WEBVTT

1
00:00:00.100 --> 00:00:12.940
[upbeat music] Hey, friend. It's David Nebinsky, the community lead here at the Chief of Staff Network.

2
00:00:13.600 --> 00:00:23.200
We help chiefs of staff through the three Cs: cohorts, curriculum, and community, via Slack with over 900 people in it. Can learn more about our membership, events, and courses at chiefofstaff.network.

3
00:00:23.640 --> 00:00:34.449
There, you'll see our upcoming Chief of Staff Connect conferences in New York in October and London in November. This episode was recorded during our New York City BrainTrust event in July.

4
00:00:35.280 --> 00:00:49.900
Uh, it is recorded with TheOrder.co Chief of Staff Ali Sardenia and CEO Zach Garrippa. You may remember Ali from a prior podcast episode called Mastering the Message: The Chief of Staff's Role in Storytelling.

5
00:00:49.920 --> 00:00:51.470
Definitely check that out after you listen to this.

6
00:00:51.900 --> 00:01:02.920
In this episode, you'll learn about why Zach wanted to hire a chief of staff, how they co-created the role, frameworks they have developed to be successful in the role as partners, not letting things fester, and so much more.

7
00:01:03.580 --> 00:01:14.760
So excited for you to level up as a chief of staff. Here we go with Ali and Zach. Ali and Zach, welcome to the podcast. Thank you for having us. Thanks so much. Um, so how did this, how did this role come together?

8
00:01:14.860 --> 00:01:24.240
I think, Ali, you've shared it on our podcast before. Um, Zach, what, what was your perspective in terms of wanting to hire a chief of staff and wanting to hire Ali? Yeah.

9
00:01:24.340 --> 00:01:38.570
So it's half better to be lucky than skilled to find Ali, but the first, the first skill part was our company was getting to a stage where advisors and people I trusted that I knew were like, "You need a chief of staff."

10
00:01:39.300 --> 00:01:47.140
So I actually wasn't even the person who thought, thought of it. I just, like, wasn't familiar with the role. C- once a couple people tell you the same thing, you start taking it seriously.

11
00:01:47.220 --> 00:01:59.080
[laughs] So my first step was, like, literally trying to find chief of staffs through my network and figure out what they do, because I was told that the, like, role is quite broad.

12
00:01:59.510 --> 00:02:09.180
And then among hires you can make, usually it's th- like if you make the wrong hire, that's on you, the hire, hire person- Mm... because the, the role is broad.

13
00:02:09.220 --> 00:02:20.560
So you have to, like, figure out what you want, and then you're gonna try to seek someone in that, uh, in that area. So I basically spoke to, like, probably 10 different chief of staffs at different companies.

14
00:02:21.870 --> 00:02:29.320
W- Order.co is a B2B software company. I was speaking to chief of staffs at not that. I spoke to a chief of staff at SolidCore.

15
00:02:29.400 --> 00:02:35.540
I spoke to the chief of cha- uh, chief of staff at just, like, other different roles because I was literally trying to figure it out.

16
00:02:35.640 --> 00:02:53.780
Thought I really, really narrowed down just, like, what would really, really work for the business, um, what would work for kind of the s- the stage, but also what would work for the next five, 10 years, and then got really, really lucky when Ali's former CEO called me and said, "My chief of staff is available."

17
00:02:54.840 --> 00:03:04.160
And what were the conversations like between you two about what the role, uh, would be like, what you needed, what you wanted? Like, how did you kinda craft the role? Yeah.

18
00:03:04.300 --> 00:03:14.060
So, uh, from, I think, like, my perspective, um, we... The first time we met, we met for coffee, and it was very... I would say, like, it was very casual.

19
00:03:14.100 --> 00:03:23.140
And the questions that I asked were like, "What problems or, or challenges is your business experiencing right now, and where do you see a chief of staff fitting into that?

20
00:03:23.180 --> 00:03:30.360
Like, why are you hiring a chief of staff, and what are you expecting this person to solve?" In that sense, then I also said, "Okay, well, here is where I'm coming from.

21
00:03:30.720 --> 00:03:40.580
You know, if you are looking to bring on a chief of staff who is going to build your operating plan or is, needs, you know, heavy financial acumen, like, I'm not your girl. Like, that's just not my area of expertise.

22
00:03:40.640 --> 00:03:51.340
But if you need someone to do, like, executive operations and, um, you know, executive team management, OKRs, you know, whatever it may be, we can definitely talk about where there might be overlap."

23
00:03:51.460 --> 00:03:59.700
So it certainly was a conversation in terms of what does the business need, but I was also very vocal about here is where I think that I can provide, like, unique value.

24
00:03:59.730 --> 00:04:09.780
And then I think we naturally found some of the synergies there. Is there anything you wanna add to that? [laughs] Yeah. One funny thing is we met in March of 2020. Oh. [laughs] Like March 7th of 2020.

25
00:04:10.440 --> 00:04:16.519
[laughs] So that- For a coffee. That coffee- Yeah. [laughs] In-person coffee. [laughs] The last, the last human I saw, uh, outside of my family for some time.

26
00:04:17.200 --> 00:04:21.850
But then the other funny thing is, like, we onboarded Ali in June of 2020. Mm.

27
00:04:21.880 --> 00:04:32.760
So she was actually the only hire we made over that kind of four or five months 'cause everyone was still just quite adjusting to a pretty abrupt, you know, change. Um, I, I think Ali nailed it.

28
00:04:32.880 --> 00:04:43.740
I would say what was very memorable was, like, how easy it was to chat the first time. And then in the same vein, both sides were very comfortable with, like...

29
00:04:43.780 --> 00:04:53.320
You know, Ali was like, "If it's the operating plan, not it." And I was like, "That's cool. I don't... That's not it either for me. What about this? What about..." Like, we almost like- Yeah... went back and forth.

30
00:04:53.560 --> 00:05:00.350
And then I remember from my perspective leaving, like, that one coffee meeting being like, "Yeah, this is amazing." Like, it, it... That was it.

31
00:05:00.400 --> 00:05:11.020
It took about an hour 'cause it was so specific, but it wasn't transactional. Mm. Like, it didn't feel, um, you know, kinda cold. Yeah. And then Ali joined.

32
00:05:11.540 --> 00:05:21.640
And maybe describe, like, what the role was like then and what it's like now. Yeah. Uh, yeah, I'll, I'll let Ali tell it from her perspective. So she joined in June of 2020.

33
00:05:22.600 --> 00:05:34.680
We just told a very true story of all the conversations leading up to it. The first week she joined, I was like, "I'm having like a... There's some, like, HR issue that I'm gonna need you to, like, jump into." So, like,

34
00:05:35.910 --> 00:05:45.800
we won't overshare the HR issue. [laughs] It was resolved favorably. But I bring that up because from day one, I think a lot of the role is, like, again, from my perspective,

35
00:05:46.740 --> 00:05:58.100
I try to go into the biggest problems of the org all the time. If there's not a problem in the org, that's great. Other people are kinda focused there. So I think naturally my role is searching for problems.

36
00:05:58.600 --> 00:06:05.484
And then as an extension, at the time, that was the biggest problem. And then the funny thing is that's then-...

37
00:06:05.494 --> 00:06:11.104
done, it's resolved, very quickly there's another big problem, and then very quickly there's another big problem.

38
00:06:11.164 --> 00:06:25.824
So fast-forward now, uh, we excitedly, you know, are, are pursuing kind of this inorganic track, so ac- acquiring companies of our own. That's a different problem than it was in 2021 when we were trying to raise money.

39
00:06:25.864 --> 00:06:38.564
So I think the one thread here is every year will come with X number of big problems, and then since that's where I'm focused, I, I certainly look to Ali to jump on in. No, I, I think that's right.

40
00:06:38.584 --> 00:06:49.624
And I think to your point, like, early days, early days are fun, uh, because there's a, a lot of things to be solved, and I think especially as chief of staff you are pointed in a lot of different directions.

41
00:06:49.644 --> 00:07:00.874
You have your hands everywhere. I think at, for me in particular, I think what helped in the early days or at the early stage was aligning with Zach on, okay, HR is a gap in the organization right now.

42
00:07:00.964 --> 00:07:09.364
I am going to assume the role, but we will align on a point in time when I say, "I have gotten the foundations as best as I can.

43
00:07:09.423 --> 00:07:17.064
I am not, like, an HR professional, so we should now bring someone on who can scale this function to the next level as, like, required by the organization."

44
00:07:17.094 --> 00:07:29.544
And I think having that type of conversation has really helped me. And I think exactly to Zach's point, as a chief of staff, you are just pointed at every business problem. You are kind of like a de facto gap filler.

45
00:07:29.584 --> 00:07:35.764
So very tactically for me, like, one, I think that's great because it's a sign that you have built really great trust.

46
00:07:35.824 --> 00:07:42.924
Like, you wouldn't be asked to do these things if you haven't proven that you're capable of doing the job and getting it done, so, like, trust is really at the root of it.

47
00:07:43.464 --> 00:07:50.454
But I think in that sense, you, at least for me, my priority is immediately having prioritization conversations with Zach.

48
00:07:50.964 --> 00:07:58.204
Um, that is really where I found that, like, I have protected myself, but also made sure that I am focusing on the most important needs for the business.

49
00:07:58.724 --> 00:08:09.524
So every time Zach comes to me, basically it's like if the framework is a problem is identified, I am pointed in that direction, and then I immediately, I'm asking questions around where should I be spending my time?

50
00:08:09.834 --> 00:08:15.974
What are the priorities? Because last week it was this problem. [laughs] But now there's a new problem- [laughs]... and I'm being pointed and pivoted there.

51
00:08:15.974 --> 00:08:20.054
So what can we deprioritize in service of, like, the latest and greatest thing?

52
00:08:20.424 --> 00:08:29.044
And I think that has really helped our working relationship, and it has made me be more impactful because I'm not spreading myself too thin and I'm focusing on things that I know really matter.

53
00:08:29.964 --> 00:08:41.024
Anybody else relate to prioritization conversa- Okay, I'm seeing a lot of head nods. Okay. Um, and then, um, Z- Zach, what are those conversations like for you?

54
00:08:42.024 --> 00:08:51.964
Yeah, I think Ali nails it, where, like, at least for, for me personally and for our business, I need someone to not go do the exact thing all the time, actually.

55
00:08:52.024 --> 00:09:02.044
Like, I don't think the chief of staff role, at least for us, is go do these things. It, it is like a gentle challenge, and in some cases a, a more than gentle challenge.

56
00:09:02.544 --> 00:09:16.373
'Cause I think Ali's right, like, things happen quickly. Uh, you know, today we're 140 people. When Ali joined, it was, like- 50... fif- yeah, 50 people. Our, you know, aspirations are to be 15,000 people.

57
00:09:16.404 --> 00:09:30.384
So I do think things change quickly, and I think something that Ali does uniquely well is, like, actually is, like, do you, do you still need this thing? Mm. Like, is this still important? 75% of the time, yes.

58
00:09:30.484 --> 00:09:39.873
25% of the time, no. And then what she also does well is not, like, rub it in my face after the fact. [laughs] Like, it's like a, "Okay, we'll drop it. Onto the next thing."

59
00:09:40.064 --> 00:09:53.984
So I actually think those two skill sets are important 'cause even though we're speaking at this abstractly, this happens, like, once to twice a week, not, like, once a year. Hmm. I can add one more thing. Yeah. Yeah.

60
00:09:54.584 --> 00:10:06.204
The other thing that I'll layer onto that that, like, helps me, even within this, like, broader prioritization framework, is, like, also as chief of staff I think we all know there is work that you do, and then there is work that you direct.

61
00:10:06.284 --> 00:10:18.984
And so also when we're having these conversations, I try to get more clarity in terms of, like, okay, w- when you are asking or pointing me in the direction of this problem, what are your expectations of, like, my role in this problem?

62
00:10:19.044 --> 00:10:23.304
So is it, like, do you want me to, like, literally do this? Like, do you want me to go talk to someone else?

63
00:10:23.843 --> 00:10:33.944
I can do it myself or I can kind of gather people together and direct them to do the work, and I will make sure that it gets, you know, through completion, um, which also helps me as well.

64
00:10:34.004 --> 00:10:41.364
If I'm doing the work, that's a significant amount of time. If I'm directing the work, it's still work, but okay, maybe I can do that thing that he asked me to do last week then.

65
00:10:41.444 --> 00:10:48.204
So that's just, like, an additional layer or, like, a thought process that I also go through. But I think frameworks like that are helpful.

66
00:10:48.254 --> 00:11:03.444
I think, like, the biggest thing, again, I think everyone in this room knows, but what has really helped me is, like, making sure I am flexible, because priorities will always change, and then when they do change, making sure how- you kind of force these priorities or prioritization framework exercises.

67
00:11:04.264 --> 00:11:16.664
And what are, what's, like, a recent top priority, and how did you decide, like, what to do? Yeah, I think, like, in the spirit of, like, company... So company priorities change infrequently.

68
00:11:16.704 --> 00:11:27.624
Priorities at the team level, tactics change frequently. So I think with that framework, entering this year, performance was good. We had a couple of tailwinds, um, that, that we're excited about.

69
00:11:27.644 --> 00:11:38.484
So we started thinking this may be a good, good year to raise a Series C. So with that as a thought process early on, we kinda delineated work, like, across the company between, like, performance and execution.

70
00:11:38.544 --> 00:11:42.894
Revenue needs to be, you know, go from X to Y, and costs need to go, you know, all that good stuff.

71
00:11:43.904 --> 00:11:54.354
On the other side, Ali and I have drank the Kool-Aid of just the importance of storytelling, and although it sounds simple, I think I personally have done that sometimes poorly- Mm...

72
00:11:54.354 --> 00:11:59.924
'cause I'll just be like, "Here are numbers. Like, read those numbers" [laughs]... and someone just looks at me with the blanks there.

73
00:12:00.564 --> 00:12:07.544
So over the last few months, I would say that that's our biggest focus area, but then breaking that down, it's not, like, chatting about it.

74
00:12:07.784 --> 00:12:14.824
Like, we, we have a book club, so we read the same book, and then we talk about it. We send each other podcasts or articles about it.

75
00:12:14.904 --> 00:12:27.020
We have two or three times a month-Like leverage storytelling meetings, and we try to, you know, take things that have happened in the company and essentially wrap it into a broader company narrative.

76
00:12:27.220 --> 00:12:38.070
So I'd say over the last three, four months, that- that's probably been the biggest one. Okay. Um, and then I can imagine over these, these four years... It's been four years? Five years. Five years.

77
00:12:38.650 --> 00:12:54.760
Um, it hasn't been always perfect. How, how would you say you two have worked through, um, challenges, either at the company level or maybe, like, disagreement on, um, some priorities amongst you two?

78
00:12:55.300 --> 00:13:09.000
F- I could take this, 'cause from Ally's perspective it's been quite perfect. [laughs] But from, but from mine, I think it's the same theme of don't let anything fester at all. Mm. Like, I think that that's really it.

79
00:13:09.200 --> 00:13:14.500
I think what both of us do well is, like, a disagreement will last

80
00:13:15.480 --> 00:13:23.520
a short period of time in the bad sense, but if we're actually disagreeing on, like, where time is being spent, that's okay if that takes a day, two days to, to think it through.

81
00:13:24.020 --> 00:13:33.600
So not to, like, overanalyze, like, that word. It's like, what's the disagreement? If we're just, like... If it's more on the bickering word choice, just avoid it, you know, no hard feelings.

82
00:13:33.680 --> 00:13:43.820
I think neither of us intend on making anything personal. If someone takes something personal, it's just like clear that up very quickly. 'Cause then, like, business disagreements are actually not bad.

83
00:13:43.840 --> 00:13:53.400
It's like we're trying to spar a little bit. Should we do this? Should we do that? I don't think, like, it's the chief of staff's job to, to agree all the time. Mm.

84
00:13:53.520 --> 00:14:05.360
I wanna kinda say that again, because that's usually not at least what I want, and I think a lot of CEOs want. Like, you actually don't want everyone to do what you want all the time. Mm. You want thought partners.

85
00:14:05.420 --> 00:14:19.270
You want, you know, different leaders in the org, like, challenging you, and then it helps you build conviction and then make a decision. So I think some disagreements, good, welcome them. But the stuff that can derail,

86
00:14:20.500 --> 00:14:32.460
I think you wanna nip in the bud/don't let fester. 'Cause those happen too. Like, I talk to Ally all day every day because of just different things. Um, there are good boundaries.

87
00:14:32.540 --> 00:14:41.419
Both of us have kids, so I think that that's, like, a a- a good kind of mutual boundary where we both have family time- Yeah... kid time, and we don't bother each other, you know, during that period.

88
00:14:41.540 --> 00:14:55.990
Um, I can hop on late or early, and Ally can hop on late or early. Like, it kinda keeps you in sync. But any sort of disagreement that, like, could cause a problem, don't. Just, like, be really proactive about it. Yeah.

89
00:14:56.060 --> 00:15:02.280
I mean, e- echoing a lot of what Zach said, I think, like, the default is, like, we always want to be in alignment.

90
00:15:02.320 --> 00:15:10.530
And so obviously, like, if you're disagreeing constantly, there is some sort of, like, question there of, like, are your priorities misaligned? Like, what, what may be happening here?

91
00:15:10.540 --> 00:15:21.380
But generally I think, like, we do feel like we are well aligned, and I think we both view disagreements as, like, a good challenge. Like, we challenge one another's assumptions. And so whether that's, you know...

92
00:15:21.400 --> 00:15:30.480
And luckily for me, I think, like, Zach has set a good culture within our team that, like, disagreements are welcomed. And so I feel like I can voice when I say, like, "What if we took this different plan?"

93
00:15:30.590 --> 00:15:37.920
Or, "I'm not really sure that I agree with the path that we're on." Like, that is welcomed, um, and vice versa. Like, he'll disagree with me and, and, and he'll push back.

94
00:15:37.940 --> 00:15:40.979
But, like, I think that is a welcome challenge across everyone.

95
00:15:41.000 --> 00:15:51.720
When we were talking about this earlier, like, we were like, we kind of, like, do have a framework that we didn't realize where it was like we disagree and then both of us hold firm [laughs] 'cause we're like, "We're not giving up that easily."

96
00:15:51.780 --> 00:15:59.320
We're not just gonna, like, be like, "Okay, you're right." We're like, "No, we're gonna, we're gonna hold firm on our assumptions here and kind of, like, challenge each other," immediately then commit.

97
00:15:59.620 --> 00:16:09.050
Like, uh, we then commit and we move on extremely quickly. I think we both know there's zero sensitivity. Um, I also, like, none of us, like, hold grudges. We, we just move fast. Mm.

98
00:16:09.140 --> 00:16:15.790
I think that is also, like, part of, like, the culture inherently is, like, things are happening, we move fast. There's not a, a lot of time to let things stew or fester.

99
00:16:15.980 --> 00:16:24.060
So disagree, hold firm for a bit, and then commit right away, and then boom, like, you're, you're onto actioning right away. Before we go to audience questions, just to, like,

100
00:16:25.100 --> 00:16:35.660
zoom in on this a little bit, like, let's say do you, Ally, do you, like, send a Slack message to say, like, "Hey, I wanna talk to you about this," or is it, like, send an email or just quick call, quick text?

101
00:16:35.699 --> 00:16:45.540
Like, how do, whenever there is this so it doesn't fester, like, what does that... Like, how, how have you figured out, like, how to start having the conversation? 'Cause c- I can imagine Zach's busy, et cetera.

102
00:16:45.600 --> 00:16:58.200
Like, how, how does that go from, like, it's internal to, like, being proactive about- Yeah... fixing it? Yeah. It's a good question. I feel like we are constantly in contact with one another over a variety of forums.

103
00:16:58.220 --> 00:17:06.780
So I guess it kind of depends. Like, if this is, like, a, a big, like, you know, q- question around company direction or something, I definitely think it's, like, let's sit down and let's unpack this together.

104
00:17:06.860 --> 00:17:13.450
I wanna share my point of view on this. Like, let's actually talk about it because I don't think that a Slack message is going to, like, resolve this.

105
00:17:13.500 --> 00:17:23.000
Like, we really need to dive in together or maybe help me understand what I may be missing, like, whatever it may be. But also, like, sometimes if there's little things we'll Slack about it. I'll, I'll text you.

106
00:17:23.060 --> 00:17:29.940
It could be, like, at 8:00 PM, like, "Hey, I've been stewing on this thing. Here, here are my thoughts." And then it's, like, either resolved right away or it's like, "Okay, good idea.

107
00:17:30.000 --> 00:17:38.980
Let- let's chat in the morning and, like, we'll move through it." Um, so I think, like, the punchline being, like, big things that we really need to think about we carve out space and we talk about it one-on-one.

108
00:17:39.020 --> 00:17:52.440
Otherwise, again, I think we default to action, so if we can action something faster or quicker over email, Slack, text, we will default to that. Yeah. I, I think a huge thing here is, like, ask your CEO too.

109
00:17:53.040 --> 00:18:02.600
Like, I think Ally does a good job of that simple thing. So on this exact topic, my personality is just tell me. Doesn't matter if it's- Mm... Ally or anyone at the company.

110
00:18:02.680 --> 00:18:13.860
Like, good, bad, or otherwise, I don't love just someone trying to n- not even, like, sweep it under the rug, but it's like, "Hey, are you free tomorrow? Are you free this week? Like, let's chat th- Just tell me now.

111
00:18:13.880 --> 00:18:22.800
It's fine." [laughs] It's like literally tell me right now and then we'll, we'll figure it out. So that's, like, almost a personality quirk for me, but that matters a ton.

112
00:18:22.880 --> 00:18:32.960
So, so Ally will literally, you know, on Tuesday of this week-... messaged me like, "Hey, I was actually thinking about this thing still." Perfect. Love it. I, I kinda was too, actually.

113
00:18:33.620 --> 00:18:39.270
Um, I think that each person is gonna have hopefully only one or two- Yeah...

114
00:18:39.290 --> 00:18:54.000
quirks on, on things like this, but actually it matters because if someone else is the complete opposite, like they want, you know, full reports as to why something happened and, you know, the root cause analysis, that's not gonna work.

115
00:18:54.260 --> 00:19:00.860
I do not want those things. Just please tell me, and then, like, I'll help you out. Like, we'll let's... This is kinda our problem, is kinda h- how I see it. Mm.

116
00:19:01.649 --> 00:19:13.840
Um, but everyone will be different on, you know, like, idiosyncrasies. What, what questions do people have? You can come on up. This is a podcast. Um, hey, I'm Alana.

117
00:19:14.140 --> 00:19:24.520
Uh, I'm curious about your team structure, both your executive team and then do you manage a team? Does your EA... I assume you have an EA. Is she EA? No, maybe not. Okay. No. No. Um, all right.

118
00:19:24.540 --> 00:19:30.420
So, I'm, I'm r- I'm just curious about your structure- Yeah... and, and how that works. Cool. Yeah, I can answer it a little bit- Yeah... and, and Ally can answer it.

119
00:19:30.500 --> 00:19:40.220
So, one, not to answer this question a little meta, um, Ally helps me with org design and team structure, so we meet on this topic constantly.

120
00:19:40.300 --> 00:19:50.040
Ally alluded to this with one of her anecdotes earlier, but it's like, okay, I can help, you know, perhaps do this problem. I can help direct this problem, but there may be a gap in the organization here.

121
00:19:50.380 --> 00:20:00.650
Like, we talk about this all the time. So, like, almost more literally have an executive team. For our org, Ally doesn't manage a team, and we do that, like, pretty by design.

122
00:20:01.320 --> 00:20:14.980
Um, we like this, like, ability to move in and out of organizations. I think that's gonna be a little bit of a skill set competency thing as well. I think, like, Ally's uniquely talented at just getting context quickly.

123
00:20:15.040 --> 00:20:26.679
So, it's, it's okay. Like, she could jump into something on the product org, jump into finance org, people org, sales org, and she's, like, got it. Ask some thoughtful questions and can kinda keep the train moving.

124
00:20:27.000 --> 00:20:39.200
Um, and then it's funny you mention EA. For me, like, I'm, I'm okay. I'm good with, I'm good with a bunch of the AI- EA stuff. So, for our kind of working relationship, like, I do emails. I do my own scheduling.

125
00:20:39.260 --> 00:20:51.169
I do all that kind of stuff, um, because I, I want, you know, Ally focused elsewhere, but again, it's gonna be, like, to each their own. Like, I don't mind doing a, a lot of that stuff.

126
00:20:51.300 --> 00:21:04.100
Like, it's just not a, a burden, but there's other things that I mind tremendously that perhaps other people just don't care about, so it'll be a little bit unique. Any other questions?

127
00:21:04.860 --> 00:21:14.980
Ally, this is for you specifically, but how do you build rapport as you're jumping in and out of different areas of the org knowing that at the end of the day none of those people actually report up to you, but you have authority?

128
00:21:15.200 --> 00:21:27.700
Yeah. So, that's a... It, it's a great question and something that I think I have honestly during my time as chief of staff, um, have, like, learned the hard way, honestly.

129
00:21:28.000 --> 00:21:34.080
I think, like, what matters most, and, like, what I have learned is it's kind of like two things.

130
00:21:34.140 --> 00:21:45.660
One, I think people understand that, like, when I am maybe providing feedback or direction to them, it is because Zach and I are in alignment, and I know that this is what he wants.

131
00:21:45.720 --> 00:21:56.050
So, I'm not giving feedback to someone as me. It is like I am, like, the conduit by which, like, Zach is kind of giving his feedback, and I am directing people that way. I think, like, I help...

132
00:21:56.180 --> 00:22:00.740
I try and m- as best as I can help, like, people realize, like, I'm actually here to help you.

133
00:22:00.780 --> 00:22:10.770
I'm giving you this direction because if you don't take this feedback, he's gonna throw down the [laughs] hammer a lot harder than I am, and I'm trying to, like, save you from that. I'm trying to save you from yourself.

134
00:22:10.860 --> 00:22:17.230
So, let, like, you and I figure it out, and then when we feel good and I feel good about whatever you're bringing to Zach,

135
00:22:18.630 --> 00:22:24.540
uh, w- we're feeling good about the outcome, and I think the probability of success there is high than the alternative.

136
00:22:24.620 --> 00:22:35.920
Um, so I think, like, really, like, pointed, like, to your question, I think it's really just about helping people understand, like, w- w- my... Like, I am motivated by helping you, and that is what I am trying to do.

137
00:22:35.980 --> 00:22:45.380
There literally is no other motive outside of I want you to be successful, and I think that there is feedback that I have for you that would help you be successful.

138
00:22:45.440 --> 00:22:49.770
It sounds like you didn't spend a ton of time together before you decided to work together, and I'm curious.

139
00:22:49.800 --> 00:22:59.860
Do you think there were specific elements that you figured out before working together, or did you just get lucky? Like, what should people look for? Do you have that? I got thoughts on a lot of things.

140
00:23:00.300 --> 00:23:08.960
[laughs] Team notes. So, like, during... Like, well, I'll reference, like, kind of the specific coffee meeting. Like, that, we met one time, and then we... You may know this better than me.

141
00:23:09.040 --> 00:23:14.960
I think we chatted one more time, and then, like, the third time- Yeah... like, a formal offer. Maybe the second time.

142
00:23:15.380 --> 00:23:30.860
I think when I was just trying to get a feel for it, I was looking more on, like, like, company value type things. So, for our organization and for me, um, you know, winning is fun, is one of our company values.

143
00:23:31.000 --> 00:23:40.800
What we mean by that is not, like, the end prize. Everyone knows that. You kinda actually have to, like, enjoy the work. You have to enjoy the practice, 'cause most... You know, I'm a big sports fan.

144
00:23:40.840 --> 00:23:50.520
Most champions, they stand on, you know, half court holding the trophy for five seconds, but, like, you don't see hours in the gym when no one's watching. That's really important to me.

145
00:23:50.900 --> 00:23:58.560
So, you know, you talk to someone, and you don't ask that specific question, but you actually can get a feel for that type of thing, you know, frequently.

146
00:23:58.620 --> 00:24:04.120
So, when I was asking Ally about, you know, things at ManageByQ, for example. So, ManageByQ had a, a, a great exit.

147
00:24:05.120 --> 00:24:15.660
Her stories were more, you know, these were things that didn't work, and this was a thing that, like, was super silly. It was more self-deprecating. I like those kind of people.

148
00:24:16.050 --> 00:24:22.620
Like, I think she could have taken a much different [laughs] tone, and she deserved to take a different tone, 'cause that company was successful and did great work.

149
00:24:23.280 --> 00:24:33.039
Another company culture thing is, like, we're probably on the sillier, self-deprecating side. Like, we take our work super seriously, but just you work a lot, have fun along the way.

150
00:24:33.080 --> 00:24:44.780
So, I won't go one by one, but-I was trying to get a feel for those things because I was like, if those things are aligned, you know, what it's applied to is easier than the opposite.

151
00:24:44.840 --> 00:24:56.820
Like, you know, perhaps if Ally had the most perfect experience going from, you know, a Series A company to hopefully an IPO company for us someday, that matters too. But to me, that was actually secondary.

152
00:24:56.860 --> 00:25:09.040
I was like, if we can align on these, like, foundational principles, you know, everything else will be easy relatively. Yeah. And I'm happy to share, like, my perspective also kind of approaching these conversations.

153
00:25:09.080 --> 00:25:20.400
So one, I think, um, in talking to Zach, I was very much drawn to the company that, that he was building and the vision that he had for the company. That was obviously a, a huge thing for me.

154
00:25:20.440 --> 00:25:22.580
I'm not gonna join something and I'm like, "Oh, this is going nowhere."

155
00:25:22.620 --> 00:25:34.380
But it's like, okay, clearly there's something really big that we are solving here, and I feel confident with Zach at the helm, and, like, that gives me a lot of confidence in this, uh, this business having staying power and me being able to have an impact.

156
00:25:34.440 --> 00:25:45.040
So I think one, assessing like the, the space that we were in, the product that we were building. I think also, personally, it was, um... I think it probably aligns with what you're saying about values.

157
00:25:45.060 --> 00:25:54.750
But, like, getting to know Zach as a person, and, like, what motivates him. Um, every conversation that we still have today, but even back in, in the early days, like, he's asking, like, how I am.

158
00:25:54.840 --> 00:26:04.680
I think at the time we were, like, wedding planning. He's asking me details about, like, wedding planning, and, like, he's asking though, like, not just to check it off the list, but he's genuinely c- curious.

159
00:26:05.220 --> 00:26:12.990
Um, and I think he, like, deeply cares about his people, and that, for me, certainly resonates of what I wanna see from a leader, so I appreciated that, and I was...

160
00:26:13.100 --> 00:26:21.980
Um, I think for me, it was like, yes, our values are aligned. I think he treats people with respect, and he deeply cares about his team. And again, that is something that I was looking for from a leader.

161
00:26:22.060 --> 00:26:32.820
So I think both of those things were, at least for me, things that I kind of, like, assessed, um, without really having a lot of time, but I could pick up on that after a couple of conversations. Last question.

162
00:26:32.860 --> 00:26:45.920
No pressure. Come on up. Okay. So this is a two-part question. [laughs] One is... [laughs] One is, uh, very practical, and that's, like, um, what are your beliefs about stand-up meetings, and how often do you have them?

163
00:26:46.440 --> 00:26:48.180
Like, what's the frequency and cadence of them?

164
00:26:48.500 --> 00:27:05.060
And then the second one is, when something does fail, and things fail, like, you have an i- you, you have something you're pushing out and it doesn't work, how do you protect your relationship so that you're not projecting the blame onto, let's say, the chief of staff or onto the CEO?

165
00:27:05.080 --> 00:27:13.180
Because failure is kind of, like, built into the system. So those are the two questions, the cadence of stand-ups and, um, projection.

166
00:27:13.900 --> 00:27:22.100
When you say stand-ups, is that, like, one-on-one meetings or, like, team stand-ups or- Uh, it's prioritization meetings. Okay. So, like, knowing that every week priorities can shift- Yeah. Yeah...

167
00:27:22.160 --> 00:27:28.380
so to stay fast-moving- Yeah... you probably need to be synced up. Yeah. So how do you stay in sync? Yeah. Okay. What's your flow? Yeah.

168
00:27:28.440 --> 00:27:37.540
So we definitely have a standing weekly meeting, and we strategically have those on Mondays so that we can be like, we have a shared agenda, but it's mostly like, "Here are...

169
00:27:37.580 --> 00:27:45.120
Here's, like, where I'm spending my time and what I believe my priorities are for the week. Are those your priorities? 'Cause I don't wanna start doing all of this work if that's not, if we're not in alignment there."

170
00:27:45.520 --> 00:27:53.660
So Monday mornings, we meet, and we review those together. Uh, if there's anything I'm missing, he'll loop me in on that, like vice versa. So we do standing weekly.

171
00:27:53.730 --> 00:28:00.690
I think for a while we were also doing, like, an end of the week touch base. That was more towards, like, afternoon of, like, "How did this week go?" Like, "How are we feeling about things?"

172
00:28:00.740 --> 00:28:09.620
Like, "What's coming up next week?" Um, so that, those two cadences I think have worked well for us. Um, do you wanna say anything on that before we kinda go on to the next one? Yeah.

173
00:28:09.660 --> 00:28:21.340
I think, like, the secret sauce is gonna be alignment 'cause everyone is different, and I kinda keep harping on that. But, like, for me personally, I'm like, if we're aligned on a Monday, I'm in the office every day.

174
00:28:21.420 --> 00:28:31.720
Ally's in the office usually four days a week. That works great because then, like, if anything changes, we sit next to each other, and then we just talk about it. Like, literally we'll just talk on the...

175
00:28:31.820 --> 00:28:40.200
Like, just turn, talk, and then we're done. I like... It's, like, the same theme. It's just, like, more, more rapid communication. I'm not even advocating for it.

176
00:28:40.260 --> 00:28:45.170
I'm just like, that's what I'm used to, and it's easy for me. Just, like, kinda quick. And it goes both ways.

177
00:28:45.220 --> 00:28:58.720
Like, if Ally was, you know, prioritizing a deck for all hands, but then something on the investor side come up, she will Slack me or turn and be like, "Listen, I may have to reprioritize," and we just, like, do it very quickly.

178
00:28:58.760 --> 00:29:04.980
And then I'm like, "Okay, okay." Ally's like, "Okay, okay. Done." Then we turn back, and then we continue to, to work.

179
00:29:05.220 --> 00:29:16.620
So I really do think it's like, the key here is gonna be alignment with the chief [laughs] of staff and the CEO because if, you know, Ally was like, "Let's meet daily in a formal meeting," I hate...

180
00:29:16.700 --> 00:29:29.640
That's a nightmare to me 'cause I don't love, like, pre-scheduled meetings that may or may not be relevant. Like, I prefer, like, one on a Monday, and then we'll meet as stuff comes up. Some week, some weeks,

181
00:29:31.060 --> 00:29:38.940
uh, you know, we'll meet on music, movies, and our kids. [laughs] And then that's it. Like, other weeks, it's like, wait a second, like, we have kinda too much stuff going on.

182
00:29:38.980 --> 00:29:51.680
We gotta prioritize a lot, a lot more quickly. Um, on the second one, I can quickly hit, and then I'll kick it over to you. I think you're right. Like, the failure side is inevitable. There's no magic bullet here.

183
00:29:51.700 --> 00:29:55.430
It's, like, the trust aspect again. Like, I don't... I've, like, never...

184
00:29:55.480 --> 00:30:06.400
I can't think of one example where I feel like Ally has blamed me for a problem, even though, like, I actually think most of the problems I ha- I am at least a party in because I'm giving direction. [laughs] And I...

185
00:30:06.440 --> 00:30:16.680
Like, not lost on me is I have to make decisions, and not all of them go well. But literally, I can't think of one where I've kinda, like, felt shitty from Ally afterwards, and then it goes the other way.

186
00:30:16.740 --> 00:30:28.920
Like, I think there's... We kinda made the unofficial deal of, like, in it together. If something fails, like, it's on both of us, but not in a pull your hair out, drive you crazy way.

187
00:30:28.930 --> 00:30:42.864
That's actually a more motivating interpretation to me 'cause then I'm like, okay, if we caused it-Then we can fix it. Mm. And then we meet on how could we have done it better, or how could we do this on a go forward?

188
00:30:42.884 --> 00:30:49.014
And when I say that, like, sometimes it's a stretch. Like, even we're in a meeting, and we're like, "I don't know, we weren't even totally involved in this," but

189
00:30:50.364 --> 00:30:56.954
we had to be involved in it in some capacity, like, given our roles in the company. So we would, like, try to kind of reverse engineer, map it, and we're like, "Okay,

190
00:30:57.944 --> 00:31:01.084
maybe this was more confusing than we originally thought."

191
00:31:01.124 --> 00:31:10.264
So it really is just, like, an interesting interpretation of it that I never quite thought about until you asked the question, where I'm like, "I don't even know. I've never... Like, it's, it's never even come up."

192
00:31:10.284 --> 00:31:13.434
[laughs] I don't... I, I can't think of a time. Yeah. Yeah.

193
00:31:13.504 --> 00:31:24.864
I think one of the things that we, like, instinctively do, and maybe this is, like, um, both of our personalities, like, maybe culture also, but I actually think in hindsight it's a framework that works pretty well.

194
00:31:25.644 --> 00:31:36.254
When something bad happens, w- the immediate thing we do is action right away. Like, the mindset is, "How do we fix this?" Like, let's action it immediately.

195
00:31:36.284 --> 00:31:41.204
And it's not so much of, like, let's point fingers and play, like, the blame game, like, whose fault is this, and, like, how did this happen?

196
00:31:41.704 --> 00:31:49.004
There is time for that, but I think we are, like, wired to be like, "How do we fix this immediately?" And let's, let's action it right away.

197
00:31:49.504 --> 00:31:54.754
And then once the dust has settled, "All right, let's go back, and, like, what were the learnings here? How do we avoid this moving forward?"

198
00:31:55.264 --> 00:32:05.254
I think that helps, like, spare, like, the emotions of, like, when something bad happens, everyone's just, like, again, they're emotional. They wanna point fingers and, like, point blame. But, like, we don't do that.

199
00:32:05.284 --> 00:32:14.624
We solve for it. We action it. And then later, when, like, emotions are better, everyone has slept on it, we can actually have, like, a thoughtful conversation around, "All right, how do we avoid that moving forward?

200
00:32:14.684 --> 00:32:28.204
What did we take from this?" So I think that kind of, like, framework certainly helps. Love it. And if people wanna learn more, order.co, follow up on LinkedIn. Right. Yep. Thank you so much. Thank you. Appreciate it.

201
00:32:28.544 --> 00:32:43.924
[audience applauds] [upbeat music]