#24: Carolyn Childers, Chief

Welcome to From Startup to Grownup, the podcast.

My name is Alisa Cohn.

I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode 24, and what a thrill to talk to Carolyn Childers, the co-founder and CEO of Chief. Chief is a private membership network focused on connecting and supporting women executive leaders. Chief has been on a rocket ship ride. After only 3 years of existence, Chief recently raised their Series B of $100 million at an over $1 billion valuation. Prior to co-founding Chief, Carolyn was an SVP at Handy. She led the launch of soap.com, and she was also a GM at Amazon. Now, I got to interview Carolyn live at Collision, the tech conference in Toronto, and that was super fun. You'll hear a little bit of background noise in this podcast. We talked about what it's like to have a successful career and then to get into your first role as founder and CEO and how vulnerable that makes you feel. Carolyn was also so honest about some of the clunky times she had with her co-founder Lindsay when they were first starting Chief and the breakthrough moment they had in their partnership. She also talked about how she handled it when many people didn't get their vision and how personal that feels when you are the founder. Carolyn and I also talked about how she learned to be a leader from sports and how she's grown as a leader as Chief has grown. We discussed how she handles the ups and downs of being a founder and a CEO and her mom's reaction to one of the most magical days she had at Chief, which includes the time that she interviewed Michelle Obama.

There's so much here.

So please enjoy this incredible discussion with Carolyn Childers, the founder of Chief. There's, there's so much here. So please enjoy this incredible discussion with Carolyn Childers, the co-founder and CEO of Chief.

Carolyn, welcome to the show. I'm so glad to have you.

I am thrilled to be able to be doing this.

This is so exciting. We, um, just to set the scene here, we are here at Collision, the, uh, conference, the tech conference here in Toronto. And we've known each other since, uh, probably March 2020.

I know, the fateful, infamous March 2020.

That's right. And we'll get into how we met and everything, but, um, we then spent some time together on Zoom and then we bumped into each other in real life. Here at Collision. So it's been cool to be here. And I was just asking you how you enjoy— are enjoying Collision. And it's like, on the one hand, it's busy. It's busy around here.

Busy. Yeah, very busy. There was this great phrase that somebody used at a dinner that I was at recently about like the increasing the surface area of serendipity. And that like something like Collision allows for that to happen. And I even feel like being here on this podcast is that. Um, so it's been fun to be here, and I hope to have more serendipity over the next few days.

I love it. That's a very good way to put it.

Definitely.

Good.

So I'm gonna dive in because, you know, my podcast is about the personal growth of, uh, founders as they grow into leaders. And you know what I'm interested in You were certainly an executive at startups and also in large companies before you founded Chief and became the CEO of Chief. And I'm curious, what was that like for you when you sort of stepped into the founding role, but also the CEO, CEO role for the first time? Can you sort of think back and remember what that was like?

Yeah, I mean, I think when you first start, I don't know that any founder really is acting as a CEO in early days. Um, so for me, like, the very first pieces of it were, you know, what is it like to be the founder now, the true entrepreneur? And I will tell you, like, still to this day, with many things that have happened over the last several years, that is still the hardest moment. Um, because I think for many people, they've done other things in their careers, they've had success, but all of that success can sometimes be attributed to other people, like the other teams or the other founders that started something. And so like, even though you may have been in a startup and it did incredibly well, there's still that question of like, well, was that the company or was that you as an individual? And so when you go and actually start it yourself, it is so like singularly focused on you that it was— I was so scared that like everything that I had done up until that point would be completely erased. Everybody would view the successes of previous to not actually be attributable to me, and that this was actually like the moment that would prove or not prove the career. I think that is actually not true, but that's what's in your mind. Yeah, that's what you think. And so I think it's one of the hardest times, and especially, you know, whether you're doing it solo, whether you're doing with a co-founder. I was, you know, you know, doing it with a co-founder of Lindsay. And I think it was the, one of the darkest times of us as partners too, because like we only had each other. And so it was a little bit of like us versus us instead of us versus the world. 'Cause we hadn't yet launched, you know?

Oh yeah. Well, that's fascinating. What, tell us more about that. What do you mean by that?

There was no, we had no team at that point. It was just the two of us. So like if you didn't agree on something, there was actually like no external validation, no internal extra person to get a point of view on. It was just the two of us, and it was the first time that we were working together. And we're very different people, um, but yet like share the same underlying values, which is what makes it work so well. So we were trying to discover how to work together. We were getting no external validation of any kind. That I actually think it's the hardest part as an individual founder, is the hardest part I think as partners. Um, and, uh, very glad to be out of that part of the journey.

Yeah, totally.

Yeah.

Actually, let me double click like a little bit on that with Lindsay. So it was just the two of you and you, you definitely, I, I, you know, from what I've heard and you've told, told, talked about this quite a lot, like you had this overarching sense of this is what we're gonna do and this is how we're gonna do it and it's all good. So that made sense that you were co-founders. But I wonder, how much did you talk in advance about how we're gonna make decisions, how we're gonna handle conflict? You know, what I call the co-founder prenup.

Yeah, I don't think we did. Um, I think we did a very good job around what do we want this to be, how do we want to divide and conquer, like what are your values, what are my values. So I think we were, we were very aligned on a lot of it. Um, I wish there actually was. You might have one of these templates. I know, but like, I wish I had truly outlined what and everything that should go into a prenup. And I think the one of the things that was like most interesting was actually our like ways of working, of just like understanding that about each other more so that we had a better understanding of how to support each other in different, in different periods of time. And I think one of the most important moments for us in our, like, early co-founder relationship was, um, I actually, uh, set up some time for us to sit down and say, like, what is the most important thing that I can do for you, and what's the most important thing that, um, you can do for me? And, like, for us to think about that over the weekend and have this conversation. And this says everything you need to know about Lindsay and I as two co-founders, because we come into this meeting And, you know, my things are like, I just need to know what you're truly handling. Like, at the end of our meetings, I need to, like, we need to have some type of summary at the end that says, like, this is what you're taking, this is what I'm taking. Like, we need to be just a little bit more disciplined in that way. That was my answer. And her answer was, I just need to know you're my friend. Wow.

Different.

It's so different. And I think that personifies what, like, makes it such a beautiful partnership, but what makes it really important in those early days in defining how you want to work together and what's important to you and all of those things.

Yeah, totally. You know, something else I do is a personal operating manual with, you know, really all executive teams, CEOs with certain executives, because to your point, we don't usually say upfront, hey, this is actually what I need from you, or this is actually how I work, or whatever, even just down to please don't call me, just text me, or please stop texting me. If it's important, just call me or whatever. Right?

Yeah.

And so I think that, that just sitting down and talking about that is super helpful.

Yeah.

So the two of you were together, you know, of course trying to develop the business model. Of course, that sort of, those founding days are very difficult. But then my understanding is that you got a lot of naysaying people who were like, no, this is never gonna work. So I'm wondering, how did you handle, you knew it was gonna work. And you went, well, you were hoping, right? Turned out to be true. But you and Lindsay had this idea, you were doing it, you had a strong advocate and a strong investor also. But how did you handle that sense of like nobody else sees your vision?

Yeah, I mean, it was, it was very interesting in early days where, you know, we hadn't yet started to fundraise and I was even going through a journey of like trying to find a lawyer to represent me and the company so that we could start fundraising. And even in like that journey of finding a lawyer, I got nos from the lawyers who were like, I don't think this is a VC-backed business. And I'm like, but I'm trying to pay you.

Yeah.

So there's, uh, there was a ton of, you know, early cynicism around the idea. Not that, not only about like, will this business be successful, but the way in which you were going and approaching it of like, should this be VC-backed versus, you know, other means of capital? And so there was a ton of that. And I would say like, I would love to be able to retell the story and say that like the entire time, like we had 100% conviction that this thing was going to be and should be the exact way that we had drawn it up. And I actually remember there was— we were out in San Francisco doing a bunch of the seed round conversations. And I remember going back into our hotel room and pulling up the seed deck with Lindsay. And, you know, we were like, oh, what do we need to change? We need to do this, we need to do that. And like the whole deck. And we had another meeting in like an hour and we were trying to like completely revise our vision.

Yeah.

In an hour before the next, before the next meeting based off of all the feedback we had been getting over the last, you know, several days. And finally, like, right at the very end, I was like, we don't have time. Like, we're going to do— we're going to continue to go into the next one and talk about it the way they were talking about it. And in some ways, like, I'm glad that we didn't have more time to be able to do it because I think it was getting in our head in a way that would have not only, like, made the business less strong, but I think made us as founders who are supposed to be passionate about exactly what you were building less passionate about that thing, um, because it came from a personal need for us. Um, and so I think the thing that I wish I had done more of is honestly like had that network of other founders that I could be like, and I got another no, and just like normalize it. Um, because it's— everybody goes through through it, um, and yet it feels very much like they're saying no to me, um, and it's about me, um, and so I'm glad that like we kind of settled into it a little bit more, but our first reactions were very reactionary, um, and, uh, found our, found our rhythm over time, but, uh, it was definitely— I wish we could say that we were like, no, this what we were building, we were always convicted. And now, like, we just raised our Series B and it was really fun. We pulled out our seed deck, the one that we actually officially got funding from, and we looked at it and we're like, things didn't change.

Yeah.

Like, it stayed true to like what we originally believed in. And that, that makes it all the more special.

Very sweet. And I think that's so powerful what you just said. Like, for, for everybody, if I had only known then what I know now, but you as a founder having to really be that vulnerable because it's about your business, but it feels like it's about you. And to really have this doubt, like, well, if no one's buying, maybe we're not selling the right thing. Right? And so the sense of having to, to go through that morass of uncertainty and how sweet it is. And by the way, congratulations on that funding that you just landed, naming you one of New York's newest unicorns, I might add.

Yep.

So it is very, I'm sure, very validating. But I think sometimes from the outside it looks like, well, of course they figured it all out. Well, that didn't feel that way early days, right?

It really doesn't. It really, really doesn't. And I think, you know, we had, it was, we had an all-hands right after to like announce the fundraise. And I remember saying to the team, like, it's actually in some ways those like early nos that makes everything more special now. And for the team, and I just think we have an incredible, incredible team that is behind Chief. And I, it actually like, I got incredibly choked up in that moment because I was like, it just makes me that much more appreciative of all of you who said yes to coming to Chief as team and employees because it wasn't always a no-brainer or easy thing, you know?

Right. They had to believe in it. Yeah, right. Yeah. So just remind me, how long has Chief been around?

So Lindsay and I started working on it in 2018, but we officially launched in 2019, the beginning of 2019. So, okay. Really, like, 3 years. Yeah.

And so— Pretty ginormous growth for you.

I mean, it has felt like a roller coaster because it's also the kind of craziest 3 years that a lot of companies have gone through. So—

I don't know why you say that, just because it was a global pandemic. So yeah, I want to talk about both those things. I think first I want to ask you, for you, in this short 3-year period, if you think about where you started as a leader, could you talk about some of the things that come to your mind when you think about how you've personally grown as a leader, as a CEO?

Yeah. I mean, I think for me, a lot of what defines me as a leader started because I played sports my whole life. And, you know, a team, a sport team, is pretty small in, in size and very deep in relationship. And so like my definition of leadership has always been like, well, you know, you work right beside each other and you're, you know, doing wind sprints next to each other. And, and that very much plays out in early days of startups. And I think for me, what I have most realized as the team has grown is more things are happening in places that I can't be a part of. It's a really hard journey to go on because I love to be in it. And I think one of the biggest things that I realize, especially as I have just an incredible senior leadership team around me, is that like sometimes that style of leadership that actually feels like, "No, but I'm in the bunker with you," actually comes across as like, "I don't trust you to be in the bunker alone." Right.

Right.

Which I didn't realize. And, you know, the feedback that I would get is that, like, I mean, I trust Carolyn, but I'm not sure that she trusts me. And I was like, are you kidding? I think you're fantastic. Like, what? What? And it was that because, like, my style of and what I know is that, you know, I never want to ask somebody to do something that I wouldn't do right beside them.

Right.

But I would also go one step further and be like, and I'll be right beside you. And they're like, no, that's not how this works. And so I think for me, it has been an ongoing evolution of how to create that level of mutual trust and to show it in the ways that are needed and to move into a place that is more around how do I create the right parameters and the right, like, broader framework and understanding and vision of where we're going.

Right.

So that I don't need to be in that bunker with you, which has been kind of a fun journey, but a hard journey, especially because, you know, you, you're going through that evolution, you're trying to start to do that more, and then a pandemic hits and you're like, okay, well, now I need to kind of go back in the bunker.

Right.

And to have to have a little bit of that ebb and flow and have the types of relationships that are okay with that ebb and flow where, you know, when you're in hard times, it's not about, you know, uh, decision by committee. It's around alignment around the decision that you made. Um, and so it's been interesting of like trying to go through a normal journey of what, uh, leadership looks like at a startup, of going from, you know, a small number of, of employees to hundreds. And, you know, uh, and at the same time going through a bunch of external factors that are changing even what you should be doing. So there's a lot of, of inputs that are coming in that, uh, you're kind of muddying through and hoping that you get it right.

Yes. And by the way, it's happening fast.

Yes.

Right. Yes. And they don't always have a lot of time to step back and reflect the way one would hope that one could. Right.

Yeah.

So good. So yes. Um, March 2020, that was a time that was quite a time, especially in New York, which is where we are.

Yeah.

And where we live. And, um, I'd love to just hear your thoughts about kind of the first days of that because, and just to clarify as, or, or to emphasize for everybody, Chief is an in-person experience, right? You had Clubhouses, you had plans for Clubhouses, you had people getting together. It was very, it felt to me very much in-person. So tell me what that was like when you initially realized, well, in-person is not going to really be helpful. It's not going to happen for the next 2 weeks, which turned into 2 years.

Yeah, I mean, I think there were so many things that were happening all at once. Um, obviously as an in-person business, we were at the very top of all of our investors' lists of what's going to happen with this company. But like, at the same time, you had a whole team who was worried about their personal safety, was worried about their job security, given we were also on the top of our investors' lists of what's going to happen.

Not in a good way.

Not in a good way. Not the top of the list that you want to be on. Right. The like, question what's happening here category. And so I think for me it was like, I am people call me a bento box all the time because I was like, there's so much happening, I just need to like break it down into the most important things that we could possibly be doing. And it kind of, you know, broke down into 3 very discrete things that we just had to do as a company and I had to do as a leader. And, you know, first and foremost was about the team and making sure that everybody was safe. Secure, um, could be set up from home to work if they needed to. But more importantly, just, you know, had a right cadence of communication. And we went to really regular, uh, all hands, uh, that like sustained for way too long. Like every week we did all hands until like a month ago. Um, and, uh, but there was just like that need for this ongoing communication and how do we support each other through this. It was wonderful to see the team come together where like we actually had like a summer camp for, for the kids of our, of our team, where like somebody else on the team would do a Zoom playdate for everybody else's kids to just support each other. So it was just like a really special moment. But that was first and foremost of like, what does the team need? The second category was like, do we have the capital? Um, and we actually went and raised it, you know, a little off of our Series A just so that I could sleep at night. And then the final was, okay, like, now what does this mean for our members and how do we pivot the business so that we can still be there for them? Because they also, I mean, Chief is a membership of senior executives who are also going through all of this. And so the amount and of support that they needed of navigating their kids being home from school, not having any idea when that was going to come back, if that was going to come back, trying to lead their teams. A lot of people were going through furloughs in those early days. It was just like the hardest. Um, and so really trying to figure it out across all three of those things. And where we talked about before of like those early days being the darkest, in some ways this was actually like the one of the most proud moments I have ever had in like the team and us as a business where, you know, we pivoted everything over to virtual engagement, went up across our member base. We added new services, we added executive coaching and gave everybody free sessions because they needed it. We added a hiring board because people were looking for new positions and people were letting people go within their teams and wanted other people within the community to know about it. And so the, just the amount that this team accomplished, all while also having their own, you know, personal journeys around an uncertain time, I, I was so proud of that team.

So that is amazing. Yeah. And, um, I'm just reflecting how I spoke on my podcast to Elon Twig, who's the co-founder and the CTO of TripActions. TripActions, a travel company.

So an easy time for them.

Exactly. Exactly. And what he said was we created 70 new features because we listened to our customers. Yeah. And during this period, like if they're not gonna travel, fine. What do they need? Sounds like you really were finger— how did you set up your company and how do you have a culture of being so nimble? Yeah. You know, because you had your roadmap, this was a massive change, but how did you actually get into We're listening to our customers, what they need. We're being smart and just sensing what people need. And then we're able to implement these very quickly.

Yeah, well, I think one of the beauties of Chief, I think a lot of— I've been at other companies and, you know, you struggle to get feedback of like what, what's happening, what's not happening. Chief never has that problem. You know, we've got 15,000 of the most powerful women across the US. Who know what they want and feel like they're on that journey with us of like, of what Chief should be and could be and want to be a part of that journey and want to. And so it was very easy to, you know, know exactly what they were going through, how we can be there for them. So that part I think was easy. The hard part is then we were still a very small team. I think at that point we were 30 people. Wow. And so that's kind of, you know, even just going back to the leadership style, that's when it— the way that you become nimble, in my opinion, in those early days is that the, you know, debate and commit became less about a debate and more about a, okay, here are the things that we need to accomplish and got into a little bit more of the like directive and cut out what is a beautiful process of collaboration and like it can make things that were good great. And there's the right time for those things. But in March 2020, it became much more of like, this is what we're going to do. This is what you need to get and accomplish. And we just got into that mode really effectively. And I think more, most importantly, every single person in the team just had so much such great alignment and desire to deliver in a hard time for our members. Mm-hmm. Um, and I think being a mission-based business, mm-hmm, we have an amazing group of people that have, you know, galvanized behind that mission, that it wasn't that part, the, the motivation of that wasn't hard. It was more about the clarity of what are we doing, right? That had to be really—

and, and I think, I think you're absolutely right. At, at those moments, those real kind of crisis those moments, you know, Ben Horowitz calls it a wartime CEO. And whether you like that language or not, it is like a moment of truth. The CEO really has to be clear, like directive. You could say, you know, what that really means, but actually the clarity is so important. But I'm just curious, so like, you weren't talking to all your members though. You must have had mechanisms for people, right, to give input, like, oh, these people are saying this. And so that helped you figure out, oh, therefore we need to do this.

Yeah. Um, yes and no. I mean, I, I talked to our members quite a bit, um, and especially early days in when we were in a physical space in a club, like you were having direct conversations. Um, but yes, it was definitely, um, you know, we have an amazing member experience team who, um, were kind of the eyes and the ears of all of it and You know, we paused all of our memberships so that, you know, people didn't have to renew. Like they were just a part of Chief and we were going to like see this time through together. And we had a ton of community events where I and the rest of the team could be there and listen to what's happening. So I'd say what was important is that everyone on the team was was hearing and seeing and understanding what was happening. But it also was, you know, not the hardest to see also, like, what do people need right now? Oh, they're going through a bunch of furloughs across the entire country. Like, you know, what might be helpful to an executive is someplace for them to share the people that they need to let go from their teams, but are— that are still wonderful people, and they want to find them a home, as well as they might be one of the people that is on that list and looking for a next big.

Right. So, right. That makes sense. So now we're, we're not necessarily past the global pandemic, although it's maybe unclear, but certainly, you know, there's a lot of markers of Chief success. So with your funding raise, your valuation, that's wonderful. I personally speak to so many Chief members who love Chief and love their coaches. I mean, really, you've created such a beautiful community. You should be really proud of that. And then like, it goes that thing everyone on LinkedIn sees. People say, oh, this— I just got accepted to Chief with that beautiful sweatshirt. I was lucky enough to speak at Chief, so I got a swag sweatshirt myself. It is wonderful. So listen, it looks amazing, right? But I know I, of all people, know that startups are filled with drama and stress and very difficult times, even when the outside world is like, oh, Chief is killing it. And I'm sure that's true for you because Chief could be killing it all day long, but you're still making tough decisions and bad things are happening inside of the company because they're just like, that's life in company. How do you personally manage that when the outside world— it looks so great to the outside world, but actually your day-to-day can just be very stressful?

Yeah, I, I actually, um, I feel like I'm going to answer this in a way that I, I wish I could have an answer that is like easily replicable for, you know, any founder out there. Um, and I'm unfortunately feeling like my answer might not be the easiest one to replicate because I actually, for me personally, I think one of the things that happened over the pandemic was we moved to a remote-first organization. You know, we have been hiring and we've been moving people all over the, the US and our senior leadership team is all over the US and it actually afforded me the opportunity to spend a bunch of time where my parents have retired to down in Florida. And I guess the like replicable part is it created the opportunity for me to like pull myself out on a regular basis from the like world that is startups and VC. And New York can become that, you know, like your entire calendar becomes like, I'm going to, you know, this VC meeting, that startup dinner, this, and like you're just in this like bubble of it.

It's very intense.

It's very intense. Yeah. And I think the thing that has allowed me to get through that period of time and everything that has come since has been like an actual, like, literal step out of that bubble. And I'm down in Florida where my parents are, and they'll keep you humble. That's right. But it means that I can go on a bike ride every single day. And listen to podcasts while I'm on that bike and just pulls me into like a completely different, like, reflective mind space. And so every single day something happens. I mean, if you fast forward to even what we were talking about of like March 2020, you fast forward and then you had the murder of George Floyd and all of these things that were happening of— and the social unrest that came with that. And almost every other, um, you know, sociopolitical thing that happened over this period of time, there's always something. It is never, never easy. And to me, I just like really try and hold sacred that like hour of getting on a bike, putting on a podcast that inspires me, and just creating a little bit of that space for myself. Mm-hmm. And I don't know that I would've been successful at that. I know I wouldn't have been successful with that if I had been in New York Um, through the whole pandemic.

Yes. Well, I can understand that the non-replica part is have parents in Florida and go, right? Be with them.

Yeah.

But the replica part is exactly like you say, carving out that time.

Yeah.

And you know, I, I talked to, um, Zvi Band from Contactually. He sold that company to Compass and he talked a lot about the need to divorce your identity from the company, for periods of time just to kind of maintain your own sanity. Yeah, yeah, yeah.

I will say, um, just to like put that in like in a funny story context, so when we were, we were raising our Series B, um, and like I probably had like the pinnacle of all days of we, you know, I'm signing a term sheet for a $100 million raise at a $1.1 billion valuation. I'm literally signing that term sheet TechCheck for a Michelle Obama event where I'm interviewing her. Like, that is the day, right? And then, you know, that was all over Zoom. Yeah. Um, so it wasn't in person. So like, pretty amazing day to have. Like, not sure how I'm gonna replicate that. Um, and then you get off the phone and my parents are like, uh, we're just gonna order some pizza. And I'm like, yep, that's my, that's my life. And then the next day I was flying coach, flying, going over to, to LA to, you know, try and get get a new hire close. Like, I think being a founder, you have plenty of humble moments, but it's actually really important that those humble moments happen because it helps to divorce some of that pressure of just like— and I actually remember it was a great story by like Indra Nooyi, who like is obviously CEO of a massive company at Pepsi. Like she would come home and her mom was there helping and she'd be like, you need to go and buy milk. We're out of it. And it's just like, it just helps put you back into this place of like, right. You know, I am, I am, you know, a part of this family is a part, is a part of my identity as much as anything else.

Right. Yeah. Right. So it also, by the way, broadens you. It's both that you're, it's so funny, of course the mothers are always the one, but also it just, it also broadens you. You're not just a startup founder. Yeah, right. Your other, your other things. By the way, what podcasts do you listen to that inspire you besides this one, From Startup to Grownup?

I do love this one.

Yes.

Oh man, I, I, there's a lot of them. So I loved your episode on the Tim Ferriss Show. I listen to that.

Thank you so much.

Um, and which is why I know that you have all of these, uh, scripts and forms and everything that probably has the, uh, founder prenup in there. Um, I listen to Pivot a lot with Kara Swisher and Scott Galloway. I listen to Masters of Scale. I listen to Adam Grant's Work Life, I think is the name of it. I could like go on and on and on. 20 Minute VC. Like there's—

I love 20 Minute VC.

Yeah, there's some— there's such good, good content out there.

You know, it used to be that we couldn't educate ourselves by ourselves, but now we can. There's so much great content. Content. I love that. Now, in your sort of leadership journey, and as you've gone through all this, I'm just curious, have there been some leadership myths that you've been like, oh, that's actually true? Like, there's some myths that everyone says, but it's actually true. And then there's some myths that you've discarded, maybe.

I mean, I think what, what most comes to mind for me, uh, this, this happened even as I was getting more senior in leadership, let alone like becoming a founder. I remember sending emails to previous founders, previous bosses, being like, oh, I am so sorry, am I allowed to swear on this? Yeah, this shit's hard. Yeah. Um, and I think the thing that has just become like most true for me is that it's better to be respected than liked, that like it is almost impossible to do something that is 100% the thing that everybody wants, um, and that like that can be really taxing and hard. And, um, you know, I think that there's often this like unfortunate perspective of, you know, people in leadership are, you know, um hungry for their own, you know, outcomes and everything. It's like, well, sometimes like there's no easy decision that can be made and sometimes like it's just hard. Yeah. And so I think for me, every step of this journey has made me want to go back and send notes to people and be like, yeah, I'm sorry I was a pain in your ass at that moment. I understand why some of these things are hard. Yeah. And so I think that that's been a definite part of my evolution. Things that like I think I am constantly trying to instill myself on an ongoing basis. Yeah, I said this yesterday when we were doing our session here at Collision where just the idea of like, don't let perfection get in the way of progress. I have—

it is—

that is a constant battle for me, um, as a, as a person. Um, and I think that, you know, I, I talk all the time to, you know, my, my board investors where they're like, you need to start planning for, you know, Plan B of what happens. And I was like, you guys need to understand, like, I have Plan D. Like, yeah, like, I've got all of that. Like, what I need and what I need to continue to, you know, push myself on is like, how do we continue to like push the envelope instead of planning for B, C, D? And I think that context switching of like that planning versus, uh, you know, creating that broader vision is, is something that, uh, is my ongoing journey.

Yeah. So how have you sort of worked on that? I think that, you know, all founders and certainly CEOs, they start and there's a certain kind of communication style and even like quote unquote vision style. Mm-hmm. Which is like, you know, it's for 8 people or for 20 people. But now how many employees does Chief have now?

About 250.

Yeah. So now it's like, ooh, it's no longer just, just you and Lindsay, right? It's no longer 30 people, it's 200 people, 250. How have you grown as a communicator and sort of focused more on the vision and like specifically, like tactically, what have you done?

Yeah, I mean, I think I'd say that there's two things that have been very clear for me is up the repetitiveness and down the complexity.

Yes.

Um, and that, you know, anything that we are presenting, that we are talking about, um, just making sure that it's in the simplest terms that it could possibly be in so that there's no ability for misinterpretation, for us all to be really aligned. And it is like actually a joke of like there's two slides that are in every single all hands that I present every single time that people are probably sick of that when I make a slight edit to, people are like, ooh, you like changed the color on that one. But it like, it is just the repetitiveness of making sure that everybody is really aligned on where we're going, why we're going there. Um, and so for me, I think the bigger the company gets, the increase in frequency and the decrease in complexity, like, really needs to be at the forefront of your communication style.

Yes, that is so well said. And then how do you think about that with your leadership team? Like, I think of the leadership team always as ambassadors, right? In terms of they're giving out your message, but also bringing back from from the team, kind of what they were saying. How do you think about communicating with them to keep everyone, keep them in sync?

Yeah, I mean, I think for me, one of the, um, really important differences that I've really tried to create has been there's a difference between, you know, a team of leadership, uh, team of leaders, and a leadership team. And I, and it's been really important to me as that team has grown that like that feels like a first team, like we need to be a team together and not, you know, a bunch of different functions and your leaders of your function. And we come together and talk, but that like we are a team and it's not always been easy because we are everywhere. You know, we have our CFOs in LA, our CTOs in Chicago, you know, our chief people officer is outside of Detroit. Like we're all spread. So it's actually quite hard to, you know, do that in a virtual setting to like, how do we ensure it? But the beauty of something like Chief is that we have access to amazing facilitators that can come and, and we try to spend a bunch of time on just like, how are we as a team and individuals as part of that team and how do we continue to bond and knowing that about each other I think just gives that trust that they are ambassadors of that same message, same message, and that they are aligned and feel a part of this. And, you know, I think honestly that is probably one of the most important things is just making sure that they feel like a unit and team themselves instead of having their own agendas, in which case, you communicate all different ways, they're still gonna say what they want to say the way they want to say it under their own agenda.

Right. Totally. So it sounds like you do work on the team.

Mm-hmm.

You know, by making sure you spend time together, probably in person and also on Zoom and using facilitators. But then also that gets me also to hiring because you can care about that all day long, but if you don't hire the right people who are willing to drop their agenda in service to the team to So have you thought about that differently over the past 3 years? What has changed in the way you approach hiring, especially more senior-level people?

Yeah, I, I do think that we have a distinct advantage, candidly, at Chief, of we are a mission-based business inherently that pulls people into our orbit that want to work at Chief, that are very likely to galvanize as a group around something is that mission. So I do think we have like a distinct advantage that way, but it's definitely a part of our recruitment process for sure, of, you know, how do we make sure that somebody that is coming in truly does display that. And I think it's, it's those classic questions about like, tell me a time when, and it's literally like, tell me a time when you didn't agree with the vision or the way in, but the direction in which a company is going. Yeah. And you can tell very quickly from that answer how much of, of it was a, I'm a missionary person versus a mercenary person.

Well, that's well said too. What's an example? What's a missionary answer and what's a mercenary answer to that question?

That's a great follow-up question. I would say like the The missionary answer to that is, you know, it was really hard for me because I really believed that this is the outcome that would be best for the company and our customers and our members. But, you know, I understood that, you know, it's better to be aligned and disagree or debate and commit, um, then, you know, continue to, um, to make those statements. But I also asked for the permission to come back to it at some other point when we had more proof points, to just say, like, I, I would really love for this one to be one that we can circle around on again. Um, a mercenary type of, uh, answer might be Well, that's why I'm talking to you right now is getting myself out of that. Yeah. They don't know what they have. Yeah. But I do think, or it is a, you know, even just like the more subtle answer I think to that is do they answer it in a way that like puts their team at the forefront of it of like, well, I knew we had to do this. I had to, debate and commit, but I really needed to make sure that my team and like going to the my team quickly.

Yeah.

Is actually a little bit of a signal for me. Yeah.

Yeah. Yeah. It's interesting because your point is you pick up these signals.

Yeah.

Right. And that's, that's part of it is the gut feel, but as it relates to the way the question, those questions are answered. Yeah. Yeah. That's very powerful. And now of course, like in all startups, you've had to fire people. I'm positive that's true. And then also, You might have hired the wrong people. How do you approach firing? You know, I talked to Matt Bloomberg about this. He was my first episode, and he really thinks deeply about the way he sets up a process for firing someone, which is inevitable. How do you think about that? And what are some, you know, moments that you've had which have been difficult but that you realize you had to part ways with somebody?

Yeah, I mean, I would love to— I need to listen to that episode because I would actually love to hear his process, because I think what has been actually universally true for me is that, and I am somebody, I am an operator at heart. I love a good process. And I actually think that it's very hard to process that type of thing. I think that creating one standard for every situation is incredibly difficult and actually not something that I have ever really wanted to do. That there's, you know, nuances to the person, there's nuances to what the business needs and all of those different things that like the universal is that I always want to treat somebody like fairly and with decency and, um, transparency, and that it's never a surprise. And so there's definitely certain things that I think are universally true, but like from a process perspective, I do think that it's actually sometimes okay to be— especially if we're talking about senior leadership, um, I think that sometimes like there's there's nuance that needs to be accounted for there based off of the individual, based off of the business, based off of a number of different things. But I guess, like I said, the universal truth is like transparency. And I think maybe I would add another one in, which is like to act with speed and decisiveness. Because what I have always said, and I say this to my team, is The second that somebody starts to talk to me about like, well, you know, I'm not sure if this is the right person. I'm like, you've already made that decision. Like you've, you've made the decision. You still have the human compassion there, which is great. And like, I want everybody to come from a place of human compassion. But when you're starting to talk about the line and you're like, I'm not— they haven't really crossed the line yet. Like the second you started to talk about the line, they probably actually are. And it's your human compassion that is actually like pulling pulling you away from that. And so how do you then get to a place of like being really transparent with that person? Um, have you been transparent with that person? Um, and I think it's one of the things that was most important to me as we set up Chief. I was very inspired by the, uh, Netflix book, um, the No Rules Rules, particularly around like their feedback, um, cycles and just how transparent they are with each other. And, you know, I hope that we have a very kind culture at Chief, but kind and nice are two very different things, and clarity is important. And so for me, like, the things that I most want to instill in every leader is that, like, if you're telling me first and you haven't said something to them, then we shouldn't even be having this conversation. And to just have that be a part of, like, the DNA of a company so that you can act with the, this, the speed and decisiveness that is important. And the other thing that I would just say that I have discovered from, uh, years of, of being in, in spaces where, you know, unfortunately sometimes you have to let people go for performance or for other things, is especially for performance, nearly every single time that person lands in a better right lot for them.

Yeah.

And that, like, we, we really struggle with it, um, but it's actually not only the right thing for the company, but oftentimes and most of the time it's better for them because they have an opportunity to go to a place that fits more of, like, the way that they like to operate and, um, you know, their skill set. So, uh, but it's never easy. Yes.

You said so many valuable things there. And importantly, if you're already asking this question, like, when there is doubt, there is no doubt. And I think that people have a lot of trouble with that, right? But you're also— your emphasis on transparency and also feedback culture is so important. And I'm wondering how you get feedback. So, you know, I just an hour ago had a meeting with a founder and he said, you know, whenever I come to the meeting, they clam up. Like, that's what it is, right? And that's normal. And you can be the nicest person in the world, but you're still the CEO and you're still the founder. How do you proactively make sure that you— your team is telling you what you need to hear and giving you feedback?

Yeah, I think that it's actually been a journey for me to even recognize that that's happening. Lindsay and I have gone on a little bit of that journey of like, we're the co-founders and now we're a senior leadership team. Like, there's a distinct journey that has happened for us as a company. And I actually think one of the like key roles that Lindsay still plays most for me is like the reminder of like, I'm in some of these meetings when you're not there, it's different, and then you're in there and it's different. And it's actually not something that like I recognize because I like to think of myself as approachable and like, of course they would say the same things when I'm in the room and not in the room. And so it's actually been really hard for me to even like recognize that. Um, and I actually think that's step one of this entire thing, is to recognize the problem, recognize that you have the problem for addressing the problem. Um, but I think that actually then comes back to like that, you know, um, senior leadership team rather than a team of leaders is— and particularly, um, I just think that I have this a wonderful chief people officer who is also very much that sounding board of, you know, what's happening that I might not hear and see of like the way people are feeling and operating and other things. That's great. And what I would most hope to do, and I don't know if we are truly successful at it, and we have our own podcast, it's called like The New Rules of Business by Chief and There was this one nugget in one of our episodes where just even changing the "Does anybody disagree with this?" to "Tell me why we should disagree with this," like actually prompting people in a way that's like, I am actively soliciting for you to tell me like, what, where can this go wrong? And just small little changes in phrase that do allow for, you know, the potential for the debate to happen, for you not to get a bunch of yeses.

I love that. Tell me what—

say that again.

Tell me why.

Tell me why we should disagree with this decision. I was so much more succinct the first time, but like, tell me how this could go wrong. Tell me like why this might not be the right decision, instead of going from an assumption that it should be a yes, but actually asking for somebody to be the dissenter. Yeah.

Yeah. Very powerful. Very helpful, actually.

Right.

When you sort of set that expectation for people and set a paradigm for we're looking for disagreement here, and then they build the muscle around disagreement. Yeah, that's great. Carolyn, Carolyn, just two more questions. What do you wish you had known earlier on your journey?

There's a few things that I would, I would probably point to. I think that from a hiring perspective, You can never move fast enough. It's easy. That's easier to say as like a company that has like had a really nice few years. But I look at, you know, some of the hires that we have made and I was like, oh man, if we had done this quicker, earlier, there's just such richness that could already be here that I know will be here over time. So I think that particularly as we went into COVID, you know, we had— we slowed down our hiring and even I wasn't spending as much time just meeting people for the maybe we will hire somebody in this, in this direction and just even starting to have some of those relationships. So I definitely feel like there's a speed of that that I wish I had done. But from a personal standpoint, I will honestly say the importance of trust in all relationships is something that, you know, I think I have, I have been fortunate enough to build with people, but it— I wasn't as like aware and focused on it as just like a thing in and of itself. Um, and even like those, that's those stories that I was telling you before of like my way of operating with people is to like, I want to be in the bunker with you, and that being perceived as, you know, a lack of trust and just like how important it is to like actually go and assess like your relationships, particularly with your senior leadership team and, you know, the people like that are your lieutenants on that team, like, and really critically look at it and say like, how strong or not strong do I think the trust is here? And how do I make those investments?

Mm-hmm. Good advice. Yeah. Yeah, that's great. That's, and it's a good, it's a good sense for you of like seeing where you are now and, and where you could have been maybe hopefully sooner and then hopefully take that with you.

Yeah.

So last question, what did, what advice do you have for other founders as they embark on their journey to grow into leaders?

Oh my gosh. So many, so many things. The number one piece of advice that I could give is to create an ecosystem around yourself that is not a startup ecosystem, that are the people that you can turn to when it's really hard, when it's a little bit darker, and you're gonna go through those. And to just have the ability to like lift yourself out of that place every now and then actually allows you to do it that much better when you go back into it. And I think so often we are like, I need to go and meet all of these people who are in VC and I need to like, and that is the ecosystem that you create around you. And I just think it's incredibly important to keep the other ecosystem that you probably have that isn't in that, that does allow you to come out of that bubble.

Yeah. And stay grounded. Right. Mm-hmm. Um, thank you, Carolyn. Such a valuable conversation. Thank you so much for doing this with me.

This was really fun.

I'm so glad we ran into each other. I did too. Here at Collision and, um, I just want you to know that I, I know people really benefit from this, so thank you.

Yeah, thanks so much. This was a lot of fun.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.