WEBVTT

1
00:00:00.100 --> 00:00:12.260
[upbeat music] Hey, everyone. Welcome back to the Chief of Staff Network Podcast.

2
00:00:12.580 --> 00:00:20.540
I'm Scott, and today I'm sitting down with Nick Greif, who has one of those career paths that I think a lot of chiefs of staff dream about but rarely get to see up close.

3
00:00:21.380 --> 00:00:29.240
Nick started in management consulting at Deloitte, then moved into city government in LA, where he eventually became a chief of staff to an LA City Council member.

4
00:00:29.300 --> 00:00:36.220
He was managing a team of twenty-five people, a multimillion-dollar budget, and serving over two hundred and fifty thousand constituents.

5
00:00:36.260 --> 00:00:46.500
He then made the jump to the private sector as a chief of staff at Instride, an education technology company, and has since transitioned into a leadership role there, overseeing corporate partnerships and government affairs.

6
00:00:47.100 --> 00:00:55.040
What I really enjoyed about this conversation is how Nick breaks down the differences and the surprising similarities between the public and private sector chief of staff roles.

7
00:00:55.600 --> 00:01:07.600
He's got a really sharp framework for building trust across an organization, some great perspective on how political coalition-building translates directly to corporate life, and practical advice on how to set yourself up for what comes after the chief of staff role.

8
00:01:08.120 --> 00:01:16.300
Let's get into it. All right, Nick, welcome to the podcast. Great to have you here. Great to be here. I was excited for this conversation.

9
00:01:16.800 --> 00:01:24.960
We don't have a lot of current or even former government chiefs of staff on the podcast to date, so I think you might be the first, which is quite cool.

10
00:01:25.420 --> 00:01:32.920
Happy to lead the way, and hopefully that means you'll find a few more after me. I think so. You've got a lot of interesting things to share, so I'm excited to jump into it.

11
00:01:33.320 --> 00:01:41.540
Walk us through a little bit of, like, your path to becoming chief of staff for an LA City Council member. What was the scope of that role? What kinda led you to it?

12
00:01:42.000 --> 00:01:51.900
My career started in private sector, then went public, then went private again. You know, I knew in college that I always wanted to do government work and public policy work. I just found it fascinating. I still do.

13
00:01:52.400 --> 00:01:58.080
But I also knew that I didn't want to get stuck in the public sector, and sometimes that happens, you know, to people.

14
00:01:58.100 --> 00:02:08.820
They get pigeonholed in that realm, and there's a bit of a, I think, a bias on the private sector side that thinks the government public sector work, you know, doesn't necessarily translate, which I don't agree with, and we'll talk about that a little bit.

15
00:02:09.360 --> 00:02:15.880
But I started as a management consultant working for Deloitte, and then went over to the City of Los Angeles, started my career there.

16
00:02:16.240 --> 00:02:26.480
Spent about eight years with the city, a few years with Mayor Garcetti as a economic policy advisor, largely working on legislative policy and business development work, and then moved over to the city council.

17
00:02:26.840 --> 00:02:30.360
Uh, there was a new city council member in the district that I grew up with in LA.

18
00:02:30.760 --> 00:02:42.960
He needed a, a full team, so I was brought on to be policy director, so anything basically that you can think of that a city has to deal with, that was my team that was responsible for making recommendations on the policy.

19
00:02:42.980 --> 00:02:52.040
And then a few years in, my boss, the chief of staff, left the office, and I was selected to be the chief of staff for the council member for the final few years of his term. Cool.

20
00:02:52.100 --> 00:02:58.760
And in that role, you managed a pretty large team, especially for a chief of staff. I think it was, what, twenty-five people? Yeah.

21
00:02:58.940 --> 00:03:06.180
Twenty-five people, you know, a few million dollar staff budget, another few million dollars in just discretionary money that we could allocate to public concerns.

22
00:03:06.220 --> 00:03:12.480
And you're serving two hundred and fifty thousand plus constituents, so, you know, no light responsibility.

23
00:03:12.520 --> 00:03:18.160
When you took on that role, like, what kinda surprised you the most about what the chief of staff in this context meant?

24
00:03:18.700 --> 00:03:27.340
You know, I think when people think about chief of staff, and certainly for the Chiefs of Staff Association, I've been a, you know, long time reader of the great information the, the association puts out.

25
00:03:28.020 --> 00:03:35.320
The private sector chief of staff is obviously the focus, and that's, you know, where I've been most recently as the chief of staff, but public sector is where it all started.

26
00:03:35.420 --> 00:03:44.740
Military is where the chief of staff concept comes from. That's why the name chief of staff really does mean what it says in the public sector and the military. It means you're the chief of the staff. That's your job.

27
00:03:45.260 --> 00:03:58.680
And so Ike Eisenhower brought the chief of staff concept over to the political realm from the military realm for the first time when he was president, and then it trickled through politics for decades before it finally became, you know, more in vogue in the private sector.

28
00:03:59.280 --> 00:04:04.360
I think the big things that surprised me was just how much authority you have as the chief of staff. Depends on the principle.

29
00:04:04.500 --> 00:04:14.100
Like, some elected officials, they operate more as the CEO, and the chief of staff's the chief operating officer. In my case, my boss was much more hands-off, so I really was the CEO.

30
00:04:14.160 --> 00:04:23.700
He was more like the chairman of the board, setting the overall direction and raising money and, and all that. But either way, whether it's a CEO-type role or a COO-type role, you run the show.

31
00:04:23.760 --> 00:04:33.900
I mean, you're in charge usually of budgets, deciding who gets hired and fired. You're expected to operate the office because the elected official has to be externally facing. They're, they're the public face.

32
00:04:34.160 --> 00:04:39.580
You know, they can set direction, but they don't have the time to do the kinds of things that a private sector CEO spends a lot of their time on.

33
00:04:40.200 --> 00:04:51.820
You've described in our first conversation the chief of staff role as being the pinnacle of staff work, almost like being the CEO. You know, while your principal here in this context is the chairman. Can you unpack that?

34
00:04:52.400 --> 00:05:01.480
When I became chief of staff for David in the City Council of LA, the first thing I did was, you know, open up all the books. It was who's making what within the office? Do we have pay equity?

35
00:05:01.920 --> 00:05:03.900
What are performance reviews? Do we even do that?

36
00:05:04.000 --> 00:05:12.540
You know, all of those things that you think of as being, you know, pretty much what a head of an organization, you know, should be doing, as well as managing strategy for the office.

37
00:05:12.580 --> 00:05:21.460
Like, how are we going to allocate resources and time to make sure the council member does what he can to move the policy issues forward that he's focused on?

38
00:05:21.980 --> 00:05:32.000
So from a work perspective, it was, like, an amazing opportunity to pretty early on in a career get executive-level experience, and that's, I think, a big difference between the private sector and the public sector chief of staff.

39
00:05:32.320 --> 00:05:40.479
You can become a public sector chief of staff in your twenties. You even come like a public sector CEO type, like an executive, because the chief of staff is [audio glitching] in your twenties.

40
00:05:40.540 --> 00:05:46.510
You can't do that in the private sector unless you're, you know, starting something from scratch. You're not gonna do that at a big company. That takes decades.

41
00:05:46.560 --> 00:05:58.740
And so that was a huge advantage because early on in my twenties, I'm taking press calls, you know, I'm in front of big groups giving presentations, managing complex staff issues.

42
00:05:58.780 --> 00:06:20.147
You know, all of that experience was incredibly valuable and has translated almost one to one over in the private sector.It's an interesting insight that the chief of staff role in a government context is almost always very senior and yet as it's evolved in the private sector, and, and we have our own leveling framework as part of the chief of staff network, and, and there are certainly others there are levels to that role.

43
00:06:20.348 --> 00:06:36.728
Everyone has the same title, but you might be a very junior chief of staff in your early twenties right out of college, you may be a very senior chief of staff working exactly like the rest of the C-suite later on in your career, and yet it can be still very hard to kinda distinguish between the two.

44
00:06:37.128 --> 00:06:42.188
And I think that's one of the challenges in the private sector that is still, you know, yet to really be resolved.

45
00:06:42.228 --> 00:06:47.248
When you moved to your kind of private sector role, what surprised you the most about how different it was?

46
00:06:47.828 --> 00:07:09.728
Coming in with prior chief of staff experience, coming in private sector experience being a management consultant, you know, I think that helped a lot where I wasn't too shocked by, you know, what I was walking into, but I also knew the questions to ask to be really clear exactly where on that private sector chief of staff spectrum from, I guess, glorified executive assistant to executive level chief of staff, you know, I was.

47
00:07:09.767 --> 00:07:15.007
That was really important to me. I knew from a career perspective, like I was pushing for, you know, more of the executive levels.

48
00:07:15.048 --> 00:07:23.668
That meant I needed to be in board meetings, and that was a negotiating, you know, requirement. I wanted to get that visibility and that experience. That was one of the things that made the role attractive.

49
00:07:23.788 --> 00:07:41.128
Having that kind of authority in terms of internal budget and actually having a team that, you know, reported to me or having special projects as being a clear part of the role, so knowing that there were gonna be some projects, even if I wasn't running those teams, that I needed to be projects that would be, you know, in charge of.

50
00:07:41.568 --> 00:07:52.927
Those were things that I wanted to make sure were clear as an expectation because that was how I was gonna grow and then be able to make the next transition that I wanted to after the, you know, kind of typical two-year chief of staff sprint than most people do.

51
00:07:53.508 --> 00:08:00.488
Would you think about kind of the ownership of projects and team as being hallmarks of like the executive level chief of staff?

52
00:08:00.528 --> 00:08:09.548
And how does that differ from like being more of an advisory chief of staff or, or these more kind of junior interpretations of the role? Yeah, definitely. I mean, I think access is key.

53
00:08:09.948 --> 00:08:13.428
Are you in the C-staff, the executive team meetings?

54
00:08:13.848 --> 00:08:24.808
Are you encouraged or expected to participate in those in addition to presumably taking notes or running agendas and the common stuff that can apply at both the junior and senior levels of being a COS?

55
00:08:25.368 --> 00:08:31.108
Being in the board meetings I think is big, right? That's not an automatic thing that, you know, all chief of staff get to do.

56
00:08:31.208 --> 00:08:44.488
Having that access to the board and mostly just hearing the conversations that are happening so you can understand the pressures the executive suite is under, the expectations and how, you know, whether it's a public or private company, the, the investment community is thinking about it.

57
00:08:44.528 --> 00:08:51.188
I think that's just a huge value add because a lot of the chief of staff role, it's-- most people think of it as a stepping stone. I think it should be.

58
00:08:51.568 --> 00:09:03.808
Your hope is you do your two years of insanity, and then, you know, you get kind of moved into an operational role where you have a budget, a P&L and all that, and people that report to you, and it's a great career stepping stone.

59
00:09:03.848 --> 00:09:12.088
But the best way to make sure that that happens is making sure you have that access to learn the types of executive mindset pieces that are gonna be relevant for that.

60
00:09:12.668 --> 00:09:20.308
I think in terms of kinda looking for leverage points that a younger, more junior chief of staff should be looking for, it's exactly that, right?

61
00:09:20.388 --> 00:09:27.728
It's access, it's do I get certain levels of decision-making powers over X, Y, and Z projects or functions?

62
00:09:28.308 --> 00:09:37.288
I may not ever manage a team directly as a chief of staff, at least in the private sector, but how much indirect authority do I have to kinda drive initiatives forward?

63
00:09:37.828 --> 00:09:48.588
These are the things that kinda make or break the role. Hundred percent. In government, you had to build coalitions across press and business interests, community stakeholders, right, to get anything done.

64
00:09:49.148 --> 00:09:59.148
How has that compared to your experience in the private sector, where kind of theoretically the CEO just decides, as we were talking about, how does a chief of staff kinda move up the levels of responsibility?

65
00:09:59.668 --> 00:10:10.108
How does a chief of staff lean in more to getting kind of that authority? I think that aspect of being a public sector chief of staff was probably the most valuable learning that I took away from that experience.

66
00:10:10.508 --> 00:10:22.908
You're playing 4D chess in politics, and I should differentiate politics versus in administration, you're a government employee, civil servants, right? The political side at a young age, you can really do a lot.

67
00:10:22.968 --> 00:10:29.048
You're expected to do a lot. It's basically a startup. Most political offices operate a lot like startups, and I don't think everyone always realizes that.

68
00:10:29.568 --> 00:10:37.848
But when you're deciding how to get something done internally, your first step is get the principal, the elected official, to agree. That's just step one, though.

69
00:10:38.058 --> 00:10:44.458
In the private sector organization, if you get the CEO to agree, you're often done. Great. Okay. We're put a budget and authority, and we're gonna go do that thing.

70
00:10:45.048 --> 00:10:52.628
In the public sector, the CEO [chuckles] the elected official wants to do something, and now you gotta get potentially the rest of the legislature to agree.

71
00:10:52.668 --> 00:11:03.028
You need the mayor or the executive branch to agree, or you need to get influence from community groups or the press to help create that coalition that's gonna get to whatever votes you need.

72
00:11:03.048 --> 00:11:05.708
For us, it was eight out of fifteen to get something passed.

73
00:11:05.808 --> 00:11:15.848
That coalition-building was incredibly valuable learning because in a private organization, you actually do need to build those coalitions internally to often get the CEO to agree to something.

74
00:11:15.908 --> 00:11:26.268
So the same skills are relevant, but how do you create those allies? How do you strategically approach something and not come in too hot, too high up in the organization, but build the groundswell of support?

75
00:11:26.688 --> 00:11:36.488
Those are all, I think, really critical, not just chief of staff experiences, but just if you wanna work effectively within a large organization. Large organizations are highly political. The larger, the more political.

76
00:11:36.528 --> 00:11:39.648
And so those are skills I absolutely took into the role.

77
00:11:40.028 --> 00:11:55.568
Being able to manage the executive team for the CEO and the folks under them and be able to manage those politics and provide information that was valuable to my boss, the CEO, without stepping on toes, all of that was really helped by the time I spent in politics.

78
00:11:56.088 --> 00:12:18.647
Were there any memorable kind of policies or projects that you worked on in your time in the LA office that kinda stuck out as huge wins that you've kinda carried forward in your career to the next stages as chief of staff and leadership?The most relevant, because I currently work for an education technology company, when I was in politics in LA, one of the big things we worked on was creating what are called child savings accounts.

79
00:12:18.868 --> 00:12:19.988
Pretty simple concept.

80
00:12:20.108 --> 00:12:37.008
Someone starts at first grade in LAUSD, biggest school district in the entire nation, and they're gonna get a $50 savings vehicle invested in by the government to help them and their families really understand how to save for college, and then understand the expectations that these kids are gonna go to college.

81
00:12:37.428 --> 00:12:41.688
And that was a huge undertaking. I mean, we're talking about 50,000 kids getting a bank account every single year.

82
00:12:41.788 --> 00:12:49.187
You're managing three different levels of government, private banking, you know, that you have to do an RFP for to get them in, getting budget authority to do that.

83
00:12:49.248 --> 00:13:08.508
Like, all of that was incredibly complex, but the upside of that long-term thinking and how those kids are gonna, you know, be much more likely to make it to college and have that opportunity was a direct tie-in to the work I do now, which is at InStride, a company that works to get education benefits up front for employees at major employers.

84
00:13:08.728 --> 00:13:17.268
So Amazon, Taco Bell, Medtronic are all partners of ours. Most organizations have a reimbursement approach, right? You go get the education, you get paid back.

85
00:13:17.728 --> 00:13:30.048
That's fine if you already have money in your bank account, but most employees don't have thousands of dollars that they can spend on tuition and wait six months to get reimbursed, or if they're doing a degree, really you're waiting four, five, six years, and so there's this huge access barrier.

86
00:13:30.148 --> 00:13:38.588
So having that same experience and being able to create access at the K to 12 level translated a lot in my work now to create access to the adult worker. Yeah.

87
00:13:38.628 --> 00:13:47.308
And the types of constituents, advocates that you have to get on board for that, has that drawn any parallels to your private experience now?

88
00:13:47.848 --> 00:14:00.108
Once I moved on from being a chief of staff at the private sector at the company I work for, I now work on our corporate partnerships side as well as overseeing government affairs for the company, and that partnerships piece is all about coalition building.

89
00:14:00.208 --> 00:14:10.088
You know, when you're on the sales side, when you're working with an organization, you're doing a fairly similar thing to trying to get a new policy, you know, accomplished in the public sector.

90
00:14:10.408 --> 00:14:19.148
You've got to build, you know, in sales they call it multithreading, right? You've got to build relationships with multiple people at the organization that you're hoping is gonna, you know, use your company's services.

91
00:14:19.528 --> 00:14:25.088
You need to show them and give each one of them a different angle that's why it's beneficial for them and the company.

92
00:14:25.148 --> 00:14:29.808
And so just having all that experience, you know, on the public sector side, a lot of that really does translate.

93
00:14:30.408 --> 00:14:39.388
Let's talk a little bit about the relationship between you and your principal and some of the differences or similarities that exist between kind of private and public sector.

94
00:14:39.828 --> 00:14:45.508
Obviously, like, you need to be a trusted thought partner to your CEO, right, to a councilman or woman.

95
00:14:45.928 --> 00:14:54.928
What does that mean in terms of being someone that, like, your executive can trust but also the rest of the exec team or organization can trust as well? Is there a through line there?

96
00:14:55.468 --> 00:15:00.837
That's the area that's probably most similar between public sector chief of staff and private sector chief of staff, if not almost identical.

97
00:15:01.368 --> 00:15:12.848
The relationship between you and the boss, right, CEO, elected official, whoever, is so tight. You're their second brain. You're there to help execute. You're there to make their vision happen.

98
00:15:12.908 --> 00:15:50.468
To do that, you have to really create trusted, deep relationships throughout the organization so that you can provide good advice and feedback both ways, and that, I think, was the biggest piece when I was applying for the job to be chief of staff at InStride that I really explained to the rest of the executive team that I was interviewing with, was, like, I viewed my role there, just like in the public sector side, as I'm trying to create a font of information for the CEO so they can make good decisions, but also help translate what the CEO wants to other people so that they are more likely to go in the right direction the first time and not have to backtrack and, and do something over again.

99
00:15:50.488 --> 00:15:55.548
And so then being that two-way safe funnel of information I think is really, really critical.

100
00:15:55.648 --> 00:16:18.707
I took a pretty interesting approach to that, that definitely drew on my time in the public sector, which was, A, I obviously met with the full executive team, but through my first year, I committed to meet with every VP and every director in the company one-on-one, and I talked to them about what, how I viewed the role, really trying to make sure we had this, this shared language and agreement as to what chief of staff meant to me and what I was hoping it would be valuable to them.

101
00:16:19.128 --> 00:16:40.268
And I explained that exact thing, that I'm here to, like, help them be able to understand what the CEO and the executive team wants without having to, like, take that risk of asking, which people are often afraid to do, but also to be able to safely, and no names, take issues that are happening in the organization and make sure that those can be disseminated either to the right person in the executive suite or the CEO, and do that in a delicate way.

102
00:16:40.578 --> 00:16:48.938
And that can be really challenging. And so I told every single staff member I met with that I would take a press approach to it, off the record, on the record, or on background.

103
00:16:48.988 --> 00:16:57.078
And so for those that aren't familiar with, like, how the press works, you assume everything's on the record when you talk to a member of the press unless you clarify it's off the record or it's on background.

104
00:16:57.088 --> 00:17:06.228
And I basically just flipped that on its head, and I said to everybody I met with, "Everything we talk about is off the record unless we explicitly agree it's on the record or on background.

105
00:17:06.268 --> 00:17:11.108
And on background means I can share it, but no names. On the record means you're happy if I attach your name to it."

106
00:17:11.498 --> 00:17:24.908
And so that meant that I could collect a lot of off the record confidential information about what was going on with the organization and still be able to, like, filter that and make those issues known without anyone ever knowing where they came from.

107
00:17:25.258 --> 00:17:33.528
And my boss, the CEO, also knew that that was my approach, and so, you know, I wasn't gonna divulge people's names, because once you do that once, it's over. You can't get that trust back.

108
00:17:33.688 --> 00:17:46.708
But that meant that I was able to really connect things that were happening throughout the organization and make sure that information, which is the toughest thing for CEOs sometimes to get, accurate information from lower down in the organization, but I was able to serve that role for him.

109
00:17:46.768 --> 00:17:52.548
It's a really interesting framework, not one that I've heard before, I think, anywhere, at least not in this context.

110
00:17:53.048 --> 00:18:01.908
When you're privy to that kind of information, obviously, you know, you've got a lot to lose, and the other side has lots to lose in terms of damaging someone's standing with you if shared.

111
00:18:02.388 --> 00:18:03.468
How do you go about handling that?

112
00:18:03.568 --> 00:18:16.248
Like, are there things that you end up just keeping to yourself and trying to back-channel decisions or other conversations to, you know, kind of make sure that the company landed the right way? Exactly right.

113
00:18:16.288 --> 00:18:29.417
I mean, you use your influence and your ability to-Touch almost all parts of the organization to provide that kind of back-channel nudge. Sometimes you just elevate stuff as if you just noticed it on your own, right?

114
00:18:29.508 --> 00:18:38.837
And so it's like no one has to know where it came from if the person who, you know, fed it to you doesn't want their name attached to it. That's okay. That's part of the role of chief of staff in my view.

115
00:18:39.338 --> 00:18:47.578
And so I think that created really good trust throughout the organization because also people pretty quickly see that you mean what you say, because nothing leaks that's not supposed to leak.

116
00:18:48.118 --> 00:18:56.238
I think working in politics definitely helped with that because leaking to the press is, like, a big part of the political world. And so, you know, I'd already built that reputation that that wasn't something I did.

117
00:18:56.718 --> 00:19:03.598
But I think you learn how quickly that that gets around. Like, in politics, you knew the people that you could trust and you couldn't.

118
00:19:04.098 --> 00:19:08.638
People gossip about that constantly, and so I think that happens in private organizations as well.

119
00:19:08.978 --> 00:19:15.518
We all can think of the people in our organization like, "Yeah, I trust that person with my private thoughts about what's going well, what's not," and you also know the person you wouldn't do that with.

120
00:19:16.078 --> 00:19:24.858
It was really critical to me that as chief of staff, I quickly cemented that I was the person you could trust because I would not automatically trust a chief of staff. I know they've got a direct line to the CEO.

121
00:19:24.937 --> 00:19:28.818
That's scary. You're the eyes and ears, yeah. How could I diffuse that up front?

122
00:19:28.898 --> 00:19:42.718
Well, I diffused it by being really explicit about how I was gonna approach our conversations and the information that was shared, so they knew that at least they understood what I was saying was how I was gonna handle it, and they obviously had to wait some time to decide if they could really trust that or not.

123
00:19:42.758 --> 00:19:49.458
But that pretty quickly, you know, went the way it needed to. And information is obviously power, right? So with that power comes responsibilities.

124
00:19:49.958 --> 00:19:59.978
You mentioned we're talking about kind of the differences between private sector and public sector at the beginning of the episode. The public sector version of chief of staff runs the staff, right?

125
00:20:00.038 --> 00:20:07.198
You've-- actually you're leading with authority. You've got management responsibilities, hiring/firing decisions, et cetera, budget responsibility.

126
00:20:07.708 --> 00:20:14.858
That is very often not the case in most private sector chief of staff roles. The phrase that's very often used is leading without authority.

127
00:20:15.398 --> 00:20:22.138
How have those two things collided in your experience, kind of making that shift from public to private, if at all? Yeah.

128
00:20:22.218 --> 00:20:32.278
In part, public sector, yeah, you lead with authority in your organization, but outside of it, you lead with only minimal authority because even if your boss [audio glitching] you gotta convince a whole bunch of other people to agree.

129
00:20:32.298 --> 00:20:34.798
And so I think that translates, and I talked about that a little bit earlier.

130
00:20:35.278 --> 00:20:45.778
But the other thing that I recommend everyone do, no matter where you are in an organization at some point, is be on the board of a nonprofit or, you know, a volunteer group. Run a volunteer organization.

131
00:20:45.818 --> 00:20:57.057
When you can get people to work at something that they're not getting paid for and that no one really can force them to do it, and you can create that motivation, like, that's gonna take you really far in any role.

132
00:20:57.138 --> 00:21:18.618
Because frankly, you can always, if you're in charge of somebody, force them to do a thing because you can say, "I'll fire you if you don't," but people are gonna work way harder, way smarter, and way longer for you if they wanna do that, whether you pay them or not, and that's hard experience to earn, and I think the best way to earn it is by being in a role that actually doesn't have, you know, kind of a I pay for your salary connection to it.

133
00:21:19.128 --> 00:21:28.218
Does that authority also, you know, government chief of staff role, does that come on paper? But there's a difference between having it on paper versus having it in practice.

134
00:21:28.918 --> 00:21:40.138
In a private sector role, you know, I think a lot of that authority is earned over time. It's not necessarily explicitly directed on a job description. Has that been the case for you in your experience? Yeah.

135
00:21:40.198 --> 00:21:47.258
On the government side, it usually is on paper. Within a political office, there aren't standard job descriptions. Like, every office can do their own thing.

136
00:21:47.578 --> 00:21:57.138
But generally, it's accepted and understood that the chief of staff is the person who's gonna be in charge and is basically, you know, running the show with the authority and direction of the elected official.

137
00:21:57.638 --> 00:22:03.558
On the private side, you know, something you mentioned earlier that I wanted to, to touch on, the information is so critical.

138
00:22:03.978 --> 00:22:13.538
Being able to be a source of information to the CEO, being able to collect information from across the organization is one of the main ways that as a chief of staff you can provide value, right?

139
00:22:13.758 --> 00:22:23.258
You're hired to manage the board agendas or executive team, you know, agendas and, and brief the boss and make sure that they, you know, are ready for whatever their public speaking events or their internal meetings.

140
00:22:23.278 --> 00:22:26.398
Whatever it is that's part of your chief of staff formal responsibilities.

141
00:22:26.438 --> 00:22:46.898
But in my opinion, the best way to show huge value as a chief of staff and then can set yourself up for whatever your next step is, is by understanding as much across the organization, having access to information across the organization, because you are one of the few people, if not the only person, who touches the operations group, the tech group, the finance group, sales.

142
00:22:47.078 --> 00:22:52.978
Very few other people can actually see where there might be silos or where there could be opportunities that aren't being addressed.

143
00:22:53.458 --> 00:23:09.958
To the extent that you can get that information and then in a productive way share or suggest kind of ideas for projects, ideas for projects sometimes you might be the one who gets to lead or could suggest that you lead, that's where you're gonna, like, really take a big step up and drive value for the company and, of course, for your own career.

144
00:23:10.518 --> 00:23:21.498
It's a great point, and we've heard other examples of this on the podcast where, you know, when those opportunities present themselves, it's on you, right, to put your hand up and say, "Hey, this is something that I wanna lead.

145
00:23:21.898 --> 00:23:30.078
This is something that I think I can own." And that is very often the most natural transition out of chief of staff roles.

146
00:23:30.618 --> 00:23:36.038
Can you talk a little bit about kinda your experience chief of staff at InStride and kind of moving out of that position?

147
00:23:36.718 --> 00:23:46.778
I'm a big believer in the mantra of, like, make yourself obsolete in your role and find the person who can replace you. I think a lot of people want to show that they're indispensable in a role.

148
00:23:47.178 --> 00:23:51.258
But if you're indispensable, no one can move you. They can't promote you because you're indispensable in the role you're in.

149
00:23:51.718 --> 00:24:12.378
So when I was policy director in government, I had worked really hard to make sure my number two, my senior manager for public policy, was ready to become policy director, and that that was clear the, to the elected official, because that way he could feel comfortable when the role opened, making me chief of staff, knowing there was gonna be a really strong policy director that would be a really clean transition.

150
00:24:12.438 --> 00:24:15.678
So in the private sector, I think, you know, the same thing applies, right?

151
00:24:15.738 --> 00:24:29.438
If you can find whoever the next chief of staff's gonna be, that definitely, you know, is a great thing to have because sometimes, you know, yeah, you sign up for the two-year, you know, sort of tour of duty, but that can stretch to three or four because obviously a CEO doesn't really have an incentive to move you.

152
00:24:30.038 --> 00:24:39.066
And to the extent that you can create a role for yourself and say, "Hey, there's this big project. Hmm, we're actually gonna have to hire a team for this," and then go run that-That's a really effective way to go.

153
00:24:39.146 --> 00:24:45.926
So, like, my predecessor as chief of staff at Instripe did exactly that. She's phenomenal, former, um, McKinsey consultant.

154
00:24:46.446 --> 00:24:59.986
But over time, we realized we had just more and more complex solutions that we needed to provide to our corporate partners, and so she ran the project to scope that, and then ended up running the solutions team and, and overseeing solutions and product for the company.

155
00:25:00.356 --> 00:25:03.446
And so that's, like, the exact kind of route you wanna create for yourself.

156
00:25:03.486 --> 00:25:20.546
The more that we talk about kind of the dynamics of both roles, private and public, it also seems, and you kind of alluded to this at the beginning, government offices and startups are actually not that different from each other in, in lots of ways, certainly not in the way that I think most private sector employees like to think.

157
00:25:20.886 --> 00:25:33.306
And I think one clear example of that is, like, government office have term limits. They have election cycles. Startups have funding runways and board pressures and imminent bankruptcy at any given time sometimes.

158
00:25:33.946 --> 00:25:42.405
How does operating under, like, an external clock shape how you work? Is the mental model similar on both sides of the table? Yeah, I think it definitely can be.

159
00:25:42.466 --> 00:25:48.846
I mean, knowing that you've got an election cycle that you're beholden to on the public sector side a hundred percent makes everything a clock, right?

160
00:25:48.976 --> 00:25:56.326
Post-election, you're like, "Okay," if it's a four-year election cycle, which is what we had, post-election, you're like, "Cool, I've got two years to go do the stuff I really wanna do.

161
00:25:56.746 --> 00:26:04.716
I've got, you know, the authority, the energy, and I know that people are gonna forget the stuff they don't like that I did during these two years by the time it comes down to it two years later."

162
00:26:04.766 --> 00:26:13.086
Once you get past that two years, well, now it's just like being a public company. You gotta constantly be just driving towards what's the next quarterly financial release do I have to hear?

163
00:26:13.196 --> 00:26:19.546
'Cause the stock price is basically the same as political sentiment and whether or not you're gonna have a good chance of winning a reelection or not.

164
00:26:19.576 --> 00:26:23.886
And so you start really thinking about, well, how does this, every action we take, look externally?

165
00:26:24.426 --> 00:26:32.546
And the same thing happens in private companies, especially as you get closer to a funding round or you get closer to a sale. It's all about, well, how do we package this up?

166
00:26:32.866 --> 00:26:40.806
The package is the value of the company and what you're, you know, what you're kinda selling, which is your enterprise value that you're raising at or trying to get an exit at.

167
00:26:40.906 --> 00:26:51.766
I think the same thing applies in government, for sure. The other thing that applies is, you know, what are the stakes, right? What is the impact that we're creating as a company or as a government institution?

168
00:26:52.386 --> 00:26:59.786
In your case, in government, you're passing policy affecting sometimes millions of people, right? And the example you shared earlier is a great one.

169
00:27:00.426 --> 00:27:08.336
How do you think about impact kinda differently now that you're in the private sector? Does it hit the same way, or are you kind of constantly looking for- [laughs]

170
00:27:08.386 --> 00:27:16.006
Yeah, you know, it is funny 'cause, like, obviously a lot of times you move from public to private sector because you grow up, you wanna have a family, you need more money to do that.

171
00:27:16.106 --> 00:27:20.186
Like, we all know, I think, that private pays better than public, often two X or three X better.

172
00:27:20.666 --> 00:27:30.906
But I hesitate to use the words like addiction, but the energy in the public sector on the political side is unmatched, I think, in almost anything that exists. You want to be at work every day.

173
00:27:31.066 --> 00:27:41.406
You're doing events every single evening because your work day goes from, oh, my regular government job, and then moves into thinking about the next campaign or the next, you know, sort of more political part of the role.

174
00:27:41.946 --> 00:27:42.846
You definitely chase that.

175
00:27:43.266 --> 00:27:56.206
I had it particularly bad 'cause when I first joined government, one of the first things I worked on in the mayor's office was raising the minimum wage in LA City, which we did, which basically moved up and immediately gave money to a half million people.

176
00:27:56.246 --> 00:28:01.946
Like, how do you go from helping a half million people get more money, then ended up becoming the state, the state followed the city.

177
00:28:02.026 --> 00:28:06.186
So you're like, the whole state of California basically, like, kinda followed what we did at the city of LA.

178
00:28:06.776 --> 00:28:12.866
That's a lot of impact to have early, and then everything you do after that, you know, kind of pales a little bit in comparison. So that's challenging.

179
00:28:12.926 --> 00:28:19.766
You have to really love the work itself, love the challenge of what you're doing, and try to find something that scratches that itch.

180
00:28:20.226 --> 00:28:27.926
For me, it has always meant that I needed to work somewhere that had impact that I thought was interesting from a public policy point of view. That's just a through line for me personally.

181
00:28:28.346 --> 00:28:37.766
So for InStride, we're helping provide education access or equitable access to education across employees in America. Like, that's easy for me to get up in the morning and be excited to go do.

182
00:28:38.246 --> 00:28:52.706
My company prior to this was a autonomous vehicle technology company, so all my work on transportation policy in government, you know, there's a lot of benefits of frankly taking not very safe human drivers, you know, a little bit less in charge of deciding when to brake the car.

183
00:28:53.206 --> 00:28:55.806
And so, you know, there's a big public policy tie-in as well.

184
00:28:55.846 --> 00:29:08.226
And so I think that helps because the impact on the private sector, it's like you maybe aren't gonna impact the same amount of people in the same way, but you make a small change, and it could be something that everybody in the US or even the world uses.

185
00:29:08.266 --> 00:29:20.146
And so that's, you know, you can have huge impact there too. I'm gonna hit you with some rapid-fire questions. Hardest decision you had to make as a chief of staff? You can pick private or public. Ooh, wow.

186
00:29:20.686 --> 00:29:41.506
Pulling the plug on policy initiatives that we were trying to get done, realizing that it just-- we were throwing good money after bad, or it was a good idea, but it was gonna not sit well with either special interests like labor or business or with our constituents, even if I personally believed it was the right thing to do for the public at large.

187
00:29:41.846 --> 00:29:49.966
That was really hard. Hard to relate, I think, unless you're in a public role. What's one thing you wish someone had told you before you took your first chief of staff role?

188
00:29:50.026 --> 00:30:01.066
I think the relationship with the principal, whether it's the elected official for me or, or the CEO, just not knowing ahead of time how personal and connected that relationship was gonna be.

189
00:30:01.136 --> 00:30:04.406
'Cause, like, you're really not just being hired to do a job.

190
00:30:04.826 --> 00:30:15.746
You are gonna be on the phone with this person or in the room with this person every single day, often multiple hours in a day, and there is just a deeper connection that is beyond a usual work relationship that develops there.

191
00:30:16.146 --> 00:30:22.646
And so really thinking hard about, like, do I want to spend all this time with this person? Like, I think is a key piece of it.

192
00:30:22.726 --> 00:30:32.566
For me, the answer was yes on both occasions, and, and it really worked out great for both of the principals I worked for. But I don't know that I had fully processed how much you're gonna be connected into their lives.

193
00:30:33.306 --> 00:30:41.474
What do you think you know now or that you learned about leadership that you didn't know when you started?The power of information. We talked about that a, a little bit.

194
00:30:41.614 --> 00:30:55.854
I think I knew information was important, but knowledge really is power, and deciding and the judgment for how you use it effectively, preferably more as a scalpel than as a sledgehammer, that was a big continued learning lesson for me.

195
00:30:56.554 --> 00:31:05.354
For someone that's listening that wants to move from a more junior to a more executive chief of staff role, what's your advice? Is it amassing knowledge?

196
00:31:06.034 --> 00:31:14.054
Yeah, I think it's amassing knowledge, working throughout the organization to build those relationships and connections with people because that's where you get knowledge and you get information.

197
00:31:14.494 --> 00:31:25.924
But being proactive about thinking through what beyond my actual scope of work can I do to create value, and then, you know, coming up with ways to propose that and, and hopefully get some of that approved.

198
00:31:26.034 --> 00:31:32.294
I think that's how you move yourself forward. Is there anything else that we didn't cover that you think chiefs of staff need to hear?

199
00:31:32.374 --> 00:31:41.374
I think the biggest thing that chiefs of staff should be thinking about when they're in these roles or they're trying to get these roles is knowing that it's a time-limited position.

200
00:31:41.974 --> 00:31:47.754
No one expects you to do this for the long term. It's not sustainable, frankly, [laughs] for most people to do it for the long term.

201
00:31:48.094 --> 00:32:05.074
And so I think you really wanna think of it as an investment in yourself, in knowing you're probably gonna work silly hours, that you're gonna get phone calls at ten PM, six in the morning, like, that that's just the role you play, and that you might have to go on travel trips that you don't wanna go on 'cause your principal's going there.

202
00:32:05.094 --> 00:32:22.724
But that you know what you wanna get out of it, and for me, a lot of that was the access to the board room, to the executive conversations, because so much of being in management is having seen something before and knowing how it went, and being able to then extrapolate or interpolate that for the decision that's in front of you.

203
00:32:23.354 --> 00:32:32.974
Management is, like, ninety-nine percent decision-making and, you know, maybe also, like, ninety-nine percent encouraging and motivating people, so maybe it's fifty-fifty. Those are, like, the big two things you do.

204
00:32:33.014 --> 00:32:43.674
You don't do actual line item work that much anymore once you're in, you know, higher level management roles. So that experience is what makes you a really effective manager, leader, executive.

205
00:32:43.894 --> 00:32:51.134
So the more that you can build that into what you're trying to get out of the chief of staff role, the better off you'll be. I love it. Nick, thanks so much for the insights today.

206
00:32:51.234 --> 00:32:59.774
Thank you for the time and for you sharing your story. Thank you for having me, and I really appreciate everything the Chief of Staff Network puts together and sends out. It's always been a resource for me.

207
00:33:00.114 --> 00:33:08.694
I'm looking forward to the next one that comes across my desk. Thanks again to Nick for joining us. I love that framing of the chief of staff role as an investment in yourself.

208
00:33:09.034 --> 00:33:16.294
Knowing for many of us it's a time-limited position, the hours are going to be intense, but obviously being intentional about what you're building towards is really helpful.

209
00:33:16.894 --> 00:33:27.074
Also, his approach to information management, using that on the record and off the record, on background framework to build trust, that's one of the most actionable, concrete things we've heard on this show.

210
00:33:27.674 --> 00:33:38.254
If you enjoyed this episode, make sure you're subscribed so you don't miss future conversations, and if you're not already a member of the Chief of Staff Network, head over to our website to learn more about the community and everything we've got going on this year.

211
00:33:38.814 --> 00:33:39.594
We'll see you next time.

212
00:33:43.894 --> 00:34:01.514
[upbeat music]