Evan Grossman, True Search MD on Landing a C-Suite Role

Michael Koenig: Hey, it's Michael. If you've been on a zoom with me lately, you'll notice that you have my full attention. It's because I'm not taking notes. Instead, I rely on Fellow, an AI meeting assistant to take notes for me, along with tracking action items and decisions, handling recordings, transcripts, and summaries all in one secure platform. It's kind of like magic. Built with security and privacy at its core, Fallow is the only AI meeting assistant that thousands of leaders and organizations trust to capture meeting notes and recordings while keeping your data safe. They're so confident that you'll love it, they're offering an insane deal to you all. Between two COO's listeners, 90 days of unlimited AI powered note taking and recording completely free. Visit fellow.app/coo to sign up today and experience the AI meeting assistant trusted by leaders everywhere. [00:01:00] Hello and welcome to between two COO. I'm your host, Michael Koenig. One of the most frequent questions I get is how do I get a C suite job when they aren't posted? Hopefully we'll be able to provide some answers today with my guest Evan Grossman, a partner and head of the CEO and board practice Search at TrueSearch, one of the top executive recruiting firms out there. Evan works closely with public, private equity backed, and pre IPO venture backed Companies specializing in CEO, COO, president, and non executive director assignments across a variety of sectors, including enterprise software, AI, data analytics, security, consumer, internet, and marketplace businesses. The vast majority of C suite roles tend to never make it onto job boards. Instead, companies contract with exec recruiting firms like TrueSearch to find the best person for the role. Who better to provide us with some insight than Evan. [00:02:00] Evan, welcome. Thanks so much for being here. Thanks for having me. So let's get to that question first. Aside from being promoted, how do folks make it into the C suite when the majority of these roles just aren't posted?

Evan Grossman: It's a great question. It's one that we get a lot. And the reality is, a lot of things are done before a search is actually kicked off, ? And frankly, companies, if they're smart, do try to save themselves the small pain of going through a search. And a lot of that comes down to network and who you know, and so you think about things like talent diasporas, there are plenty of organizations out there in consumer and enterprise software, all over the map, really, where you've grown up with a peer set of folks who are more junior and they've grown into these SVP C level roles. A lot of those folks know each other well. It's a smaller world than many people even realize, and even if you're one click outside of it, the odds of you knowing somebody who knows somebody who is a decision maker [00:03:00] or has at least a strong position in one of these companies is actually higher than a lot of people realize. And so it's positioning yourself within your network as somebody who's really ready to be in a C level role and jump into a C level role. And we can talk about, what that looks like and how to kind of look inward to know that you're ready for something like that. But it really starts with a few different avenues around your network. One is the folks that you've worked closely with in the past who have a pretty clear vantage point on what your strengths are, what your weaknesses are, where you are in terms of your career journey line. Then it's talent partners in the venture world or in the private equity world. These folks are always one click removed from just about everybody. And it's their job to try to put great folks in front of a CEO or a board long before we even get to search, for things like calibration. So being part of those conversations earlier on that's a pretty direct route to actually circumvent a search and become involved in those processes earlier. I'd also say because the market is so dynamic and shifting, this is actually a pretty good time for folks with slightly less traditional backgrounds to think about jumping into the C suite because what has worked for the [00:04:00] last 20 years. is not necessarily what's going to work for the next 20 years, 10 years, even five years, as we think about AI, as we think about the growth and consolidation of a lot of these different industries across the board in tech and non tech. And so the combination of all of those factors means that if and when somebody's right for a C level role, it starts with the network, and then it also, it's also a lot of time interfacing with folks like myself and my colleagues.

Michael Koenig: There's a lot to unpack there. Okay. The first is the network, kind of the people that you come on up with. Where, then, does An exec recruiter or a talent partner at a VC firm sort of step in if, the, that network, that CEO or that COO already knows, Hey, I want this person.

Evan Grossman: Yeah, it's a good question. So the reality is a lot of the work that we do in the early phases before we go to search is validation, right? So for example, Michael, you and I worked together at a company for 15 years, you go off and you're a CEO somewhere and a need comes up for somebody on your team. You're going to naturally think of me, I would think, but you might also have [00:05:00] 10 other people that could potentially play that role as well. So as long as I'm keeping top of mind, I'm saying, Hey, here's how I'm thinking about my career journey. It's a more friendly conversation, it's not transactional. Hey, I'm trying to land this gig, but it's really, here's where I think I'm going to be. I'm going to be top of mind. And then. And if you need , thoughts on how to really build out the criteria of what this person is going to do, then you would look to your talent partner, then you would look to your trusted search partner, somebody who can say, hey, this is what we're really solving for. I've got somebody in my network who I think solves for 80 percent of this. Can you sit down with that person and validate and give them your point of view on where they spike on these different areas of need, it really all comes down to core need. It was a lot of great people out there for whom there might not be an immediate need. And a big part of our job is narrowing that funnel down to make sure that that person is going to be the right person to drive maximum impact.

Michael Koenig: You're talking about talent partners at VC and private equity firms. Their job is to find people. When do they decide, you know what, I got to bring in a firm like True.

Evan Grossman: So there's a couple different flavors of talent partner. Uh, and I don't want to bore you with the nitty gritty details of the [00:06:00] search world, but there are talent partners for whom their job is to really keep a finger on the pulse of the network, and those folks tend not to do search work. They tend to outsource as much as they can to, to folks like myself. If there are two or three folks that they know well, They'll try to put them in the mix again before a search comes on. If those two or three don't land, or more likely if a search is incredibly complex for one reason or another, in a nuanced market, in a space that people don't know as well, if the company's a bit of a turnaround player, and you need somebody who's got a deep network, then you pretty quickly move on to search. There's another breed of talent partners that actually do search, and so they might run a search for three, four months. And if they don't get anywhere, again, they don't have the same level of network. They don't have the infrastructure. They don't have the team. That executive search firms do, then they'll quickly move on to search after that, but they will run their own prolonged search in this.

Michael Koenig: Let's talk about the network then. What if you don't have that network, not everyone necessarily, has that group of peers that they come up with.

Evan Grossman: [00:07:00] Yeah it's a lot of, it comes down to. In the conversations I have, and I get probably 15 to 20 inbound LinkedIn's or emails a week from folks who want to be a CEO, COO, sit on a board. And so as you think about a lot of those things you do have a broader network than you think. If you are an attorney, and you've spent a lot of time doing M& A law, for example, even if you're not as close to the day to day operators, you likely have CEO, COO, board level contacts you can draw from that can put you in touch with folks who are doing the job you want, if you come completely from a different ecosystem entirely, you're going to have to work a little bit harder to make a case that this is the right thing for you, and that's ultimately a lot of these searches come down to risk mitigation and every client has a slightly different level of risk they're willing to take when it comes to bringing on a new person. A lot of that risk is mitigated by. Having a great network that you can validate through, things like back channels or blind references if that person is good. A lot of it is, hey, this person spent 15 years at [00:08:00] least adjacent to our space, we have conviction that they get a sense of it. If somebody lacks a couple of those things, But they're really smart and gritty and willing to maybe take a lateral step or even a step down to get into a new field. Those can become more compelling, but it takes a little bit longer.

Michael Koenig: Let's talk about the LinkedIn messages that you just said. You only have so much time, how do you decide, hey, You know, this is really interesting. I'm gonna kind of dig a little bit deeper on this one.

Evan Grossman: Yeah, it's, so this is one of the things that I go back and forth with myself a lot. If I had infinite time, I would respond and give thoughtful guidance to everybody, the reality is between managing a large number of clients, between managing a large team, between, being a person at home, there's only so much time you have. And so I often tend to take a look at folks backgrounds. And if I know that I can help them, I will do so. If, and my sweet spot, my background is very much in sort of the B2B world. I've done consumer. I know that industry well, too, but if somebody comes to me from, say, pure play logistics or healthcare or large cap financial services, they could be [00:09:00] great. And somebody out there will be able to help them, but it's just not me. And so what I don't want to do is mislead them or give false hope of, hey, try these things. When in reality, I may never have a search that could be relevant.

Michael Koenig: Right. Makes a lot of sense. And then I'd imagine that as part of such a prominent firm, there's, there are also a lot of partners that specialize perhaps in healthcare versus B2B SaaS. So, you can pass people along when and if it makes sense.

Evan Grossman: Exactly. And I think that's one thing that True does maybe better than some of our competitors. We do tend to have folks at the scale we're at today that specialize in almost every area that growth would touch, whether it's. It's tech, whether it's CPG, you name it. And so a lot of it is just directing traffic, this person reached out to me from the CPG world. They're an A plus. I'm going to make sure they get in front of our top search people on the consumer side. And I know that I'm not going to be the right person for them, but I want to make sure that they have a good experience with us in that regard.

Michael Koenig: You talked about LinkedIn and some of the things that I think every executive feels like they have to do is be on LinkedIn. Post, et cetera, et cetera, et [00:10:00] cetera. What role does that play? Is this really something that people need to be investing time in and trying to be a thought leader? If everyone's a thought leader, no one's a thought leader.

Evan Grossman: Yeah, look, I we see a lot of that. And I think that's a really astute question. The, there are a lot of great people who don't use LinkedIn at all, and some ways that signal to the market is I'm actually too busy. being the CEO of this company to jump in and be really thoughtful on LinkedIn. I think LinkedIn absolutely does have a place and a platform where you can provide your point of view. You can add a lot of value. We all see the kind of sales influencer folks on LinkedIn. And so much of that is, you can even read it, it's a lot of it's canned, a lot of it's chat GPT with a wrapper on it, those things I think hurt more than they help in a lot of ways, having a voice, but having nothing to say. Okay. It's going to be less impactful than really making fewer posts or having a smaller voice, but really targeted to your area of expertise.

Michael Koenig: Just out of curiosity, when we think about this hidden job market, [00:11:00] why does it remain so hidden? What is the purpose there? You've got these talent partners, oftentimes, companies like the company I'm at. We have a pretty robust talent department. Like.

Evan Grossman: Yeah, I think there's a few reasons for it. At the end of the day, I think efficiency is a big factor, if you think about the c level landscape, there are only 20 ish, 25 percent of folks at any given time who could make sense for a C level role. Whether it's CEO, CTO, COO, CRO, you name it, it's a very small pool of people relative to the people who want that job and that opportunity. And if you run that process the same way that you run a process for a sales manager, you're going to get a similar result, which is you're going to get inundated with Folks of varying degrees of quality, you're not going to be able to be as targeted. And even if you do find a few folks who are really strong, you're likely not going to have the resources to go as deep with them as you'd like to run a really architected and well tailored process. And that leads to settling at the end of the day.

Michael Koenig: So we're [00:12:00] talking a lot about scale and efficiency to be able to find, the candidates that are relevant for the role. We're basically seeing with AI every single function get disrupted. What have you seen so far? How are you guys within TRUE thinking about this and talking about this? Because, one, on the one hand, You have a lot of candidates who can pop into chat GPT and generate something that is totally, misrepresentative. But then at the same time, what does AI do really well? It deals with things at scale. It's

Evan Grossman: well said. And one of the hallmarks of true in our culture is that we're only 12 years old, but we're the sixth biggest firm in the world. And a big part of how we got the way we are is through just raw innovation, so we've always been a little bit further ahead technically than a lot of our competitors. And AI is no different. And so we, several years ago put together a very strong data team. And that data team is a proxy now for a lot of the AI work that's going on. The way that we're thinking about using it internally, it's never going to replace the one to one human [00:13:00] connection. If you're recruiting a C level executive, you need to be able to look that person in the eye and understand their motivations and their thoughts and where they are in life and why this is compelling. AI won't really be able to do that. What AI is better at than we are is ingesting tons of data. And so we have a platform that we built called Thrive. It's now used by Google, Starbucks, many large corporations, a lot of venture and private equity firms, and a lot of our competitors use it as well. Everything that we do rolls into Thrive, right? And if we're good about the data, I mean, you're only as good as your data, and I know every sales manager in the world wishes that their team was better at using Salesforce. We all wish that we were better at using Thrive for the details. But if we ingest all of that data we can then use AI to pull, Hey, here are the 20 criteria we're thinking about. We want somebody who's based in Chicago, who's been a COO for 20 years, who's got financial underpinnings who spent time, maybe three of these, I don't know, 50 companies, and across the board, that'll help pare down the list and do a lot of the manual kind of clicking through things like LinkedIn, things like Thrive to give you a more curated sense. And then [00:14:00] it's over to the search professional who look at that list and sort of draw the insights.

Michael Koenig: And that's one of the things that I find so interesting about True is this business is diversified. I mean, it's not just an exec recruiting business. There's this entire platform that you're talking about. How much of that played into, you know, you mentioned we were only six years old or excuse me, 12 years, no, six years old, but we're 12, we're within the 12 largest. Was that the metric? Yes. So we're. We're 12 we're not

Evan Grossman: the sixth largest company.

Michael Koenig: Yeah, how much of that, you're talking about data and using data, likely, in a much more sophisticated way than some of those big players out there. And now you're talking about, hey, we have a platform that we've actually productized and turned into, a money generator.

Evan Grossman: Yeah, it's, I've got to give credit to our founders who've always been, you know, very thoughtfully ahead of the curve on these things. And because tech is really our roots, and for, for the first several years of the True journey, our real sweet spot was VC backed companies. And those are the most innovative folks on the [00:15:00] planet for good reason, and so we needed to innovate alongside them. And what that drew to the platform was almost a different type of search professional. It was not this quota carrying salesperson who can fly in and out of calls and win business and have their junior team do all the work. It was people who really did the work themselves and really cared about it, right? And they might've been earlier in their career. They might've just had a passion for the actual execution versus just driving revenue. And if you give those people who care a lot and who are good at the work, all the data and the tools to go do that work more effectively, what you get is, you know, A lot of growth very quickly because that's not what you're seeing from the other firms.

Michael Koenig: When we first started chatting, you mentioned that it's a really interesting time for people with less traditional backgrounds. What do you mean by that? One, two, why is it a good time? And the reason why I'm asking is, say I make a B2B automotive sales. You know automotive sales platform, right? I'm probably going to want someone who has experience pitching [00:16:00] to you know The big autos if i'm looking for a cro or something like that. So is this an exception not the rule or just talk to me a little bit about those trends and what was behind that statement

Evan Grossman: Yeah, so we talked a little bit about risk mitigation here, and a lot of search can be paint by numbers If we are an 100 million dollar software company selling into financial services Who better than somebody who was just a CEO of a, of a hundred million dollar software company selling a financial service, who took it to 250 million. That is as black and white as it gets. The reality is, in this world and in this market, a lot of these proven CEOs, even proven number twos or C level executives, have done so well in the last four or five years that they may not want to do that again, on top of that the world has changed around all of us, we think about things like COVID, return to office or not, we think about the rise of AI and the way all these tech tools play. There are some seasoned operators out there who just either want to go sit on boards or play golf, so the world has shifted and it's created a little bit of a talent delta at the top. [00:17:00] And what that does is it gives opportunity for all those. Folks who are a little bit earlier in their career to step into these larger roles and that will variable effect will continue right such that the folks underneath that think the VPs of the world, there's not a natural pyramid of folks who are going to be who are going to be advancing year over year over year. As, as one might think that'll create opportunity for folks who haven't quite had the same level of experience to come in and get in at that, right? Because we're at a place where the black and white is starting to become a little bit more gray, if somebody is a seasoned professional in a, in, for example, services, there are services folks who are now joining software companies in mass, because things like profitability are a lot more important, and they've spent a lot of their time focusing on profitability, whereas folks in the pure SaaS world, have not, with the exception of the last few years, unless you're a deeply private equity held company. And so that skill set is starting to translate more and more. And I think what that does is it does create that opportunity. Now, if you are so far afield that it's a pipe dream, you've got to be honest with yourself and with [00:18:00] the team around you, the professional you're working with, on what might be realistic. But we're seeing boards and hiring managers for the first time get a lot more creative.

Michael Koenig: How interesting. Now, let's clarify on this risk mitigation, it's, I kind of always have said it's riskier and more problematic to hire the wrong person than it is to take a little extra time and find that right person. When we're introducing new non traditional backgrounds, like you're talking about, there is that inherent risk. How do you mitigate it? How do you make sure that, yeah we're bringing in a fish out of water. Let's hope they can swim or rather walk.

Evan Grossman: It's another good question. That's where a great search firm is an advantage, and I can give you an example of a search that I recently completed. It was a CEO search for a 100 million software company. And we had two candidates who both fit that exact profile. They had some domain expertise. One had been CEO of a larger company. One had been CEO of a slightly smaller company. And. [00:19:00] We listened about the core areas of need here, things like getting to profitability, things like expanding into new markets what we weren't, things like some product marketing, as opposed to retrenching the product and having to go through a lot of technical debt, what we weren't hearing Was things like this person needing to have experience out in the market raising funds, they didn't need to have experience Doing a lot of the deep technical work They didn't really need to have experience Deeply on the go to market side because the business had a great CRO And so as part of that we were introduced to what I would call a very non conventional candidate This person was a career investor and a very good one Sort of a mid career level person who for the last five years had been running value creations And as part of that value creation had been very, very deep with companies on the reacceleration of growth, which is what this company really, really, really required was a reacceleration of growth. And who better to be thoughtful about the reacceleration of growth than somebody who would just help 15 other companies do the exact same [00:20:00] thing. Even if they weren't leading the teams, they brought up a certain playbook. And so that got me thinking ordinarily five, six years ago, that person probably wouldn't have made as much sense. In this context, let's give them the chance to compete. Let's give them all the data that we've given the other candidates. Let's show them the board decks. Let's let them go deep on the financial profile. Uh, let's have them spend time with the founders, spend time with the board members to really understand the nuances of the problem. And let's have them do a working session with the board to really show what they can do. And I think that puts everybody in a level playing field. And even if somebody does come at it from a different perspective, I think those perspectives can be additive.

Michael Koenig: Yeah, that's quite incredible. This is an evaluation of skill set, and how they think about things, what flavor do they bring differently. There's also this sort of, evaluation of culture fit. First off, what does that even mean now? We hear it all the time, but also second, like how do you evaluate that?

Evan Grossman: So culture fit is really interesting, especially in the context of the work that I do. Often if you're looking for [00:21:00] a CEO or a number two to a founder, the culture is probably okay, but it can be optimized, right? So somebody who is a purely 100 percent culture fit may actually not be the ideal person because the culture needs to be shaken up a little bit, there might need to be some high performance injected into the business. There might need to be more rigor around certain processes, things like that. So somebody who's just going to sort of show up and go along to get along may not be ideal. Now, there's also the notion of sort of bend to break, if somebody is way on the other end of the spectrum and they're, culturally completely misaligned, that risks organ rejection, which nobody wants, because to your point, we'd rather take a little bit longer and hire the right person. Now, evaluating culture fit this is where, people call search sort of an art and science. This is really more of the art form. We spend a lot of time, and I spend a lot of time, up front with the directors and the folks of the companies that I work with, and yes, it's what they say. It's also how they say it. It's their body language. It's their values. It's, in essence, it's the mission of the company and what the company's aiming to solve for. [00:22:00] If it's a MarTech company, that's one mission. You know, we've done vertical SaaS searches for companies that were in the brewery space, and so if the CEO doesn't enjoy a beer every now and then, they're probably not going to be a great fit with the broader team. And so all of those things allow us to get a sense of what the current makings of the company look, feel, and sound like. And then we're out in the market, we're meeting folks, and we do make it a big point to meet folks in person, I think that's, that's a little bit of lost art post COVID, but it's really important to me that, that we are able to look a lot of these folks in the eye. Um, we can get a sense pretty quickly of their style. And then the last thing that we do, which, you know, is, is crucial is we run blind references, right we'll call folks who they've worked with at different points in their career and just get a sense of this person sounds great. They feel like a great fit, but how are they when, uh, when they're in a tough situation, right? How do they lead when things aren't going incredibly well? Occasionally we'll call folks that they fired and just ask, simple questions around that. And all of these things are taken in context, right? Nobody's, you know, Nobody's hearing these things in a negative way. But it gives us a very, very strong 360 degree [00:23:00] view of kind of the good, bad, and ugly. Look, we all have blind spots. You can back channel me. I'm sure you hear good, bad, and ugly as well. It's true for all of us who spend a lot of time in and around the ecosystem. But it does help us get as close as we can to really nailing that culture effect.

Michael Koenig: You take a lot of these first time calls, you're constantly meeting people. Someone's made it through. They've made it in your door. And you just said something really interesting around the art, not the science of this, but the art of evaluating not just what they say, but how they say it. What does that actually mean? But also what are some of those pitfalls that you see people, you talk to them and you go, okay, nice person, but not so much.

Evan Grossman: Yeah. Look, I think there's there's a certain level of gravitas, or of executive communication that, that folks have, and you can feel it in some ways that the folks who grew up in large, potentially now a little bit stodgier companies, they're trained to speak in such a way, or the old, the old school salesperson who might use your name 15 times in a given conversation. Like that [00:24:00] is a way of communicating, right. It is not necessarily the way that I think. With the world being what it is today would resonate with all audiences. And so that's something to take into account. You can be almost too formal or too polished in some cases. Now I'd say in terms of Frankly, it's sort of just being yourself. It's a conversation like this, it's just an honest one to one dialogue. If I can feel that you have a bit of an agenda behind the conversation, you can't really hide it. It's what I do for a living. I can pick up on it, and I'll question, what is that agenda? Right? And why is that the case? What are you trying to get out of me? I'm trying to help you. The things that I think separate candidates who I'm meeting for the first time, who I come away with a really positive point of view versus less so, is somebody who's Very honest about not only where they've been, what they've done, but what they want to do. And not only what they want to do, but also their strengths and weaknesses, we think about a lot of folks and a lot of COOs, frankly, a lot of COOs are classically trained, great pedigree, you know, worked at top tier eye banking companies and, or [00:25:00] managed consulting firms. They're polished. They've got this presence and they've excelled in life. A lot of them have been student athletes. A lot of them have been part of, you know, great universities. And so they're used to succeeding at most everything they try. And so when I talk to them, they say, Hey, I just took a company from, you know, 2 a COO. I'd love to be a CEO of a 50 million company. And the reality is they don't have the self awareness to understand how big of a gap that actually is. And if somebody doesn't have that self awareness. It's hard for me to corral them in that regard. Because I'm meeting them for the first time or the second time. I can give them my point of view, but nobody's going to tell them they can't do something if they've been successful through all areas of life. I think it's the self awareness to say, Hey, I've, again, for example, taken a company from 2 million to 10 million. I'd love to do the 10 to 25 journey, and that might set me up for my next one, and so I think it's being honest. It's being realistic about where you spike and where you don't. And I ask this question of CEOs a lot. Where do you need a strong lieutenant? No CEO who is successful has ever told me I'm perfect and I'll do it all myself. They say, I need a great finance person or I need a great CRO. I want to spend [00:26:00] my time on product or I love to be on the road and spend a bunch of my time with customers and the team. So I need some sort of chief of staff to help me keep my life together or else there's no way I can be all the places I need to be at the right times. That level of self awareness and depth allows not only me to make a stronger case for them, but also once they get into the seat, It ensures they're going to be more successful because they know where the gaps are and how to supplement them.

Michael Koenig: You said something really interesting here about, okay, I took a company from, 2 to 10 million dollars. I'm really looking, I want to take a company from 10 to 25, wouldn't a company want someone who's already done that in another space? Like, how do companies decide, This person hasn't done exactly what we want, but we think maybe if, the stars align, they'll be able to do that. How do you decide, when to take the plunge on that?

Evan Grossman: Yeah, it's something we're seeing more now than I've ever seen in my time at Truth. Which is folks who have gone from X to Y, and we're calling them and seeing if they can go from Y to Z. [00:27:00] As opposed to doing the same thing they just did because of that talent shortage we're talking about of folks who've seen that level of scale before. And so what that creates is opportunity. But when you get that shot, you've got to be buttoned up and really thoughtful about how to approach it. So, for example, calling out the fact that you haven't done it. Hey, I just saw 2 to 10. I'd like to do the 10 to 25. I've not done it before. But here's how I would approach learning the things I don't know, so if you're having conversations with the CEO, with the board, with the broader executive team, you, you can and should call that out. Because if you make it seem like you're just going to be able to walk in and crush it day one, that's actually going to raise suspicion. On top of that, Everybody who's been in a C level role, SVP level role, you have some level of strength. And if you play to those strengths, if those happen to be where the company is weak, then the fit's even better, if we're talking about a CEO, for example, who's amazing on product. And that company that's going from 10 to 25 has a great cheap product officer. You're not going to add as much value as somebody who's world class on go to market. So it's a lot about finding the right fit and allowing [00:28:00] folks like myself to help guide you to that fit on those dimensions. It's also about betting on yourself. And there are a lot of folks out there who, because the last three ish years have been as hard as they've been, they maybe don't want to take a bet on themselves. A lot of them are comfortable taking sort of larger public company roles, which don't get me wrong with that. It's great work, but if you want to do something a little bit more innovative and get your hands on in more of a build mode, you're going to have to take a little bit of that risk. And that's where, a lot of folks careers begin to really accelerate.

Michael Koenig: We'll be right back. Okay. Does this sound familiar? You wake up, take a look at your calendar and see it's filled with meetings, project meetings, standups, weekly check ins, one on ones, town halls, and those are just the internal ones. Some are productive, but some are total waste of time and treasure. Be honest with yourself. How many times have you thought this meeting could have totally been an email? Now, consider that in the U. S. there are 55 million meetings happening each day, and [00:29:00] 85 90 percent have no agenda. Fellow is on a mission to solve the meeting problem by offering the only meeting management tool that covers every part of your meeting workflow. By offering 500 meeting templates, integrated action items, collaborative meeting notes, and AI recording and transcription, Fellow helps teams and organizations get more done with less. Between two COO's listeners, yes you, get five free AI meeting recordings. Go to fellow. co to start your free trial and start having better meetings today. Something to remember for everyone out there who's just thinking, how do I get to that next level? When you're in a C suite role, you haven't done everything before. But you as an executive recruiter the hiring team here, they're not just vetting. Hey, does this person have the experience, but it's more along the lines of Hey, this person is going to see new things. Do they have the capacity to make the right decision at the right time? So it's really [00:30:00] interesting how it's, as you just said it. It's the approach to learning what they don't know. So fascinating. And it's so true for COOs. Today I, of course I can't talk about it, but before this call dealt with something I've never dealt before. And you're like, ah, I think this could be the right decision. Of course, this isn't a decision where anyone's going to die or go to jail. So we can reverse course, that type of thing, but super, super interesting. And so, you know, very, very relevant for this audience. Now you started talking about process previously. You talked about how you gave I think it was a CEO from services company, the same data, and then you put them in front of the board and you work through things. Like now we're further down the process, but maybe can you take us through the process of great Evan had a call. You love this person. You're like, wow, maybe I have one or two roles that I'm thinking cool. I'm going to put them in touch with. Who, what happens next between that first, you know, [00:31:00] exploratory call to I've been hired?

Evan Grossman: Yeah, it's a, it's a good question. So the way this typically works is, and I hate to say it's like a stereotype of search, but it very much is like, we'll call you, right? We have this advanced database. And if the needs been identified, and we feel like you're a great fit, we're going to reach out, and we're going to get a sense of a few things. The first is, Timing and interest, is it the right time for you to think about something? Is this thing the right thing for you at a high level? And then we'll set up a lot more time to go very deep on the ins and outs of the business. And my team and I spend hours. We try to approach each kickoff as if we're management consultants trying to uncover the problems for ourselves. So yes, we'll listen to the board and get their point of view on, um, You know, what needs to be fixed, what's going well, you know, the strength of the team, all of those things. And then we'll ask for all the board decks, all the financials, we'll go away and we'll form our own conclusions. And those are the questions that we'll ask folks. So if we reach out to somebody, we have a great couple of conversations, we feel like this is the right fit. Uh, we'll use a CEO search for an example, from there, we will introduce them to each Board, if the process is being run thoughtfully, there will be one person who's [00:32:00] sort of the initial screen, of a search subcommittee of four of a board of eight. And so they'll meet that one person. Um, that's primarily more exploratory. It's getting a sense of, again, the issues that business is solving from that person's vantage point, getting a sense of, uh, the candidate's background, experience, excitement, desire to approach this challenge. And then from there, if that goes well, they'll likely meet each of the rest of the search subcommittee. And those people will all be probing, uh, with guidance from myself on different areas. It could be, Hey, this is a company that is bleeding money, right? How do we think about this person's point of view on profitability or our churn is dramatic? You know, what is this person's point of view and playbook on fixing things like churn? And so if they make it through that broader gamut and circuit, we will then likely deliver them all of the data that we can. And again, this is back to the board decks, back to the financials, uh, back to product decks, roadmaps, and allow that person to kind of go to school on the business and unpack their own theses and be really thoughtful about what things might look like. So,

Michael Koenig: this is very timely. After we speak, I'm [00:33:00] getting off a call, and I'm hopping into an interview. No joke. I have gone through so many different ways of evaluation. I've tried very You know, objective measures. I read this book, who, and they had this whole, matrix that was weighted based on the core competencies you want based on the values. And here I am trying to give numeric scores to every single thing and designing questions around. Those core competencies. And then I've said, okay, I'm going to take just objectively. I'm going to take the highest score on this thing. I've done that. Sometimes it works. Sometimes it doesn't. I've also gone through much more subjective measures. And the thing that I always struggle with now is. How do I do this? I have a list of 13 questions. I will actually put them on LinkedIn. So anyone who comes and interviews with me, they can know they can put their best foot forward. This is exactly what I'm going to ask. Maybe I'll do that. How should I [00:34:00] think about evaluating this person in this interview in 30 minutes?

Evan Grossman: There's a lot of different schools of thought on this, there's a notion of, again, it comes down to art and science. Some folks think that if you have enough science, but if you feel a certain way, you've got your answer. Other folks are much more rigorous where they take their emotion out of it and really use a rubric, a scorecard. In my experience, the answer is always going to be somewhere in the middle. I think about this when I hire for my team, when we bring partners in externally as well, I think in some ways interviewing, um, can be over complicated. You're trying to solve for all things in a pretty short amount of time. What I found works for me, and this is the advice that I give to founders who are hiring eStaff maybe for the first time or even board members who call me and ask, Hey Evan, what do you think of the CEO candidate? How should I approach this? You're hiring somebody for a reason, and as simple as that sounds, underpinning all of that, there's probably two or three very simple core needs that you need this person to do. That's true of even a CEO role. And so I know it's largely true of the rest of an organization as [00:35:00] well. From SDR all the way on up. That's where I think spending the most time can yield the most impact. Things like culture fit, you'll feel along the way. Things like aptitude will come out on the questions that they ask you. Things like enthusiasm will come in the form of follow up notes, with good hygiene or additional calls. But really, it's about what are those two or three core areas and what is your experience and desire to go solve those specific problems. And if you spend most of your time talking about whatever those two or three areas are and getting their input in a first or second conversation, you'll know pretty quickly whether that person is worth going deeper on the other areas with, and so it's less is more in that regard. And going deeper on three things is, in my opinion, going better than going deeper on nine to ten. Because you're solving for something really specific.

Michael Koenig: I always take the approach of those behavioral questions that are open, and tell me about a time when you had a conflict with someone on a team. How did you, and my favorite question always is, as a follow up, what would you have done [00:36:00] differently? I love that introspection, but really interesting, super helpful. Let's talk about board. A lot of folks, a lot of CEOs in my network, we're we've accumulated knowledge and now we're kind of like, Oh, this board thing. That could be interesting. I've dealt with my board members before I've been, in that hot seat and taken that fire. And now I'm, I'm interested. Two questions here. One, how do you evaluate when a C suite is ready to make the plunge or jump to the board member? How do you evaluate, okay, this person has something to contribute?

Evan Grossman: So when someone's ready and what they might contribute. So the, the reality is everybody wants to be on the board. A lot of the inbound that I get is exactly that, it's, hey, I'm thinking about adding a board seat. Board hiring is, it's limited, if you think about the amount of companies out there, only so many private companies are at a scale where they even need to bring on a true independent, and beyond that, yes, there are a [00:37:00] lot of public companies out there too, but if you're not a multi time public company executive and officer, it's unlikely you'll get a shot to be a public company board member. And so that takes out about 90 percent of the ecosystem almost immediately. As we think about private company boards, and maybe we start there, you are ready to be on a private company board when you have really been the key decision maker in a much larger scale and context, so there's a level of complexity. And no one's a board member until they are, and we, probably half of the board members we place are joining a board for the first time. And what I would say is, there is a, again, because everybody wants to be on the board, but a lot of people don't really know what it entails to actually be on the board and do a lot of that work, and so if, I'll give you an example, I just kicked off a board search yesterday with a 100 million company in the infrastructure space more broadly. And the primary purpose of them bringing on independent is twofold. One is to really re accelerate, go to market and build out the channel strategy. And have a lot more depth around different areas of marketing [00:38:00] and help the CEO build this foundation for a pivot in their go to market, and so that's a pretty specialized point of view within other infrastructure companies. The real reason that companies are looking to bring on independence often is to supplement that founder. Because a CRO is great, but the delta between a great independent and a great CRO can be 15 years of experience. And a lot more scale and a lot more battle scars to show for it, so you really have to have specialized experience in a very core area that board is trying to solve for. That's where athletes tend not to do quite as well, great athletes who can do a little bit of everything tend not to do as well as folks who are specialized, who can add really deep rigor on the audit committee. If they're a CFO. Or really deep rigor on areas like regulation or cyber. They come from that world, and so those solves are pretty specific and that's where the black and white has not gone away in executive search. The other piece of it is you have to have experience working very closely with a board and managing a board. A big part of being on a board as an independent is also helping to manage the board in tandem with the founder or CEO. A lot of founders [00:39:00] look, call me and say, Hey, I want to bring on a board member just to have that person rubber stamp that they're not crazy, and to push back on the investors. But that's not how it works, like it's a two way conversation. That board member has to be able to sort of call BS in some ways and the founder and say, Hey, you're actually wrong here. Here's how we should be thinking about things. If you've not led those yourself, you're not going to be as effective in a board facing role.

Michael Koenig: So let's talk about, you do COO searches, you do CEO searches. What do you look for in a COO who maybe wants to move into that CEO spot?

Evan Grossman: So a lot of the data, and this is true of larger public companies, but a lot of the data suggests that COOs are becoming CEOs in a faster clip than ever before. Now when I think about growth businesses, which is we're all tailoring this question because that's really area of expertise There are two spectrums. One is value capture. The other is value creation, capture being go to market, creation being product and tech. If you are to be a CEO and to sit on top of the entire organization, you really do need to have experience ideally on both value capture and value creation. [00:40:00] And this is a little bit different than the trains on time COO, that person who's managing OKRs, KPIs, making sure the business cadence runs really smoothly. It's one thing to do that, but if you're not actually touching and owning the functions that create. Revenue and that drive revenue, you're going to be lost in a CEO seat. And I, there are very few instances in which I've seen a trains on time, COO at a growth company, step into a CEO seat. And so the advice that I give a lot of COOs who are incredibly bright, who see the business from every aspect is try to get some of that hands on experience in product or in go to market. And even if it means jumping down a level and becoming a VP of sales, or becoming a VP of product. That foundational training that you have, uh, insert COO who's incredibly bright and has seen this stuff, that translates really well into territories, comp plans, quotas. It can translate really well into the nuances of the business. For product and roadmaps, and so yes, you'll get some more hands-on experience, but that usually becomes a situation where then they become a CRO or a CPO and then they look even better as a CEO candidate than somebody who's [00:41:00] just been a, a functional lead in revenue for a long term, or a functional lead in product for a long time because they're cross-trained, if that makes sense.

Michael Koenig: Right. How interesting. And, some folks don't want to take a role that they feel like would be a step back, a COO may not want to take a role that's at the VP level because they've hit the COO spot. But in this case, look, that's beneficial. Play the long game is essentially what I'm hearing. If you want to make it into that next level or CEO, whatever your career ambition may be. Evan, this has been awesome. It's time for my last and favorite question. We've all had those moments where we've seen just something completely off the wall and we've just thought, I have never thought I'd see that. Do you have one you can share with us?

Evan Grossman: So I appreciate the question and giving it a fair bit of thought. I mentioned a couple times how tight knit this ecosystem really is without people realizing it. And I've realized that a couple times the hard way. I'll give you an example. I'll give you two examples, actually. The first was we were doing a CEO search for a company in Chicago. Chicago [00:42:00] has a pretty robust tech ecosystem, but it's not It's not the Valley, it's not New York. And so there are a couple of great companies you can look at. And we had two candidates go in to give their finalist presentation on the same day. We knew that they'd overlapped at a certain point in time to specific company. What we didn't know is that they were essentially best friends. And so usually you try to add like a 30 minute buffer in between presentations to avoid anything like this. And now we do it every time because we learned the hard way. But one of the candidates was leaving the presentation as the other one was coming in and they did not know that they were part of the same process here, our two finalist candidates. And so the, uh, the awkwardness that ensued led to the, the number two, who had worked with this other person for a long time as their number two, to essentially say, Hey, I know this person's more experienced than me. I don't know if I'm the right person to do this, if that's who you're considering. And then the more senior person said, Hey, I want to give this person the at bat to go run the company. I think they'd be great. And so we had a week of back and forth on calls, in some cases with the three of us, trying to figure out [00:43:00] what to do here. And ultimately, Yeah, ultimately the board decided the more senior person, um, had this level of depth and expertise that we needed. Uh, it was messaged very appropriately, but I'd never seen that before.

Michael Koenig: That's nuts. And one of the things that I love about this story though, is that both said, you know what, you should take this other guy. Like, that's incredible. Let's talk about selflessness. Let's talk about, you know, humility. Let's talk about, you name it, that is someone that you want on your team. So I could see how that'd be a hard decision.

Evan Grossman: Could not have said it better. I, I keep in touch with both those folks. Both have gone on to great careers, obviously but they are standup human beings and it really speaks to the culture of that company. And it also speaks to the thoughtfulness of, of the two of them. And we do not see that all the time. And to kind of dovetail into my other example, this is another small world environment. We were doing an earlier stage CEO search for an infrastructure company. And we had had candidates present. They were, they were the finalists. And then it was a Thursday afternoon. And I had called, there were [00:44:00] two candidates in the mix. I had called the first of the two that didn't get the job. And we're very timely with feedback. We always try to give candidates feedback as quickly as we can. So I'd called them to say, Hey, you're just not the preferred choice here. They preferred X, Y, and Z about the other candidate, uh, left it in a really good place. I then called the second candidate right after and said, Hey, you're the preferred choice for these reasons. It was a hard decision from the board, but they're excited to move forward. We'll talk about the offer. It turns out that they were on the sidelines together of their kid's soccer game. And so I had called one, And the second person knew that call was coming from me because they were literally standing right next to each other. And I got a call later on, the week later, telling me that, and I thought it was the funniest thing in the world. And they handled it incredibly well, but what a small world we live in, where two folks come from the same world that are, that are in this, their kids are playing soccer, right as I'm trying to deliver this information.

Michael Koenig: Yep. It's, it's the soccer sideline. You never know who you're going to meet. I have met some really fascinating people, especially out here at University of [00:45:00] Michigan in Ann Arbor. And you just get all walks, I got a fusion scientist. I got a fission scientist on the same sideline and just got to it was almost like sitting in the middle of a fusion fission type of thing. Anyways. Evan, this is awesome. Thanks so much for joining me. Where can people go to keep up with you?

Evan Grossman: I'm on LinkedIn. I don't post much, but it's out there. And then You're too busy. Yeah, exactly. LinkedIn's a good place to find me. And then obviously, Trude's got a great website. If you've got anything you need, you can see the work that we do across the board. We're international as well. So if you're listening to this and you're global please do still keep us in mind.

Michael Koenig: Thanks for listening to Between Two COOs. I'm your host, Michael Koenig, and a very special thank you to Evan Grossman for joining us. Tune in next time. Time for our next COO chat, um, between two CEOs and be sure to subscribe on Apple podcast, Spotify, or wherever you listen to podcasts. So you never miss an episode. Just visit between two COOs. com for more. And if you have a minute, please, please, please leave a review and let other people know just how awesome the show is. So [00:46:00] thanks for listening and until next time so [00:47:00] [00:48:00] long.