#22: Sarah Dorsett, Nanit

Welcome to From Startup to Grown up, the podcast. My name is Alyssa Cohn. I'm an executive coach, an angel investor and the author of From Startup to Grown Up. 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 22 and I am thrilled to have Sarah Dorsett on the podcast. Sarah is the CEO of N. Nanit is a suite of products that lets parents track the health, wellness and development of their baby so they get insights and advice about how their baby is doing. Nanit was founded by Tor Ivory, Andrew Berman and Asaf Glaser. Sarah Dorsett joined the company and took over as CEO in 2019 after having been an executive at Bed, bath and Beyond, Century 21 and bloomingdales.com Sarah and I have an incredible conversation. We talk about what it's like to step into the CEO role in the place of a founder. A complicated transition, but one that's gone very well At Nanit. We also dive into what it's like to be a first time CEO and the way she developed a robust playbook with a lot of different options and how to lead and manage. Sarah talks about how she built trust with the team and how she's created more white space to focus on bigger questions, which is a tough thing for so many CEOs and leaders. Sarah shares how to build your own situational awareness and how her role as a parent has helped her be a better CEO at work. This discussion is so valuable and you're going to learn a lot about how to grow as a manager and a leader. So please enjoy this incredible conversation with Sarah Dorset. Sarah, welcome to the show. I'm so excited to have you today.

Thank you so much. I'm thrilled to be here.

Great. So I guess I want to really start with your background before you came to Nanit. Tell me about your background and maybe if there were entrepreneurial roots at all inside of the background that you had in career wise.

First 10 years of my career were really spent in the beauty industry where I learned, I really got my training wheels there. And the second half of my career was spent in sort of big E comm. So I was, I was early in the days of building those sort of massive E commerce sites for big retailers like Bloomingdale's and Century 21 department store. You know, I partnered with Macy's when I was at Bloomingdale's and then Bed, Bath and Beyond. Bye baby, baby. So really spent quite a bit of time learning how to sell things online and leverage the digital space. And I would say that the reason I sort of fell into it, that wasn't what I wanted to do with my life when I was, you know, when I grow up. Kind of my roots as a child are definitely kind of half art, half science or engineering, if you will. So my dad was a big engineer and I spent a ton of time when I was a kid tinkering around with the stuff that he would build, especially when he got into computer science and engineering. And then my mother was always very artistic and I always thought I'd be doing something much more artistic. But somehow this is E commerce and building businesses sort of taps into everything, all that history.

So that's so fascinating that as a kid you could have sort of saw yourself do, you know, sort of sciencey things and artsy things, and then you came to Nanit. That's fascinating because it is sort of a combination of the things together as well as E commerce. So then how did you find your way to Nanit and what was your first role inside of it?

I ended up at Nanit mostly. Well, interestingly enough, I was selling nanites before I joined Nanit. So I was at Bye Bye Baby in Bed, Bath and Beyond, and Nanit was one of the products that was sold there. The world of baby monitors at the time was a little bit nascent, if you will. It had had kind of its roots in sort of your traditional monitors that sort of did what they were exactly what they were supposed to do, which was just give you a way to hear your child when you weren't in the same room with them and you largely use them just within your home. And then as these smarter monitors started to emerge, or the smarter technology started to emerge, I think in other devices like security, home security, Dev, and keeping in touch with electronics, of course, it started to make its way into the baby monitor world. And so I was approached by recruiter and various other investors for this particular business. My name had popped up because of, I think, both the understanding of the market, because this market is really interesting and it's very nuanced. And I had a lot of experience in the market and understanding this customer base and what people want in this market. And then on the other side, I think I also knew technology, so I understood what this technology could do, even though I wasn't necessarily a builder of it.

So then I think you were recruited in to be the president, is that right?

Originally, yeah. So originally I was. I was asked to be the president, which really Meant that I would take on the commercial side of the business. So the go to market strategy, all of the things that go along with, with, with really building a business and selling to a. And then about six months in, things were going really well and we decided to make some changes. So I moved into the CEO role. This was a VC backed startup at the time and the founder moved into a chief product officer role. So we did a little bit of shuffling.

Yeah, so of course I want to know about that. And as I think I told you when we spoke initially, I know Assaf, of course, and I know what a fantastic founder he is. And, and also, you know, I certainly know that about sort of his own growth journey. And then at some point this is not unusual, you know, at some point a founder decides this is not maybe for me to be the CEO. And it makes sense to have someone who has like more experience, especially in the commercialization and especially in maybe larger companies. So I'm curious, what do you want to tell us about that transition? Like how did that happen and what was the, what was the parts of it that were easy and what were the parts that were hard?

You know, transitioning into taking over for a founder led company is never easy. When we talked about moving things around, it just felt like it was a better fit. You know, I think, I think Assaf being one of the co founders, but the CEO at the time really wanted to stay focused on developing a really great product. It was a product led company that was, that was the reason it was so significant successful and that was where he really thrived, was, was sort of in that, in that role of developing products. And then I think he saw the benefit of having someone who had maybe a broader scope, you know, more strength on the business side, more strength on the marketing side. And that, that was, that would give him the opportunity to stay more focused. He was also more of an academic type of person. So I think being in a product role also allowed him to do more of the, the research side of the business as well. So I'd say from, from right fit and finding where you belong in a company, I think that was the part that made a lot of sense to both of us. I think one of the challenges is always, you know, when you've built something from scratch and you're so invested in it as a founder, it's hard to say, okay, you can have this now and you know, you can go do this and you can be the face of what I built, you know, and where does that sort of balance Come in. Like how, how do we still remain really respectful to him as a founder and give him the credit for what he built? Because it wasn't my idea, you know, it wasn't my technology when I came into this business. So really trying to find that balance between, okay, I'm going to be the CEO, I'm largely going to be the ultimate decision maker in this organization now. He no longer will be, but. And the rest of the company needs to understand that. Whereas, you know, so now we're both here together, but we're in these different roles, which is very unique at the, you know, the top of a company. And then how do we also. So how do we make sure the company understands that this is what's happening? That was probably one of the biggest things we had to, we had to adjust to. And then it was just kind of figuring out our leadership styles and sort of how to work together and, and what the final mandate for the company was going to be. So I spent a lot of time, I remember at one point the co founders were both in Israel at one point and I had them on the phone and I was whiteboarding with them and just saying, this is what I think could happen here. And they both were just giving me feedback, oh, that's great. Or this looks good, or how should we think about this? And so it was really a collaborative transition, I would say overall. But I will note that it is never ever easy. No matter what anybody says, it's never easy to kind of make that transition, especially in kind of an original founder led space. But it is one that's often necessary, just depending on the stage of the company and what the company needs. And if everybody is really committed to the success of the company, that's often where I think there is a successful outcome.

Yep, totally makes sense. And I think it's so honest just to say, you know, how could it be easy? It's not easy. It's complicated. There's complicated emotions around it and there's both like, the complication is like bittersweet. The notion of like on the one hand, probably someone coming in and doing something that probably is not my natural swing, or maybe I have too much of a realm to grow. But at the other time, it's like as you said, giving up your baby, so to speak. And in this case it's kind of an ironic thing. What kinds of conversations did you and Asaf have? Like, was there a moment of truth conversation you had where you really came to terms with or really hammered out together your leadership Styles and how you're going to interrelate. Is there one you should remember?

I think when we first. When we first started working together, it was very much what I loved was he was extremely committed to making it work. So. And so was I. So I think it was, you know, Sarah, you. You are calling the shots now. You know, help guide me, help figure out, you know, how we get this, how we get this done together, how we hold hands and link arms. And I think there was a. There was this aha moment. I remember where Assaf started seeing the opportunity, other opportunities that the company had, and so did I. And I remember him asking and saying, look, I would really love to be a part of this over here and no longer be a part of this over there, the things that I'm doing right now. And it was this very healthy conversation where we said, okay, yes, this feels like it's kind of. It needs a different resource, it needs a different lead. There needs to be someone new coming into this space who understands this, that and the other. And then there was a moment when we sort of said, okay, well, how do you see leadership in the organization? And because we were both CEOs of this company at one time, there were people in the organization who still remembered him as the CEO, and now I'm the CEO. And so we have these. These people who in some, in some cases are kind of. They've had both experiences. And we also had to sit down together and say, okay, whose style is really going to win here? Because. Because we need to do what's right for the company and right for the organization. But we can't have two people who have had this title making decisions about what the ultimate culture of this organization should look like. And at the end of the day, the one sitting in the CEO spot, which was me, had to say, it really needs to look like this, or at least we need to go down this path and if it doesn't work out, we can make a change. And that was another factor in the decision to say, okay, maybe it is time for me, Assaf, to. To step aside and sit on the board and, you know, and manage from a distance and see where you take this thing. So that was another big transition in the company when he finally said, okay, I'm just going to move off from, like a line role and just sit on the board. So various transitions. That isn't always the case with a lot of startups. A lot of times it's one and done. You know, a new CEO comes in, the founder steps Out. So that was not the case with Nanit. We very much had the, the love and commitment of him as a founder and we still have, you know, his co founders still in the organization.

Yep. And so it sounds like it was a process, you know, probably for better and for worse, it was a process. But there's, there's something about that glide path that was possibly helpful. And then you pointed out about the organization maybe possibly, like, definitely needing to know. I won't say being confused. You could, you can sort of share that, but like needing to understand what the new reality is. So how did you approach that? Different, like different time points. Right. The milestones and the communication you had to do to the organization.

Well, a big shift in the organization, I think was coming in and I think many startups are like this when it's small. Everybody's involved in every decision, so.

True.

And I come from a world where I knew there was kind of a turning point where the team gets just a little too big and you need everybody to stay focused on what they're doing. And you can't have everybody in every meeting making every decision. It just ends up. You almost end up not making decisions. So I think the first big shift in the organization when we changed into our new roles was, look, everybody, I value all of your opinions, but we're no longer going to have everybody in the room for every little thing. We are going to be able to move a lot faster if we get the right people in the room making decisions. So let's talk about that. And then how do we still make everybody feel like their voice is heard and they still have input because we're still small and, you know, I don't want to exclude anybody, but I also feel like we're not being very, you know, we're limiting our success by continuing to make decisions this way.

Right. Sarah, let me ask you specifically that. How do you both make sure responsibilities are delineated but also make everyone feel included?

So first thing was making decisions in a smaller group. So taking a few, identifying a few key players and getting in a room together multiple times and saying this is kind of how things are going to work. So the pyramid heads, if you will, and there weren't very many, and saying we have to try to make, we need to come to a decision. We haven't been able to get there. So now we're going to see if a smaller group can make this decision. So really making or helping the company adjust to really, really building TR amongst a smaller group of people who I felt were confident enough to make decisions, who are sort of craving the opportunity to make the decision and really leaning into those people first and then starting to do that with a few others in the organization. Interestingly enough, the company was so was small enough that almost everybody still got to be in one of these smaller pods making decisions. So at first it wasn't a huge culture shift where everybody was like, wait a minute, how come I don't get to be a part of that? Because they had their moment and they had their part of it. And then the other side of it, when we started to get a little bit bigger was, okay, how are you going to cascade this information down? This is one of those opportunities where this feels good. We've all made this decision. But the next step would be that you meet with your teams and help them understand and get some feedback and maybe and bring that to the group. And then ultimately we would identify, because in many cases there were just one person doing each job. We would identify moments when somebody who maybe wasn't always in those decision making pods would be invited in to share because they were the ones. We quickly realized that making decisions in a smaller group actually meant that some of the experts were left out. And not everybody who was in that small group knew everything because we just couldn't. So how do we invite people in? And then that became, oh, another mushroom group was too big. So it was kind of this constant iteration on, should this meeting change? How does this, you know, how do we shift? Should we. Should we break this apart into smaller things? Should the topics change so that all these people are not included? So it has definitely been an evolution over time. And I really encourage that because I don't think we could have scaled and grown the way that we had if we hadn't had some of the people in the room at the right time and then made some decisions to move past that and change how we were all making decisions repeatedly.

Yeah, I think that is so important because I think what happens is you set up a meeting and then, you know, regular standing meeting or a regular meeting of this kind of group, and then, you know, time goes by and things change, but that meeting stays the same. And everyone's now complaining about that meeting. It's not working, it's not effective, Whatever, whatever. But, you know, what's important is what you just said, which is to test and learn and to not be afraid to iterate and move away from what had worked for me in the past. Because what got you here won't get you there as you scale fast.

Yeah, yeah. And I mean, I think that that holds true for almost everything in an organization. I find myself almost on a daily basis saying, do I still want to do this thing right that I've been doing for the last three years, or was I doing it better two years ago and should I revisit how I was doing it? So I'm kind of constantly kind of assessing what's going on. But I'm also very transparent, I think, with my team now. Whereas before I sort of wanted to be seen as the leader and, you know, and the decision maker and be respected for that because the company needed somebody to, you know, to lead it. But now I actually asked the question, like, do we like this meeting anymore? Like, are we finding any value in it? Should we be thinking of a new way to do it? Or does anybody have any ideas? Like, let's spend our time thinking about that instead of just reporting the news and not getting as much out of this as we could. If you're constantly evolving as a leader and learning from, you know, the past in your own company, you also have a much better shot, I think, at driving success because you're, you're sort of self evaluating along the way.

Totally. I mean, that's my religion.

Right?

Sort of constant personal and professional development. And I'm really curious for you, when you came in to net, I still, I would love to just hear a little bit about how you approach kind of your first day as CEO, like how you thought about that, what you, you did specifically. But then as you just said, how your leadership style has evolved in the years subsequent.

Well, interestingly enough, my first day at Nana as president was in Las Vegas at ces. And I highly advocate for starting your first day at a company at a huge trade show in Las Vegas. But when I transitioned into the CEO role, the interesting thing is it was a bit of a slow roll. So we had been testing the idea, so I sort of under the radar, had more of an interim CEO kind of approach with the investor base. So let me test the waters here a little bit. I'm a first time CEO. Everybody felt like, let me get my sea legs. And for several weeks actually, as we were going through the transition and making sure we were doing the right thing for the company and for the founders, we didn't tell anybody. So I was functioning as a CEO and learning and I was really, I think fortunate because, because no one knew, I was able to start to ask questions as though I was the CEO and, and Assaf was kind of Supporting me in that. Like, let's make sure Sarah has this information and. And, you know, and let's invite Sarah into this conversation. So able to learn before we actually made the official announcement that I was the CEO, I would say that my very first day when I made that transition, it's not the first time in any company where I've moved into a new role. The first few days are often a lot of FaceTime, so spending a lot of time, starting with your direct reports. Okay, you're now reporting into me. How do you feel about this? And just kind of getting to know everybody a little bit differently. Even though I'd been in the company for six months, so everybody knew me already, but now in this capacity, I think, frankly, when I started as the president, I was probably a bit. I came on a little strong anyway, so. So people probably didn't, you know, didn't. Didn't see it as a big. A big shift.

What do you mean coming. What did you mean coming on a little strong?

I think when I came into Nanit, I just immediately knew what I wanted to do, and I felt that way about a lot of roles that I've stepped into where I just have this sense that I want to do this. And oftentimes it's just a couple of decisions I want to make. It's not I want to change it all. It's. There are two or three things that I really want to get done and I really want to do. And somehow it's worked for me. You know, I found the right people and said, you know, I really want to try this. I really think there's success in this, and I sort of sell it in. And that's really been the key to a lot of my career success, is just identifying a few things that I can rally around and get alignment on so that everybody's sort of focused on that and instead of focused on managing through change and all the emotions that go through everything. And I think that's really sort of what happened with the CEO role too, was I had, like I said, I had spent a lot of time with the founders kind of identifying a plan for the future. So that when we. When we announced that I was the CEO, I would be the CEO of the company, I could also roll out some key initiatives and some plans.

And so that's. That's fascinating. I appreciate that you had the slow roll. And also I appreciate that, you know, you're reminding me of Robin Matlock, who was on this show, who was a marketing executive, and she ultimately became the CMO of VMware. And she talked about having to kind of re enroll people around her. Even though it like she just same company, stepped into a new role, had knew the same people, everyone knew her, but actually it was different. And so you have to sort of promote yourself and have a new kind of relationship with all these people who used to know who you, who you have known for a while. So that's very interesting because it's akin to what you're talking about. And can you relate to that?

Absolutely. You know, when I was almost on my roles, in my roles at Bloomingdale's, I stepped into various roles where I would have the same team. You know, it might not be bigger, I might be absorbing other functions. But now my role is, is different, you know, and same with Century 21 department store and coming in. And I was given more responsibility throughout the years and my, my title changed over time and so you know, I would, and I would always have the same people but then a new group too. So it was always that shift. So I can absolutely relate to what that looks like. And over time I have changed how I approach that transition. So I've learned in different ways. Each experience has taught me something different. But I'd say that every, every culture is a little bit different. So sometimes you have to work a little bit harder on what it is that you're going to say and how you're going to present yourself in this new role. And other times it's, it's a bit more fluid, a bit more organic, a bit more natural and, and, and you just sort of have to find the pockets where you need to, need to give a little more attention and love.

Yep. Oh totally. And so as you've now progressed in the role of CEO, how has your leadership style changed? What specifically have you done differently? How have you experienced yourself differently?

Well, I think it's twofold. One is working for sort of a high growth startup. You almost have to be committed to change all the time. I've always been a lover of change. So I think being in the E commerce world, that's one of the things that I love so much. Anything in technology is constant change. So you get sort of obsessed with it. So that embracing change was always something that I did. But what I started to identify in the CEO role and as I took on bigger and bigger sort of leadership roles even before this one was I can't just be one type of leader. So whereas I used to have in my, in my, when people would ask me that Question. I'd be like, oh, I'm very collaborative, and I like, you know, leading from the back. And I love. I love promoting leadership at all levels. And I'd have all these, like, catchphrases. And then I started to realize that if that was a one size fits all approach, and especially at Nanit, where you have an office in Israel and you have this huge team of people that you don't get to spend very much time in person with, and then you're spending a lot of your time in person, you know, in the. In the U.S. but those two cultures are very different, and how do you bring them together and how do you think about them? You start to realize that as a leader, you actually have to have if, you know, if you want to be. If you want to be a good leader, which I think all of us want to be, you have to have a pretty good playbook with a lot of different options to tap into. So I sort of test a lot of different ways to motivate and lead people, I would say. And I think I've gotten much better at identifying, okay, what situation am I in right now, you know, and what type of leader do I need to be today? You know, are these guys, you know, are they able to make decisions on their own? Can I. Can I really push them and step away? Or is this a moment where everybody needs to. To feel that their CEO is here and supporting them and do they need some additional guidance? Because, you know, I'm just kind of starting to see the wheels fall off the bus a little bit, and everybody's getting a little shaky and uncertain. So it really is situational at this point. I would call myself a very contextual leader.

That's very good. A contextual leader with a playbook of moves. What advice do you have for people if they're trying to build their situational awareness or, you know, their context, as you just said, and also build their ability to sort of feel the nuances of what is needed here. What advice would you have for somebody to build that level of context and nuance?

Oh, listen. Learn how to listen really, really well. Oftentimes I would find myself wanting to fill the void, like, fill the space. Like, you know, there's empty, dead space, nobody's talking, or somebody is craving feedback. You know, they just want you to give them the answer because they've just presented this whole thing to you, and the whole room is waiting for you to speak. And sometimes I just wouldn't because I just wanted to hear, like, who was going to speak up first and who was going to step in and fill that and start to talk. And in many cases, I think my advice would be, overall would be really focus on getting to know your team and building trust first and foremost. Because when you start to ask them to do things that aren't as familiar. So when you start to step away from meetings and, you know, you know, you tell them, you know, please take this one without me, or I'd love for you guys to go off and make this decision and bring back a recommendation. I think that if the trust is already there and they know that they can come back to you if they get stuck or if they're uncertain, I think it builds a lot of confidence that they can go do it. And then over time, you end up starting to feel like you're not making every decision, you're only making a few kind of key, critical ones. And you can spend a lot more time kind of understanding what it is that people are bringing to you. And then you can start, I think, to guide them on what it is that might improve it. So I think the feedback that I get today sometimes is, oh, Sarah, we always think that we're going to walk out of the room and everything is perfect because we've done so much. And you always have that one other thing that you want, and you start to just get really good at that because you're not making all the decisions and you're not building everything from scratch. So my advice would be listen, build trust with your team and start to see if you can recognize when you can push them a little bit to go off and make decisions. And the other thing that I learned sort of the hard way, was not to expect the result that I wanted and to be very open to what they were bringing to the table, because I would always go in with the perception of what I wanted to see and how I would have done it. And then I wouldn't say anything, but I felt like internally I might have been a little disappointed, you know, in the fact that, you know, I wouldn't have presented it that way or I would have thought about these 12 questions and. And I started to teach myself to just be very open and listen and understand if their result could potentially also yield as good a result as I thought mine did, or even better, you know what I mean? So I really had to remove my ego, I think, from everything. And that takes a lot of just, I think, self discipline. So I would also recommend that just. Just, you know, practice that silence and, you know, take that Take that moment before you say anything to just, you know, sometimes less is more.

I love it. I want to highlight something else you said, because a lot of CEOs that I coach, and especially founder CEOs, but really CEOs everywhere, they feel like if they're not doing things, making decisions, stepping in, they're not doing their work like it's laudable, right? They don't want to just do nothing. They want to contribute, they want to do their work. But what you just said is so powerful. If I'm not making decisions, if I have the blank space that I could see something they haven't seen. And actually, as a CEO, that's actually your most powerful movement, really, your most powerful motion.

It really is. It's shocking, actually, because I am a doer. I am an operator times a thousand. I love doing things. And over time, my team, as I've built trust, I've sort of. I've encouraged those moments and given them the space to say, sarah, stop doing that. Sarah, please don't touch the website. Sarah, please don't go in and tinker with my calendar. Sarah, we will tell you when it's ready. And I have people who've worked with me for years who know how to do that. Sarah, I just am not going to tell you yet, because I want it to be a certain way and give me one more day. And I've used those people to help coach newer people so that they can feel really comfortable saying to me, I would like to own this. Sarah, I don't want you. Even though you seem like you really want to be involved, and I don't want to take it away from you, I want to do it. And I love when people come to me and have that conversation. But on the flip side, what's really nice is what the team starts to do is they start to. Because they own it, they start to bring you more. And when you have that space, when you're not full, when you're meeting, you don't have 14 meetings a day, you can actually open up whatever it is that they delivered to you, whether it's in a PowerPoint or an email or a Slack or whatever it is, and you can read it and actually let it, you know, let it sink in and digest it a little bit, and then maybe ask a really thoughtful question. And then as they get even better, what's my favorite thing now is when I get to just say, great job. That is amazing. You know, like, that is excellent progress. I can, you know, you just. You've really caught on to what the goal is here. And, and all I have to do is offer encouragement. And that's probably one of those. One of my favorite things to look for is where can I just not give any more feedback and just say, great job, team. You're doing amazing. Keep it up.

Yep, I love it. That's so great. Now one thing that you've said in other podcasts is that you bring your mom to work every day. And I'm so interested. How does your role as a parent inform your leadership style?

Oh, my goodness. Well, in some cases, I feel like I have to really not be a mom just because I will treat my team like kids. So I have to remember that I'm not, you know, giving life lessons all day long. And, and sometimes I think I slip a little on that one because I'm so used to, you know, trying to figure out how to keep my kids on the straight and narrow and, and then it just like glides right over to work. But, but I would say that one, I'm very lucky that I work for a family company. So a lot of what I experience I get to actually bring to the product itself. And we get to have conversations every day about that, which is something that's very valuable for this particular role as a mom. But then the other piece I think that I've maybe mentioned before is I reflect a little bit more. I would say I'm much more self reflective on kind of of what's happening. I think a lot of this conversation today probably represents that, I think a lot more about what impact I am having and how what I say might just like with your kids, like if you say something and you think, oh, maybe I shouldn't have said that, that probably wasn't the best thing or, you know, or I'm being perceived and just, you know, your kids absorb you like a sponge. And so I know adults, not necessarily the same way, but it is, is, it is. Especially if you're, you're the CEO of a company. You know, everybody's looking to you no matter what, even if they don't spend any of their time with you. The minute you're visible, everybody's waiting to see what, what is she going to say? You know, and that happens everywhere. It doesn't matter who, it doesn't matter what company you're in. If, you know, if this, if the CEO has something to say, most people are going to, you know, perk up and, and listen. And I think that being much more aware of the impact that what I Say, has how I present myself publicly, how I treat, you know, the people around me. And the company has definitely been very influenced by what I've experienced as a parent. So big shift. Whereas I think before I was just a. I loved being part of a team, and I was just a. I just loved making stuff, and that's how I came to work. And people reacted really well to that. They loved that. But then when you had to start to say, I shouldn't be doing everything and I need to be, you know, more of a leader of leaders, you need to. There's definitely a benefit in taking a step back and evaluating how your day went and what you thought your impact was and where you might have a little cleanup to do.

Yes. So reflection is so important and sort of looking and I think also just acknowledging, like, that didn't go so well. The good news is that you often get a chance to make up for little mistakes you made. But the bad news is, to your point, you know, CEOs are always under surveillance. Everyone's watching you. It's always showtime when you're the CEO. I think that's the way it is. What, you know, on the topic of being the CEO, what do you like best about being the CEO and what do you like the worst?

What I like best has always been. It's never changed. And as a CEO or not, has been discovering what people are capable of. For me, you know, the most exciting thing is to either I have an idea or, you know, large. Mostly it's. It's. It's. It's the group having ideas. And I love being surprised. So my favorite thing about being a CEO is how many people come to you with amazing stuff. You know, just really, really great thoughts and ideas and things they want to try and things they want to do. And so you get to spend your whole day if you're in a company where you embrace that, which is because I love it so much. I do. Oftentimes, actually, that's a big health measure of the company, too. So if I'm not hearing from people, if people aren't bringing me new ideas, and a lot of what we're talking about is not things that we're proud of or excited about, then I pay very close attention to, okay, we need to make a shift now because something is going on, and I need to pay closer attention to how we find our way back to that excitement and that energy, because that is my favorite part of being a CEO. So that is a little bit selfish when I say that working for A VC backed startup. My least favorite part is probably making sure that the company stays in business. So it's different from other roles where you do have a bit of a safety net. Even though I felt like I often built built companies within larger companies from scratch where nothing existed before, there was a bit of that net underneath you because the larger company could kind of hold you up. This is sort of one of those you're swinging without a net scenarios. And as much as I feel like I sort of thrive on the excitement and the risk that that brings, I also every day remind myself that there are, are a lot of people who, you know, who care about the paycheck and what that means for their families. So I would probably say that that's the most. Well, it's maybe not my least favorite part. Probably the part that keeps me up at night if I'm trying to tackle a heavy problem.

Yeah. You mean it's like the most stressful in some ways. Yeah. Yep, I can see that. Sarah, what advice do you have for executives who come in and are replacing a founder? What suggestions do you have to make that go well?

It really depends on the scenario. So in some cases I think there's a clean break where the CEO comes in and oftentimes maybe doesn't have a lot of contact with the founder. There's just kind of a, okay, come in and that founder needs to head out. So if that's the scenario you're in, largely there's two scenarios. One is that one or the one where you really collaborate. I think the one where you come in. I guess this might apply to both the one where you come in and there's sort of that clean break. I think the thing I always advise first is to set expectations. One of the, I just, it was a trial and error early on where I sort of, of did that as just like a fluky thing, not, not as a CEO, but way back several companies ago where I just had expectations. You mean? Yeah, where I just, I just came in and I said I'm going to do a PowerPoint about kind of what I expect and it's going to be really simple and really easy and I'm going to try to make it fun. It's going to be four whole things, you know, that everybody. So that everybody just knows where they stand with me, you know, that if they just toe the line on these, these simple things, they'll probably be successful. And I just had this idea in my head of what those could be. But I think coming in and transitioning into that role, you have to do a lot of caretaking. I would say it really depends how the transition works, because in some cases, I think the transition happens with a founder who says, okay, I want to move out of this business now, but they have such strong ties with the people in the organization that it's almost, you know, there's that severing those ties. You really have to have to almost coach the founder or partner with the founder on how to make sure that everybody feels embraced. So really understanding what it was about that founder that was so important to the people who are really embracing or really struggling with the change. The other side of it, I think with a founder who may or may not still be involved in the business is also setting expectations. But in that case, I think there's more boundary setting than there. You know, it's expectations, but also boundaries. So saying, you know, in this case, even though this founder is sitting right next to me today, the decision is going to come from me. I'm the tiebreaker. You know, we're going to collaborate, but at the end of the day, the final decision is mine. And really working closely with that founder, if they're still engaged in the organization on a regular basis, to help the company understand where the decisions are actually coming from. So that you're not actually, you know, so that the company doesn't actually have two CEOs or, you know, two. Two heads of the company and potentially a fork with the decisions. Yeah.

Because that can be very confusing, obviously.

Yeah, yeah.

Anything else you would suggest in terms of, you know, the first few days or how you approach it or what you need to. How you need to toughen up, maybe, or how you need to maybe be more sensitive. Like what. Anything else in terms of. Of a mindset?

I think I remember having to. Having to do a lot of. A lot of learning early on, but also a lot. I had to sort of embrace what I didn't know. So there was a lot of embracing the unknown. And oftentimes I think sometimes I had to. And I kind of advise everyone on potentially saying, okay, I really need to. I don't know these 12 things, but only three of them are really important to what I believe needs to happen right now. So even though There are these 12amazing, you know, really important things, and frankly, there are 60 people who want you to focus on the 12 things, you have to figure out what are the three most important and how do you make the rest of the organization understand that you can't focus on these things on the Other nine that are so critically important. And I think one of the things that really helped me do that was to, I mean, like I said, I spent a lot of time with, with the people who kind of had the history in the organization and being really, really present and learning. And in many cases I had to plug holes and just look for resources, not only in the organization, but tap into my own network and say, listen, I need something here. I need to kind of figure this out on the emotional front. I had been fortunate enough to have moved into, like I said said, roles, new roles in other companies. So I felt pretty good about transitioning into that. But I remember every single role that I transitioned into, a new, a bigger role with any company that I'm with. I always, I sound like a broken record, but I sort of take stock before I actually make the announcement of how do I think everybody's going to react to this? What do I think is going to be, you know, the first question that they're going to ask and what have I learned before, you know, before stepping into this role and now that I self reflect a little bit. Almost every role that I've stepped into, I've had a little history in the company. So even in this case, I had a little bit of history so I could prepare for what I thought people might expect and what they might say. And the number one thing I did, like I said earlier, was embrace the unknown and say, look, I am not going to be able to solve all the problems tomorrow, you know, and all the things that you've been grafting, grappling with and all the things that you've wanted to do. But I promise you that I've heard them and in many cases I've written them down or I've committed them to memory and we will talk about them, but we will be successful, you know, if we, if we all are committed to what we know this company can do and just constantly kind of offering that encouragement to the team as we were managing through the unknown.

So, last question. What do you wish you had known.

Earlier on your own journey? I wish I had known earlier how to advocate for myself. This sounds like, I feel like it's such a woman thing to say, but, but I think really, you know, really early on I would just, I would be so overwhelmingly grateful for the opportunity and I think I still cherish that. I'm glad that that was my mindset. I was always like, oh my gosh, I get to do something else. It's a privilege to be asked to do these things, and I do think it is. But I think along the way I started to forget that I needed to also advocate for things that would help make me successful. Right. So whether that's, look, I'm taking on way too much. I can't solve every problem right now. In some cases, it was advocating just for compensation, you know, and trying to understand where I needed to be in order to feel like I could make the commitment that I was being asked to commit to. And there was almost no guidance, I would say, in my, in my role, almost every place I've worked, I've worked largely for men. Not that it's a man woman thing, but I think I watched men advocate and do a much better job of it than I, than I would feel comfortable doing. But back in the day and there was no coach, you know, in these, in these roles to say, no, you really should, you know, before you, you just go running down and thank everybody for this wonderful opportunity that you have, you know, take a minute and, you know, and really ask some, ask some questions, make a list of questions that could potentially lead to, you know, what would be maybe best for you as they clearly think that, you know, you're going to be, you're the right thing right now. But how do you feel about that? You know, And I think, I think that I probably put myself through a lot of pain and suffering by not knowing how to do that for a long time. I don't even know if I'm an expert at it today.

Well, your point about, you know, there aren't always role models around us to show us how to do that. And I think that the gender question is like, when you see other women, when you see men doing it, you don't always see yourself doing it. And so when you see women doing it, and that's where I think we need more of those kinds of role models and also put a plug in for coaches, for coaches who help people in all aspects. Sarah, thank you so much for talking to me today. This is so valuable and so useful and it's just wonderful hearing about your journey and it's. I know a lot of people are going to benefit from this, so thank you so much.

Thank you. It was a pleasure. I really appreciate it.

Thanks for listening to From Startup to Grown Up. 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, alyssacon.com.