step I've taken to stay in it has been very much on purpose since. [laughs] Yeah.

127
00:20:14.696 --> 00:20:28.126
Um, I, I really feel that I've found my, um, you know, piece of the market where I wanna play. Yeah. And I think it like leads to interesting questions and commentary around specialization with chiefs of staff. Yeah.

128
00:20:28.126 --> 00:20:36.866
Yeah. Um, I know like a lot of chiefs have asked me these questions of, you know, when is it time to specialize? Do I have to specialize? Um, all those, all those questions.

129
00:20:36.936 --> 00:20:46.476
And I guess to the, to the question of specialization, I do not believe that you have to specialize. Um- Yeah... I think that that's like a newer train of thought, uh, for the role.

130
00:20:46.536 --> 00:20:51.536
But, um, I really just don't think that you need to. Um, I think that generalists rule the world.

131
00:20:51.796 --> 00:20:59.586
Um, and also too, um, your founder or your executive that you're supporting, your principal, will absolutely have to be a generalist always- Mm-hmm...

132
00:20:59.596 --> 00:21:05.096
in some sense of the word, because like I said, the buck stops with them, and they'll- Yeah... there'll always be different hats they have to wear. Yeah.

133
00:21:05.355 --> 00:21:11.196
So, um, you being a generalist as well and supporting them, um, um, is not a bad thing at all.

134
00:21:11.256 --> 00:21:34.966
And I think, you know, on the specialization topic, um, if you are feeling like maybe it's time for me to specialize or, um, you know, a lot of my mentors are telling me it's good for my career, whatever your reasons are that you're starting to kind of think about it, but it's spooky to you a little bit, um, I would just like challenge you to expand what you think specialization actually is, because it doesn't have to be- Yeah...

135
00:21:34.976 --> 00:21:41.876
you know, I was chief of staff for two years and did a lot of projects with the product team, and now I'm gonna go work on product and be a product person.

136
00:21:42.396 --> 00:21:51.626
Um, it can be maybe more similar to my journey of I'm a generalist, but there is one sector that I, that I play in and I hope to play in for, you know, the rest of my career.

137
00:21:51.756 --> 00:22:01.236
So specialization doesn't have to be based on a function in the organization. Mm-hmm. It can be, you know, a piece of the market that you, you're an expert in that way. Yeah. Um,

138
00:22:02.316 --> 00:22:06.496
what other questions do chiefs of staff ask you? [laughs] I wish they were here to ask the good questions.

139
00:22:06.616 --> 00:22:18.476
But what else do you think you like typically get either on LinkedIn or in the chief of staff network that like either keeps popping up or that like has stood out to you? Yeah. I think, um,

140
00:22:20.056 --> 00:22:27.396
I mean, tactically I get a lot of questions about annual planning [laughs] Because I know it's like a huge tranche of work for a lot of chiefs of staff.

141
00:22:27.456 --> 00:22:32.216
So like annual planning is just the absolute cross-functional Olympics of a business- [laughs]...

142
00:22:32.226 --> 00:22:40.876
of like all of the, you know, SMEs need to be in the room for us to come up with an annual plan that will turn into our budget that needs to ladder to, you know, our five-year vision.

143
00:22:40.916 --> 00:22:50.126
So that, that's-- I get a lot of questions about, um, that from, um, chief of staff who've been doing this for, you know, only a few months or a couple of years. They're just like, "How do I do this really well?" Yeah.

144
00:22:50.126 --> 00:22:59.126
I get like a lot of operating cadence questions. Um, but I think a lot of people, um, a lot of the questions I get around chief of staff type work is, how do I get into the role? Mm-hmm.

145
00:22:59.136 --> 00:23:06.336
And I think probably a lot of people who are listening to this podcast might be like in that same boat of how do, how do I get into this role?

146
00:23:06.456 --> 00:23:17.516
Um, and I think, um, you know, the, the role has absolutely exploded, which is so great 'cause I'm obviously a fan. [laughs] I've done this enough times that I'm definitely a champion of the role.

147
00:23:17.536 --> 00:23:27.016
It's been amazing for, for me in my life- Yeah... and my career. Um, but I think what's awesome is seeing how many companies and founders are really seeing and valuing this role.

148
00:23:27.036 --> 00:23:32.856
There's just, you know, go on LinkedIn, there's JDs for every startup is looking for a chief of staff right now, which is so awesome.

149
00:23:33.516 --> 00:23:46.976
And, um, I think like the best way for you to get into the role is to really be great at, you know, storytelling and explaining your experience, even if you don't have the direct background that the JD is looking for.

150
00:23:47.036 --> 00:24:00.936
Just showing, um, you know, the different sizes and stages of companies you've worked at, what you yourself learned in your role during, um, those different, uh, different stages or the different, uh, things that you've, you know, operated through.

151
00:24:01.056 --> 00:24:10.866
Um, and, uh, showcasing your resiliency through those things, your passion for, um, uh, working with founders or executives and, um, being that right hand.

152
00:24:11.316 --> 00:24:19.896
I think all of those things, just showing and storytelling, even if you don't have the direct background of why it's transferable or, um, translatable into the role. Yeah.

153
00:24:20.156 --> 00:24:28.656
Um, that's how you can really storytell of why you would be the best candidate for the position. Cool. Cool. Um, anything else on annual planning?

154
00:24:28.736 --> 00:24:34.456
Is there like a template or a resource or like anything that you've developed or that like...

155
00:24:34.936 --> 00:24:42.796
Or I guess like, yeah, why, is it just that everybody wants to get better at this or has to do it so, but then since you've been in the space for a while that people come to you?

156
00:24:42.876 --> 00:24:54.132
Or like, or have you developed up something that like- Mm... is your special sauce? I can't sayMaybe I have. I don't know. Have I developed a special sauce around- [laughs]... annual planning?

157
00:24:54.792 --> 00:25:00.002
Um, I think it's just such a huge project, and it's always a huge project, and you have to do it every year. Mm.

158
00:25:00.002 --> 00:25:10.212
And, um, it usually gets, um, in some ways, in some ways clearer as your company grows, but some ways more complex, um, as, you know, the organization grows and the targets get higher.

159
00:25:10.792 --> 00:25:19.672
So, um, I just think it's, it's one of those necessary evils. We have to do it every year. Okay. That, um, it's never, it's never going anywhere, and that's why, you know, there's always gonna be questions around it.

160
00:25:19.972 --> 00:25:36.712
Cool. Um, summer 2023. Mm. What, what, what was that like for you? Ooh, that's a great question. Are you referring to my... Yeah, so David's referring to when I got laid off.

161
00:25:36.952 --> 00:25:53.701
Um, it was, uh, in many ways the most difficult time of my professional career, but also the most expansive and rewarding thing that's probably ever happened to me professionally. Wow.

162
00:25:53.812 --> 00:26:01.102
I know that might sound kind of woo woo- [laughs]... and wow, she's really just, like, putting a spin on this and branding that. But, um, I think that

163
00:26:03.212 --> 00:26:11.852
it, it really was, like, one of the best things that ever happened to me because I had to prove to myself how resilient I actually was- Mm... and how resourceful I could be.

164
00:26:12.322 --> 00:26:22.192
And I think, um, in this role specifically, I'd spent a long time, uh, happily so, being resilient and resourceful for, for others. For- Yeah...

165
00:26:22.372 --> 00:26:30.212
for either my founders or my executive team or, you know, all, all the people that I, I worked with that I, you know, loved and wanted to be the best chief of staff that I could for them.

166
00:26:30.352 --> 00:26:36.772
But, um, it was really something expansive for me to be that for myself, um, and

167
00:26:38.232 --> 00:26:49.312
go out there and, like, start a consulting business and, like, file LLC [laughs] paperwork, whatever the hell that means, and just, like, get an EI- like, the non-sexy stuff.

168
00:26:49.332 --> 00:27:01.612
Like, get an EIN number and, like, uh, like just have to really be, uh, be my own boss and, you know, um, bring home the bacon for myself, I guess. Um, so it was really amazing, and it was expansive for me.

169
00:27:01.652 --> 00:27:09.192
And I think it was also a very, um... It was scary, but it was really creative too. Mm. Um, and I was just, uh, really seeing that there are...

170
00:27:10.492 --> 00:27:22.652
This is, I'm gonna go on a tangent about how cool fractional work is, but there just really are different ways to make, uh, money and be your own boss, um, but to completely own your own schedule and be the captain of your own ship.

171
00:27:22.772 --> 00:27:29.231
So, um, it w- it was really cool to, um, just experience this new thing and kind of build it for myself.

172
00:27:29.892 --> 00:27:41.752
And, um, yeah, I, I found that, you know, I wanted to go back to being a full-time chief of staff, um, for another company, and that's where I, I landed at my current gig, which I'm, I'm so happy that I did.

173
00:27:41.852 --> 00:27:53.012
Um, but yeah, I think that, um, David's asking me this because I wrote a vulnerable post on LinkedIn about, like, what being laid off, you know, was like and what it did for me, or what it did to me and how I had to grow.

174
00:27:53.212 --> 00:28:08.882
But, um, I think that, you know, there are just so many talented people that- Mm... have been laid off. And I think that's why I wanted to post about it, is because, um, really talented people get laid off too. Yeah.

175
00:28:08.882 --> 00:28:18.112
And it isn't personal, and it has nothing to do with you. Mm-hmm. And the market is down, and that's why these things happen. And, um, there's nothing wrong with you if this happens to you.

176
00:28:18.152 --> 00:28:28.072
And also, I think it can be, like, a really lonely time, um, out there interviewing, getting rejected, all the things. Yeah. Um, it can be a lot.

177
00:28:28.172 --> 00:28:37.572
But also too, just knowing that, like, other awesome, smart, resilient people are out there doing the same thing. Uh, you will find what is meant for you.

178
00:28:38.012 --> 00:28:49.892
And also too, sometimes, um, you are meant to go do other things anyway. Yeah. Yeah. Yeah. Yeah, it's a really great post. I remember- [laughs]... when you posted that, I was like, "Oh, shit."

179
00:28:49.912 --> 00:29:00.192
[laughs] Like, Maggie is dropping some knowledge here and putting her heart out there. Some wisdom. Yeah. Just like this podcast episode. Yeah, totally.

180
00:29:00.822 --> 00:29:17.062
Um, but that's so interesting about, like, it's not about you, but yet we think it's about us. Totally. And we feel it so much. Yeah. It's not about you, and it's not about your team either too. Mm-hmm.

181
00:29:17.352 --> 00:29:24.832
Like, if you're part of, like, a team that got cut, like, that sucks too because, you know, you, you usually, you love your team and think that they're so talented 'cause they're your team. Yeah.

182
00:29:24.972 --> 00:29:35.372
Um, but I think also too for founders, um, laying people off is the worst thing ever. Mm. Like, just like, you know- Mm...

183
00:29:35.412 --> 00:29:48.232
in candid conversations I've had with the people that I've, like, worked with, um, it's, like, devastating. It's gutting, and, um, of course no one wants to do it. Yeah. And, um, it is just, it really is just business.

184
00:29:48.352 --> 00:29:58.712
But, um, it's tough, and I think it's part of, you know, layoffs happen in any sector, but particularly in startups when you're, you know, growing at different rates.

185
00:29:59.012 --> 00:30:09.492
Um, unfortunately it can be part of the gig that, uh, you know, you're not a solid, stable corporation yet, so, uh, you can't, you know, always have job security for every single person on the boat.

186
00:30:10.092 --> 00:30:12.512
Um, which is tough, and it sucks. Yeah.

187
00:30:12.972 --> 00:30:22.792
So the only thing you can do is, um, be the best leader and operator that you can be, that your company doesn't get into those situations if you can avoid it, and, uh, take care of your people. Yeah.

188
00:30:22.832 --> 00:30:35.602
And wait, what was the song that you shared on that LinkedIn post? [laughs] It's this old song called "It's Amazing." It's probably from like 2005 or something. It's, it's, it's good stuff. Oh, yeah. Like, you- Yeah...

189
00:30:35.602 --> 00:30:47.632
you guys, you can go find me on LinkedIn and- Yeah... find the post. Um, it's, it's, it's good. It's pump-up music. Yeah. Um, we've covered a lot of ground here. Um,

190
00:30:48.932 --> 00:31:00.832
is there anything else that you really wanna share, uh, that you think that really stands out about your chief of staff experiences?Maybe you wanna shout out the wine- Mm. Wine, wine shop. Um, if you wanna...

191
00:31:01.232 --> 00:31:10.822
Yeah, I just like, I don't know how you've done so much. Like, I just- [laughs]... feel like y- you've been everywhere ev- like, everywhere, anywhere, all at once. And then when you were like,

192
00:31:11.772 --> 00:31:22.092
"Yeah, I also sometimes, like, hang out here," like, I just was like, I... Like, classic chief of staff. [laughs] It's just like, "Yeah, of course. Like, I'm just doing this, this, this, this."

193
00:31:22.252 --> 00:31:32.252
Then like, "Yeah, what's up? Oh, you... Yeah, I'm down to come to that event. Oh, you wanna meet for coffee? Cool. Yeah, yeah, yeah." So always, like, that's what has been so cool getting to know you more, is just, like,

194
00:31:33.332 --> 00:31:44.212
so much more is even happening and you're doing than, like, I see. And, like, you're my client, and I'm, like, trying to get to know you more, and, like, the more that I do, I'm like, "How? Like, she's just a rock star."

195
00:31:44.312 --> 00:31:57.462
Thank you. Oh my gosh, David. Wow, thank you. Um, I think it's like... It's probably what draws me to the role, is that, like, I feel, um, I feel such a sponge. [laughs] Mm.

196
00:31:57.462 --> 00:32:01.592
My life is that of a sponge, and I just feel like there's so much to learn and grow and do.

197
00:32:01.672 --> 00:32:10.782
And that's why I love this role so much, and I'm just such a champion of it, is, you know, the way I frame it is you're literally getting paid to learn. [laughs] You're usually earlier in your career.

198
00:32:11.332 --> 00:32:23.312
You show up, you get to be at the founder's table, and your counterparts that you're working with every day are, like, the topmost leaders of their function. And, um, you just get to be in the room.

199
00:32:23.392 --> 00:32:31.522
And, um, maybe I'll start a podcast about why I have no time for imposter syndrome. Doesn't mean I don't- [laughs] As I- it doesn't mean I don't suffer from it sometimes. That's gonna...

200
00:32:31.522 --> 00:32:39.872
That might be the subject line, or that might be the episode title. No- Yeah. I have no time for... I have no time for imposter syndrome. Because the point is, like, you're...

201
00:32:39.912 --> 00:32:48.712
Everybody knows that you're younger in your career, usually. The- Yeah... you know, when you're taking a chief of staff role. Everyone knows that you're not the foremost subject matter expert. Right. You're not the CFO.

202
00:32:48.772 --> 00:33:01.712
Yeah. You're not the CMO. Um, but the point is that you are, have obviously done something right enough that the principal trusts you and has you in the room as well with those executives to be here and create value.

203
00:33:02.232 --> 00:33:12.992
And, you know, if all else fails, and you're just nervous as hell, just remember that, that you're in this room for a reason. Um, and there's obviously value that you provide.

204
00:33:13.072 --> 00:33:24.872
And, you know, on days when you're feeling just so imposter, and you just, you know, can't get past it, whatever, you're like, "Oh, my gosh, can't believe I, um, am front row to this right now," um, you've made out like a bandit.

205
00:33:25.022 --> 00:33:32.332
Mm. They haven't figured out yet, I guess, that you're so bad at your job [laughs] or whatever. [laughs] So just, you know, get in there. Yeah. Fake it. Learn as much as you can.

206
00:33:32.572 --> 00:33:42.022
Um, take everything you can from the experience. And, um, just keep going. And, you know, learn whatever you can, and then, you know, if they figure it out that you're a fraud, they'll kick you out.

207
00:33:42.052 --> 00:33:52.071
But of course you're not, so, um, that's why they have you there. Love, love, love, love, love. So people can find you on LinkedIn. Yes. Um, Maggie M on LinkedIn.

208
00:33:52.332 --> 00:34:02.852
Um, and I'm, uh, made some commitments with David around myself to be posting a little bit more. Ooh. And this is my first foray into doing that, so, um, yeah, um, check me out on LinkedIn. Follow me there.

209
00:34:02.932 --> 00:34:15.032
And for chiefs of staff or aspiring chiefs, uh, if you have questions, send me a message. I have many battle scars and stories- [laughs]... and just, uh, you know, wisdom to share if you ever need it.

210
00:34:15.082 --> 00:34:19.072
So, uh, please reach out. Aw. Thank you so much, Maggie. Thank you. Thanks, David.

211
00:34:21.452 --> 00:34:39.492
[outro music]