Winnie Wong: You Don’t Have To Look The Part, Workplace Vulnerability and Personal Storytelling vs. Bamboo & Glass Ceiling - E289

· Women,Southeast Asia,Purpose,Podcast Episodes English


"There's a gap between men and women, but an even bigger gap between white women and Asian women. What is an Asian woman supposed to be like? A lot of reports in Western society show that women fulfill more emotional needs for their colleagues and are expected to get involved in diversity and inclusion efforts, which can sometimes turn into additional unpaid roles resembling human resources. It's fascinating to learn about these issues faced by women, especially those who belong to double minority groups." - Winnie Wong


"Initially, my book centred around the stories of East Asian female founders and the lessons we learned from them. I did a pre-order campaign and shared the first drafts with my friends. They said it’s great, but they didn’t understand why I’m writing it and there wasn’t enough of myself in the book. It was scary to open up about my past experiences. The tough part is that I didn't want to portray myself as a victim, point fingers or blame anyone, and I wanted to maintain a positive perspective. It helped me reflect and share my experiences as objectively as possible." - Winnie Wong


“In some ways, Southeast Asia can be ahead of the Western world in supporting women in their careers. The future diversity in the region is still uncertain because visas have been declining, the Singaporean population is becoming a lot more educated over time, and the middle income is growing. It's great that region is growing and I hope that representation will also grow eventually.” - Winnie Wong


In this discussion between Jeremy Au and Winnie Wong, significant insights emerged including women's challenges in the workforce, the glass ceiling versus the bamboo ceiling, sponsorship and mentorship, and the role of diversity and inclusion. Winnie’s book, “You Don't Have To Look The Part”, played a prominent role in the conversation, blending personal narratives with research findings.

One significant aspect explored was the apprehension and vulnerability associated with sharing personal stories. Winnie expressed her concerns about potential backlash and cancel culture. However, she emphasized the importance of authenticity and acknowledging the challenges faced, while maintaining a positive and constructive outlook.

The conversation also highlighted the issue of representation, extending beyond gender diversity to encompass race, ethnicity, and disabilities. Winnie stressed the need for organizations to actively include underrepresented voices at all levels and explore diversity metrics. By doing so, companies can develop improved products and services that cater to a broader population.

Feedback received led her to include more of her own experiences in the book, striking a balance between objectivity and subjectivity. She aimed to avoid victimhood narratives and instead presented her reflections and the realities encountered throughout her life.

Overall, the discussion shed light on the significance of supporting women in their professional journeys, promoting diversity and inclusion, and embracing individual narratives to foster a more inclusive and equitable society. Winnie’s book serves as a valuable resource, providing insights into the challenges and triumphs of East Asian female founders while encouraging a broader understanding of diverse perspectives.

Supported by Esevel

Do you manage your own IT for distributed teams in Asia? You know how painful it is. Esevel helps your in-house team by taking tough tasks off their hands and giving them the tools to manage IT effectively. Get help across eight countries in Asia Pacific, which includes onboarding, procurement, device management, real-time IT support, offboarding, and more. Gain full control of all your IT infrastructure in one place with our state-of-the-art platform. Check out and get a demo today. Use our referral code, "BRAVE" for three months, free. Terms and conditions apply.


Jeremy Au: (01:28)

Hey, Winnie. Excited to have you on the show. You are writing an important book on double minority representation in entrepreneurship, and I thought it would be a fun way to get a mixture of both the personal and, of course, academic, from your perspective about what is happening and also what needs to change. So on that note, could you please introduce yourself real quick?

Winnie Wong: (01:47)

Hey Jeremy. Thanks so much for having me. So my name is Winnie and I'm originally born and raised in Canada. Growing up in Canada, I had a very multicultural upbringing. I had friends from all over the world because people were just immigrants from everywhere, but the cool thing about growing up in Canada was that I was a product of scholarships. So I got to study in French-speaking Canada, the United Kingdom, and China, and that was an amazing experience for me to just understand what the world was like outside of the Western world and to find a part of my own identity in China and Asia. So, after working a couple of years after graduating from school, I decided to drop everything, quit my job, get rid of my lease and move with just one suitcase to Singapore and give myself six months to find a job.

So, that's kind of how I ended up moving to Singapore. I ended up just networking, getting coffees with a ton of people, and just sharing my story with them. And that's also the basis of how I ended up writing a book too. My book's called “You Don't Have To Look The Part” and throughout writing this book, I got to learn a lot more about the subconscious reasons for why I ended up writing this book and why I ended up moving to Singapore. But I'm happy to share more about it throughout this chat.

Jeremy Au: (03:08)

Yeah, and I thought it was interesting because you chose the title, “You Don't Have To Look The Part”, and it's interesting because I think there's an element of stagecraft, right? You don't have to look the part, wherever the part is. So could you share a little bit more about how you came out of the title and what it means to you?

Winnie Wong: (03:25)

Yeah, honestly, my working title initially was called “East Asian Woman in Entrepreneurship”, and so I have gone through a hybrid model, in hybrid publishing, this book where I had gotten a ton of pre-orders early on back in November 2022 to help fund the publishing of the book and at the time the working title was “East Asian Women In Entrepreneurship”. At the time it was just a stale title because I didn't know really what anything catchy was. People thought it was going to be a textbook, but it sounded like a textbook. So I think it wasn't that easy, like as a sell back then, but now that I've changed the title to “You Don't Have To Look The Part”, people get why I'm writing it and it came about because when I was researching this book, I went through researching and profiling a ton of like East Asian female entrepreneurs, and one of them, her name is Vicky Tsai,, she's the founder of Tatcha, a beauty company. As she told, she shares a story about how she founded her company after nine years.

She got private investors on board, and those private investors told her that she didn't look like a CEO even though she went to Harvard Business School. She had worked in the beauty industry for many years before that, and the company was growing by double digits every single year. So because of that, it was the name of a sub-chapter, like a mini-chapter in the book. And then it just resonated with me when I was thinking about the book because I realized the bigger picture about this isn't just about East Asian women's entrepreneurship, but it's about anyone who's diverse or is a minority.

Whether you are homosexual or whether you are, black, latino, whether you're a minority as a woman or transgender, it is about not being part of the majority and that you don't have to be, you don't have to see someone who looks like, the role you want to have to go for that. You can build it yourself, build your path, and you can be a role model for others, who follow you afterward. So yeah, that's kind of how the title came about. It was just a subsection of one story that inspired me the purpose of the book is really about diversity, equity, and inclusion.

Jeremy Au: (05:53)

I think there's an interesting piece they talk about, which is, I think the word majority, right? And I think there are so many different majorities. So when I'm in Singapore, for example, my Asian identity, I'm the majority, and in America, it's a minority, for example. So, I think you kind of shared a little bit about how you've moved right between Canada, between Singapore. So you know, different identities can be different majorities. Different professions have different majorities as well. So how do you feel about that? Is it natural for majorities and minorities? Is it natural for outsiders and insiders? What do you think about that?

Winnie Wong: (06:32)

Yeah, that's a great question. So, when I think about my own experience in Canada and growing up in the Western world, I also studied in the UK. I also studied in France. I went to INSEAD and I remember when I was at INSEAD, I was thinking about moving, I was moving to France. I speak business-level French. So, yeah I was sitting in one of these luxury goods companies, their info sessions, and I was thinking like, oh, maybe I'll explore luxury goods. I love it, I'm super interested in it. And I noticed they were saying, you know what? We love women. 90% of our companies are made up of women. And then they showed in the next slide, and it shows like their leadership. And it's like, they're like, oh yeah, but all of them are in the junior levels, basically like shop floor, like salespeople.

None of them are in management. None of them are in senior management or the executive, and it's a family-owned company. So I was like, okay. My initial reaction was, this is so grey. And then it's like slowly, like you even track, you even track your leadership and the gender representation in leadership and you're showing this to us and it's like so negative for me. And as an Asian woman, especially if you're living in France, there's an expectation that you bring this Asian perspective as well. Like you've got networks and in Asia or whatever, and you can bring the business in and you can speak Chinese. I don't know about you, but my Chinese, it's worse, it's worse than my French.

Jeremy Au: (08:17)

So less business subprime level.

Winnie Wong: (08:21)

Yeah, that's kind of how I realized I got to stop this process. I don't think this is the right fit for me. And that's also how I ended up steering back and returning to Singapore after my MBA because I noticed terms of the majority and the expectations of Asian people in the Western world are a bit different, like in the tech industry as well. There's a huge, there's a ton of research about how like East Asians, they're recruited and they're very, their income levels relative are like, as a minority, are extremely high, higher than the majority, the Caucasian majority. But then there's like a broken rung for them where they don't get promoted into managerial roles. So that's subconsciously how I end up doing up back in Singapore and Singapore.

Although the majority of, the population here in Singapore and in Asia is like visually Asian. I do remember like I was, I was having dinner at this restaurant, it's called Sear. It was called Sear, it was like on the top of Singapore Landtower, a great steak restaurant, and was a Caucasian man serving me at the restaurant. I remember it being like how are you serving me? And so the fact that I even had to question that in my mind, because internally I'm so used to minorities, like non-Caucasians like, being in the service industry, it really kind of taught me a lot about my own, like how we kind of have been programmed. And this translates to a lot of companies here in Southeast Asia. I've worked in I think maybe four companies now since I moved to Singapore. And what I've seen across many of these multinational companies is that like when I look up, there's a lot of, or when you look at the senior leadership of them, a lot of them are Caucasian.

You see very rarely people at the junior levels who are of this Western background. And so I think that also like inherently as an Asian makes you feel like, am I not good enough? As Asian am I not? Like, do I have to be more Western to fit in for me? I actually kind of believe that in multinational environments, there is that expectation to be a bit more Western. I know you have a degree, you have a couple of degrees from the West myself too. And I feel like this Western perspective is very respected. The assertive culture is very respectful, but I feel like it's important to also recognize the strengths that we bring as Asians as well, and the Asian culture too. So, yeah, I do feel like even though we're part of the majority here in Asia there is still, in a lot of ways, a bit of a broken rung for many Asians to progress into higher levels of senior leadership.

Jeremy Au: (11:07)

Yeah, and what's interesting is that you're not just talking about, for example, kind of like racial in terms of equity and inclusion, but also talking about, the double minority, right? So for example, about the bamboo ceiling times the glass ceiling, right? So what happens in that situation? Like what, I mean, you've done quite a bit of research, right? And so tell me more about that.

Winnie Wong: (11:30)

Yeah, so I do have some facts and figures about this.

Jeremy Au: (11:35)

Shoot away.

Winnie Wong: (11:36)

A bit of research.

Jeremy Au: (11:37)

Only years of research. There we go.

Winnie Wong: (11:41)

Yes, so globally, like, for my book I had like, I was really researching and just learning a lot about representation. Firstly of women in leadership and so, what I found was that women of course, only 15% of Fortune 500 CEOs are women and a big one for me in the tenant of this book was about entrepreneurship and only 2% of venture capital funding goes towards women also. One-third of businesses are owned by women, so it's hyper-under-indexed. I looked into a lot of those factors behind it. Some of them are internal versus external. Internal could be like as women, we're a bit more risk averse in some ways we're we don't per, we're very careful about what we say. Even you can tell as I'm speaking to you as well, right? I'm trying to be careful, and very thoughtful about anything that I say and of course like. There, there's that aspect of it as a woman of like, if you show too much emotion, you can be considered too dramatic and, it's a big issue about women's issues and like how women are portrayed. So that's one part of it, like what you're talking about, the glass ceiling.

Then there's just this whole bamboo ceiling of, how is Asian being Asian or being a minority, any type of minority affecting people as well. So that double whammy as I call it, does have, like a compound effect on people's careers. So, LeanIn and McKinsey, have this 2022 report about the gender gap and they describe it as a broken rung where for every 109 men who are promoted, I think it's 87 women are promoted, and 82 women of color are promoted. So this is industry-wide and this is how they look at it as color. There's another research report from Ascend, which is like, a Californian organization of Asian professionals and they looked at five major tech companies, Google, LinkedIn, HP, Intel, and I think it might have been Yahoo, but I forget the last one.

Where it showed that one in 285 Asian women in the organization holds an executive position compared to one in 125 white women and one in 87 white men. So it really shows when you look at it, there's a gap between men and women, but there's an even bigger gap like the gap even extends even further between white women and Asian women. So like, it shows and it's a lot has to do with the expectations of what is a woman, and there's a lot of it, it's ingrained when we're young as well, but also what's, what is an Asian woman supposed to be like? And a lot of reports like in Western society, women fulfill more emotional needs for their colleagues, which is actually, I get it. I get it. I see it myself too. Right? They're seen as the person that people can confide in. They're expected to like to listen to all of this. They're expected to get involved in diversity and inclusion efforts, which a lot of the time these DNI roles end up being like, they end up being their like roles themselves, like unpaid, but a completely different job, it's like an HR job. So, it's kind of fascinating to kind of learn about all these issues that people face, not just as women, but also as double minority women.

Jeremy Au: (15:00)

Yeah, that resonates with me. In my last company, I had a Caucasian co-founder woman and myself, and I think l pitched and we had a VC one, so I was like, he was kind of offhand, but he was like, oh, we get count you twice. He meant for the diversity score. Right. I was like, haha and I was like, wow, that's an awkward joke to make. Right. Not the one I would've made. I think there's that interestingness, which is, it's not bad that they have an explicit goal, I guess, to increase diversity. So they have, they're saying like, we have an accounting diversity score, so it's good to have you. But I think the same, I don't know what it is word system or structure goalposts do make you feel a lot more transactional right? In that conversation all of a sudden. Right.

Which is like, we're making scoring points for them towards diversity. And I think that happens a lot for a lot of different initiatives, right? So there's like, there's like, we did this initiative, we did this event, we had this thing, and some of my female colleagues and friends are, kind of get a bit frustrated Right, about, kind of like the sponsorship and mentorship aspect about, like there's a lot of like stuff happening, but it's not coming together. Right. So I'm just kind of curious about how you feel about that.

Winnie Wong: (16:12)

Yeah. I think in terms of diversity and inclusion I've worked in a bunch of organizations and I've been really like I really like some of them where you know that they really take it seriously and you know that they take it seriously when the training that they give their managers. A lot of organizations, and I've worked in like the startup industry before too, the startup industry, honestly, for me, I didn't really enjoy as much because I felt like there's like a lot of egos and people who've just started the company and have a lot of legacies. They end up becoming managers, but they're not always the best managers at times, but they're there because they just have the legacy. But what I found was like some really great organizations take diversity and inclusion very seriously, and they track, first off every rung of the organization.

Like what is the diversity representation at those rungs? And as long as like, just being aware of it really like allows people to consider, when I'm interviewing, make sure that there's half women, half male. It doesn't have to be exact, but just being aware of it really helps, especially because for me, I notice the biggest, one of the biggest reasons why women are a bit pushed back in the organizations of being promoted and progressing in their careers is because of childbirth. Only women are capable of childbirth. And as a, whenever you go and you're pregnant or, and you give birth, it's a two-year journey where you're basically out of career progression. The first year you're basic, you've got a bit of a parasite-like growing in you, and you're tired all the time. You're throwing up and you can't even tell people what's going on for a, like until halfway through.

Something along those lines and then you, after you give birth and you're recovering, you're away for somewhere between three to 12 months, depending on which country you're in and it's very rough because a lot of things change the longer the maternity leave or the difference in the maternity leave versus the paternity leave really sets a stage where managers are, they going to just cover for two weeks or four weeks for men. But for a woman to be away for six months is like a big deal. They have to hire someone new and I caught myself actually once where I was working at a big tech company we had hired a woman and on her third day at that company, she took maternity leave and I was like, why did we hire her? Now we have to hire a contractor. And it was, I was like, oh, this is the worst. Like, I can't believe she would do this to us. But at the same time, like what? Like you, I know you have two kids, like it's tough planning pregnancies, you just don't know when it's going to happen. People try for many years and I have a lot of friends who've gone through the IVF journey as well, so it's a complicated journey and so for women, often they don't feel like they can move jobs when they're pregnant or when they're trying to get pregnant because it's a sign of disloyalty or it's difficult to interview when you're pregnant and you're big and people don't want to sponsor that.

So I think that's the biggest issue for women and like that, that they're facing is this whole paternity. So in terms of inclusion, a lot of inclusive policies are really about, decreasing that gap between paternity and maternity leave. So some countries allow people, like couples to share the birth share that full year. Or even two years. And they can allocate back and forth between the two of them, but also other inclusive policies are really about like, okay given that people have, we work, let's say in an organization, your contract says you work from 9:00 AM to 5:00 PM every day. How do we make it so that whenever we have these social events, they're within that timeframe, so that people who have to go home and pick up their kids or have child-rearing responsibilities? They can do all these things, but it could also be other things like maybe you need to go to the mosque and pray, or you need to, have other activities outside of work. Right. So I think in terms of inclusion, celebrating inclusion and allowing it so that whatever is considered work activities, whether it's social activities within work, are contained to the hours that are agreed to from an employer with an employee. So I think there are some other inclusion points as well as having people in the promotion.

Those promotion committees actually share and mod moderate how those conversations go. Like for a woman, They're often promoted based on past performance versus men are often promoted based on potential. So really monitoring, like how is this conversation going? Are we talking about this candidate's past, their potential that they were great, that they could lead if they, but how have they actually shown this in the past? Right. So I think there are different policies that, different organizations have researched and have fortunately, Been a part of in the past that have really shown to me what inclusivity can be like and that can also be like, some of these great tech companies create like accessibility features on their like laptops or, even I remember I was sitting in a conversation with a paly, Singapore's Paralympic athlete. And she was sharing about how during Covid like a lot of malls, they'll have like only certain doors that are open to manage the crowds and a lot of those doors were not automatic.

So for her as a Paralympian who is going and she has to use a wheelchair to get in, she couldn't enter a lot of these malls and she ended up staying home a lot during covid, which really horrible for your mental health to begin Right. And also people with oxygen masks as well. She was sharing with me because there's a lot of regulation around the masks. Even wearing them outside they couldn't wear one of those masks because they needed an oxygen mask and they'd have to go back and forth. So I think a lot of it really starts with just being aware of different needs and accessibility, not just for East Asian women, but also for people who are accessible or other minorities.

Jeremy Au: (22:20)

You had previously mentioned, something called over-mentored unsponsored, and I think there's actually a great encapsulation right of feeling. Right. Could you share a little bit more about what that meant?

Winnie Wong: (22:32)

Yep. So there's a Harvard Business Review article that shares about how women are over mentored, but unsponsored, and in this article, and I refer to it in my book as well, In structured programs of mentorship within organizations, they find that women have very different experiences than men do For women in these structured mentorship programs, they often, they might ask hey, I'd love to learn how to grow or develop in this area and they say hey, yeah, if you'd like a role in that, you need to show past performance and therefore, We're going to put you on all these extra assignments. You can be the diversity and equity inclusion manager while also doing your full-time job. You will also do these like three extra projects that will be shown to senior leadership down the line later on and so these women feel like they're just piled on more work, but then they don't really see much results after that. They're just exhausted because they also are taking on a bit more work at home that's unpaid, versus men, what they find is that they are openly sponsored where.

They'll sit down with their men, their structured mentor, assigned mentor, and their mentor will just say, Hey, like where do you want to go in your career? And they're like hey, I'd love to one day be the CMO of this organization, chief marketing officer and so their sponsor will say, yeah, let me connect you with a bunch of people who are in marketing, whether it's inside and outside of the organization so that you can learn more about it. You can also gain connections about it, and maybe you'll find a role in that area. So it's as if the men are already deserving of it and the books already the black book is already open to them where they can pick and choose who to connect with, versus for the woman, they still have to go and shoot and like show and prove that they can do it before they can even get a contact or build a relationship with anyone and many, and most of the senior leadership roles are with men too.

So for them, they're, even with networks, the way that networks work within our organizations is that they're a bit gender-based and a lot of men, actually, I remember Michael Spence, former vice president of the United States, he had a policy where he would not take a one-on-one meeting with any woman because he never wanted to be under the spotlight of having, sexually harassed her or assaulted her or anything like that. So, as a woman, for myself, not having access to senior leaders, and the majority of them are men, is a very challenging situation to be in, because what we know is that. Actually, your progression in an organization is heavily dependent on your network in the organization rather than you know the projects you've done. Because a lot of it really is the spotlight that you get and the platform that you get, which is really about who's willing to listen to you as well.

Jeremy Au: (25:20)

Speaking about, speaking and listening, Shao Ning from Angel Central, who was a prior BRAVE guest and interview shared how she felt like, The world of business was very masculine language from the perspective and she felt that the people and the founders who struggled to fundraise were often their languages didn't match. Right? And so she spent a lot of time coaching them to be more from, in her words, masculine in their language and she also shared that actually what was interesting was that the investors that she works with as well actually also had the same bias in looking for the same masculine language as well and so she ends up kind of coaching both sides of the table towards that, say norm, right? In that sense. I know you have a lot of thoughts about this. What do you think about it?

Winnie Wong: (26:06)

Yeah, I listened to that podcast as well, way long ago, before this one actually. But it was, so there is a lot of research out there about like, even just job descriptions. So Glassdoor has published research on how a lot of the job descriptions are about independence and leadership. Leadership is like not so much mentoring others, but more so being independent and some of those words. I remember one of them was rockstar, and I actually use this word myself. I'm always like, oh, you're such a rockstar to like other people when I'm cheering them on. But I realize I have to change my own tone as well because the research shows that women don't feel like rockstar describes them. Rockstar seems like you're on your own island and you're just killing it. Versus women are a bit collaborative. They really seek collaboration and I know in that podcast she was sharing that women ask questions a lot.

They want to understand, they seek to understand and to adapt accordingly and so when they speak, they might have their tone go up in a question like, oh well, I actually ask a lot of questions but they could say, I always ask for confirmation like, oh, is this okay? Or how is this, hope this is okay. Versus for men, they're just like, this is the way it is and I think it's because also society's expectation of women is to be a lot more collaborative than to be independent and Sheryl Sandberg also talks about this too, whereas a child, a woman might, and a girl and a boy might be exhibiting the same like behavioral features and the boy will be considered like a leader, a strong leader, very, an assertive and like independent versus the woman might be considered aggressive, right? Because she's not fitting the gender norm, but like, I believe that women, and I do believe with that podcast guest about women being a bit more successful if they understand how to communicate to men and live in this masculine world because men are make up the majority of senior leadership roles and therefore they dictate what is expected of other people in the way that they see the world, which is as a man and very masculine, whether it's a language even for myself, I speak.

Relatively at a different pace to you even then I would speak to my girlfriend, I would speak at a way higher pace. I'd speak a lot more freely to her. But I think the language, to begin with, like job descriptions is one example of why a lot of roles can be very gender-based also when we think about a nurse versus a doctor, for example, we think about a nurse being a woman and a doctor being a man. It's actually untrue. In Singapore, the majority of doctors, are actually females, it's really interesting. But we would think about the job description as even just like we might say some. The most extreme in the worst-case scenario, they'll say he is good at this. He's good that when they're like writing the drop description, I think people are relatively smart enough now or more like understanding to drop those pronouns, but at the same time, they're very masculine based because they think that there's a man in the picture versus for the nurse. They might think, okay, we need to be more collaborative. She needs to be very caring, but they don't put these adjectives with the doctor.

Although doctors and nurses actually have very similar. But actually similar capabilities and roles where they're doing a lot of nurses. Actually, I trust a nurse more than a doctor because nurses just see so many more cases. They're triaging so much that they can make decisions very quickly or they can diagnose a lot quicker than waiting for a doctor. So, yeah, I think a lot of it has to do with job roles, how they're written, not just about pronouns, but also about verbs and actions and ad verbs about our adjectives about them.

Jeremy Au: (30:04)

Yolanda from Uncommon, she's building a community for female leaders, right? So for them to help each other, but also to mentor each other as well to climb that. I think there are also other communities like that. For example, I know the co-founders of Chief, which is a female leadership community in the US and I remember sitting in their first clubhouse it was still being half constructed, and I was thinking to myself like, oh is this like, young YPO, right? Young President's Organization is like EO Entrepreneurs Organization. So I think it was interesting to see, I think the birth of these communities, right? So what do you think about the right approach to sponsorship and mentorship that you think makes sense for the next generation?

Winnie Wong: (30:50)

Yeah, I think for women in particular, it's very tough as a senior woman to mentor others. They're exhausted generally because there's only usually one woman, maybe there's two or three who are at the absolute top echelon of an organization. They're exhausted from having to attend all these diversity events and just represent that there's a woman at the, like in leadership, and I remember when I was in consulting, it was usually one woman to 10 to nine men out of like a room of 10 people. It would always just be one woman, and so they have to like, rather than the men, they can just rotate around. They have to attend every single event, so they're exhausted already.

Then all these like female junior employees are asking them for mentorship and there's only so much that they, these women can do. They're also trying to like, continue on, become senior partners. Like, they've got to sell work, all these things. So it's tough. I would say Sheryl Sandberg actually really originates this whole like, lean in circles where you have. When you're not able to get the mentorship of people above you, you build out these circles of women who are at the same level as you or slightly above or below where you can talk about different things. So actually, Jess Lee, the former founder, and CEO of Polyvore, started this organization called All Raise. Where female venture capitalists can join and they're placed into different cohorts of co-mentorship so that they can share and build their own networks in the venture capital space. Because I think venture capital only has something around like 9% women in the space. It's very man driven. I think it's something like 40% of venture capitalists come from three schools in the US. Harvard, Wharton, and Stanford. So it's a very homophobic organization.

So by creating this All Raise platform where like they meet kind of, they have their own little circles and or their cohorts based off of their level, they're able to actually like do also like work on deals together as well, build this network across the woman. So I do believe in some respects that. I've also heard a bit of negative feedback about some of these circles as well. Not all raised, but some other ones that exist here in Southeast Asia where sometimes there's not enough of the same like level of people in the room because let's say like there's only so many tech companies, let's say major tech companies here in Singapore, there's a lot of conflict of interest where you don't really want to share too much about what's going on in your organization. There's not enough diversity to create a safe space actually, because, you might be in the same circle as someone who might be hiring you at the next organization. That's not safe and there's a difference between mentorship and sponsorship.

Mentorship is really when you can fully trust in that person and have that person share their own experiences and you share your experiences to problem solve. And usually, the best mentors are outside of your organization because they don't affect hiring, or promotion decisions, but they can help you problem-solve with your manager what to do in these situations sponsorship is usually best in your organization because they're there to fight for you or to advocate for you in those, because most of your career, most of the decisions that affect your career are made in a room that you're not a part of like promotion cycles or promotion committees or performance review committees. So regarding your question about mentorship and sponsorship, I believe that one part of it is yes, having a community of women. Different organizations that are going through similar things can help. I also believe in that this is not just a woman's issue, it is a gender issue where, and it's a gender initiative. And I agree with not saying women's initiative, but more gender because men also need to feel comfortable supporting women. And just like I shared with the example of Mike Spence, he didn't feel comfortable supporting women because he was scared about sexual harassment lawsuits, for example.

So I can understand that point of view, but we have to find and create a safe space where that kind of communication, that kind of sponsorship can be made or whether it's having male sponsorship like allies that are in structured programs so that women can build their networks and like I said women are over mentored and unsponsored, so they won't necessarily get fully the sponsorship that we have defined, but at least it does start to build their network. But just having, involving men in the conversation, because men have their own issues too. Men also feel like there's an expectation that they need to be strong. They cannot be vulnerable, they have to be the breadwinner. They have to earn more than everyone else. They have to be hyper-masculine. They have to be big and take up space. They have to be dominating. So, it is a gender conversation rather than just a woman's conversation.

Jeremy Au: (35:55)

What does the path look forward in Southeast Asia a lot of these concepts and themes for example, are obviously very much prevailing, for example, on Twitter, which like say represents the West and so, so forth, and then of course China has its own set of conversations altogether and so does India has own set of conversations within the Southeast Asia context, and I think we alluded to this earlier, is obviously not only different cultures but different countries, different identities and everybody's just like, I know one hour away, right from each other. Right. So I think that's an interesting dynamic for this region. So what do you think about this melting pot slash flow of folks in Asia?

Winnie Wong: (36:37)

Firstly, I think the biggest advantage for Southeast Asia, or at least in Singapore, or actually in a lot of countries in Southeast Asia, is this foreign domestic helper situation. I actually, it really helps progress women in the workforce because women, like if I were an employer, I wouldn't have to think twice about sending a woman to, let's say, Taiwan for work for a week because she likely has helped at home and by equaling the playing field of the opportunities for men and women by having in-home support, it means that women can progress and women can be seen as leaders and they, it's normal for them to work. And I think Singapore's great about this too. Like the population has been dwindling. It's like the biggest national security issue here in Singapore, right?

It's like, please give us more babies. It's part of the national parade every year. It's very clear so the Singaporean population, what the agenda is, right? So they make a really great job of encouraging women in the workforce and there are actually a lot of Singaporean companies where women are leaders too. So I think Southeast Asia can actually be a bit ahead in some ways than the Western world in supporting women in their careers. Yeah, so I think in the future of Southeast Asia, I'm actually not sure about the diversity here because I understand that visas have been declining, but it's also because the Singaporean population is becoming a lot more educated over time and this middle income is growing within Southeast Asia. So I think it's great that Southeast Asia is growing and I hope eventually in terms of representation, it will.

Hopefully, we'll see a lot more Singaporeans or Southeast Asians taking on leadership roles in even multinational companies as well. Because that's something that I described earlier in this podcast where, when many people look up to these multinational organizations, it's often imported talent. But I think our talent is getting strong enough. It's even since I've been here over the last eight years, I have seen it, and when I worked in consulting, like I worked with people who were like Oxford, Cambridge, Harvard, like graduates, and they're so sharp. A lot of them were presidential scholars that like cut their bonds to go into private industry. So I really think that. Singapore and like, they're doing a really great job of investing in people, sending them to some of the best schools in the world, and then bringing them back to eventually become the leaders of these organizations.

But at the same time, I think it's great to also start looking at every rung of the organization actually having, just testing out, what is this DNI? Can we report how many people are a woman? How many of them identify as like other minorities or colors or races? I think in Asia, it's tough to do a race actually because in Singapore I think it's something like 70 to 80% are Chinese themselves. There are other, differences that people have. Accessibility and disabilities are huge ones that I'm starting to learn a lot more about and I'm getting interested in them because apparently, 25% of people in the world have disabilities. So you could have a disability but not know about it by the way. But how can we include these people in our organizations to make better products so that we can reach more people so that we are actually serving the general population even better? So, yeah. I hope that answers your question a bit.

Jeremy Au: (40:15)

Yeah, definitely. So when have you personally been brave?

Winnie Wong: (40:21)

Yeah. I think there are a couple of times that I've been brave, one of them was moving to Singapore by myself. I had one friend here, she's since moved and interviewing and just finding a job and building a life here. But I think actually the biggest thing and the scariest thing that I've done, which is the definition of being brave to me, is sharing stories about my life and reflecting about them, whether on this podcast, but through this book that I've written called "You Don't Have to Look The Part", because it's scary when you're actually sharing something that, there's a cancel culture out there these days, right?

You say the wrong thing and you're canceled for like three to five years and recording a podcast like this, it's going to forever be out there in the world. You can't change what you've already said. At the same time, writing a book, this is something that there might be something that a lot of things people don't agree with and it's kind of scary. You're putting yourself on the line for people to give you negative reviews or to criticize your book or to say it's, it doesn't go as deep as they would like and everyone's going to have their own opinion. But I realized that being yourself, It's very hard to be yourself. But yeah, I think stamping and like putting this permanence in, sharing my stories publicly.

Jeremy Au: (41:41)

Yeah. I think that's very reflective and real of you to share that. Could you share why you think it's hard for you to put yourself out there in terms of the writing, and the like, was that feedback, was it scary? Because, but cause you started the process to write it, no one forced you to write it. So you're writing it and it's scary. So how does that work? Yeah.

Winnie Wong: (42:02)

Initially, my book was primarily centered around the stories of these East Asian female founders and what we learned from their stories and then I layered in a lot of research as well on top of that. And I'm like, great, this book is going to be out there, I'm very proud of this book and I had gone on a pre-order drive, so I had crowdfunded the first print of this book and had many people like. Who wanted to become beta readers and give me feedback as I went along. So I had, I submitted these first drafts to a bunch of my friends or a bunch of these like people who've pre-ordered and they would come back to me and they would say, this is all great, but I don't know why it's you that's writing this book. There's not enough of Winnie in the book and so I think it was very scary to open it up and open and think about past lives. I think the tough part is, I don't want to be a victim in my life and I don't want to point fingers and blame people for anything. That's a big core tenet and value that I have. So I didn't want to say in this company, this is what happened to me. I was, systemically discriminated against. I didn't want that to happen.I wanted to be more of a positive one.

And so it helped me to reflect and share and I tried to share as objectively as possible, like this is my experience. Like when I was recruiting in France, these are the facts that they presented to me, and this is how I felt. I felt like I couldn't be myself. They were expecting me as a woman, I, well, me as an employee, as a woman, I have to be better than the male candidate they could hire because they might think that I might take maternity leave at some point. Then as an East Asian woman, I also have to be better than a Caucasian person. So I have to offer networks, language, all these things. So, yeah, I think the scary thing was just sharing my deep thoughts that I've never really shared with anyone about my life. Whether it was the segregation that I felt in school, which, that maybe my school won't, or my undergraduate might not want to invite me back to speak because I'm sharing this.

So it's scary because there's a big cancel culture here happening, at least in the Western world, that once you say something, it can be turned against you later on in your life. And people change over time too. Something that was used that someone said 10 years ago might not be representative of what they represent now.

Jeremy Au: (44:29)

Right. On that note, thank you so much for sharing so authentically about what you feel and what your personal experience has been. I'd like to summarize the three big themes I got from this conversation. The first is, thank you so much for I think, sharing about your exploration and research on the glass ceiling versus the bamboo ceiling. I thought it was a very nice way for you to share why you cared enough about it and also about what started you on that journey and also what was the research and findings that came up. So I thought it was interesting to hear a lot of the different aspects that show up in terms of promotions, in terms of retention, in terms of different work scenarios. So that was really interesting. Secondly, thanks for sharing about being over-mentored and unsponsored.

I thought that was a whole theme about how folks can really help support women in their journey. Either you're a male or female executive, but was is it that you need to do to help sponsor folks and vice versa? If you are a female employee, what you need to do in order to get that sponsorship and move forward is clear lastly, thanks so much for sharing about your own personal writing experience and I guess it's not so much about writing because you can type and so, so off, but more like writing your own story and interweaving that with the stories or other folks. So thank you so much for sharing all of that, Winnie.

Winnie Wong: (45:50)

Thank you for having me, Jeremy.