Adam Torres and Katy Trost discuss CEO leadership.
Subscribe: iTunes / Spotify
Apply to be a guest on our podcast here
Show Notes:
How do you build a healthy aligned organization that scales? In this episode, Adam Torres and Katy Trost, Coach and Advisor to CEOs, explore what it takes to become an exceptional CEO.
About Katy Trost
Katy Trost is a coach and advisor to tech CEOs in London and New York City. They partner with her to become more effective leaders and build healthy organizations while navigating the challenges of scale. Understanding the responsibilities and challenges that come with serving a company and its people, her mission is to support CEOs at Series B and beyond on their growth journey.
Her clients include companies backed by leading investors, including SoftBank, First Round Capital, Primary Venture Partners, Felix Capital, Octopus Ventures, Inflexion, Maven, and more. Katy is a coach and judge to Tech Nation Future Fifty and Upscale, Octopus Ventures, Founders Forum, Techstars, Harvard Alumni Entrepreneurs, PwC Fintech, and the Mayor of London Mentoring Program as well as an advisory board member of various startups.
Full Unedited Transcript
Hey, I’d like to welcome you to another episode of Mission Matters. My name is Adam Torres, and if you’d like to apply to be a guest on the show, just head on over to missionmatters. com and click on Be Our Guest to apply. Okay, so today I have Katie Trost on the line, and she is a coach and advisor to CEOs and founders at Series B level and beyond.
Katie, welcome to the show. Thanks so much for having me, Adam. I’m looking forward to it. All right, Katie. So we have I mean, that’s our audience. Lots of CEOs and entrepreneurs that are listening to this program. And I want to know how you are helping them and how you are helping individuals through your coaching.
So maybe just start off with a little bit more about like how you got into advising CEOs, because I don’t know about other CEOs listening, but I know I can be tricky and I know they can be too. How’d you get into that? I actually really love it. I feel like it’s my perfect client and I really just am so grateful to be able to do this work.
I actually started out as an exec coach in corporate America when I lived in New York City, 2017, 2018. And I got into the whole tech and startup ecosystem around the same time and I was just so much more drawn to work with entrepreneurs and CEOs and lots of early stage startup coaching and advisory and then in the past 5, 6 years, I feel like it’s just been lots of the latest stage tech companies.
Most of them go through hyper growth, anywhere between 100 and 1000 employees and yeah. Usually around the 10 to a hundred million dollar revenue, Mike, and very similar challenges on that journey from 10 to a hundred million. And most of them who are listening probably know exactly what I’m talking about, scaling people, scaling ops and building out the exec team, building out your, your board, et cetera.
So lots of challenges and obviously lots of you know. Opportunities and exciting times, but yeah, you’re kind of a little bit alone on that journey. And so I made that my mission. Let’s stick in the challenges a little longer because I feel like that’s the fun part. and what I do like is that you’ve also I know now you work primarily with CEOs that are at the series B level. but that being said, you did work with early stage in the past. So talk, let’s talk a little bit about some of those nuances and the differences, especially after that hyper growth, because it’s two different seats, right? Very much so. And oftentimes it’s not even the same person.
So if it’s a founder, CEO at the Series B, C, D they oftentimes really have to up level and CEO leadership is a big topic. So I often get asked the question, like, do you have a CEO toolkit? How do I know I’m a great CEO? and not my CEO leadership look like and what is it supposed to look like?
I have nothing to measure it. the big corporate CEOs and then obviously set up founders and it’s just very, very different. Before series B. So the C and a company is usually finding product market fit, getting their, you know, MVP, right? And then selling to the first customers and their whole go to market strategy.
Building up the core team, your first 10 to 25 people or so, and requires just very different very different skills and you just. Really try to get the baby off the ground and for some of them, it works for some of them. Obviously, it doesn’t. And once you have funding and investors really put tens of millions into your business, actually, this becomes so much more challenging and all of a sudden you have executives who’ve worked in bigger companies before, but you have to lead them.
How do you facilitate that? And how do you. Yeah. Yeah. Sure, they work well together as a team and you have a culture that can scale as well and you don’t just, you know, have 10 people in the office and everybody else is at home and you don’t really have that team spirit or you have a nice culture. Two performance cultures.
Usually I find the companies lean either way and it becomes really apparent once you hit the 100 people mark and the challenges on both sides can be quite, quite big and that’s usually when I. Supporting the founders. You said something interesting to me. You said many times, it’s like, it’s two different people.
Like, what do you mean by that? Like go further into that. Cause I think the identity portion of what a CEO goes through is, I mean, I could tell you at every rung or every zero, and I can’t tell you, cause we we’re not at that a hundred million. So don’t be involved by these listeners. I don’t want to know.
Emails coming in asking for things. We’re not, we’re not there yet. All right, but, but I do find the CEO mentality fascinating, even from the standpoint of who would want to do that at that level, like it takes a special person, so when you say a different person, like talk a little bit about the psychology side of things.
Yeah, totally. So I find that a founder is oftentimes much more successful being a visionary and entrepreneurial and, you know, just basically running through walls and whatever it takes and that inspire people and you get them behind you to support your idea and work for you. Like, how do you even get people to you know, to Put all of their eggs basically in your basket, and especially at the earlier stage, maybe you have 10 million in funding, but that doesn’t mean you’re going to be around in 6 months.
Right? So how can you convince people of your vision and really just have that excitement and just. Go forward and whatever it takes, a good CEO is almost a little bit like a celebrity. I don’t know if it’s the right analogy, but you have to have a personal brand internally and externally, and you you have to manage, right?
So you don’t just lead them and you, you have to bring structure and that’s not necessarily natural for a founder and for an entrepreneur. And that’s why oftentimes you get professional CEOs come in. Especially post a hundred million dollar mark, who can just take the company to, you know, two or three thousand employees.
It’s very, very different. And it’s interesting because I do work with a lot of late stage founder CEOs. And they actually always tell me, Oh, I just left the product development. I just, you know, really liked the building stages zero to one, or maybe one to 10. And then after that, I just, I just want to have a really good management team that can execute and that can, you know, drive.
Drive execution and drive the results through the teams, but I don’t really, you know, enjoy it that much. So I find them often going back to product development and to the, you know, maybe they have an innovation hub within their big corporates and and they just kind of hide their, so it’s definitely a different, different kind of skill set.
I so one of the things we do here is I run, and I personally run this, so per, it’s a, I work with CEOs, but not in the manner that you do, by the way. It’s, all on branding. So I run a personal branding accelerator, and I can say that from my end I look at things and one of the things that I find many of my, you know, cohort members, as I like to call them they struggle with is imposter syndrome.
With getting to, especially as they hit new rungs, like, I’m working with, you know, really. Visible people, let’s say and, and it hits everybody. And I always find that really interesting because by all means, when I’m the individuals I’m working with, I’m like, okay, they’re definitely more educated than myself.
They’ve definitely more like they accomplished in many different ways. But other than branding, which they’re coming to me for, obviously, but imposter syndrome, maybe creeping in as, as the CEOs from your vantage point hit these different tiers or different levels? Yes, I would say probably at that point they are kind of past that, but you do have a lot of pressure and you, you know, you have your investors who gave you hundreds of millions and all of a sudden you have to be that CEO and they need to have the confidence in you to.
Make a return, right? In the end, you’re almost kind of employed again by your investors. And if you don’t return, then you’re out of your role, basically. And the same with your team, right? You need to usually when things go wrong, you usually take the responsibility for it, right? When things go right, you usually let other people shine and you, you know, I appreciate them and thank them on LinkedIn, et cetera.
So you’re kind of the punching bag from, from many directions. I like your analogies, by the way, I think they’re great. They’re accurate. They’re accurate. And they’re, and they’re real. I appreciate that. Yeah. You are. That’s a, that’s what happens. Go ahead. Yeah. So it’s, it’s not, you know, and oftentimes people think that it’s a really great thing.
Title to hold, but I am not envious. I’m not envious either. I don’t know. I’m like, wait a minute. I do hold it and I don’t want no. Sorry. We’ll throw my employees. I do want it. I’m sorry. Hopefully they don’t listen. I will. Who knows? So, tell me about as I say that I don’t want it. Talk to me about building culture.
Let’s switch the topic. We all heard it, culture eats strategy for breakfast, right? You can have that strategy and you know, your, your business plan is very sound and and then you just don’t have a good culture and it just ruins everything because all of your attention all of a sudden gets drawn to personnel issues and.
Most of them HR cannot deal with. Most of them is really some something that needs to come from the top and cultures, in my opinion, definitely under responsibility of the CEO and the whole company is an extension of how the CEO manages and what the CEO wants to see. So I oftentimes, recommend to use values, not just as like, beautiful words on the wall, but use them as a management tool and your performance reviews and your one on ones and your town halls and just keep referring back to them and enforce certain behavior. Do you want to. Build a team culture, do you want to build a culture where individualism is more celebrated and you maybe have lots of individual contributors as well.
And that’s the management career path and just making it very clear what behaviors you want people to show at work it can, it can just. Make your life so much easier. And oftentimes people wait until it’s almost too late or they can’t ignore it anymore. Or there’s real issues that come up and they’re like, well, actually, okay, culture might be the reason why why this is cropping up and then they address it.
And it’s pretty hard. Like, so, or I should ask you is for that type of CEO that let’s just say, put some pack into product development or more on the product side and has that strong management team that, so that’s just one archetype. Let’s just say for that, is it, is it, is it, do you find that maybe that type or different types maybe struggle with culture more than others or.
No, I don’t think so. But I would say that oftentimes when you can afford a really good management team, and you get people from, you know, the, the nice Silicon Valley companies to join your executive team, and they’re very accomplished, what do you do? You give them, you basically have the keys to the castle, right?
And then six months later, you find out that you may be you can’t hire the wrong person. They might not be a good culture fit, but you kind of just turning your, you know, yourself away from it because you have to fundraise. You have to you know, do some firefighting and a different department. And so one person can just spoil the whole culture within a very, very short time.
So I would say it’s really what kind of behavior do you reward and who do you fire and who do you hire? And to just be really on it and make it very clear what the expectation is. I think it’s quite important. I probably would see a big difference between CEOs who have a different background. So somebody who has a management consulting background or a commercial background, they weren’t sales before, they have a very different personality than an engineer, right?
And so I find that oftentimes engineers are a little bit more On the humble side, and they don’t necessarily need to have the big presence and they usually don’t. Voluntarily build personal brand to stereotyping here, right? It comes with its own set of problems and oftentimes they’re not necessarily people people.
But I find that usually their leadership is quite genuine and sometimes the sales leader or the commercial leader has been different challenges and they might be a little bit too pushy or there might be a little bit too performance driven and they, you know, they’re kind of lacking this empathetic element of their leadership and the more conscious leadership style.
And so I think it’s more about having the awareness, where do I lean and how can I balance it out to, to make sure that people resonate with my leadership style. Yeah. And, and I’m all right with an understanding and I know everybody listening, come on, there’s going to be exceptions, right? Like that’s a given.
But that being said, I do appreciate your, your, your insight from your vantage point, working with so many leaders and kind of maybe even affirming some of the things that, you know, are actually true. Right. That we may have thought, but that now we know I’m curious in your end, what, like, what do you, and obviously we’re in again, doing a little bit more generalization.
I know things change. Right. But what are some of the traits that you think make an exceptional CEO? Oh my goodness. So many. It’s a big one. It’s a big one. It’s okay. We got some time here. Go for it. And again, I understand we’re generalizing a bit. We have to, right? It’s a podcast. We got to get, we got to get somewhere, okay, to the audience.
I love it. You know what? I think the way I would summarize it is a good coach. And it’s funny because I am a coach. Wait a minute. A good coach is going to ask me a question back. You don’t get to do that. No, you’re not. What do you think? No, I don’t think you go. So, I would say that the leader is a coach, right?
If the if the CEO coaches the team, and that means that they are developing their team. That means that they manage each of their direct reports in a different way. So they don’t necessarily have one style, but they understand how different people react or respond to. Different leadership styles and for some of them, they may need to take more time to just, you know, help them solve issues and hold them by the hand a little bit longer and other stages want to fly and therefore their leadership side with that person is very different.
So I find that training the CEO to, to become the coach of their team is usually in a, in a summary. And that’s what I would say makes a good CEO. And, yeah, I think sometimes you have to have this balance where you’re directive, but then also give give them autonomy. Right? So these there’s a great article on HBR.
I forgot the name of it, but it’s really about the opposites, right? Pushing people and, and really challenging them. And then at the same time, knowing that they that they can lead themselves as well. So. Yeah. It’s really this coaching mentality. I find that makes a good CEO. That’s on the leadership side, I would say on the, on the fundraising side of managing investor relations, which becomes very, very important.
I would say at that stage, you receive the you know, usually have an institutional board and you know, they just need to have a hundred percent confidence in you and I think managing that. Quote unquote team that boards very well and requires it requires, I would say, a different kind of leadership and a different kind of confidence to, to make sure that you’re, you’re good with the board because that’s that becomes very important because they can vote you out any moment.
Yeah, and I know we spent a lot of this kind of only so much we can get done on on you know, on a podcast episode, but we, we did leave some of this out, like talking about the investor side, some of the board side and those whole other topics that are super important with in relation to what you do and how you’re, and how you’re helping CEOs navigate those Sometimes choppy waters, but Katie, that being said, I know people want are going to want to follow up and learn more about what you do and maybe have some more of those more expanded conversations.
That being said, how do people reach out to you? The easiest way would be on my website. That’s katytrost, K A T Y T R O S T dot com. And you can find lots of articles there and resources and books I recommend. And you can also find my email there and reach out if you have any questions or if you would like to set up a call.
Fantastic. for my audience, we’ll put all of that information in the show notes. And speaking of the audience, if this is your first time with Mission Matters and you haven’t hit that subscribe button, I don’t know what you’re waiting for. Just do it. It’s it’s right there. Hit it. It’s all good. We have many more mission based individuals like Katie coming up on the line.
We want you to get this information. We want you to get their knowledge. Definitely come back and see us again. Katie. It’s been a pleasure. Thank you so much for all the work. You do dealing with those CEOs. That could sometimes be a little I’m gonna use the word tricky. So thank you. Katie. Thank you.
Thanks for having me.