WEBVTT 1 00:00:00.100 --> 00:00:12.720 [upbeat music] Hey, friend. It's David Nebinsky, the community lead at the Chief of Staff Network. 2 00:00:13.260 --> 00:00:23.700 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 upcoming events and programs at chiefofstaff.network. 3 00:00:24.200 --> 00:00:32.280 You can also subscribe to our newsletter there to learn more as well. This episode of the Chief of Staff Podcast is with Kyle Hege, the chief of staff at Morning Brew. 4 00:00:32.920 --> 00:00:45.860 This episode was recorded live at our July New York City Brain Trust, a six-hour intentional gathering to help chiefs of staff level up in their roles and their careers through peer-to-peer problem-solving and connection. 5 00:00:45.900 --> 00:01:02.720 In this episode, you'll learn a- about how to be an effective chief of staff in your first ninety days, developing influence without authority, meeting cadence with your principal, why the chief of staff role doesn't have to be a bridge to something else, and lots of other juicy chief of staff hot topics. 6 00:01:03.500 --> 00:01:11.380 Uh, would love to hear what you think. Send us an email at hi@chiefofstaff.network. So excited for you to level up as a chief of staff. Here we go with Kyle. 7 00:01:12.040 --> 00:01:20.720 Welcome to live podcast recording at the Chief of Staff NYC Brain Trust. Let's give it up for Kyle. [clapping] There we go. 8 00:01:20.780 --> 00:01:32.640 [chuckles] So, uh, the topic of this episode is around the first ninety days as a chief of staff role. Um, Kyle, how'd you get your chief of staff role? Uh, well first, thanks for having me, David- Yeah... 9 00:01:32.660 --> 00:01:42.560 and nice to see everyone. And also, this is throwing me back. So I started a podcast myself like s- what is it, like, six years ago? Seven years ago? Yeah. 10 00:01:42.960 --> 00:01:50.300 When I was, um, uh, in, uh, my master's program at Marquette University. So if there's any Midwest people here, shout out to you all. [laughs] And we'd rent... 11 00:01:50.410 --> 00:01:57.360 Because we had no money, we'd rent these from, like, the Marquette library. Whoa. And I remember my first ever podcast, I-- we actually had something like this, and I put it right... 12 00:01:57.780 --> 00:02:08.140 We were interviewing someone next to a window. [laughs] And cars were, like, zipping by, and ambulances were going by, and the audio was so terrible. Um, so this is, this is a nice throwback. But- Cool... 13 00:02:08.240 --> 00:02:16.000 uh, I love podcasts. Um, what was your- I'm sure this is good audio. [laughs] Yeah, it'll be fantastic audio. Uh, what was your first question? I totally don't know. [laughs] Already going on tangents here. 14 00:02:16.140 --> 00:02:26.660 [laughs] Yeah. Uh, first question was, how did you get your chief of staff role? You weren't- Okay, yeah. Um, you had a prior role at Morning Brew, and then you became the chief of staff. Yeah. How did that happen? 15 00:02:26.980 --> 00:02:38.810 So I'd been at Morning Brew for three and a half years, and started as a community manager, actually, at Morning Brew, where we were, uh, launching a new business unit focused on building one to eight-week mini MBA courses. 16 00:02:39.460 --> 00:02:47.480 So basically, it was, uh, one of our first paid products directly to the consumer. Uh, it was me and three other people building that business unit. It was super fun. 17 00:02:47.640 --> 00:02:56.920 I, I don't know how I met David, but maybe through that community- Audley Specific... community manager space. Yeah. Audley Specific, maybe we can talk about that. Um, and then we scaled that business. 18 00:02:57.000 --> 00:03:08.040 We had about thirteen people on the team. We put four thousand professionals, uh, through these programs, both direct to consumer, but we also did some B2B deals and, and came in and trained people at companies. 19 00:03:08.680 --> 00:03:16.800 And in November of twenty twenty-three, we shut that business unit down, so we can also talk about that if that's interesting. RIP to Morning Brew Learning. 20 00:03:16.880 --> 00:03:29.360 Uh, and at that point, Austin, our CEO, had asked me, like, "We really like you. We want you to stay on. What's a good role for you?" And so I, one, had to really evaluate, like, do I actually wanna stay at Morning Brew? 21 00:03:29.500 --> 00:03:37.890 Because I've had a lot of friends who, their teams get laid off, they stay at the company, but there wasn't really a role for them. And then, like, six months later, they're like, "Why did I do this?" 22 00:03:37.980 --> 00:03:47.220 Like, it actually wasn't a good fit. So really thought about, you know, what talents I have, what were the business problems that I saw at Morning Brew, and what was the Venn diagram of those where I could be effective. 23 00:03:47.740 --> 00:03:59.140 And really was drawn to the chief of staff role mainly for the breadth of it, and we had just brought on a new COO who was fantastic and had been in media for a couple decades, and thought I could learn a ton from him. 24 00:03:59.360 --> 00:04:12.860 So we settled on chief of staff to Robert, our COO, who's now also our CRO, and have been in that role since December, January. Okay. Woo. That, that, that's, that's good. That's good. [laughs] Um, 25 00:04:15.120 --> 00:04:26.420 so you had that conversation with Austin. Yeah. And then did you have a conversation with Robert? Or, like, how did that kind of piece happen? Yeah. We, they, we didn't just throw me at him- [laughs]... 26 00:04:26.430 --> 00:04:32.800 without having spoke to the guy. Yeah, I had a lot of conversations with Robert. He was actually consulting with Morning Brew for about eight months. 27 00:04:32.870 --> 00:04:41.830 We've kind of transitioned to when we can bring on consultants and kind of test them, make sure that it's a fit for us or... and it would be a fit for them. 28 00:04:41.860 --> 00:04:48.100 And he was doing amazing work, so he had a lot of already great reputation at Morning Brew. I talked to him, like, four or five times. 29 00:04:48.200 --> 00:04:54.460 I remember, like, getting on a whiteboard and drawing out, like, what his priorities were, where I could fit in, like, making sure this is a good fit. 30 00:04:54.980 --> 00:05:06.770 And then about four or five months into the role, he also came to me and he was like, "Just letting you know, I, like, back channeled, like, a ton of your Morning Brew employees, like, asking about you, and they all said good things, so, like, good for you," 'cause... 31 00:05:06.810 --> 00:05:10.010 So he did his due diligence as well. I wasn't aware of that, but- [laughs]... 32 00:05:10.010 --> 00:05:23.360 um, yeah, had a lot of conversations with him and, um, you know, loved the company, loved the role, but more importantly, with chief of staff, you're working so closely with an executive, I think it's really important to, like, work for someone who you ultimately want to become in some form or fashion. 33 00:05:23.810 --> 00:05:33.064 And so it's nice to get to know Robert both professionally and personally, and, and I really like the guy. He was really brilliant, so it's been great working for him.When you, um, 34 00:05:34.004 --> 00:05:44.454 like, decided to work together, was there, like, initial scope or initial, uh, projects that say, like, "Okay, in the first 90 days, uh, here's what we want you to work on?" 35 00:05:44.504 --> 00:05:48.094 Or, like, how did you kind of decide what, what to, like, work on? 36 00:05:48.484 --> 00:05:54.734 Yeah, it's a great question, and I'll maybe just reframe it as, like, you know, how to be effective in those first 90 days and figure out what to work on. 37 00:05:55.344 --> 00:06:02.684 And for me, this is not just advice for chief of staff, but it's advice for any employee is you're not working in a vacuum. 38 00:06:02.824 --> 00:06:10.264 Like, ultimately, the work you are doing is laddering up to the company's, you know, strategic mission, their, their vision statement. 39 00:06:10.784 --> 00:06:22.544 So I think it's really important that you understand how everything you're doing ladders up to a really important rock or KPI or metric at the company. And I would never create a JD just for me, like, based on... 40 00:06:22.564 --> 00:06:24.184 I heard vibes earlier. Based on vibes. 41 00:06:24.214 --> 00:06:36.523 [laughs] Like, it, it, it, it should if you wanna have career growth and career, like, uh, uh, protection, it's really important you can articulate why you're valuable to the company and how you're moving important things forward. 42 00:06:36.564 --> 00:06:47.264 So I kind of flipped the question on him. Mm. Like, "You're coming in as a COO, new. Like, you're gonna have probably a different set of priorities than our exist- or previous COO. What's important to you?" Mm. 43 00:06:47.354 --> 00:06:54.024 And so we outlined a few things. One was our event strategy. I'd been doing a ton of virtual events in my previous role, so that was a easy fill-in. 44 00:06:54.224 --> 00:06:59.544 One was taking our data and analytics team and really supercharging them. We have a really fantastic team. 45 00:06:59.584 --> 00:07:10.304 We wanna create more net new research at Morning Brew that we can sell to sponsors and inform our sellers, so that was a, a key piece. And then we had just really solidified our professional sales team. 46 00:07:10.324 --> 00:07:22.424 So we have seven B2B franchises: HR Brew, CFO Brew, IT Brew, et cetera. We have a dynamic sales team around them, and he really wanted me helping to oversee that team, providing them the resources they need. 47 00:07:22.984 --> 00:07:36.464 Um, and so it, it's, like, what I'm hearing is that sounds like that conversation was that you went to him, um, and said, let you know, "What, what's important to you?" and stuff. Yeah. It sounds like it was really easy. 48 00:07:36.584 --> 00:07:43.924 Was it easy? Um, I think it's easy if you aren't dead set on having the job. 49 00:07:44.284 --> 00:07:51.684 And, you know, I was in a lucky position where I was transitioning from Morning Brew, so I knew the company very well, but I've never been a chief of staff before. 50 00:07:51.744 --> 00:07:57.784 Like, if you asked me maybe eight months ago what a chief of staff was, I would've given the world's worst answer. It would've been terrible. 51 00:07:57.794 --> 00:08:08.254 [laughs] So I didn't even really know what the role was supposed to be until I started this process. And what I told Morning Brew, I was very explicit, is like, "I'm just looking for fit here. 52 00:08:08.844 --> 00:08:22.484 And if we get to the end of this process and we decide, or I decide, or you decide, like, this isn't the right move, you know, I'd rather go work somewhere else where I can be in the right environment, there's a good fit for me, 'cause I'm only gonna be more impactful and grow my career, uh, somewhere else if that's the case." 53 00:08:23.044 --> 00:08:28.944 And so I think if you have an open mind that it might not be the right role for you, you're able to be a little more transparent. 54 00:08:29.084 --> 00:08:33.694 You're able to be a little more confident in telling people what you want and what you expect out of the role. 55 00:08:33.694 --> 00:08:42.944 And I was able to do that, and I think both sides were willing to walk away from it if it wasn't a good fit, which in some ways actually makes the process a lot easier. Mm. Um, so it was de-risked from that perspective. 56 00:08:43.144 --> 00:08:55.584 Uh, so I, I think it was pretty easy, and that probably has a lot to do with Robert's personality as well. Cool. Cool, cool, cool. Um, and did you, uh, set up any kind of structure? 57 00:08:56.304 --> 00:09:02.124 Did you have any, like, "All right, let's check it, check in on these in three weeks, two months," et cetera? 58 00:09:02.204 --> 00:09:12.024 Like, what was that kind of like getting up to speed and, um, kind of making sure you guys are, like, firing on all cylinders together in the beginning? Yeah. So I can definitely talk about cadence. 59 00:09:12.084 --> 00:09:18.284 So it's funny you ask that. Before, as I mentioned, I was building these courses, and one of our courses was New Manager Boot Camp. Oh, sick. 60 00:09:18.344 --> 00:09:28.824 And, and before at Morning Brew, I also had direct reports, so I was running my own team. And I was so big, and I still am, on, like, process and structure. It just creates clarity. It creates expectations. 61 00:09:28.864 --> 00:09:33.864 It creates acount-accountability, and I think it helps the whole team grow. So that's definitely something I wanted. 62 00:09:33.944 --> 00:09:42.534 I think a lot of chief of staffs oftentimes can feel like they don't really know what they're supposed to be doing. There's so many things to juggle. How do you prioritize effectively? 63 00:09:42.564 --> 00:09:54.464 So the cadence me and Robert set up is, I don't know if it's rare, but it's worked very effectively, is we meet Monday morning, and we basically talk about, what are we going to accomplish this week? 64 00:09:54.984 --> 00:10:02.324 All of those things should ladder up to... We use, uh, a system called Rocks at Morning Brew from the book Traction. All those should ladder up to, like, a quarterly Rock. 65 00:10:02.744 --> 00:10:08.694 And then Friday rolls around, we meet Friday morning, and we look at the list. Like, did we get done what we said- Mm... we were gonna get done? 66 00:10:09.044 --> 00:10:17.074 What happened during the week that might inform next Monday's meeting, uh, and to hold ourselves accountable. So we're in constant contact, at least at the beginning of the week and the end of the week. 67 00:10:17.544 --> 00:10:27.414 That's been a great cadence for us. Is that in person or virtual? It's in person for the most part. Cool. Uh, and, and we can talk about that as well. Uh, I, I do- Yeah, let's dive in. 68 00:10:27.424 --> 00:10:32.384 [laughs] You're smiling, so [laughs] Yeah. So we're, we're both in the office. Yeah. Uh, I go in five days a week. 69 00:10:33.004 --> 00:10:40.504 Uh, he's in pretty much five days a week, although he's a little more senior and, uh, a little cooler than me, so he also has a place in the Hamptons he occasionally, uh, calls in from. 70 00:10:40.534 --> 00:10:49.754 [laughs] Uh, so one day maybe we can all get there, but, uh, yeah, we're in person. Cool. Yeah. Um- And, yeah, I can give m-maybe more of a hot take on that if you want. Yeah. Yeah. Yeah. 71 00:10:49.754 --> 00:11:05.984 Uh, uh, at least for me, I found it really important that obviously if you're chief of staff, you have to really understand your executive, your principal, and I've just found that that's so much easier to do in person because so much of that understanding is gonna happen outside of work. 72 00:11:06.044 --> 00:11:16.964 Like, we got drinks a few times. We've got meals a few times. Um, and I think that kind of deeper understanding of who you are as a person is so important, and that is harder with remote work. 73 00:11:17.204 --> 00:11:23.524 I don't think it's impossible. You just have to be a lot more, uh, structured, like almost set aside time to get to know each other if you're remote. 74 00:11:23.584 --> 00:11:34.504 So if I had to pick, all things being equal, of being a chief of staff with an executive that was in person versus remote, I would choose in person 100% of the time.Um, are there other hot takes you have? 75 00:11:34.764 --> 00:11:37.844 [laughs] Um, you had asked me about this before. 76 00:11:38.464 --> 00:11:53.104 Um, I, I think something I hear often from people that want the chief of staff role or are currently a chief of staff is they view it as, like, a bridge to another job, and I just think that's stupid- Mm... personally. 77 00:11:53.144 --> 00:11:53.384 Like, 78 00:11:54.384 --> 00:12:06.904 maybe you have aspirations that are outside of the chief of staff, but I think taking any job and viewing it as, like, a bridge to something else, I feel like you're gonna miss really understanding maybe that job is right for you forever. 79 00:12:07.544 --> 00:12:20.204 And I think there's so much more, uh, so many more things that are important to your career than just moving to different roles. If you love the company and love the mission and, like, you wake up- Yeah... 80 00:12:20.213 --> 00:12:31.194 and you're like, "I'm excited to work for this company," if you love your executive, you probably will never have another role that's more intimately tied to another person. Like, that's probably a great reason to stay. 81 00:12:31.204 --> 00:12:39.494 And so I would just go in with an open mind, and like, if I'm a chief of staff 10 years from now, I, I would be thrilled. If I'm still working with Robert, I'd be thrilled. If I'm still at Morning Brew, I'd be thrilled. 82 00:12:39.924 --> 00:12:44.124 So I don't think it necessarily has to be this trampoline. A lot of people talk about getting stuck. 83 00:12:44.724 --> 00:12:54.804 To me, like, getting stuck right next to a really great executive that understands a ton and can mentor you, that's a great place to be stuck. Cool. Cool. Cool. Um, so you mentioned these... 84 00:12:54.984 --> 00:13:07.564 the goals, the weekly cadence, um, how to be effective. Is there anything else about the first 90 days, um, as you kind of look back now that, like, were really impactful, important, or things that just sucked? 85 00:13:08.024 --> 00:13:12.064 Yeah, two things I would say. The first is understanding communication styles. 86 00:13:12.884 --> 00:13:22.104 Uh, Morning Brew is hybrid, so we are Slacking, we're emailing, we're talking in person, and every person has a very different philosophy around how they wanna receive information. 87 00:13:22.204 --> 00:13:29.724 I remember once sending Robert this Slack that, like, you had to scroll to see everything. Like, whenever you're sending Scra- Slacks that you have to scroll, like, that's bad news. 88 00:13:29.784 --> 00:13:36.124 [laughs] And he literally was just like, "What the fuck is this?" [laughs] Like, "This is an email. Like, don't send me this over Slack." And that was a good learning. 89 00:13:36.184 --> 00:13:47.264 Like, okay, Slack for him is, like, quick updates, like, check-ins, maybe so- send him a cool song on Spotify. Email is stuff, because he manages his schedule basically based on email, it becomes a to-do list. 90 00:13:47.324 --> 00:13:55.864 If there's something important that requires a lot more context kind of outlining next steps, that should be an email. So I've, I've totally adjusted my communication style based on that feedback. 91 00:13:56.524 --> 00:14:18.024 The second thing I would say is super important, probably in any role, but most important for chief of staff, is you're interfacing with a lot of different business units that have a leader of those business units, and I think the last thing anyone wants is this person coming in who doesn't understand your business unit, doesn't understand your team, and just immediately starts going like, "Hey, you guys are, you guys are fucking up." 92 00:14:18.093 --> 00:14:26.994 [laughs] "Like, let me tell you exactly what you should be doing. This is why that's wrong, and let's do this." You're not gonna set yourself up for success, and you're probably not right. Like, what do you know? Mm. 93 00:14:27.004 --> 00:14:34.304 You should come in with some humility. So I think the number one skill for a chief of staff to develop is influencing without authority. 94 00:14:34.313 --> 00:14:39.984 You're gonna be in a ton of environments where you don't actually have, like, titular authority to tell anyone to do anything. 95 00:14:40.044 --> 00:14:52.504 You have to persuade them, and part of that persuasion, first and foremost, is really getting to understand what happened in the past, why they're doing what they're doing, what pain points they see before you start giving a ton of recommendations. 96 00:14:53.164 --> 00:14:56.873 And, uh, I think that's going to engender a lot of trust with those teams. 97 00:14:57.364 --> 00:15:08.593 And again, like, you could be really smart and, like, really effective at the chief of staff role, but if all the business units that you're interfacing kinda hate you and don't wanna work with you, like, you're screwed. 98 00:15:08.754 --> 00:15:12.724 Yeah. So maintaining those relationships is super important, and I think that's a big mistake. 99 00:15:12.754 --> 00:15:19.984 People come in, they wanna prove themselves, and oftentimes we think of proving ourselves like, "Oh, I have to have this sick idea that transforms- Yeah... this business unit." 100 00:15:20.024 --> 00:15:30.404 Proving yourself to me as a great leader is coming in, listening, being humble, hearing what they've done in the past, and I think that's gonna set you up for success well past 90 days. 101 00:15:30.464 --> 00:15:39.304 Has there been anything else about, like, kind of where you're at now? Uh, so now it's six to eight months? Yeah, I think it's, like, eight months or so. Eight months, yeah. Yeah. 102 00:15:39.424 --> 00:15:52.904 Um, anything about, like, how things have shifted from the beginning towards n- now that you wanna talk about? Yeah. I think one thing that's shifted that comes to mind is just more trust. I think trust is a... 103 00:15:53.204 --> 00:16:02.604 and, and relationships are a function of time. I think when anyone starts a chief of staff role and they're sitting close to an executive, like, you want all the tea. [laughs] You want the gossip. 104 00:16:02.704 --> 00:16:10.994 You wanna, like, be like, "Tell me, like, what you can't tell anyone else." [laughs] Like, "Trust me, I'll keep it confidential." And I think something like that is just earned over time. Mm. 105 00:16:10.994 --> 00:16:17.364 And I think you're not gonna get that stuff right away because, like, what are you gonna do with it? You don't have the full context. 106 00:16:17.484 --> 00:16:26.744 Um, so I think more trust over time and developing a strong relationship with Robert and stakeholders has allowed me to gradually expand your scope. I think i- right away it's gonna be narrow. 107 00:16:26.784 --> 00:16:37.484 You kinda have to prove yourself in the, in the categories you've outlined at the start. But eventually that, that role expands. And I think the second is you quickly assess, like, where you can have the most impact. 108 00:16:38.064 --> 00:16:47.404 And right away you're kinda guessing, but if you go through that process that I alluded to before where you're talking with a bunch of different business units, you're understanding their pain points, you're, you're seeing over months, like, who... 109 00:16:47.564 --> 00:16:55.004 what's working and what's not, you can kinda plug yourself into the overlap of a business problem and where your talents intersect. 110 00:16:55.024 --> 00:17:08.804 And so I've definitely taken a step back from a few roles and, and stepped up into, uh, some more roles that just needed more help. Cool. Um, who's got questions? Come on up. Wow, a quick question. There we go. 111 00:17:09.864 --> 00:17:18.284 Shout out. [laughs] Um, I'll say it now to the podcast, Kyle. Huge fan of your content. Um- Thank you... very, very helpful. 112 00:17:19.524 --> 00:17:32.884 So, um, what really resonated with me with what you said, uh, was, um, about, you know, if you could work with Robert and work in your role, and if you wake up and you're really excited to do what you wanna do and you could do it for 10 years, right, that's... 113 00:17:32.944 --> 00:17:39.024 it's super, super important. Yeah. Um, I resonate with that so much. I'd work for my principal for 25 years if I could. Yeah. 114 00:17:39.384 --> 00:17:53.812 Um, I'm curious-With that kind of feeling, how much emotion you show in your relationship with your principal? Ooh. Whether it's personal, professional, if you're frustrated, do you show that frustration? Um, 115 00:17:55.252 --> 00:18:04.792 do you show... You know, do you cry? Do you vent? [laughs] Do you just- Every day. I just, you know- Yeah. [laughs] I think, I think the, the relationship could be so personal- Yeah... and yet it's business. 116 00:18:05.172 --> 00:18:15.392 So I'm just curious, like, where emotions come into play. Yeah, that's a really great question. Um, I'd say two things. I, I'm, I'm not in the camp of, like, bring your whole self to work. 117 00:18:16.052 --> 00:18:28.612 Um, I just think that there's some things that y- are probably not appropriate to share in a professional setting. That's highly contextual, but I do think it's good to understand that, like, you are doing business. 118 00:18:29.232 --> 00:18:34.532 They ultimately can, like, let you go or y- they can move on from you, and, like, you should be thinking about that. 119 00:18:35.112 --> 00:18:45.992 So, uh, I, I wouldn't say, like, I keep everything close to the chest, but I, I, I come in with that mindset. That being said, like, I'm a pretty enthusiastic, emotional, sensitive person, and that's just how I am. 120 00:18:46.552 --> 00:18:56.572 And so, you know, being conscientious of not taking that too far, I think that's where I shine. Like, I get energized, I get up, I get down when things aren't going well. 121 00:18:56.652 --> 00:19:02.472 And I think, you know, the best thing you can do, again, within the confines of outlined, is, is be who you are. 122 00:19:02.492 --> 00:19:11.012 Because if you can show up every day and feel confident, like I'm crushing it and I feel good about how I'm showing up, that's just gonna lead to better business outcomes. You're gonna have a, a stronger relationship. 123 00:19:11.572 --> 00:19:22.092 The other side of that is, like, it probably depends on your principal. They're also gonna have expectations of how you show up and the emotion you show and, and if you, if they want you crying or not crying. 124 00:19:22.132 --> 00:19:30.442 [laughs] Uh, and so, you know, e- maybe having a conversation early on, like, one of the best pieces of advice I have for people is, like, create something like a personal user guide. 125 00:19:30.892 --> 00:19:40.011 I don't know if anyone has heard of this, but Claire Hughes Johnson, the former CEO of Stripe, has a great, uh, book called Scaling People that she talks about this, uh, and there's a few other versions out there. 126 00:19:40.072 --> 00:19:42.352 But basically, it's like the guide to you. 127 00:19:42.832 --> 00:20:01.072 So if I was a new coworker and I was coming in and, and someone had to work with me, what could I give them that would outline, like, maybe what my Myers-Briggs are, what my, uh, CliftonStrengths are, how I prefer to communicate, how I like to get work done, email versus Slack, all of those things that just make it easy to understand who you are as a person and how you like to work. 128 00:20:01.112 --> 00:20:10.252 And you don't need to create, like, a, you know, 100-page dossier, but I just think having those conversations early is super important just so you're all aligned on expectations. 129 00:20:10.272 --> 00:20:16.312 And then the last thing I'll say is, again, like, relationships are a function of time. It's like when you meet a new friend, you're probably not telling them everything about your life. 130 00:20:16.372 --> 00:20:22.772 But once you've known them for five years, like, you're probably much more of an open book, and I, I think that's pretty natural. Who's up next? 131 00:20:23.672 --> 00:20:37.692 It sounds like you're really succeeding in the role now, but I imagine the first 90 days had some hiccups. What do you wish you had done or not done in your first 90 days to better set you up for success- Yeah... now? 132 00:20:38.332 --> 00:20:45.692 Thank you. Good question. [laughs] I, I... You've already been on the pod, so I know you're, you're trained. Um, gosh, what would I do differently? 133 00:20:45.772 --> 00:20:54.732 I mean, I think the communication thing was a big piece, and I, I had to find that out the hard way. I mean, it wasn't, like, a hard conversation, but I think aligning earlier on that would've been helpful. 134 00:20:55.832 --> 00:21:08.302 I think we talked a lot about the first, like, six-month plan for Morning Brew, and now we're getting to a point where we're talking a lot about, like, the 18-month, the, the two-year, the five-year vision. 135 00:21:08.332 --> 00:21:20.792 Maybe bringing that up earlier, just so you kinda have a, a general roadmap of- Mm... uh, where you wanna go. Something I think I did good but could do better, and I think this is really underrated, is it... 136 00:21:20.932 --> 00:21:30.832 I didn't talk to Robert just about Morning Brew. I talked to him about his 20 years in media, and I really wanted to, like, know, like, what excited you about Morning Brew? What did you do in the past? 137 00:21:30.892 --> 00:21:35.032 You sold a few media companies. Like, what worked for you? What were the lessons you learned? 138 00:21:35.652 --> 00:21:41.292 Um, you know, the same question, like, w- what are you doing now at Morning Brew that you maybe, like, fucked up in the past and, and that was a lesson? 139 00:21:41.752 --> 00:21:50.072 And I think you just have such a unique opportunity as chief of staff to extract so much historical knowledge out of your executive and principal. 140 00:21:50.092 --> 00:22:01.182 And oftentimes we get so laser focused on, like, the mission in front of us, what we're doing at the company now, that we just forget that these are really successful people who have had lives and careers well before you knew them. 141 00:22:01.272 --> 00:22:08.412 Like, just... It's almost like a cheat code. Just, like- [laughs]... steal all their knowledge and all their information out of them as fast as possible. I did an okay job of that. 142 00:22:08.552 --> 00:22:18.612 I'm, I'm still definitely doing that, but, like, yeah, one thing is just, like, if I could just take Robert's brain and, like, put it in mine, I would be way smarter and more effective, so, like, trying to get as many reps in as that as possible. 143 00:22:18.632 --> 00:22:26.492 And I've had meetings where I've just asked him questions, and he answers them and at, at the end he's like, "Why..." like, "Why are you asking this? Is it, like, relevant to something you're working on at Morning Brew?" 144 00:22:26.512 --> 00:22:34.792 And I'm like, "No, not at all. Like," [laughs] "I, I just wanna, like, know." And he's like, "Oh," like, I think it also makes them feel good, like we all like to... 145 00:22:34.832 --> 00:22:41.172 Like, David invites me to a podcast, it makes me feel good. I'm like, oh, he thinks I have something that's valuable to share. Like, it's a, it's a nice emotional touch. 146 00:22:41.232 --> 00:22:49.252 So I think the same goes for people, uh, in the C-suite. So that, that, that's probably my answer to that one. Great question. How's it going? Thank you for- Yeah... doing this. Yeah, man. 147 00:22:49.551 --> 00:23:01.452 [laughs] Um, my question is how you would approach someone who is an aspiring chief of staff. Yeah. And you mentioned things like alignment for with the mission, alignment with the principal. Mm-hmm. 148 00:23:01.552 --> 00:23:15.722 But what would you say are the often overlooked red flags, overlooked green flags- [laughs]... that you consider or that they should consider when they're thinking about- Yeah... taking an opportunity? Damn. Okay. 149 00:23:15.852 --> 00:23:21.682 Overlooked red flags and overlooked green flags about chief of staff. This is a hell of a question. David, you should've had this question. As I was gonna say- 'Cause he-... 150 00:23:21.682 --> 00:23:29.092 that's why they ask questions and I don't [laughs] He's beating you at your own game. That's why they're chief of staff and not me. Um, overlooked red flags for the chief of staff role. 151 00:23:29.212 --> 00:23:35.222 I mean, I think it goes back to I, I came from having a team, and, like, I grew up playing team sports. 152 00:23:35.312 --> 00:23:46.452 Like, that was a big part of my identity growing up, and so it was really nice to, like, have a team, feel like you were all marching towards the same mission. You, like, you, you had direct reports. 153 00:23:46.492 --> 00:23:52.234 Like, it, it felt much more cohesive. I think chief of staff can be, like...W- Weird and, like, lonely. 154 00:23:52.884 --> 00:23:59.684 Um, you have a relationship with your principal, but then, like I said, like all the other relationships you have with different business unit leaders, you're not on their team. 155 00:23:59.704 --> 00:24:10.464 You're kinda helping them, and that relationship can sometimes get a little fraught. And so I definitely miss, like, having a, a team, a little more sub- substantial team that feels like we're in the trenches together. 156 00:24:10.524 --> 00:24:18.304 You kinda have to, like, make that happen with a chief of staff. It's kinda given to you if you're, if you're on other teams. So that's maybe, like, a, an overlooked red flag. 157 00:24:18.484 --> 00:24:30.234 I think the other one is, like, I would never take a chief of staff position if you don't wanna become, like, the executive. Like, i-i- who cares what role y- or title you have? Like, I... 158 00:24:30.234 --> 00:24:38.234 It just seems weird to be like, "I need to be a chief of staff no matter what." Like, why? Are, are, are you excited about the company you're working for? Do you like the people you're working with? 159 00:24:38.264 --> 00:24:42.864 Do you like the executive? If you have all of those, like, whatever the title is, it's gonna be fine. 160 00:24:42.904 --> 00:24:55.644 So I think callously just being like, "I need this title," and accepting it without doing your own due diligence, because you're gonna spend so much time with the executive, and whether you like it or not, you're gonna become something like them because you're around them a ton. 161 00:24:55.664 --> 00:25:10.544 So that's definitely a red flag. Green flag about the chief of staff, uh, in terms of, like, underrated, like, upside or- Yeah, I mean, I guess primarily, um, what is a benefit that you didn't foresee- Hmm... 162 00:25:11.184 --> 00:25:20.374 a- after taking the role? Yeah, I think the [laughs] benefit I didn't foresee is like this is definitely a buzzy title. Like, and, and maybe- [laughs]... you know, like... And I came from community. Like- [laughs]... 163 00:25:20.374 --> 00:25:27.614 holy shit, man, you... Yeah. So that's, like, an underrated benefit. People are super into it for whatever reason. So [laughs] 164 00:25:27.804 --> 00:25:36.964 I probably get hit up, like, once in a while to do a talk like this or, like, people have so many questions about, "Can I m- meet with you for 30 minutes to talk about how I become a chief of staff?" 165 00:25:37.024 --> 00:25:45.004 So it seems to be a really hot title, which is, like, selfishly, like, awesome for me. [laughs] Um, so th- so that's... There's some upside there. 166 00:25:45.664 --> 00:25:57.154 Um, the other green flag about it, I mean, I, I think in the structure that Morning Brew has, and this might not be relevant to everyone, but Morning Brew's owned by this giant German conglomerate called Axel Springer. 167 00:25:57.784 --> 00:26:01.684 Christina, who's here, works at Politico, same, uh, same parent company. 168 00:26:02.304 --> 00:26:13.884 Um, it's cool because when I was not the chief of staff and a little farther away from the executive, like, I knew of Axel Springer for a few other reasons, but if I didn't have those other reasons, I would've never known this company existed. 169 00:26:13.964 --> 00:26:27.494 Like, this German company called Axel Springer? Like, no, I'm not interested, whatever. Now, like, I just get a little more [laughs] Oh, sorry. [laughs] Hey, Berlin is great. I've been. Uh- [laughs] 170 00:26:27.644 --> 00:26:33.874 No, no disrespect to the German people. Didn't expect me to have to say that on the podcast, but, um- [laughs]... 171 00:26:33.874 --> 00:26:50.124 I, I, I now get a little more exposure to that, and I think that's something that is also pretty eye-opening from a chief of staff perspective, is you can kind of, like, parlay that into understanding the ownership or the owners of your current company, whether that's, like, a PE firm or it's venture-backed or it's owned by another company. 172 00:26:50.133 --> 00:26:55.184 You kinda get exposure to, like, the next level, and before I was just like, "It ends at Morning Brew." 173 00:26:55.244 --> 00:27:04.504 Now I'm like, "Oh, Morning Brew is kind of owned by Insider, but it's also kind of owned by Axel Springer," and it's like there's levels to this shit. Like, okay, this is interesting. So that's definitely another upside. 174 00:27:05.104 --> 00:27:13.264 Awesome. Yeah, great question. Oh, here we go. Axel Springer to Axel Springer. Axel Springer to Axel Springer. [laughs] I have not a question, but a compliment. Wow, here we go. 175 00:27:13.584 --> 00:27:21.904 [laughs] Well, you were saying that, you know, I think all of us have been sort of saying it can be a nebulous role at times. You don't have a team of your own. Yeah. 176 00:27:22.624 --> 00:27:26.714 We met a couple of months ago, and you were the first Axel Springer... 177 00:27:26.764 --> 00:27:42.184 Outside of Politico, you were the first Axel Springer chief of staff that I had met, and you really inspired me because, you know, we've talked in this today, we've talked in this session a lot about, you know, how you come to meetings when you're the youngest person in the room, and the, the sort of buzzword of polish. 178 00:27:42.524 --> 00:27:48.913 Yeah. You have the buzzword of, like, charm. [laughs] You are like a, you are a magnetic personality. Wow. There we go. You really are. Thank you. 179 00:27:48.913 --> 00:28:01.184 You're a magnetic personality, and you make it impossible to be lonely as an Axel Springer chief of staff. Yeah. Because you reach out to people, you create community, you attract it- Yeah... 180 00:28:01.194 --> 00:28:13.464 and you, you sort of inspire it. Um, after you and I met, I started to think about, "Okay, what can I do within Politico to get our chiefs of staff together?" We have a few. I'm not the only one. Yeah. 181 00:28:14.584 --> 00:28:23.484 And we had a dinner, and we all got together, and then that sort of grew, and the snowball rolled into weekly sort of like touch bases- Yeah... 182 00:28:23.524 --> 00:28:32.124 where we all talk and exchange ideas and think about how can we help each other. And, you know, you inspired some of that. Yeah. 183 00:28:32.184 --> 00:28:41.144 Because you have that personality of just connecting people, and I think that, um, that's a very special touch that you bring. So I just wanted- Thank you... to give that compliment. Wow. 184 00:28:41.204 --> 00:28:50.444 This was not a plant, I pro- [laughs] I promise. No, not, not planned at all. [laughs] Thank you, Christina. A- and, I mean, I think there is some, like, overarching really good insight in what you said is... 185 00:28:51.144 --> 00:28:54.344 And, and, and- [laughs] And it's... I'm lost now. 186 00:28:56.084 --> 00:29:13.024 [laughs] Meaning, like, I think, I think I was at a bit of a benefit because I had, I had been a community manager and then a lead community manager and then a director of community at Morning Brew before starting, uh, as the chief of staff, and I think you just take away so many lessons from that experience. 187 00:29:13.084 --> 00:29:20.754 David, obviously you know them quite well and, and you're, you know, an ultimate example of the same kind of, uh, attraction and magnet for bringing people together. 188 00:29:21.364 --> 00:29:31.024 And I think oftentimes you feel like you have to do that if there's, like, an external product that requires community. But viewing your company itself as a community, it, I mean, it ultimately is. 189 00:29:31.044 --> 00:29:47.384 You gotta, you gotta, you gotta get along and, you know, i-if you can take that role as a chief of staff or any position in the company, if you can bring people together, you can make them more comfortable, if you can get to know people, I think that's really powerful and it's like, y- people joke about, like, a personality hire, but, like, it's a, it's a thing. 190 00:29:47.544 --> 00:30:02.120 Like, if you can bring people together and get people talking and get people comfortable, like, that is such a valuable service that you could be, like, so mid at your job and, like-People would be like, "No, you're actually great at your job," 'cause you're doing all these other benefits and, and those are just as important. 191 00:30:02.220 --> 00:30:15.640 So, um, yeah, I think that's a really smart thing you're doing at Politico. Thanks to you. Yeah. Thank you. Um, how do you balance diplomacy, tact, and honesty? 192 00:30:15.840 --> 00:30:26.710 In other words, do you realize when it's time to shut up- [laughs]... or you're just like, um, to your principal, you know, "I don't agree with what you're doing. Um-" Mm-hmm... you need to do something different. 193 00:30:26.780 --> 00:30:31.880 You're doing it wrong," or you just keep it to yourself and let them do whatever they think is right? Yeah. 194 00:30:31.940 --> 00:30:41.120 This is a really good question 'cause, like, you aren't gonna always see eye to eye with your executive, with anyone, your, your spouse. Like, even if you have an identical twin, you're gonna think differently. 195 00:30:41.200 --> 00:30:43.780 Like, there's just no way you're 100% gonna see eye to eye on everything. 196 00:30:43.840 --> 00:31:00.920 I think, like, I, I would put it in the frame of, like, a, a president and a vice president, where, uh, it's, it's the president's administration, and you're a trusted confidant to help craft what that vision is. 197 00:31:00.980 --> 00:31:02.580 But ultimately, like, it's their decision. 198 00:31:03.200 --> 00:31:16.920 And, like, if I had to bet, if I had an idea and Robert had an idea, and all I knew about us was like, this guy's been a chief of staff for eight months, and I've sold two media companies and been in this industry for 20 years, he's probably right, to be honest. 199 00:31:16.930 --> 00:31:27.200 [laughs] He's probably right, so, like, come in with some hu-humility. But, uh, to the broader point, I think it's, like, criticize in private and support in public, and I think it... 200 00:31:27.460 --> 00:31:31.960 you owe it to your executive to be honest. Like, if you're in private, there's no reason to lie. 201 00:31:32.060 --> 00:31:39.480 Like, you'd be like, "Hey, I want you to view me as a trusted confidant, and the only way you can view me and trust me is if occasionally I'm telling you, 'I don't think you're right.' 202 00:31:39.540 --> 00:31:43.240 If I'm always agreeing with you, like, also, what am I doing here?" So I, I think that's cool. 203 00:31:43.300 --> 00:31:49.400 I think in public, like, you want, you know, whether you like it or not, faith in the executive is faith in the company, and I think 204 00:31:50.380 --> 00:32:10.960 w- whatever they decide to do, if it's gone through the right process and they've listened to stakeholders and they've said, "Look, I'm in charge and this is what I'm deciding to do," you either, you do either have to decide, "Okay, I can get behind that," and it's like disagree and commit, or if you're like, "I really think this is a problem," or, like, there's a moral or ethical reason you can't support it or, or whatever, it, it just might not be the right fit for you. 205 00:32:11.020 --> 00:32:15.480 And you, you kinda have to have those boundaries of saying, "If, if push comes to shove, I just have to leave." 206 00:32:15.600 --> 00:32:23.860 I think most problems in business don't get there, so I would say, you know, yeah, critique in, in, in private. Support the enterprise in, in public to the best of your ability. 207 00:32:24.940 --> 00:32:35.000 Um, I know time management and sticking to schedules is important- [laughs]... for chiefs of staff [laughs] around here, um- Is this a podcast ad? [laughs] Um, no, it's not. No, no. 208 00:32:35.220 --> 00:32:46.820 Um, how do you think we should, uh, wrap this up? [laughs] I have no idea. You're the host. [laughs] You- How, how to wrap up the pod? Yeah. Yeah. Mm. What... 209 00:32:47.080 --> 00:33:01.560 A final takeaway, a final closing thought, a final green flag, red flag. Um... Hmm. [tsking] Take your time. I feel like we switched roles. [laughs] I'm now the host. 210 00:33:01.740 --> 00:33:07.950 Uh, fi- I mean, o- on, on, I have a sh- Not about, now, but not, not about with me. No, I know, I know. I'm just saying. Yeah, yeah. 211 00:33:07.950 --> 00:33:13.250 I have, I have a show on Morning Brew, and one of the things we do at the end is, like, tactics. Like, we just had this kind of wide-ranging conversation. 212 00:33:13.470 --> 00:33:23.090 Like, if I was listening, mentally, like, you're not gonna remember everything I said, and if you did, like, it's probably half stupid. Like, what are the two or three things you should, like, walk away with? 213 00:33:23.640 --> 00:33:34.000 I would say the first is, uh, this developing influence without authority. Like, if I could have everyone just remember that, I think I would feel good about this. It's such an important skill. 214 00:33:34.010 --> 00:33:45.600 Like, you're, you're rarely, unless you're the executive, be a- to, uh, you're rarely gonna be able to deploy, like, a command and control type structure. And this isn't just professionally, like, personally. 215 00:33:45.680 --> 00:33:56.380 Like, you're always negotiating with friends or with partners or with parents, and you can't just tell, you know, your parent, like, "Do this." Like, you're gonna have to have a conversation. 216 00:33:56.400 --> 00:34:05.480 And I think the more you can be open-minded and try to understand their point of view first before articulating your argument, the, the more successful you're gonna be in business and in life. 217 00:34:05.900 --> 00:34:08.209 So I think developing influence without authority is super important. 218 00:34:08.840 --> 00:34:20.100 And then I think, uh, the number, the number two takeaway, the last one I'll say is, understand deeply how what you do at your company helps the company make money. 219 00:34:20.280 --> 00:34:27.840 I think a lot of us have, like, pretty fuzzy jobs where ROI can be hard to articulate, and that's fine if the company's growing. 220 00:34:27.860 --> 00:34:37.000 But you know the second that the company's not growing and they, they s- they look to make, you know, layoffs or something, like, they're gonna basically go employee by employee and be like, "Okay, 221 00:34:38.020 --> 00:34:46.380 Jimmy," like, "Jimmy does this. Like, how is that making us money?" And if they can't come up with a quick answer, like, you're probably gonna be at risk, and I don't wanna see anyone at, at risk. 222 00:34:46.460 --> 00:34:50.510 So really being able to tie your job to, like, a clear ROI. 223 00:34:51.180 --> 00:35:07.180 And it might be a bit fuzzy, but I think you should just have the mental model of, like, how you plug into the company, how you help the company make money, uh, and be able to articulate that frequently to your boss, your manager, and executive because I think that just puts you in a, a really stronger position. 224 00:35:07.260 --> 00:35:17.300 And if we wanna get, like, really tactical, if you can do the math on that, and you know how much they're paying you- [laughs] Like, if there's a delta- [laughs] Okay? 225 00:35:17.380 --> 00:35:24.800 Like, if the delta's really big, you can go to them and have a pretty great argument. Like, "Look, I'm making us 500K and you're paying me 100K. Like- Whoo... 226 00:35:24.820 --> 00:35:31.140 I get there's overhead and I get all that, but, like, can we do a 50K raise?" [laughs] "Like, can we get a little closer to that?" 227 00:35:31.319 --> 00:35:42.350 [laughs] And, and, like, if you're truthful about it, like, and you're willing to be like, "I need this, this or, like, I'm outta here," their math is like, "Okay, well, you make us 50, uh, 500K. 228 00:35:42.380 --> 00:35:45.920 If we lose you, how long is it gonna take to replace you? Is that person gonna be able to j..." 229 00:35:45.980 --> 00:35:52.900 Like, there is just a mathematic equation that I think puts you in a stronger position, so I would have that in your back pocket as well. Let's give it up for Kyle. 230 00:35:52.940 --> 00:36:14.620 [claps] [upbeat music]