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The TechCrunch ‘Lean In’ Roundtable: Full Video And Transcript

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This past week, TechCrunch TV was honored to host an intimate roundtable discussion of Facebook COO Sheryl Sandberg’s new best-selling book Lean In: Women, Work, and the Will to Lead.

The idea behind this was that while there has been a lot of buzz about the book and the larger movement being born out of it, much of it has come from established women in Sandberg’s generation and above. While that’s been valuable, we at TechCrunch wanted to find a different perspective.

So we pulled together a small group of Generation Y women who are part of the Silicon Valley’s rising new guard: Leah Busque, the former IBM engineer who is now the founder and CEO of TaskRabbit, the startup that has built a platform for outsourcing errands, tasks, and deliveries; Ashley Mayer, the senior director of communications for cloud-based enterprise storage technology firm Box; Megan Quinn, the Google and Square alum who last year made the leap into the venture capital world as a partner at Kleiner Perkins; and Pooja Sankar, the Stanford MBA and former Facebook engineer who is now the founder and CEO of educational Q&A platform Piazza.

We broke the roundtable into four segments which were posted this past week: Part one on Tuesday, part two on Wednesday, part three on Thursday, and part four on Friday.

Now in the video embedded above, you can watch the entire discussion in full. Below, we’ve posted a written transcript of the talk, which includes time stamps that correspond with the video.

Thanks for watching, and we’re hoping this is just the beginning of this discussion here at TechCrunch.


Transcript:

Leena: Hi, I am Leena Rao. Welcome to this TechCrunch TV roundtable discussion on Sheryl Sandberg's much talked about new book, "Lean In:
Women, Work and The Will to Lead." I am joined by my colleague here at TechCrunch, Colleen Taylor, as well as a number of influential women in the technology world.
I would like to introduce everyone first. Please welcome Pooja Sankar, CEO and founder of Piazza, Ashley Mayer, Senior Director of Communications at Box, Megan Quinn, partner at Kleiner Perkins, and Leah Busque, founder and CEO of TaskRabbit. Thank you all for joining us here today.

Pooja: Thank you.

Ashley: Thank you.

Megan: Thanks for having us.

Colleen: We're going to do this in several short segments, because there's a lot to pull apart in this book. But just a start, I think both Leena and I wanted to thank all of you because I think there's one thing that Sheryl says in the book. A little bit further on in the book, page 146, she says when she was thinking about making her first speech about being a female executive, she said, "Friends and colleagues both male and female warned me making this speech would harm my career by instantly typecasting me as a female COO and not a real business executive.
So it takes a lot of courage just to even speak about being a woman, period, and pointing out the fact that your gender is a minority in a lot of the upper echelons of tech and business. So thank you for coming here and being on camera and talking about the book.
The first thing that I think I just want to bring up is the controversy surrounding this book. In The New York Times, Jodi Kantor and Marine Doubt, two very influential women kind of had their daggers out in some ways for this book before it came out. I just want to start off by asking you all since you've read it now, what you think about all that buzz that had happened before the book came out.
[00:02:04]

Maybe Megan you can start.

Megan: Sure. To be honest, I was a little bit skeptical because I did read all of those articles in advance of the book actually coming out, and it turns out a lot of those writers had not read the book either. I have to say, upon reading the book, I found myself vigorously nodding in agreement with much of what I read and many of Sheryl's circumstances and experiences.

Leena: Pooja, what did you think?

Pooja: So when I pick up a book, I often look to things that I can take for my own particular case, and there were many of those. It actually validated, many points I felt very validated. So I understand that not every point can be applied or is applicable to everyone, every woman out there, and I didn't want to read it with that in mind. I often find many of the criticism is around, well, these five points aren't applicable to everyone. But I really enjoyed reading it for the points that were applicable to me.

Ashley: Yeah, I have been a bit of a Sheryl Sandberg fan girl for a while, since her Barnard commencement speech. So I was a little taken aback by all of the criticism before the book was published. The best part, though, is after getting the book and reading the introduction, she pretty much addresses and predicts every counter argument that was out there. So either those people hadn't read the book, or they hadn't read it closely enough. I mean, Sheryl knew what she was getting herself into when she wrote this, and she knew that she was taking a somewhat controversial stance. I think she framed things in a way that addressed and even validated all of the criticisms against her, but then that helped clear the way for her to actually make her argument.

Leah: I found that point fascinating as well, and kind of near the end she tells a story about a female officer in the service and how that female officer was sort of bracing herself to be part of this very male contingent.

[00:04:02]
Actually, it was the men in her group that really embraced her, but it was the wives of those men that ended up attacking her and being a little bit harder to deal with. Sheryl's point at that time is that it's often the women that aren't supporting each other and helping to build each other up. So when I read that part of the book and I thought back to those articles, that kind of struck a chord with me as well.

Leena: I wanted to just add to what you said, Ashley. I hadn't read the book, of course, when I read many of those articles, and it was clear that those people hadn't read the book because she addressed things like I know I'm lucky. I know that I am lucky to have someone who takes care of my children, and I can afford multiple people to take care of my children. I know I've been lucky in my career as well to have mentors like so and so and so and so. So I think that it was a little bit, I guess, odd to me that there was that criticism even after reading the book because she did do so many, she had qualified the book so well I felt like when reading it.

Colleen: Yeah, people would talk about, well, she doesn't say any, what about poor women or women who it's not even a question whether they're going to work or not. They have to. I said that just shows you didn't get to page five where she mentions that yes, there are bigger, there are many fundamental problems that we should still be working on getting up Maslow's hierarchy. That's one thing she said, "Knowing that things could be worse should not stop us from trying to make them better."
I also want to get into a point that she talks about kind of throughout, and it seems like this underlying concept of fear and fear being something that really holds women back. I wanted to see what you guys all thought of that sort of personally. I think page 24, she says, "Fear is at the root of so many of the barriers that women face. Fear of not being liked. Fear of making the wrong choice. Fear of drawing negative attention. Fear of overreaching. Fear of being judged. Fear of failure and the Holy Trinity of ear, the fear of being a mother, wife, or daughter."

[00:06:12]
That's just a huge . . . we could probably spend 45 minutes just talking about fear. But I wanted to see what kind of parts spoke to you guys when she talks about those things.

Megan: What was interesting to me was her comparison between fear and also self-doubt, and she really wrapped those two up together in the same chapter and in the same thinking, which is a lot of the fear that women feel, particularly around likeability honestly, which I think women do spend more time focused on and making sure their colleagues, their family, their community at large finds them likeable, is also wrapped in the self-doubt that they have over whether or not they can perform or whether or not they are performing up to the standards that they hold themselves to. So I thought that the combination of those two things really resonated with me as someone who, yes, has worked very, very hard and believes that I've earned the roles that I have, but has always sort of doubted in my head whether or not I worked hard enough. Could I have worked harder? Could I have done better, and could I've been more likeable in the same case? So that fear I think really does translate into not just a lack of sort of self-confidence, but also this question of likeability more broadly.

Colleen: Yeah, it almost sounded like she was saying there is going to be fear there, but it is not unfounded. You are totally right to have these fears, and actually if you speak up, people aren't going to like you that much, because you're . . . I don't know.
Pooja, has that been your . . .

Pooja: Well, if I think about the biggest difference between the 22- year-old Pooja and now today who I am, at 22, I was afraid and I was afraid to stand up for what I believed in, to even dig deep into understanding what it was that I believed in. In fact, it was actually really reassuring to hear that she was married once at a younger age, because at 22, I had entered into a traditional arranged marriage, and I was too scared to tell my parents I didn't want to.

[00:08:00]
At 26 and a half, after 3 and a half years of trying, that was a very big moment where I had to stand up to an Indian society, an Indian community and relatives and say, "This isn't going to work for me." Since then, it has been trans formative because since I longer fear what others think or believe I should be doing, but I dig deep into what I want and what I believe in.

Colleen: Wow. Yeah, I think I heard that from a few other people that I talked to that they were just about that personal revelation that she had in that book, and it was such a small little thing. But you're not the only person who has kind of found a lot of strength in that.

Leah: Yeah, I think the other piece that she mentions, in that same chapter, besides fear is ambition, and she makes the point that actually if you talk to a lot of millenials today that just as many women will admit that they're ambitious, and that's actually a change. It's interesting, because that part really resonated with me. I remember when I was at IBM and working with a mostly male team and being an engineer and a programmer, I was always told that I was too ambitious as if it was something that was negative, and I never understood that. I was always kind of like, "Well, isn't ambition a good thing, you know?" So I think it is sort of this next generation that's taking that ambition by the reins and saying like, "This is a good thing." So I love that portion of the chapter as well.

Ashley: I also really loved the whole part about the imposter syndrome because I personally related with that quite a bit, and it's nice to know that the COO of Facebook still doubts herself. I mean, when I joined Box, we were 50 people, and I was 24 years old. So I was terrified that I couldn't do the job. But even today, I think a lot of us especially who get into careers pretty young and then maybe grow with a company, I'm always constantly thinking, "Okay, am I just here because I happen to join young enough, worked really hard?"

[00:10:04]
But it's very easy to dismiss that, and there are a lot of people who are in positions that maybe are a little bit higher up than what their experience levels would be, and it was really comforting that Sheryl sort of opened up about her own self-doubt and whether she could do, whether she could take on each new challenge in her career.

Megan: I think that fear is compounded in Silicon Valley and in the startup community at large, where you do see people of different ages, at different roles, and different levels than you would see in the traditional corporate society.

Ashley: Well, it's funny in my case, because I went to high school with our founder. So technically, it shouldn't be that weird, but I think and maybe this is something that women do more, but there is that sort of innate doubt. She does a really good job of saying address it, acknowledge it, and then just fake it until you make it, which I love because I feel like that's kind of what I do and probably what a lot of people do. We're sort of making things up as we go along, and maybe one of the benefits to being in the startup world is that you do get to sort of challenge or even ignore sort of corporate norms. So you have a chance to make your corporate culture or your career into what you want it to be.

Colleen: That's a great way to wrap up that segment. We have a lot more to talk about too.

Leena: In this segment, I want to talk about a feeling that she, I think Sheryl talks about throughout the book, and it's something that she says she's felt very much, and I know it's something that I feel and maybe Pooja feels as well as a new mom is guilt, and the feeling of guilt whether that be by doing things at work or by making sacrifices at work at the expense of spending time with your partner or your family or your children. She writes that guilt management is as important as time management, and I think that's really an interesting point, because I'm sure we've all felt guilt at certain points in our careers.

[00:12:01]
I'd loved to hear, I guess, what you thought about that and if you agree with her. Pooja, why don't you start?

Pooja: Yeah, actually I am looking at a sentence right here in the book that really stood out for me. "There is always an opportunity cost, and I don't know any woman who feels comfortable with all her decisions." I struggle with that every day. I have an eight and a half month old son, and every day he is learning something new. I get text messages and little video clips from my mother-in-law, who lives with us, about his progress, and it's very difficult. I am in the middle of a meeting with my team members and I want to watch the video, but I can't take away from what's going on in the office. It's really difficult.

Leena: You know, it's also and Pooja, you talk about it from a mother's point of view, but Sheryl also addresses the fact that we make sacrifices even in our personal lives if you're not a mom. You are going out to network. You are doing things on your own. You have to have a life outside of work, and it's not all about work, but yet we feel guilty when we do spend that time away from work and we go and enjoy a nice meal or go and hang out with our friends. I'm just wondering if anyone else feels the same way or if they had those experiences.

Megan: Absolutely, and I think guilty goes both ways, right, because when you are with your family, your friends, you're having a life, there's always that nagging question of, "Oh is there more I could be doing at the office? If you are the office and you are there late, especially the in a startup culture and it becomes your life because it is your life, you start to have friends who drop off, and your family start to say you never call anymore. So the guilt actually goes both ways.
For me personally, I never been a big believer in work-life balance, the phrase, not the concept to be clear, which is because I believe that if you really enjoy your work and you work really hard, it becomes your life, and if you enjoy your family and you love your family and hopefully you do, that becomes your life. So it's more about weaving the two things together than having a clock that you clock in and out of. Especially with mobile devices, it feels like you're always on now.

[00:14:03]

Leena: That's right.

Megan: You're always on as both friend, a sister, a parent, a partner, and you're also always on as an employee, a manager, and a boss. So I actually think it's not so much the guilt of one or the other, but sort of the "I wish I could be in many, many places at once," and in some ways we're lucky that, with phones, we can be.

Leah: Yeah, I think that's a great point. I mean I've definitely felt it myself. Sheryl talks about being a good daughter and a good wife and a good partner and a good mother. I remember when I was first starting TaskRabbit and transitioning out of IBM, where I had a lot of time to spend with my family. I remember my parents just coming over on the weekends, as they normally did in Boston, to come visit me, and I just did not have the capacity or just the mental stamina to do the whole family like chill out, relax, catch up thing. I was just so wrapped up in getting this startup off the ground. I just remember them leaving and just having a breakdown, like just really upset that I felt guilty about not being a good daughter and not being able to spend that time with them.
So I think the thing is you can't win, because like you said, Megan, if you're spending time with friends and family, then there's always something at work you're thinking about too. I think just realizing that and embracing it and finding the best way to weave both things together, what's right for you is going to be different at different times as well.

Ashley: I think it's all about setting the boundaries with yourself. So I used to have a really hard time leaving the office until everything was done, but of course nothing was ever done. I don't think that's sustainable for multiple years. So now I forgive myself for going to dinner and spending time with friends, knowing that I'll be back online from 11:00 to 2:00 a.m. So I still have the guilt, and I can't go to sleep if I have unanswered emails, and I get a lot of emails between midnight and two.

[00:16:02]

Colleen: Sometimes from us.

Ashley: Yeah, sometimes. But I think that Sheryl does a much better job than I personally have. She calls it taking control of the situation, and what's really admirable on her part is not only did she set certain expectations for herself, like leaving the office at 5:30, but she was bold enough to make those public however sort of embarrassing and scary that was, so that other people could feel comfortable doing the same thing. I think having control over your own schedule is sort of the best way to balance sort of the guilt, and I don't mind working crazy hours as long as I can decide when to take that time off and spend it with friends or family or whatever.

Leena: I think that's a really important point that she makes throughout the book is that you in very many ways have control over this, and if you set the standard, that's not only the way that it's going to affect your life, but it's also going affect the lives of women around you and for generations to come. It's funny we have this, going to back to fear, I had this fear when I was going back to work at TechCrunch that, after having a baby, the hours that I work, there's just no way that I could do that and have a baby and be a wife and do all these things and have it all.
I remember I set down with our TechCrunch's co-editors, Eric and Alexia, and I just wrote out all these notes beforehand, and I was so like mentally prepared to say like, "I can't do this all," and for them to push back on me. But when I talked to them about it, they were completely reasonable. I think I, in my own mind, had these insecurities and I created this for myself. Not to say that every work environment is like TechCrunch's work environment, but I do think that she made the point that you have control over your own destiny, and sometimes it is about your insecurities. If you just are open with it and confront it, then sometimes things can actually change.

[00:18:00]

Pooja: So something she talked really inspired me today at the office. I was on a trip to New York last week and starting to feel very guilty that I wasn't spending enough time with my parents, who moved out to India for us and grandchildren, and I started to block 2 hours every morning, 7:00 to 9:00 a.m., saying, "I'm not going to actually work. I'm going to go on a walk with my dad." Today at lunchtime, I told my team. They asked what did I do over the weekend, and I said, "Well, I've been blocking my calendar now and going out for a walk with my dad every day. Sheryl inspired me to say that.

Leena: And what was the reaction? I am curious.

Pooja: I think it was a shock to people. They've always known me to wake up at 6:00 a.m., start working, be on email, working hard until I go to sleep. So I think people were taken aback, but I'm sure they could appreciate me talking so openly about the importance of family.

Colleen: Leah also, as someone who has built a business, is there anything that you think you brought to make it easier for the people who work for you as well for that guilt?

Leah: Yeah, I mean I think being open, like I'm sure your team really appreciated that story and thought about ways that they could work that into their own lives. For sure, at Task Rabbit, I've been open about my schedule. My parents now have moved out to California to be closer to my husband and I, which is fantastic. So nights and weekends, we'll do dinner with them. We'll go to up to Napa with them and do weekend trips. My team knows that, and they always ask about like, "Oh how are your parents doing? How are they linking it out here?" I think it's just important to be open and transparent to make people feel comfortable about their own work-life balances as well.

Ashley: My boss has three little kids, and right now she is single parenting it. She is an amazing inspiration, because I mean no one takes calendars into consideration when they schedule a meeting. So we have a lot of 7:00 p.m. meetings, and she will say, "No, this is one of the days when I have my kids. I am leaving at five." And that's that.

[00:20:02]
I remember the first couple times she did that, I was like, "Whoa, what are you doing? How can the world go on?' It turns out that actually nothing falls apart, nothing breaks, and people are maybe even more productive with their time than when they have sort of a limitless calendar. So she has been a really amazing inspiration for that.
Then I have to say having a team has actually been the best thing for me. There's someone on my team who has kids, and some days he wants to pick them up from school. I feel like I need to lead by example and sometimes having my own life so that they can feel comfortable having theirs. Hopefully, I am doing an okay job of that. But I think that Sheryl really makes people conscious of manager's responsibilities and setting that example in a way that I never heard anyone do before.

Leena: I am just curious, if you did, my question is I like that she said that, that you have to sort of be in control over your schedule. But I realize the criticism is that not every boss, not every leader is going to say, "Oh yeah, it's fine," when you leave at 5:00 p.m. every day to go see your kid. I'm sure we've all been in situations where we've bosses that are like that. I'm just curious how you guys react to that and do you agree with Sheryl that you have that control? What do you do if you're not in control?

Leah: I think being in the startup world helps, in my opinion, because there is a lot of flexibility and control. I do feel like the startup culture embraces that flexibility. Even when I was at IBM actually, IBM has always been rated one of the top 100 places for women to work. When I was thinking about leaving, I would be lying if I didn't say that that didn't go through my head. I mean, this is a great place for me to build a career. But I think in startups, in particular, people embrace that flexibility, and I can't imagine someone not being supportive of it in this type of community.

[00:22:06]

Megan: I also think it is generational. I think that our generation has expectations that we will pass on as managers, as bosses, as CEOs and founders that you don't have to be physically present in one geocode, one lat and long, to be able to be very capable and competent at your job and be able to perform your job. So I think that the conversation that I've luckily never had to have, but that I would encourage someone who was in a situation you were describing to have is: How can you make sure that you're meeting all of your obligations and responsibilities and also able to take care of life's necessities? If you can't find a position like that, if you're not fortunate enough to have a role like that, you need to think about what other options there are. Of course, this isn't applicable across the board. There are lots of people who have to punch in and punch out. So it's definitely unique to our community.

Pooja: My mother-in-law is a nurse, and she's the primary caretaker of my son, actually, and she has a very strict schedule. She was the one to actually have to take three months grand maternity leave off because I was back in the office in a week, and ever since she's been back full time at Standford Hospital as a nurse, she doesn't get a lot of flexibility. So I understand that it's really difficult for people in jobs like that. I don't think she has alternatives.

Leena: Well, that's a good sort of segue into our next segment, because we're going to be talking about finding the right partner and how important that is in your support network as well as mentorship. So stay tuned.

Colleen: In this third segment, I want to talk about partners and mentors and the sort of human element here that Sheryl really spends a lot of time talking about in the book. She talks about how women have a bit more of a hard time maybe getting mentors, and it's not because they're not out there, but it's because they kind of ask in the wrong way. It's just a very complicated mentorship situation.

[00:24:00]
I want to ask all of you, have you guys have mentors along the way? Maybe you can talk about who that is. Ashley, if you want to start.

Ashley: I was going to ask Sheryl to be my mentor, but apparently that is absolutely the wrong thing to do. It's funny. I don't think I've had a mentor in the traditional sense. So I have a boss who is enormously supportive, so a mentor/manager. But then the type of mentor I've had have been more for the specific questions I've had. So sort of what Sheryl talks about, don't ask someone just straight up to be your mentor. Go to them with a specific question. When I was building my team, I asked Margaret, at Andreessen Horowitz, if she would sit down with me and sort of talk about how to structure that. She was immensely helpful. Or Jane Hynes who runs communication for Salesforce and has been there since day one. So people who I felt could help in a very sort of specific way, and I have always been blown away by how receptive people have been to doing that.

Coleen: Yeah.

Megan: I've always had mentors as well, though none of them have ever been women, and I don't exactly know why except that perhaps all of my bosses have been men and some of them are former bosses, or just those are the people who have been able to be most helpful and applicable to my work. But I have to say I have never say the words to somebody, "Will you be my mentor?" I don't think I could.

Leah: That's very awkward.

Megan: It's a very awkward phrase, and in fact, if you actually said to any of these men, Megan considers you a mentor, they wouldn't be shocked, but they might be a little bit like, "Oh, I never thought about it that way." So I'm not going to name names here, but they are people who I make a point - and I am actually someone who is religious about my calendar - of meeting with on a regular basis. One in particular from the product world, who is very senior Google, basically in many ways got me through my time at Square, leading up product there with advice and guidance, not on the specific products, not even on how to build out my team, but just on how to think about growing with the organization and growing with the product user base.

[00:26:08]
That was because we put time and calendared to meet every other week, every single time, and we never failed to show. So I think it's more about finding those people who had the experiences that you want to have and then just being religious about making sure that you check in with them.

Leah: Yeah, I mean I've talked a lot about mentors in my life, and they've made a big different to me and making that transition from being an engineer into an entrepreneur. One of the folks that I always mention is Scott Griffith, who is the CEO over at ZipCar. He kind of took me under his wing from the beginning and even gave me free space to work out of the ZipCar office. But I think the point that really struck me in the book was that instead of going out and looking for mentors, build relationships, ask great questions, be strategic. If you do those things, then people will want to help you, guide you, and they'll seek you out. When I look back at my relationship with Scott, it all started with a 30 minute coffee chat about how I was thinking about TaskRabbit, and it just kind of snowballed from there. I think that was a really important point. It is not like she says a mentor is going to come in and be your Prince Charming, swoop you off into the CEO sunset, and I loved that analogy. I think that is the most important thing.

Megan: And I also do think that you grow out of mentors, right? You need mentors for different stages of your career and candidly your life, and so it's not necessarily a relationship that's for the long term. But it's how can you have a relationship that will help you understand and excel in the portion of your career that you are at, at that time?

Pooja: So my turn to share a rather embarrassing story. I was an engineer at Facebook in 2008 and overlapped with Sheryl, and I remember she held a gender issues in the workplace session. Soon after that, I was faced with the dilemma of, "Do I stay and be an engineer at Facebook, or do I go to Stanford Business School where I got admission?"

[00:28:04]
She gave me some great advice, and at the end of it, I said, "Will you be my mentor?"

Colleen: You're the one?

Pooja: I don't know. I think she gets many of them, but the point is I'm glad she talks about this, because since then I went to Stanford Business School. I started a company, and I got genuine, true great people who took me under their wing because I was really curious and I wanted to learn and I ask lots of question. But my background, I grew up in India in a small town where women just knew how to cook, tend to a family, and get married at the age of 16 or 18. So if this book can influence other young women, well, seek mentors by learning about others and asking great questions and genuinely be curious, maybe I could have avoided asking her, "Will you be my mentor?"

Leena: I loved that chapter about mentorship, and what I loved about it is that I'm really excited for my daughter to read that, because I wish I had read something like this when I was 16 years of age and thinking through my career and thinking about mentorship, because I feel like I've made the same mistake of confining myself to the notion of how a mentor should be and then trying to pigeonhole someone into that. What I realize after reading this book is that I actually do have a lot of mentors, but just they're not in the traditional form, including my husband, for example. I find him to be a mentor to me in so many different ways, professionally, personally. So I really liked the book, and it opened my eyes and it also made me realize that this is going to make a big difference I think in other women's lives.

Colleen: And this is a very young panel, and we did that on purpose. We wanted the younger generation, because we've heard a lot from the Marine Doubts of the world about what they think about this book.

[00:30:00]
So we wanted to get this young group together, but I think that all of you were at these points in your careers where maybe you should be someone's mentor as well and reaching out. It's not just about someone coming up to you and asking, but going and talking to a younger male or female and seeking them out too and talking to them, even though we're all so busy I can't even imagine.

Megan: It is something you have to put time aside for. I mean, what's happened, as I moved from Google to Square to venture capital at Kleiner, is different people with different interests have come out and said, "I'm really interested." I have actually received emails that were, "Will you be my mentor?" It feels like a lot of responsibility, a proposal in some sorts. You can fill an entire calendar with coffee dates. So sort of the action item I gave myself, again because I am a slave to my calendar, is okay, I am going to put aside an hour every week and I'm going to fill those up with 15 to 20 minute slots and I will meet with those people who email me out of the blue, or I will do phone calls - actually, a lot of them are phone calls, because there are a lot of folks east who want to come out to California - and have those conversations. I can't be an ongoing mentor for all of these folks, but making the time, especially since so many people made that time for me, is really important.

Ashley: Yeah, and I mean given how interconnected Silicon Valley is, it's also a selfish decision, right? I mean, I love chatting with entrepreneurs who are really early and wanted to learn about PR. I'm always a little baffled when they ask me because I'm still learning how to do this, or talking at incubators. There is a whole new crop of people who may go on to do really cool things. So I like that Sheryl sort of breaks down the really rigid definition of mentorship, because by no means would I want to like an hour with one person each week. She has that funny anecdote where she thinks she is mentoring this girl, and the girl says, "Oh I wish I had a mentor." Sheryl is like, "What do you think I have been doing?" She's like, "Well, a mentor is someone who will talk with you for an hour each week." Sheryl is like, "No honey, that's a therapist." So I'm not being someone's therapist, but I do think there's a lot of reasons for spending some time and information sharing and meeting new people.

[00:32:04]

Leena: I thought another interesting part of the mentorship angle was sort talking about her husband and making your partner into a real partner. I am curious what you guys think about that. She said in the past the biggest business decision you will make is who your partner is, who your husband, your wife, your long-term partner will be. So I am curious what all of you think about that.

Pooja: Yeah, absolutely. The reason I'm successful with Piazza and the reason I can have a baby today and also be running a company is in my case not only just my husband, but also his parents and the extended family support I get. I know, I tell myself so many days that if I had not left that first marriage, I would not be anywhere near having understood my full potential.

Colleen: I thought it was that was one part of the book that I thought of all of things that are controversial, I think this is probably it. She is very straightforward in saying to the point where it's almost dating advice. She is saying you can mess around with the bad boys and go on a few dates with the sensitive but toxic artist or something, but when it comes to who you settle down with, it should be a man or a woman who is stable and invests in you and stuff like that. It was just so frank I thought that she said that.

Ashley: She actually said it was the number one thing, and it is a little bit shocking because it almost sounds anti-feminist, right, that you should have to like rely on a man in order to reach your full potential. I love that whenever it's a question of going for pragmatism or saying something that's comfortable and politically correct, Sheryl picks a pragmatic argument.

Leah: Yeah, I think, in my case, that really resonated with me as well because my husband has also helped come up the idea for TaskRabbit and has been involved from the very beginning. Early on, he was the one that stayed at the stable, full-time job so that I can go off and not take a salary and bootstrap a company.

[00:34:05]
Years later, after we raised our A round, he came on full time, and now we work together full time at TaskRabbit. So there is no question that, in my case with Task Rabbit, having my husband Kevin be a partner, not only in the business but also in our marriage, has been a huge reason why we've been successful.

Colleen: She also brings up an interesting statistic of the Fortune 500 CEOs, a very small percentage of them are women obviously. It's like 28 women who are Fortune 500 CEOs, but 26 of them are married. One's divorced, and only one has never been married, which I personally hope that's something that changes, because I'm sure we have Fortune 500 CEOs who are male, a lot of them have been divorced, a lot of them are unmarried. So that was actually, that whole section was kind of disheartening to me, because you would hope that there would be more diversity in that group.

Leah: Well, I think even more controversial is the point she makes about everything will be in balance when half of those fortune 500 CEOs are women and half of the people that stay home with the kids are men. I mean that's actually really a balance, and that is like the ending point that ends the book and starts the continuing conversation.

Leena: Right.

Colleen: Yeah, so speaking of continuing conversation, we've got more. So please stay tuned for the next segment.

Leena: In our last segment, I want to talk a little bit about what Sheryl sort of claims that we are possibly our own worst enemies. Women tend to criticize each other and hold each other back, which as she said it was very sad. It is a sad sort of state of affairs, but very much the reason she wants to create these Lean In circles. So I am curious, in all of your experiences, have you felt that? Have you felt that other women have held you back in some way?

[00:36:04]

Leah: I don't know about other women holding me back. What I have noticed at TaskRabbit is when I've interviewed female execs that have come on board, in my case a lot of them, all of them actually have negotiated hard for the job, which I appreciate actually. But she makes the point in the book that we don't do that enough, and we don't actually push ourselves enough to say, "You know what? I'm worth more." It's the fear of likeability. It is the fear of being too aggressive or being an antagonist.
Actually, when I was reading it, it was interesting because one of our newest executive, our COO, Stacy Brown-Philpot, who just came on board, she worked for Sheryl actually at Google. So she negotiated hard for her role at TaskRabbit, and again, I respect that. After she came on board, she said, "Prior to joining TaskRabbit, I was looking at other opportunities." The timing wasn't right for her to come on there, so she was exploring other options. She was accused of negotiating too hard somewhere else, and it was an all male exec team. She decided after that it just wasn't a great fit for her, and she moved on and thankfully, and I'm very grateful she ended up at TaskRabbit. But I thought that was just an interesting story, an interesting point and something that I see happen again and again. When women do negotiate, I celebrate that, like go for it. That's what we need more of in business.

Leena: That's right. Absolutely.

Megan: The one example I have, because by and large I actually haven't experienced women holding me back or even exhibited it that much.

[00:37:54]
However, there was an exception, which was in my first two weeks at Google, I was barely 22 years old, and another women pulled me aside and said, "You're really abrupt on the phone. You sound very aggressive. You should really soften your tone." I was shocked because I'm the middle of five daughters. My father and mom raised us to be empowered women, and my boss at the time, who was the only woman VP at Google at the time, had never mentioned that to me. So this was someone else. So I told her. I actually went right to her, because I thought, oh two weeks on the job, I'm already getting negative feedback. She was furious, and she actually went and found that person and said, "You never talk to my employee that way again, and you never give that advice to another young woman again." That was the only example I had, and I so appreciated the senior woman coming to my defense for something that was just so ridiculous.

Ashley: It's funny, because I almost have an opposite example where when I started at Box, I was pretty young. I was 24 or 25, and my boss pulled me into a room and she's like, "I'm going to say something. It might be a little hard to hear, but hopefully you can just take it as constructive feedback." She said, "Like a lot of women, you are saying smart things, but you're framing your statements as questions. You play with your hair a lot during meetings." Really embarrassing classic sort of feminine things, but I was taken aback, but I was so grateful for that. I haven't felt being held back at all by other women, but I do have this very strange like I don't understand why I am so shocked, but every time I do ask some powerful woman or someone for help or not a mentorship but a question, I'm always a little bit shocked when they say yes, like I expect women in positions of power not to be open to helping me. Given that I haven't had any of the opposite response, it's strange, but I am conditioned to think that women are competitive and probably will not be supportive.

Colleen: I thought that it was an interesting point, and she probably made it earlier in the book just about how women are naturally, biologically maybe they are going to be more nurturing, or that's how women are because we have babies and we can nurse them and things like that.

[00:40:07]
But that is so far back in evolutionary time that that doesn't mean we shouldn't work against that now. So even if it is, I think a lot of people would say, oh women are naturally competitive with each other because there is a short time relative to men for conception, and you need to fight for the best mate. We need to all be catty to each other or something. Even if that is the case, and they haven't proven it in either way, that's not something that we should just use as an excuse and feel like we're going to hold each other back. But I think what I've heard a lot of times is that of course women are competitive with each other. That's just naturally how they are. I think if that is nature, then it's good that Sheryl is saying we should work against it.

Megan: I also think it's potentially generational. So when you had very few women in positions of power, it seemed like there was only ever going to be very few women in positions of power. So it was more women fighting for a smaller number of spots. But as we get closer and closer towards Sheryl's vision of this 50/50 split, that notion goes away, and there's more opportunity to help actually actively pull up women into higher ranks and not have to feel competitive, which in some ways is just innate human feeling whether or not you're a man or a women, because there's going to be more positions and more opportunities to share.

Ashley: Yeah, and that's where the ladder versus jungle gym metaphor for careers is really interesting, because if you think of a ladder, it is obviously very linear. To move up to the next rung, you necessarily have to displace someone, right? So it's a very sort of zero sum way of thinking about careers. Whereas jungle gym, you're going all over the place. Maybe you're going into a role that never existed before or creating it. So I think it's a generational thing. It could also be a sort of a startup world thing, where nothing is zero sum here because everything is growing and evolving and changing. So it's very silly if we do have these sort of more zero sum mentalities about careers because that's absolutely not how the world works.

[00:42:01]

Leena: I love the ladder and jungle gym comparison, because I think that is such a good way to kind of describe what a career is and how she said she had taken different roles at different places. Some may have been interpreted as a demotion or something lower, but ended up advancing her career, and I think that's a lesson that is great for all women to kind of realize that there are all different paths to finding that professional happiness.

Pooja: For me, how I would answer the question actually if I really wanted to be very honest is I'm the person who might hold myself back the most and really the guilt issue, she says, "Guilt and insecurity makes us second guess ourselves and in return resent one another." She hasn't met any woman who is comfortable with all the decisions. I'm not comfortable with all the decisions I make, and I'm constantly trying to balance so many things. If one thing I can take away from this book is be comfortable, be comfortable not feeling comfortable because I'll never feel comfortable.

Leena: That's a good lead in to what I wanted to ask all of you about the book. How do you feel about it? I mean, it was a very controversial book as we mentioned earlier in our conversation. Did you enjoy reading it? Is it something that you will take away and actually learn from? Are you going to start Lean In circles anytime soon?

Colleen: Right. Right, because what's important to point out is that this is part of a larger movement, LeanIn.org.

Leena: That's right.

Colleen: This is one component of it, and then the hope is that there is an actual going forward, Lean In circle being formed by every women out there.

Leena: Right.

Megan: So I appreciated the book for two reasons. One, it's an incredible almanac of stats and statistics about women in the workplace. So I think almost a third of the book is footnotes. This is an incredibly well-researched and footnoted book. So I found that interesting to have that consolidated.

[00:43:55]
Then the other piece was really the distillation of a lot the things that I have thought about, that my friends have thought about, I'm the middle of five daughters, that my sisters have thought about, but broken down into really small nuggets of advice and guidance. So perhaps not every single page was revolutionary or new, but it was the distillation of something that I or someone I know has thought or felt into a way that was very, very clear and crisp. If that's useful for other women, that's wonderful.

Leah: Yeah. I found the book to be really refreshing honesty. I felt like it was a different perspective than what we usually hear, but is actually a perspective that I share. A lot of people have interviewed me about, "What is it like being a female in tech? What is it like being female CEO?" She mentions actually the San Francisco magazine article that came out with my head on Mark Zuckerberg's body, which I was appalled by, by the way. So it was just nice to have a refreshing look at the issues. I, for one, am really exited about having every single person at TaskRabbit read the book, manager, individual contributor, executive, everyone. We ordered 60 books, and I think it's just great for men, for women, for everyone to read and really internalize.

Ashley: We ordered it at Box as well, and I'm reading it in my book club. So I will have many future discussions on this. I did, I really liked this book. I think a lot of times, every now and then, the women in tech or women in leadership topic bubbles up, and usually it ends up being totally counter productive and nothing meaningful happens. I like that Sheryl, from the onset, said there are lots of institutional things that we need to deal with. Other people are fighting those battles. I'm going to look at what individuals can do. As an individual, I really appreciate having advice that I can directly apply. Whether or not this will become a campaign or a movement will be very interesting, because it's so nuanced.

[00:46:01]
So usually if there's a big social movement or uprising, it's because there's some sort of extreme view. At the aggregate, it is extreme, right? Going to 50% Fortune 500 female CEOs would be extreme, but all of the little pieces and steps we need to take to get there are so nuanced and subtle. So it will be interesting to see where this book goes from here, but I certainly appreciate it as an individual.

Pooja: Well, I felt very validated. It was really refreshing as I was going through many points and I could resonate with what she was saying. There's a young 22-year-old who just graduated from Cornell last year, and she's bright, talented, ambitious, and I'm, the same thing, encouraging her to read this book and we'll talk through it. There are other young women out there at the age of 22 who could read this book. It's like there's a lot to think about, digest, reflect on.

Megan: And not just women, men. There are so many men. I'm going to give this to my entire partnership, men, women, everybody because it is actually very helpful for both genders I think.

Leena: I agree. I was going to give this, I told my husband as I was reading it, like you have to read this because there's so many interesting points she makes about work-life balance and mentorship, as we were talking before, your partner being helpful, that men can definitely appreciate as well. What did you think Colleen? I'm curious.

Colleen: I absolutely agree with the facts and figures, and I had the same experience. I was calling out to my husband in the other room, "Did you know that we talk to female babies more than male babies?" That was just a scientific tidbit that I didn't know. So yeah, I thought it was packed with everything, and I think the overall message to me seemed to be why it's important, because I think a lot of people would say, "Well, why is it important to have more women in leadership roles at all? What if they don't want to be? What if they want to lean out? What if they want to be moms full time?" That's fine. But I think that she made a really good argument that it would have a trickle down effect if we have more women in leadership positions, and that's the thing that I'm kind of taking away from the book. That even the way the role of women in the world, there are a lot of problems and just having more women at the Fortune 500 level, it is the top 1% problem, but there will be a trickle down effect from it.

[00:48:10]
So I guess I'm starting a Lean In circle.

Megan: I can't wait to see the TechCrunch TV panel of men discuss "Lean In." I will tune in to that.

Leena: I also loved how honest she was, and I think that was refreshing because I think it would have been easy for her to say, "Things are great. My life is great. I'm lucky to have the life that I have." But she was very honest about how she still has battles with guilt all the time, and for a mom that battles with guilt on a minute by minute basis, being away from her child, it made me feel better. If the COO of Facebook is feeling the guilt that I am, then there's something there and something that we can do at least to change it or battle with it. I found it really refreshing how honest she was.

Megan: Yeah.

Colleen: And it is great to have a conversation with all of you super established women being honest as well. So hopefully more people will follow in her footsteps, and we'll have a Lean In by Leah Busque, a Lean In by Megan Quinn, a Lean In by all of you, talking just more about this in the next 10 or 15 years ahead.
It's been great. Thank you for watching this roundtable discussion of "Lean In," and hopefully this is just the beginning of a conversation about these important topics. So thanks.