Keith Cowing: 0:04

Welcome to another episode of Executives Unplugged, a show about leadership where we explore how to perform at your best, how to get the most out of your team and how to stay sane and enjoy the ride. I'm Keith Cowing, executive coach to CEOs and product leaders, and on today's episode I have the privilege of talking to Sarah Liebel, who is president and chief operating officer at Naya. She is an entrepreneurial operator with a multidisciplinary background. She has run organizations from product to marketing to sales to operations, and she has helped multiple founders in the tech industry scale their companies from early growth stage through IPO. She has learned a lot along the way and she shares much of that with us here on the show. We kicked off by talking about Paul Graham's essay on founder mode and when it's helpful for entrepreneurs or operators to get into the details and when it's not, let's get started. Sarah, welcome to the show. Thank you for joining me.

Sarah Liebel: 0:56

Thanks for having me.

Keith Cowing: 0:58

So excited to talk to you. We met 10 to 15 years ago when you were at Groupon in CorpDev and you've been through a lot in your career, seen some really interesting things, had some amazing leadership moments. One of the things we were talking about before we kicked off recording was this new founder mode discussion that's up and about and it really points at some of the different aspects of leadership and how people think about it. You've got some strong opinions here. Maybe we just open it up there. What kind of chords did this strike with you and how do you think about what makes an effective leader in a high growth environment?

Sarah Liebel: 1:34

I have a very hard time with that article because I think it is a false framework. I think it's really about good leadership and bad leadership, or subpart leadership versus great leadership. I also think it is very isolating to the founder and it neglects the concept of a team and a founding team. I spend a lot of time talking to founders of late because what I do I'm a multidisciplinary generalist and so people bring me in because I can be an operator who can help them scale. But I also operate like a founder and I'm really hands on and I'm really passionate. I resonate emotionally more to a founder than I do to. This is two years of my life and I'm moving on. I'm going to flip this company and one of the things that I've talked to a lot of founders about is there's people who you found a company and the point before scale could be three years, the journey of a company could be a lifetime or could be 15 years, and so you know that zero to three being the isolating moment and then coming in for year three, you know when you're at five, 10, 20, 50, whatever million dollars and taking that to a multi-billion dollar company is kind of like founder phase 2.0 is how I've been thinking about it, and so I think it's kind of discrediting the fact that you still need to operate like a founder with that hustle and that grind and that passion, because it's all about getting into the details. But I think the nuances is that with experience you often know which details to dig into and I find oftentimes in some camps the extreme, if you were to say, founder mode, where you're in the details of everything, you lose trust of your team who don't feel like they have any sense of empowerment or relationship with founder. On the flip side, you've got professionals coming in to scale business who don't spend any time and they say if you can't do your job, I'm just going to fire you and move on to the next because this isn't my job. I'm just going to fire you and move on to the next because this isn't my job. I'm just a leader. I think there's somewhere in the middle is the happy space.

Sarah Liebel: 3:26

What's really critical is this concept of accountability and being in the details enough to know what to hold people accountable for and how quickly to hold them accountable.

Sarah Liebel: 3:34

And it's really critical to make sure that you're making the choice of not being in the details just to be in the details or not creating whiplash speed just to have speed. So I find you know, on one end, more experience of knowing which details are going to be the biggest levers for growth can come with more experience. Same thing from a speed point of view knowing what is fast for the sake of fast and what is fast for because there's real macro impact that's requiring speed to market can come with experience. On the flip side, I've also seen operators where they are not in it enough and they are not passionate enough to get into those details, where they're delegating, where they're looking this as a two-year stepping stone to either liquidity or to another position. So I see both sides of it. I think I would much more focus on the issues around like accountability and speed and getting into the details, than putting it in a, I think, false framework of a founder mode versus a manager mode.

Keith Cowing: 4:29

A lot of what you're getting at is judgment of. How do you make judgment about, assuming you're passionate and interested in getting into the details and able to when do you do that? When do you not do that? And not all moments are created equal.

Keith Cowing: 4:41

I had an experience working at LinkedIn, where Jeff Weiner was one of the best CEOs I've ever worked for and he was not the founder, but he certainly acted like one, and Reid Hoffman treated him like one and he was in the details. He really was even when it became a public company. I remember one specific thing that he did that I found really useful is that he learned at a certain point in time that he would say something in the room and then he would leave, and all of a sudden, people scurried and changed all their priorities because he just said something. And he found out and was like that's not what should happen. You shouldn't have rechanged all your priorities because I said something in the room. And so he went back. He actually wrote a blog post about it, talked to the whole company about it and said okay, from now on I'm going to be clear when I talk in a room.

Keith Cowing: 5:24

Most of the time I'm just another opinion in the room and you probably know more about your product and your details than I do. And it's your call and I expect you to make the call. Take that input, but just as you would take anybody's input. And then there's another one that's a nudge, where I think that this is the right direction, but it really is your call and I truly trust you to make that call and I want you to and I want you to learn from it.

Keith Cowing: 5:46

And then the final one is executive mandate, where I do have that card and I have the right to play it and I will occasionally, but only when I think I have unique context and perspective or experience and there's really high value or risk or something happening where it's worth it. And that shouldn't happen most of the time, but it will and I will tell you which one it is. And if I didn't and I forget, then it's your job and your responsibility to ask me and clarify and that's how we're going to operate from now on. I think that really said a lot about leadership and judgment, of being able to have a conversation, to set expectations, that I will be in the details, but not everywhere all the time.

Sarah Liebel: 6:19

Yes, I love that it resonates so much with me. I have a tendency, I know as an operator where I can speak with a lot of feedback I've gotten from some colleagues in the past. I can speak with a lot of conviction and I can speak with a lot of confidence and even as an president role I'd be in the room and say something and all of a sudden roadmap gets changed. And so, very similar to Jeff, what I do is I'm very clear about labeling. So when I'm in the room with colleagues I always say I'm in curiosity mode or I'm in conviction mode. If I'm in conviction mode, that means I'm pushing for something, and then I think the step three on top of that is commander's intent mode, and so it's usually like curiosity, conviction or commander's intent when I work with my teams.

Sarah Liebel: 7:00

I also my career. I've spent a lot of time with founders and before working with a founder it's really critical for me to understand what are their non-negotiables. And so talking to a founder, usually working at some type of a present capacity, they may say 90% of the time. I trust you deputize you to make this decision, this 10%. This is where I have commander's intent, this is where my focus is, but I think a lot of this is around exploring those expectations up front, labeling them when you're in the middle of conversation. Otherwise you see whiplash, which is usually not the intent of either founder or manager.

Keith Cowing: 7:34

I love that framing curiosity, conviction, commander's intent. I actually think it may help leaders that are taking on a really big challenge also just manage their inner feeling and dialogue as well, because there's this balance in leadership between conviction and humility and it's really hard to balance both. How do you get people's respect if you don't have commander's intent at times and how do you keep people engaged if you don't take their feedback at times and just internally to be able to say I'm still in curiosity mode, I don't have conviction because I don't have the context. When I have the context, I'll get conviction and then when I really lean in, I'm going to be in commander's intent when I need to to get stuff done.

Keith Cowing: 8:14

I love the way you frame that.

Sarah Liebel: 8:16

Yeah, and I'd say I think about things. Think to your point. You can't be in one mode all the time. That's where I see people fail completely and lose trust of an organization. I think about it in two ways.

Sarah Liebel: 8:27

One I am big into portfolio approach. So I think about what percentage of time the same way founders will say to me is 10, 15% of time this is my ball, don't touch it. Or the rest of the time. Here's how we think about expectations. So portfolio of how much time do I want to be in curiosity conviction? What are the things that really matter? My non-negotiables. And then the other way I think about it sometimes is from a funnel point of view. But it's just about creating some process. And I think from the funnel point of view it's really curiosity top of funnel. When we start ideating as a team, it's like we are in curiosity mode. Let's explore every avenue so we can get to commit. As we start moving further down that funnel, as we start to actually lay out what are those okay objectives. That's probably going to be more of a conviction mode. And then when we get to actually some of these KPIs or some of our key results, then if we have a disagreement, I might get into commander's intent and push forward.

Keith Cowing: 9:27

And do you share this with your team members? Let's say you're starting a new role and you're building that relationship.

Sarah Liebel: 9:30

Have you shared this framework and you talk to them about it, or does that just come out in the way you behave? I like both. I'm open to flexibility. In these frameworks. I feel like hindsight's always 20-20. It's always easier to come up with a framework as you reflect back as you're leaving, so sometimes that funnel may change, where conviction may go further and further down the funnel. I definitely do upfront say to anyone I work with that I'm a Socratic learner and expect a lot of curiosity upfront. It's not undermining my expectations of you or the expertise that I think you bring to the role, because my leadership philosophy is hire the best people for the role who are experts in something I can't do. I'm a multidisciplinary leader and so I know there's people who can do every part of an organization better than I can. But I'm going to ask them a ton of questions. My job is to be able to create the context, alignment and accountability frameworks to make sure we're all rowing the same boat and hitting our goals. So I label that part up front.

Keith Cowing: 10:19

And you've been through a lot of senior leadership roles, different contexts, different environments, different positions. I'd love to rewind a little bit. You cut your teeth in corp dev, which frequently means buying companies and acquiring, though it can mean many different things. I'd love to hear a little bit about what you learned there and how that has influenced your view on leadership and your personal leadership style today.

Sarah Liebel: 10:43

Well, I think both my time at Groupon which was I started interning and working with that company in 2010, and they started in 2009. It was just growing so rapidly at the time fastest growing company of all time and working in corp dev were really the most formative pillars of my career and the way that shaped me as a leader and how I think for CorpDev. I'd say a couple of things that it has transcended into how I lead. One even though Groupon was in marketing SMB space, we spent a lot of time looking at adjacencies of how we could expand, add synergies to the company, different business models, so it could be payments. There was point of sale systems we were looking at. We moved into e-commerce and then all the infrastructure around e-commerce. So it wasn't just buy another coupon company and to be able to do that really fast, I had to ascend learning curves at a really, really quick speed. To be able to be in the room with folks like yourself who are experts and not know the space they were in and sound credible. You had to feel really confident and ascend the learning curve fast, and so that's something that's allowed me to have taken that.

Sarah Liebel: 11:49

I've worked in a wide variety of industries post Groupon, and people are always like how do you move industry to industry? That was very formative. To that I'd say number two would be it also taught me to make decisions with fast, with limited amounts of data. So if you think about when you're going to buy a company, you don't get six months to sit in there and work side by side with the CEO and understand all the nuances. There could be competitive situations where you've got a week to get an LOI out there. You've got one data request and you only get as much data as the company is able to provide. Data is the company is able to provide and usually earlier stage companies that are series ABC probably don't have the level of rigor and financial resources that you're expecting in a data set. So how do you make a decision on should you buy the company and how much to value it really quick, and that is we all know as operators of early stage through growth stage companies critical. How do you make decisions with limited data?

Sarah Liebel: 12:43

I was very fortunate to be able to see what great looks like. So in 2010, 2011, it was just the boom of so many remarkable e-commerce companies and social network companies that were happening that I got to meet with founders on day one, day two, the first weeks of their job, and get to see those companies expand over time. So I saw how different teams were structured, what different leadership styles were, how people were measuring their businesses and KPIs and dashboards, economic models. I was very fortunate to be surrounded by some phenomenal people and see what great looked like.

Sarah Liebel: 13:15

And then, lastly, as an operator, I've worked a lot with founders and I can't think of a harder challenge to be able to gain the confidence, the respect and trust from a founder within a very short period of time, as in CorpDev, you're talking about the most sensitive moment for a founder. So do I want to sell my company? Do I want to take investment from a corporate strategic? Do I just want to tell them about my business and that might be competitive. I don't know why they're calling me and so you know I was pretty green.

Sarah Liebel: 13:45

I was just out of my MBA when I was doing this and I think my amazing boss at the time, jason Herenstein. He would give me feedback that my superpower was garnering trust very quickly with these founders who would be able to tell me a lot about their businesses, and we'd build a great relationship that maybe we didn't buy the company that year, but three, four, five years down the road those companies would come back and have a strong relationship group on and that has paid forward as an operator where if I want to work at some of the best companies and be a right hand to a founder, they've got to trust me with their baby and I learned a lot about empathy for founders and what they're looking for in a partner.

Keith Cowing: 14:20

You're getting one of the great dichotomies in leadership of listening and having empathy and being patient and, on the flip side, being very decisive. You have to have conviction with limited information. I'd love to hear, on that decision-making process a little bit about how do you make decisions today, given what you learned then, when you have limited information, you have to make a call. It's going to be imperfect, but you have to move. How do you manage that psychology? How do you manage other people?

Sarah Liebel: 14:46

How do you just get to a decision and move some of the principles that I have one really important that you share as much context about the decision, the information that you have at hand with the team that's involved in making that decision. With information comes ambiguity, and so I think that's a really important thing that a lot of employees need to understand and learn is they want to be in the room, they want the transparency, but that's going to come with that ambiguity. But I do try to involve people with as much context as possible, upfront, caveating that there's going to be that. I think, too education-wise was in computer science and sciences and I'm a big believer in hypothesis testing, setting up micro goals, and you can do that from everything, from a hypothesis and a test, not just A-B testing and growth. I do it with sales, organizations, design, I do it with messaging, I do it with how you build a product.

Sarah Liebel: 15:36

I think it's really important in that decision making what is the smallest decision you can make today with the largest learning you can have as quick as possible. And then I think it's also really important to explore with your team. You know what's the downside, what is the worst that's going to happen once you set that up. So here's all the context what's the quickest thing we can do, learn the most information and, if all goes wrong, what's the worst case scenario, and kind of laying that out as a team helps with confidence. I'm a really big believer in team-wide decision-making, or at least alignment and holding hands and disagreeing and committing to whatever those decisions can be. And so if that's your executive team, if it's your senior, whatever your team structure is and whatever the note of that decision is to be made, making sure everyone's around the table and aligning that we're going to have each other's back on this decision and we're going to learn as quick as possible and be comfortable with failing fast and moving to the next decision if needed.

Keith Cowing: 16:32

I really love that. I think a lot of people could learn from that. How do you coach people that are, let's say, a new director, have direct reports, trying to figure out how to get their conviction and their commander's intent mode but go through that curiosity mode first, but maybe quickly, so that they can make the decisions they need to make? What kind of coaching do you give people so that they can develop that internal compass?

Sarah Liebel: 16:53

I think one thing that's important on that is time boxing. I see a lot of analysis, paralysis happen on the curiosity phase and so I think it's really healthy and important that you say, for example, you have a quarterly planning structure and you're trying to figure out what your roadmap is going to look like. Two weeks, four weeks, whatever the time period is, come up with a plan for how that's going to work. Feel comfortable. If you have one week, I dedicate at least a week or two weeks to just really broad exploration of ideation and let people ask as non-adjacent types of curiosity questions as they want. So we feel like we get it out on the table. Then we start to move really fast down kind of the decision making funnel, but at least you feel like you've done a lot of exploration. So I'd say time boxing is a really important part of it. On the conviction side, I think it's making sure people feel like they have the support that if the conviction is wrong they're going to be okay. And then also it's really critical that the conviction is in the hypotheses, not on the solution, and I think that's very freeing. You can feel very confident to say I believe I'll give you an example, a better up.

Sarah Liebel: 18:00

We had questions about how do we improve our users' experience with coaches and make getting a better match. So a very simple example If we had a hypothesis that you know we show them three coaches, if we showed them more coaches, they would have better retention, better satisfaction scores. Someone else might have a hypothesis that it's about deeper profiles on the coaches that they're showing. It doesn't really matter to me which one is right or wrong, because we really don't know consumer behavior at this point. What's important is, as a team, we agree on the hypothesis to test, we size them and we figure out based on how much conviction we have and how much effort is in this potential hypothesis. Then we make the decision and we have a very clear time box of when we're going to decide. Was this the right hypothesis or wrong? But I think freeing yourself it's not about are you right or wrong in the solution. Do you have conviction in what could be true on a hypothesis is the most important part.

Keith Cowing: 18:56

And it sounds like I'm hearing a few things in there where I love that you break out conviction in the hypothesis Also sounds like I'm hearing a few things in there where I love the breakout conviction. The hypothesis also sounds like you have conviction in the process of there's a funnel, you're actually stepping through the process.

Keith Cowing: 19:06

You're doing a week here, you're moving forward, so you're never moving backwards, you're always moving forward. And then eventually I believe this is the right process, I believe this was the right hypotheses. I don't have conviction, the exact predictability of the outcome, because you never do, that's okay. But I believe we made the right bet and we'll see what happens. And then I'm comfortable with that. And a lot of people don't have comfort with ambiguity and ambiguity is hard, but I think breaking it down that way at least constrains the ambiguity to the outcome and not the process and the scientific method, if you will.

Sarah Liebel: 19:36

Exactly Because, like I said, the biggest fault I see is when and this is manager, founder as well founder will move, oftentimes Manager side, where I see people just get paralyzed by fear of making the conviction in what the solution is going to be, and so it's really just about getting movement to get more data to get to the right solution.

Keith Cowing: 19:55

I frequently find when we're making hard decisions, especially ones that impact other people in some way, we overestimate the value of more time and we underestimate the cost of delay. And time boxing is a really nice tactic to be able to say we need to move, we need enough information, we need enough rigor, but we have to move quickly because if we do that all the time, we're better off being really fast and 90% accurate. Absolutely yeah, we have to move quickly because if we do that all the time, we're better off being really fast and 90% accurate, absolutely, yeah.

Sarah Liebel: 20:24

And another buzzword du jour, right In a world of Gen AI, there's so much pontification of how do we test this, what's going to happen with why? And there's a bunch of industries and companies I talk with. If you're not moving and testing, you're just going to be irrelevant. There's an existential threat to what's happening to your business. It's totally getting upended. So if you're focusing on how do I move lever A 10% and you're not focusing on just getting something out there and moving fast, it's a moot point.

Keith Cowing: 20:52

So let's talk about that a little bit. I do think that AI is going to have a big impact on leadership and my hypothesis is that and I don't think it's wildly controversial, but the value of knowledge has already gone down a lot. It'll continue to accelerate. The value of performing a task, where somebody tells you what to do and wants you to do it in a white collar, digital information world, will start to deteriorate rapidly. But then judgment, leadership and creativity will become 10X more valuable. They're already valuable, but they'll be even more valuable because you can get that much more leverage.

Keith Cowing: 21:24

But you have to be thinking independently and making judgment, and a lot of what I hear and what you're saying around leadership is really about having great judgment and having great communication and these kind of things. How do you think about training people today for their leadership job? Let's say, five years from now, where things have evolved and tasks are less valuable, judgment's even more valuable, does that change anything in the way that you're coaching and training people, or do you think it's the same skills? It's just so much more important that they actually have them and they're good at them?

Sarah Liebel: 21:55

That's a great, great question. I think that it's I mean it's definitely even great question. I think that it's I mean it's definitely even more important. I think it's something that's been a focus for me.

Sarah Liebel: 22:04

The biggest challenge I see with employees oftentimes is when this doesn't happen, is they just get so stuck in the day to day and it's like you're still moving but you're treading water, you're not swimming across the lake.

Sarah Liebel: 22:18

And so if you're so focused on execution and you're not taking the time to step back and realize, you know, is this laddering up to our overall strategy, to sometimes make the direct connection for their day-to-day work all the way back to what are the overall company priorities and is the success in the near term and then even long-term, strategically happening? So I think at a senior leader level, it makes it even more critical that we've got to really focus on making sure people understand how to make that connective tissue. But I think if you're so focused on the execution and you're not taking the time to pause whether that's through deliberate monthly one-on-ones with your manager, whether it's skip levels, whether it's coaching to be able to figure out am I making the right decisions, how is my work laddering up to the overall company, and how am I communicating what I'm doing in a way that's effective? You're going to just get left in the dust and in the world you're talking about.

Keith Cowing: 23:21

And what are you doing personally to make sure that you're prepared for these leadership roles, challenges of the future?

Sarah Liebel: 23:29

I spend a lot of time thinking about what I'm good at and how that can help companies or that can help transform industries. I don't really have a good answer for you except thinking about kind of how the industries themselves are evolving and what I'm good at and how that could plug into it.

Keith Cowing: 23:43

Well, let's take that thread, which I think is really helpful for people that are developing their personal leadership style. It sounds like you have a strong inner confidence in who you are, what you're good at Generally, from a principal's perspective, where you want to go. The details of that will sort of work itself out. Help our listeners understand what are you good at, what is your leadership style, because I think that can be really helpful as an example for other folks over time to articulate theirs.

Sarah Liebel: 24:10

I'm a multidisciplinary leader who understands how to scale high growth technology companies across product marketing, sales and ops. I've led every function. Am I the best person to be a CMO, a CRO, a CPO? No. Can I hire and retain the best talent in the world? Yeah, I think I can. Can I develop some of the best directors who become SVPs at some of the best? Yeah, I know what great talent looks like and a lot of that. Back to CorpDev. I've been so fortunate to be around people like I. Also know, from a human empathy point of view, what is going to motivate talent and how to give them enough structure or framework to empower them, but with while still setting them up for success. You know that it's kind of a ambiguous role, but I think leadership, making decisions with limited information, creating process to be able to scale companies are some of the areas that I've been able to succeed at.

Keith Cowing: 25:09

And let's tease apart a little bit. We talked about this dichotomy earlier of having conviction versus having humility. When it comes to your personal style, I heard a quote this morning that resonated a lot, which is the most important thing you can do for your career is show up as yourself, and if you're just leaning into, this is who I am, how do you help other folks understand what do I actually need to evolve and change versus what is like? This is unapologetically me and this is what I'm good at, and you may like it, you may not, but this is my style and I'm going with it, and I feel like it's really easy to go wrong in one direction or the other on that, and so talk to me just a little bit about how listeners could think about where they're unapologetically them and where maybe they should evolve a little bit.

Keith Cowing: 25:52

Before the conversation we were joking around you being a leader that's gotten some feedback about being badass, but you show up with your son's blue headphones on and you're like hey, this is my background. Like you like it or not, these are my kids books. Like let's roll. Where does that confidence come from internally and and how do you help other folks balance where their confidence is versus where they should grow?

Sarah Liebel: 26:14

yeah, um, I have no idea where the confidence comes from, but it didn't happen. Honestly, again back to group. I feel like until I was in that experience and I was around so many smart people who I read about on papers and in there were them off, there were their own authentic selves. I also found that when I talk about building trust with founders and that being pivotal to my earlier career in CorpDev, that was because I was authentic. I find my leadership style. I garner trust very quickly with people because I'm very authentic. Life's too short. I'm a mom, I've got two kids, I have a family who's gotten through lots of challenges over the years, and we have one life and so it's not worth hiding who you are to appease people. I also believe that everybody has a lot of value to bring. I truly believe that. Of everyone I've ever worked with, I think everyone's excellent at something and if something doesn't feel right about a role or an opportunity, it's probably not the right one for you. That's just like a principle I believe in which allows me to feel comfortable being authentic.

Sarah Liebel: 27:16

I did try to change for a long period of time, especially as I ascended more senior leadership roles. It's funny, one of my the CEO at first did. David Rosenblatt gave me good advice where he's like you're incredibly professional, intense even, but you're very informal and I often conflated those two things. Where I thought to be able to be professional and be successful, I needed to be very formal and I'd been around investment banking. I had my MBA, I've been, and maybe why I resonate with founders because I'm very informal I'm not your traditional consultant banker MBA mentality, but that's something I worked on, that I thought I had to change to be able to be successful and to ascend the leadership curve. But I actually found it's a superpower that my informality has been thought of as a sense of authenticity that has allowed me to garner trust really quickly, to be able to build amazing leadership teams and to be able to scale businesses.

Keith Cowing: 28:07

That resonates a lot with me, particularly that one-liner having such a big impact. I think leaders maybe underestimate the value of that little piece of feedback they could give somebody and when you see this in other folks, don't hold it back. Share it with them, because that can be gold for somebody else. I remember a business school professor, similarly Risa Mish, told me one time Keith, your superpower is building trust with people. Don't forget that, because it's really valuable and everybody has their different styles and you don't want to lose focus of the part of your style that maybe by accident you may cover up or try to evolve, but is actually extremely valuable.

Sarah Liebel: 28:42

That's yeah, and you do garner trust very quickly with people.

Keith Cowing: 28:46

So I'd love to hear, maybe as a final topic area we've talked a lot about personal development and leadership and all these different ways to think about balancing conviction and humility and leading teams. Now, when you make a change as a leader and you take on a new job and a new leadership challenge, I have found the hard way that when you change jobs as a senior leader, it's very different than changing jobs as an individual contributor earlier in your career and you don't really realize that until you go through it. The process from searching to interviewing to making a decision, to onboarding, to exiting all of that needs to change if you want to do it really well, and you've developed a framework for how to think about that. I would love if you could share that with listeners.

Sarah Liebel: 29:29

It is. It's really hard as you progress in your career to think about. You have to rethink how you think about work. I grew up in tech, my whole career tech companies and I've always thought about just moving up the ladder. It's just how do you get a more senior role, how do you get to C-level and how do you get your organization to become a public company? And I've been very fortunate that I've been able to move up to C-level executive positions and I've been able to be a part of two companies that went public.

Sarah Liebel: 29:58

When I was in my last role, when I was at First Dibs and we went public, I realized that wasn't really the thing, right, like it's just the beginning of a whole new journey and a whole new way to operate. Being a public company. That's not the brass ring that everybody thinks it is in tech. So I've thought about it and then I also have realized that, especially for myself, where I'm this multidisciplinary leader who has run lots of functions. But it's not hey, I'm going to go be the chief, the CFO, I'm going to go be the chief, the CFO, I'm going to go be this. That's not what's. You know the progression that I'm looking for. So I think about it, less about title. I get a lot of questions from venture capitalists, from recruiters, that would say what stage do you want to work at? What role are you looking at? What industry? And I tell them that's irrelevant. So my framework I love alliteration, so I force it into a four-piece framework and I think about it as the problem, the product, the people and then my personal ability to impact. So first, on the problem side, I need to work at a company where, first, the problem's big, there's a really large market size, the total addressable market's massive. Is there real pain in this market? Is there a problem that has to be solved? Is the market crowded? You could use your B-School SWOT analysis, you could do whatever you want, but to me, however you get there, it's just is this a real problem that is big and needy and needs to get solved? And also, under problem nuance, to me, I think about it as is there a purpose to it.

Sarah Liebel: 31:25

I am at a point in my career you know better up was my real first foray to focusing on this and where I'm at. What I'm looking at right now is I need to sit at the intersection of purpose and performance. I know I'm very performance oriented. I want to work at a company that's making an impact in the world in a social impact way, and so for me, problems size and purpose. Seconds, around product, and for me, I want to work at a company that has a really defensible product, that has data. Moats are a big piece of that right now. I've worked at a lot of companies that have human in the loop. I'm looking for things that are more traditional product SaaS, product SaaS and everyone might have their own definition. You could be working in CPG and it could be about having the best luxury experience in a hair product. I don't know whatever your business is, but for me it's about defensibility and about core technology components to it.

Sarah Liebel: 32:19

Third is around people, and this gets trickier as you move in your career. It used to be who's my boss going to be, but now it's okay. You know I'm looking at president things, I'm looking at CEO things. I'm looking at founding my own company, so it could be the board, it could be your peers, it could be partnering with a founder. It's all over the place and I want to work with people who I'm going to learn from and I think, people another thing in your career as you move up. It's not just about people who have more experience than you and can teach you. I learned just as much from my direct reports or multi-layers down as I do from the people who are my leaders or my direct manager, so it's really understanding what is the expertise with an organization. If you're at BetterUp, there are so many IO psychologists and people who are talking about behavioral science that I didn't know as much about and I learned a ton there and that was fascinating, could be an insurance and you could learn about a new industry and get the point. So people, different levels what are they bringing to the table?

Sarah Liebel: 33:13

The other two parts of people for me, I love to mentor. I'm so blessed that I've worked with people who have phenomenal careers and have taught me so much, and there's nothing more rewarding to me than seeing people bloom in their career and they just need that structure and they need the support and someone to believe in them, and so I love to be able to be in an environment of that. And then, lastly you touched on this earlier in our call I realize I want to have fun. I miss having fun. I worked remote for the last couple of years. I live in New York City. I want to enjoy New York City. I want to be able to be with people in my community. I want to be able to be with people in my community and I want to be in an office. And that's to. Everyone has their own point of view on that. For me, I want to have office time.

Sarah Liebel: 33:53

And then the last one, probably the most nuanced, which is around my personal ability to impact. I just squeezed the P in a little bit there, but my role is tricky. So for me it's where do people see that they're not going to pigeonhole me as just a sales leader or a marketing leader or a revenue or a operations leader? They need, they understand that my superpower is being able to think across various levers and they look at me as truly a thought partner in building and scaling the company. For certain folks, they may say I really want to double down on something that has a certain stage that I'm great at, or mentoring is a big component to it, or there's a niche part of their background that applies. Whatever that can be, I think it's just really important that the scope is reflective and that's not title. It's not the title but the scope and the partnership with your colleagues and the strategy of the company is going to allow you to have the best ability to impact.

Keith Cowing: 34:47

And what about when you actually make that transition? You're onboarding to a new position as a senior leader. What have you learned you need to do during that transition to make it successful for everybody?

Sarah Liebel: 35:01

My team I actually my direct reports when I first went to BetterUp did something that I loved. They all sent me a one pager of ways of working with them and I found it so helpful. It had personal anecdotes and it had things around. I know I'm talking to a founder now. I'm a verbalizer. I can tell I'm a verbal processor. I work with other people who are writers and they'll write you a 10 page email at night If you don't know that about one another. Know your question earlier about flexing your style for people. When should you or should you not? Somebody could be spending hours uncomfortably on Loom sending me a video and I could be spending 10 hours on writing a memo that I could have just sent them a quick Loom for. So having that kind of that one page memo was really helpful for me of what are your working styles, what are things to know about you. I need positive affirmation. I don't need positive affirmation. I like public setting, private settings. It was really useful.

Keith Cowing: 35:53

And that all comes back to communication again of this is me. This is who I am. I'm going to set expectations for your role, but here's expectations that you can know of me and how to interact with me and how to get the best or the worst out of me. So you know up front where predictability matters so much for leaders.

Sarah Liebel: 36:08

So much.

Keith Cowing: 36:10

Sarah, I learn an incredible amount every time I talk to you and greatly appreciate you sharing your insights here on Executives Unplugged.

Sarah Liebel: 36:18

Thanks for chatting with me. This was fun.

Keith Cowing: 36:21

If you enjoyed that episode, please share it with a friend or provide a five star review. I love helping people through their leadership journeys, and you can find more content from me at kc. coach. Until next time, enjoy the ride.