How to Create a Leadership Style That Blends with Your Personality

Guest: Lily Sarafan, CEO of HomeCare

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You’ll recall in that in the last episode of FemgineerTV, I interviewed Maria Giudice, the VP of Experience of Autodesk and author of The Rise of the DEO. We talked about how traditional CEOs have been replaced by a new breed called DEOs.

In the latest episode of FemgineerTV, I’ve got a great example of a DEO for you: Lily Sarafan, the CEO of HomeCare.

Lily began her career when HomeCare was just a startup, and has been integral to its growth and eventual acquisition.

But that’s not all! Lily is also very active in the tech community as a startup advisor, mentor, and investor, and she’s involved with a number of nonprofits, holds a political office, and avidly travels.

As you watch the episode, you’ll see how she manages all her projects and has learned to cultivate a leadership style over the years that resonates with her personality. Lily definitely exhibits many of these DEO traits:

  • Evaluating and taking risks
  • Being a systems-level thinker
  • Using her intuition to guide her decision making
  • Having a high level of social intelligence
  • Caring about getting shit done!
  • Influencing and shaping a company’s culture through her unique leadership style

Even if you aren’t a leader, this is a very valuable episode to watch, because you’ll learn the following from Lily:

  • Why it’s OK if people don’t expect much from you and how you can use that to your advantage;
  • Why having a leadership oriented personality is very different from being an effective leader;
  • Why the best advice isn’t necessarily what you’re supposed to follow;
  • How you can lead and built a support network even if you’re shy or introverted; and
  • Why it’s important to value people over product.

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How to Create a Leadership Style That Blends with Your Personality Transcript

Poornima Vijayashanker: Welcome to the 14th episode of Femgineer TV, brought to you by PivotalTracker. I am your host, Poornima Vijayashanker, the founder of Femgineer. In this show, I host tech innovators and together we debunk myths and misconceptions when it comes to building tech products and companies. If you’ve ever wondered how people juggle multiple roles and create an authentic leadership style, then you’re in for real treat.

In today’s episode, I’ve invited Lily Sarafan, who is the CEO of HomeCare. Lily began her career at HomeCare when it was just a startup, and she’s been very instrumental in its growth and eventual acquisition. But that’s not all—Lily is also very active in the tech community as a startup mentor, advisor, and investor. And when she’s not involved in startups, she’s also involved with a number of nonprofits, holds a political office, and avidly travels.

So, I don’t know about you but I’m really curious to hear how she does all of this, while still having a smile on her face.

Lily Sarafan: Thank you so much for having me here, Poornima. Well, you always have a smile on your face as well.

Poornima Vijayashanker: Thank you.

Lily Sarafan: So, we’re in good company.

Poornima Vijayashanker: Yeah, thanks so much. We’ve been friends for a long time now. Since like maybe 2006 and I’ve just enjoyed seeing you blossom as a leader. But I want to go way back to the beginning when you had just graduated from Stanford and you had started to work at HomeCare. Maybe if we can talk about first, what HomeCare is and then your initial role?

Lily Sarafan: Definitely. When I graduated from Stanford, I had the opportunity at the university to do a coterm degree. So, I did undergrad in Science Technology in Society and I did a graduate program in Management Science and Engineering. Afterwards, I was interested in so many different eclectic things when I was that the university that, it wasn’t clear what path I was going to take. But I did think, I was eventually going to be the Technology Policy Advisor to the president. And for that, I figured the next step was to go to law school. So, I applied to law school and I got in. And that was when I took my first strategic risk and I deferred for one year. In that one year, I decided, you know, it’s a very short opportunity, where I can explore one of the passions that I didn’t have the opportunity to, while in college and that’s when I met two clinical psychologists who were starting to provide HomeCare services to the Palo Alto California community really close to the campus.

And so, since it was only going to be about a year, I figured this isn’t too much of a risk. What if I joined them and worked to try to build a company before I go back to law school, and suffice it to say that after the first year and the second year and the third year, the company experienced such explosive growth that by the time my LSATs expired, I didn’t in fact go back to school and that’s kind of how the journey began.

Poornima Vijayashanker: That’s awesome. Yeah I had a…not quite the same experience but was definitely lured into startup and didn’t go on to deal with graduate degree because of it. Now tell us a little bit more about HomeCare, what exactly do you guys do and how have you grown over the years?

Lily Sarafan: Sure and I’ll use the acronym for simplicity, HCA. We are the largest consumer health company in aging services today. At the end of the dayn we’re a consumer service. Technology is the backbone of our company, but the end service is that we’re allowing seniors to live independently at home and not have to be institutionalized by sending health care into the home. So a lot of the health care that we assume takes place in nursing homes or rehab facilities or hospitals, we’re actually deploying it to the home. And what’s interesting is today this is called on-demand health care. It’s a massive exploding industry with a lot of venture capital being poured into it, but at the time, you know we’re talking ten and a half years ago, that wasn’t even terminology and so the idea really was as out-of-the-box as you can think, especially since our original team, none of us had traditional health care backgrounds.

Poornima Vijayashanker: Oh that’s great. So yeah, I was going to ask you, what was your initial role at HCA?

Lily Sarafan: Sure and so it was kind of like just pulling things out of a hat I think. We just assigned ourselves some titles at the time and I was the Chief Operating Officer. I had almost near full operational control, meaning setting the strategy for the company and setting the direction as a 21- or 22-year-old.

Poornima Vijayashanker: Yeah.

Lily Sarafan: I was able to do that and now thinking back I can’t believe the opportunity I was given to do that, but my role included signing retail contracts, hiring our initial field employees, setting up our corporate intranet. Any number of things that you can imagine, I really had to be a jack of all trades because when you’re that small, you don’t have the infrastructure to necessarily specialize, but of course that changed over time.

Poornima Vijayashanker: Yeah. I mean given that you were 22, most C0Os, you know, we think of Sheryl and so on, are much older, so did you ever…were you ever concerned that, “Oh, I’m only 22, I don’t have as much experience, how my going to get all this stuff done? How am I going to learn how to grow this company?”

Lily Sarafan: So the truth is that I didn’t and I should have probably.

Poornima Vijayashanker: OK, good.

Lily Sarafan: Now looking back I wonder where the competence came from to do this and I think that with almost anything in life you can grow into it and I definitely had the chance to do that and in fact, I really sometimes felt like I was playing a role, like I’m not actually leading a company. I’m just playing the role of doing so. Until a few years pass and we had generated tens of millions of dollars of revenue and I’m like, “No, like, this is a real thing,” and I think for me the switch happened when the LSATs expired and I realized this isn’t just a temporary thing anymore, we’re going to go all the way, we’re going to be the dominant player, we’re going to be the industry champion, and I think that’s when I really came into the role.

I didn’t have any concerns about myself but certainly I met with people where it was a red flag, you know, here is someone who wasn’t born in the US, who’s a woman, who’s young, I mean all the, you know, the attributes that you can imagine that someone can shortchange you for. But I always use that as an opportunity. If someone doesn’t expect much of you, it’s very easy to fill that gap, right?

Poornima Vijayashanker: Yeah.

Lily Sarafan: It’s very easy to fill the delta when you open your mouth and you say something and they realize that you can in fact generate value and so it was also nice to be able to play that role.

Poornima Vijayashanker: Nice. And your role has changed a lot over the last ten years. So tell us a little bit about how that’s happened.

Lily Sarafan: Yeah, so we were a very small team. Now we have about 500 management-level team members—

Poornima Vijayashanker: Wow.

Lily Sarafan: —across 150 global markets. We have 6500 or so field employees and so the role has really transformed and I’ve transformed with it. I would say that probably the primary difference and what I did ten and a half years ago versus today is that I operate at a much higher level and I had to learn to let go, I had to learn to delegate. And one of the things that really became valuable for me is realizing that even if I imagine that someone could do something 80% as well as I could, by freeing up 100% of my time, I could focus on a higher-level functions that maybe no one else is equipped to do because they don’t have, you know, the vision for what this company could be. And then what was interesting and what I learned is that, that individual didn’t do things 80% as well as I could, they ended up doing 150%—

Poornima Vijayashanker: Oh, awesome.

Lily Sarafan: —because now this is their single task, whereas I was really spreading myself thin across a lot of functions and so, you know, just starting small, letting go of billing and payroll, letting go of the retail offices, letting go of employee training. I mean slowly that happened, until today I’m sort of really working on our global expansion, working on strategic high-level hires. So, I guess that’s a little bit about the transformation of the role.

Poornima Vijayashanker: Nice. So during that 10-year period, you’ve done a lot, I mean you’ve been doing a lot of the work and then you started delegating. How did you in that span of time cultivate your leadership style?

Lily Sarafan: I think, and I don’t remember exactly when it happened, but there was a time that I almost had an internal conversation with myself and I said, you know authenticity is really going to be important to me. I will not operate in silos, where this is how I am when I go to work and this is how I am when I go to all of my many other roles and functions, some of which you alluded to earlier. And so once I realized that I wanted my team to be fully aware of everything I was passionate about, it kind of eliminated all of those circling thoughts of, “Now I’m playing this role, now I’m at work,” and I think that that really helped and it helps people to work with you and to align with you when they understand the whole picture and not just the vision for the company. So some of the things that I did, that I helped cultivate, that I believe helped cultivate the style is being really open and honest and transparent about what’s going on with the company and also what’s going on with me.

I mean, I had a health scare a year ago and it’s not something that I kept independent because it affected, you know, my ability to work during that time and so you know just being really open with people and that’s my style in general. I can’t imagine that everyone has to operate within the same formula, but that’s something that was really important to me. Another thing that I would share is I think starting high school, most people in this country end up taking a personality test at some point and when I took mine, you know, back in high school, and it’s been the same on the M B T I—it’s the E N T J—and so when I read the description, it’s like, “This person is just a born leader,” and so what I could have done in reading that, is just imagine like, “I’m done.” You know, I have a leadership personality, but what I came to find is having a leadership-oriented personality is very different from being an effective leader and in fact all the leaders that I admire in the world are introverts.

And so it’s kind of amazing that it’s not about just following like your personality, it’s about figuring out how you can inspire others to follow a vision and that takes time and that takes energy and also it takes a lot of good luck. Right now our industry is hot, it’s exciting, everyone wants to transform health care. John Doerr said the smartest people you know are working in health care and so it’s very bizarre because that’s not the environment we started in, it’s a lot easier to recruit and inspire people today than it was early on for sure.

Poornima Vijayashanker: And you’ve also been very instrumental not only in the growth but the recent acquisition. So tell us how that came about and how are you going to lead the company going forward?

Lily Sarafan: Definitely. And so we were very fortunate a few months ago to have a real milestone event for the company and were, you know, our previous investors were able to see their healthy return and as a company we were able to have the resources to move to the next chapter and so it was a grueling process and primarily because you’re always looking for the partner that is going to help you get to the next level and it’s not just about numbers, it’s not just about a term sheet like this level of investment and change is really going to propel the company in some direction and hopefully a good one, and so for me what was most important is finding people and finding partners that believed in the vision but could also make contributions that we either don’t have the infrastructure or the know how to do. And so that process is not too different from raising seed funding or interviewing a high-level recruit.

I mean it’s all about finding a good match and I’d say that that number one metric that I used is figuring out how risk averse a partner would be, because we’re dealing with regulatory industry, the landscape is changing and it wasn’t going to be healthy for the company to work with someone that wanted to put in a lot of constraints or wanted to be risk averse, and so finding that right balance and finding that right partner, who understood the on demand space, who understood the healthcare space and wanted us to chart a new path that was going to be critical and I lead the process. Pretty much by myself and one other team member, and so it was a huge learning experience for me, because there does come a time when you’re running a company that everything kind of happens like clockwork, you sort of understand this was a huge pivot for me, because I’m not just spending my time operating a company, I’m spending my time trying to find the partners and resources to take us to the next level and I’m so happy with the outcome.

Poornima Vijayashanker: Yes, there are probably a lot of times where you were saying “no,” where somebody was saying “no” to you. How did you handle that process and kind of keep your head in the game?

Lily Sarafan: Yeah, I don’t know if I handled it all too well. I hope I did and I think probably the things that I kept in mind is that, this is not to do with ego and it’s not to do with me. If it’s not going to be the right partnership, that has to do with philosophies on both sides they don’t always have to match. You know, two people on this earth aren’t always going to agree…

Poornima Vijayashanker: Yeah.

Lily Sarafan: And I actually enjoy that. I learned a lot from those experiences where something wasn’t going to work out and I feel like as long as those, you know, political failures help you reach a positive outcome, then you can’t call them failures at all.

Poornima Vijayashanker: Yeah, well that’s great. So you’ve kind of come full circle now with HomeCare, but aside from that you’re also very active in the startup community as a mentor, as an advisor, and as an investor. How do you find the time to focus your roles on your HomeCare versus doing that sort of stuff?

Lily Sarafan: Sure. Well, I think we’re all very fortunate to live in an area where there isn’t a traditional time clock and it’s not about “9 to 5 is work and the rest of the time is something else.” I kind of consider my 24-hour period to be very fluid, and so sometimes I’m doing mentorship activities in the morning and I’m working on HCA stuff well into the night. And so, I think not having sort of rigid structure in the day, helps me to figure out at what point I need to prioritize one thing versus another. When we were running the transaction, my focus was like 150% on HCA, and when times are a little bit easier, I could focus on some of the other activities. At this point, I’ve been involved with, you know, more than 25 companies at some level and I’d say that the thing that really helps me manage my time is leveraging experiences for other experiences.

So, instead of reinventing the wheel, if I learned something through an experience with one company, I try as quickly as possible to apply it to every other applicable case, and I think in that way we can kind of scale our energy by not operating with, you know, here and then starting over and resetting, just kind of taking what we’ve learned globally and universally and applying it to every other arena where we’re involved. Whether it’s nonprofits, investments, running a company, etc.

Poornima Vijayashanker: Yeah, so it ends up becoming a very similar problem or a solution becomes applicable in all those instances, so it’s not like this nonprofit is operating so dramatically different from your startup…

Lily Sarafan: Correct.

Poornima Vijayashanker: Or from your own company…

Lily Sarafan: Yeah.

Poornima Vijayashanker: You might be at different levels.

Lily Sarafan: It’s true and I think the mindset, you know, that bifurcation that we do of, “This is this world and this is this world.” I think it’s a mistake, at least for me. At the end of the day, almost everything that I do is an organizational structure, right?

Poornima Vijayashanker: Mm-hmm.

Lily Sarafan: And figuring out how to optimize that structure is pretty accessible and universal and so whether it’s a tiny startup or a large enterprise or even a university, there are amazing ways that one can really leverage energies and efforts, and I think that I’ve been very fortunate to kind of be able to step back and see that interconnection among all the things that I do, and that’s probably the reason why I always have a smile on my face. I think if I really did have to treat all of these things independently, I probably wouldn’t be able to sleep and probably not be in a really good mood.

Poornima Vijayashanker: It makes sense, yeah. So aside from all the startup work that you do, you’re also involved in politics and I assume it’s because you have this dream at some point to be a technical advisor. So tell me what your current role is and what do you do?

Lily Sarafan: Sure, so I’m not sure if I’m going to be be able to aspire to be technology advisor to the president. I was really fortunate during the cybersecurity conference in Stanford last year I had a chance to meet the technology policy advisor to the president and he’s way too brilliant for me to ever fill those shoes. But my interest in politics has always been ever present and I think these days when you have a lot of Silicon Valley folks going to DC as part of the US Digital Service and other efforts, it’s kind of an even more exciting time to see the nexus between politics and business, politics and technology. So, I think that politics is a way that we organize as humans to govern, and again, I find the application to running a company and running a country and running the world and so my involvement is really just an opportunity to be civically engaged. I’m an immigrant to this country and I feel that my US citizenship was hard earned and it’s something that I want to honor through involvement at every level. And sometimes our involvement really does make a difference.

I think it’s easy to be apathetic about politics until you are actually involved and you can see that a few phone calls, a few signatures, and a few meetings actually results in change across different legislation or different bills. It results in change with bringing in a leader who supports innovation versus doesn’t. And so, it’s always been a passion of mine. Right now, I’m a commissioner and local government and I’m also the board chair of a very large advocacy slash think tank in DC.

Poornima Vijayashanker: Nice. So you’ve got a pretty full plate, but we’ve figured out that because you come up with the organizational structure, it helps you at least have a sense that you know you’re dealing with a number of things that are very similar, but do you have any other philosophies that you practice on a daily basis that help you lead?

Lily Sarafan: Definitely. Some of the conversations I have with mentees are around this topic and some of the advice that I give, number one: have your primary focus. If you’re just graduating from school, you probably don’t want to spread yourself so thin that you cannot create a platform for success. I have the opportunity to be involved in a number of different nonprofits and social enterprises because of my leadership role at HCA. So first, you have to develop the platform where people see you as an effective leader who is able to produce change and then you can do everything else. That’s number one. The next thing I would say is, again, find the opportunities to leverage one experience for another. I think people assume when they see, you know, an individual involved with many different efforts that they must’ve been like independent efforts trying to get there, but in fact, when you create a large network of people and they can see the value that you bring to one enterprise, those are the individuals who are going to invite you to be involved with others.

And so, I will sometimes get a question like, “I would like to serve on that board, how do I do that?” and it’s not that transactional—you know, show value, demonstrate where you can make a difference, someone will notice that and hopefully offer you the leadership opportunity that you’re looking for. I would say that none of the things that I do today I could have predicted, but as I look backward, I can see exactly where I planted those seeds, so that after several years you know we’d be able to see this outcome. So this kind of goes back to pretty cliché remarks on hard work, it really does happen that way and it’s not all going to just fall in your lap when you need it.

Poornima Vijayashanker: So there’s probably some level of mindset that you started to practice either early in your career, as you were thrust into growing an organization, right? Were there ever times where you had a mindset and then somebody challenged you and said, “Lily, you’ve really got to change that, you’ve really got to delegate,” or, “You’ve got to let go,” or what not?

Lily Sarafan: So, I think that sometimes when you hear people talk about the best advice they ever received, It’s advice that they received and then decided to implement. And for me it was actually the opposite…

Poornima Vijayashanker: OK, good. Yeah.

Lily Sarafan: The best I ever received is when I had an older gentleman who shall not be named who came and said, “Lily, you can’t chase two rabbits at once,” and I kind of heard that, I stepped back and I said that I would think about it and then I would consider it. And so, I went home and I thought about it deeply and I realized why are we using these old expressions, slash proverbs, slash idioms to dictate our lives. We’re all different, we all have a different capacity, we all have different energy levels and if I can chase two rabbits at once, like who are you to tell me, right?

And, of course, I mean you might want to chase the big rabbit first and then find the opportunity to bring them in, but look at the world in which we live where you know Elon Musk is transforming multiple industries in parallel, like we do have these people who are creating the alternative blueprint that we can follow, and so sometimes the best advice that you receive isn’t what you’re supposed to actually implement but what you’re supposed to consider deeply and then figure out if it does or doesn’t apply to your life.

Poornima Vijayashanker: Yeah, that’s a good way to distill feedback and it’s the rebirth of the renaissance person.

Lily Sarafan: It’s true, it’s true, and another thing that I would say is, it’s really important that you’re surrounded by people who are different from you, and I think sometimes our instinct as humans is to gravitate toward like-minded people and there’s no way we would have the level of healthy debate and tension in our organization if we didn’t have a lot of different perspectives, same values, you know everyone is aligned toward a goal. But really really different and I enjoy that I don’t want people to acquiesce to one position, at the end you have to but in the process you’re going to iterate many many times to get there, and one thing that I always say to sort of teams that are hiring is if two people are exactly the same, one of them is unnecessary. So consider that.

Poornima Vijayashanker: Yeah. That makes sense, especially with co-founders.

Lily Sarafan: Yes, yes. Exactly.

Poornima Vijayashanker: Now are there ever times where you feel like, “I have too much on my plate,” and you know there’s a feeling of overwhelm or I’ve just bitten off more than I can chew? How do I juggle all this?

Lily Sarafan: Yeah, most definitely. I think that, that feeling of being overwhelmed really came to my head when…for personal reasons, I couldn’t devote time or energy to almost anything for two weeks and I’ve always lived my life with quite a bit of energy and I didn’t have to operate in structure, but what was amazing is learning that I’m surrounded both professionally and personally by amazing people who really can step in, and so learning how to delegate not just at work but in your life is also going to be really important. And I would also say that, we always talk about a board of directors for our company and I think it’s also important to have a board of directors for your life and in those moments of crisis or change or where you’re at a crossroads being able to turn to a group of people who each known you in different capacities but who you really trust, that’s what’s going to help you sort of figure out how to get through that period of feeling overwhelmed or that feeling of crisis.

And so I’ve really relied on some really amazing people on my life and what I talk to new entrepreneurs about is, in addition to the directors for your company, figure out who you’re going to turn to when you have questions about life in general.

Poornima Vijayashanker: Yeah, all right. So last question for you, Lily. For our viewers out there who want to do more both professionally and in their community, what’s one piece of advice that you want them to walk away with?

Lily Sarafan: So beyond all the things that we’ve discussed so far I would say that the headline motto is, “people over product.”

Poornima Vijayashanker: Yeah.

Lily Sarafan: Because people, those are your mentors, your advisors, your colleagues, your hires—they make or break everything. And so not focusing so much on the end game, the technical product, but the people in your life, creating that network is going to be the most significant thing. And for people who are shy or maybe introverted and don’t know how to create a network, they’d be amazingly surprised at how kind and generous people are with their time. And so, if you reach out and just ask for 15 minutes of someone’s time and give them a value proposition, for them to consider, you’d be amazed and by creating that network you have people to rely on. They’re going to give you opportunities to serve and be of value and I think the whole thing just becomes a domino effect from there.

Poornima Vijayashanker: Yeah, that sounds great. I’m sure our viewers are going to find that valuable. So anything else you would like us to know?

Lily Sarafan: Well, I would also say that HCA is always hiring, we’re growing rapidly and across right now, product, marketing, there’s ops, analytics, technology—

Poornima Vijayashanker: Wow.

Lily Sarafan: Almost every single team is looking for members and so that’s one more thing that I would mention to anyone out there who wants to join a super fun, fast-growing consumer health company.

Poornima Vijayashanker: Awesome. We will put the link in the show notes for people to access.

Lily Sarafan: Perfect.

Poornima Vijayashanker: Yeah, well thank you so much for joining us.

Lily Sarafan: Thank you so much, my pleasure.

Poornima Vijayashanker: Yeah, it’s been fun.

Lily Sarafan: It’s been so much fun.

Poornima Vijayashanker: Yeah. And thank you to all you viewers out there for joining us today and special thanks to our sponsor, Pivotal Tracker, for their help and support in producing this episode of Femgineer TV. If you’ve enjoyed this episode, then please share it with your teammates, your friends, and your boss. And join us next time where I’ll be hosting Kim Malone Scott, who is formerly the director of Google and is currently writing a book called Radical Candor. Subscribe to Femgineer’s YouTube channel to get the next episode.

This episode of Femgineer TV is brought to you by Pivotal Tracker—build better software, faster.


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