Karen Tay: Leading Equitable Transformation, Government’s Role in Tech and Avoiding Burnout - E121

· Singapore,Thought Leaders,Southeast Asia,Women,Podcast Episodes English

 Sometimes the bravest thing to do is to step back from your productivity and value yourself. I didn’t realize it at the time. At that time, I thought it was being selfish. At that time, I thought I was not being a good leader. After that, then I realized that it was the hardest thing to do for me, and I think you would empathize because it’s easy to build your identity on how much you contribute and what you do for other people and the underlying question is what am I if I am not doing all these things. That is sometimes the scariest question for any of us. - Karen Tay


Karen Tay was formerly Smart Nation Director (North America) in Singapore's Prime Ministers Office and Regional Vice President at the Economic Development Board, based in the Bay Area. She started and grew the Singapore Government's global tech talent recruiting function, boosting its pipeline by 20X, and was later hired by EDB to build its global talent platform for the tech sector in Singapore. She's passionate about transforming workplaces to be conducive to human flourishing, which she believes is the best strategy to attract and keep great talent. Her past experience includes implementing $2B preschool reforms to increase equitable access, starting up Strategic Communications and Engagement for the 40k-strong Ministry of Education, and serving as special assistant and speechwriter to various Ministers. She most enjoys full-stack work: bridging strategy, operations and team building.

Jeremy Au: (00:30)

Hey, Karen, good to have you on the show.

Karen Tay: (00:31)

Hello, Jeremy, good to see you again.

Jeremy Au: (00:34)

It’s always good to see you. I think we’ve always had such wonderful, deep, and thoughtful conversations on time. I think it’ll be nice to chat about some of the things we’ve learnt along the way, I guess, as operators and executives on one level, and as human beings as another. I thought that would be fun.

Karen Tay: (00:51)

Yeah, looking forward to it. 

Jeremy Au: (00:53)

So, Karen, for those who don’t know you yet, could you share about who you are professionally? 

Karen Tay: (00:58)

My most recent roles were held concurrently with the Singapore Prime Ministers Office and the Economic Development Board. I’ve been in the Prime Ministers Office role for four and a half years now, starting when I came out to the Bay area, and I was the first one to be hired out of here for the Smart Nation Office. I was looking at partnerships, talent, and various other initiatives, but we pivoted very strongly towards the talent piece because, more and more, you see governments and big organizations needing to insource some of these tech work. They don’t just program project manager out anymore because tech is changing so fast, and so, what you need is really good people who understand your business and also your technology; you don’t really want to buy solutions and partners like that in such a big massive ‘waterfall’ way anymore. So, I’ve really been working on that global talent attraction for the smart nation initiative for the Prime Minister’s office. 

Then two years ago, I started the EDB role. For those of you who know the EDB, our overall objective is to bring investment to Singapore; getting the world’s best companies to incorporate in Singapore, set up the incentives for that, but we never really worked so coherently on the talent front, institutions and individuals, I think, and I started to build up this individual strategy with the Singapore Global Network. I was one of the founding members there as well and I built up the US and UK operations, and overseeing the Singapore team; and I focus on tech talents specifically. Those two roles kinda overlap, so, that’s why they asked me to do it concurrently.

Before that, I was in Singapore and I was working in many various different roles – I was in the Prime Minister’s Office Strategy Group; I was in the Ministry Of Education working on preschool policy, higher education policy; set up the strategic comms and engagement teams for MOE. Back then, corporate comms was very much like – “Let’s do all the policies and then tell people what it is”!

But, really, we wanted to engage the stakeholders a lot earlier and bring that process upstream, and I was one of the founding team members for that. 

One of my most memorable experiences was in my first job - I was in the Ministry of Finance, working on social policy reforms. Looking at how you make the preschool sector more equitable, not just private sector driven; we still have that, but how do you ensure that when people enter P1 they’re not just miles apart in their foundations because preschool education has a huge bearing on your future. We looked at that, and at making healthcare more equitable, retirement adequacy more equitable and I guess that was formative for me in realizing that I have a huge passion for equity in organizations, in society, and in things like that.

Jeremy Au: (03:52)

So, it’s interesting because I see and I’ve known you for so many years now, you have two loves – you have this passion for equity and you also have this love for individual human beings, right? It’s been such a joy every time to chat with you about it, we always go on to have these deep conversations. We also knew each other in junior college as well, but, obviously, we didn’t know each other that well. I’m just kinda curious, where did these two loves, these two passions begin because they’re different – one is equity and the other is human. Let’s start with the equity side first and after that we’ll talk about the humans.

Karen Tay: (04:26)

Yeah, you know me from junior college. I was a swimmer back then, and swimming took up 15 – 25 hours out of a week and we were just doing that all the time, but finally, I got a break in junior college because I started winding down back then and started doing more volunteering, whether it was working with children with special needs or going on volunteer trips and starting to expose myself to a wider spectrum. By that time, I was kinda disillusioned with this whole achievement mentality because I was in elite sports and I win all these things but for what? What good do I add to society? 

So, I really went into it thinking about these questions. I started to wonder how was it that as a society back then, it didn’t seem to inherently value people even if they couldn’t contribute economically. This was related specifically to the children with special needs or juvenile delinquents, for example. It’s been more about mitigation and making sure that they don’t become a burden to society rather than saying these people are inherently valuable and what does it mean to have a society that respects that. That’s a tough question for Singapore because – small country, scarce resources, every resource counts, capitalist society, right?

Some of our principles, people argue we couldn’t be so abundant towards these groups of people who maybe couldn’t contribute as much back then. So, I wondered and thought a lot about these questions and I was originally intending to apply for medical school, but I ended up applying for a government scholarship specifically because of this issue, and I used to volunteer at a school for children with Down’s Syndrome in the year after junior college, before college, and I spoke with all the parents and they were all struggling. They’re not trying to game the system, but it’s incredibly difficult; somebody has to stop work, single income household…if you are lucky. I thought about it and there’s so much that needs to change in our paradigm.

That’s for equity. That’s the origins of my interest in equity. When I became a lead, I also started to think about that question because, sometimes, it seems like the leader is more important and people kinda defer to you because it seems like your view is more important, but I never actually believed that and because I was pushed into leadership when I was quite young, I knew that other people would know better than me and the fact is that they would need to feel valued despite me being in charge. So, it becomes a question of how do you enable that, how do your really be a leader who makes sure that people feel valued so that they can bring their best and always feel like they can tell you the truth, and that has always been at the back of my mind as I managed different teams along the way.

Jeremy Au: (07:16)

It’s interesting because there’s these two loves that you have – the equity that you talked about, it’s really about the organizational level, and I’ve seen you get a coaching certificate and you coach people individually as well which is very individual. So, I was wondering, how do you contrast and how do they feed into each other because you work at an organisational level and even all the way up to the national level, which is a plane higher than most people because you’re working at all levels – national, societal, organisational level which is like the ministries, the teams you’re part of, the teams you’re coaching and meeting, and then there’s the individual level that you’re working on. So, how do they work with each other, how do they flow, and how do you switch between them?

Karen Tay: (08:03)

I think that is ‘the’ question that I’m grappling with right now – How do these two interests come together? I would say that I intensely enjoy the individual level work because I think that any deep transformational work requires a safe space to reflect and be vulnerable, and for many of us, once you reach a position of leadership, there’s just no space like that… especially in certain cultures. You have to be strong. You have to be sure. Even if you’re insecure, you try your best not to show it, although it is obvious to everybody.

So where do you get space to think about it and grapple with the things you know you’re not good at or that you know you’re struggling with? Most of us who have managed somebody will end up in that situation where we struggle with certain types of people. Do you just use your powers and shut that down? Do you use that as a way to grow and develop a new type of productive relationship? The latter is so hard when you don’t have support. 

For me, when I see something that is not quite right, like one of my team members or a manager under me is struggling, I’m always thinking what is the safest way to provide feedback to this person so that they are willing to change. Often that means providing a safe space for them to unload huge emotions even if they might not admit it that come with dealing with all these interpersonal conflicts. I see that as a space that is incredibly effective and can turn situations around. It’s just not incredibly scalable as compared to a policy change or an organizational change. You need a good organization and policy, but you can’t rely on it. You can’t just say I’ve done that, and we’re good. You still need to be creating these spaces for your key people and hopefully for everyone to be transforming in the way that you want them to and they want to. 

Jeremy Au: (09:53)

Yeah, that totally makes sense and that’s the tricky part that all of us have as people who have been coaching and mentoring. The transformation is really one on one and it’s deep, but it doesn’t feel scalable and so we’re often working on another plane…and, of course, you get to work on a plane that most people don’t get to work at, right? Which is at a national level, working with millions of people. Probably if you stack up the fact that these policies will last for the next ten, twenty, thirty, forty years, it’s orders of magnitude larger than individual contributors and teams would be. I’m just kinda curious, do you ever feel like it clashes or creates moments of great joy?

Karen Tay: (10:44)

I think the question is always “How do I do this in a sustainable way for myself”.

I think because of my personality, if you give me a work situation I’ll ask who are the people working on it, what are their motivations, and how do I bring out the best in them and that’s my main operation question and, of course, how do I achieve the outcome by doing that. If you take a hundred people, 99% of them all want to do a good job, but sometimes the environment is not conducive. Be it a lack of trust or things like that. If we assume that they want to do a good job, then by enabling them to do a good job, you’ve achieved your outcome. That explains a lot of what I’ve done in the last few years. Even when I came out here, I had nobody under me as a start. I started to work with people who were not reporting to me, but had slightly similar objectives whether they were in the community or other government agencies, and I started to build a movement based on that – the first Singapore Tech Forum, for example. We were all working part time then and we just launched this thing with Facebook, in Menlo Park…I think we got 700 signups in a few weeks. The question was what was everybody’s incentives and who’s super excited about this and let’s go unlock all of that. Let’s do it and let’s share the credit generously. So, that’s generally been my approach towards leading people. 

As for moments of distress, the flipside of that for me is that I’ve had to learn that I can’t be responsible for everything. Whenever someone is unhappy, I always ask if there’s something more I could have done better and the answer is always yes, but we have to look at it within the boundaries. On the upside, almost everybody I’ve worked with have a good sustained relationship because it’s not just built on mutual interest, but we really enjoy working together. We’ve found a way to not only win-win, but enjoy ourselves in the process. I think that’s my super power when it comes to work and that’s something that is deeply meaningful for me, personally.

Jeremy Au: (13:19)

Yeah, that’s so true. Those deep moments of connections are transcendental. So much more than just transactions, it’s something meaningful. It’s also important, what you said about knowing the boundaries, I totally resonate with that whenever I hang out with people of the same archetype, it’s always something to think about. How do you prevent yourself from getting emotional burnout in that scenario?

Karen Tay: (13:54)

I think about the idea of stewardship and how I’m actually stewarding many things. My own energy is one thing, my family is another, and all the other responsibilities I have, I need to remember that I am a very important part to steward as well because my energy is going to flow in and circulate around this ecosystem and so I have to keep my energy in check whether I am enjoying my work, whether I am getting frustrated with a certain person and if I am, then something is wrong and I’m probably crossing that line, that personal boundary of personal responsibility and taking on too much of somebody else’s and that includes with your family, not just work and teams, and knowing when to consciously put those feelings down.

Having people to talk to helps, but it is hard to find people as you go up the levels especially at management. It’s hard to find someone who can give you that objective view and someone with whom you can share very openly with whether it be at your own level peers or plus one level ups who you can share with.

I’ve also learnt that I don’t have to take care of everything and sometimes it’s good to include my bosses in the brainstorming and problem solving instead of shielding them from that.

Jeremy Au: (15:42)

You brought up an interesting point in that we have a responsibility for ourselves and the closest analogy is that you have to put the oxygen mask on yourself first before putting the oxygen mask on your child during the drill. I always thought it was bonkers thing to say that you’d be more important than your child, but I saw a documentary recently that visually explained it to me that in that event, you’ll pass out in about 3 seconds, and trying to put the mask on your child would possibly cost both your lives since you can’t take care of yourself so how are you going to take care of your child. This harkens back to your talk about conserving energy and I don’t think I really understood that until I personally felt burnt out. At that time, I was consulting at Bain and running a social enterprise on the side and I just burnt out. In the end, I just chose one and I think it was the right call. I mean, people warned me about burning the candle at both ends, but it just didn’t occur to me at that point in time.

Karen Tay: (17:06)

Sometimes you don’t know it until it happens to you lah. I think that is, unfortunately, how we learn. We all think we can power through it and then boom, we can not.

Jeremy Au: (17:20)

So, you’re saying the only way you understand how to maintain your energy is if you get close to burning out or you burn out, is that one way we can think about it?

Karen Tay: (17:29)

I won’t put it like that as the ‘only’ way, but that was the case for me as well. It took two kids, two jobs, and a pandemic for me to burn out. In a sense, it is an eye-opener to be at the end of your rope and seeing that this current philosophy of life is not working, so…let me go re-examine myself. That was also the first time somebody told me that I’m working too hard. I have two kids under five, I’m taking two jobs, on call at 6AM, 7AM, 11PM and all hours in between. I kept saying it’s alright and finding the positives because that’s my personality, but when I really burnt out, I realised that it was bad and I should have listened earlier, but I was not the kind of person to listen at that point in time. Do you empathise with that? 

Jeremy Au: (18:30)

Oh, yeah, totally, I empathise with that. The tricky part about taking care of people and lying to people, whether intentionally or not and there are lots of reasons to do so like managing reputation or sparing their feelings, but at the end of the day, there’s a fundamental desynchronization between who you are and who you are projecting. Often when that happens, you end up drinking your own kool-aid and you lie to yourself in that moment as well that you can manage this thing.

Karen Tay: (19:07)

Yeah, and I think as Asians, we’re also skilled in the art of emotional suppression. Lying to ourselves becomes second nature and we’re not even aware of what’s really happening and as you’ve said, there’s so many layers to it.

Jeremy Au: (19:21)

Yeah, yeah, I didn’t mean consciously meaning to lie, but maybe subconsciously where you say to yourself that everything is alright or as you say, suppression. What I think is crazy about the human mind is that we are able to think of multiple things at the same time. We can say to ourselves that we’re exhausted while simultaneously saying I’m going to crush it and at the same time say that we’re going to take care of someone else…all within the span of several seconds.

Karen Tay: (19:50)

Right. There’s a proverb that says – the purposes of a man are like deep waters, but a wise man draws them out and I think about that when it comes to coaching because you’re right. On the surface level, all these things can be true at the same time, but what’s really at the base there? I think that is at the heart of the deeper work of coaching.

Jeremy Au: (20:23)

Yeah, I think that’s the truths. The truth in the moment and the deeper truth about who you are and why you are the way you are. Even I find it hard to catch myself in the moment whenever I get angry or frustrated about something and then later sit down and I don’t even understand why I was frustrated on a deeper level. I don’t know what you’d call that, self work…but it’s definitely some form of work, right?

Karen Tay: (20:49)

Yes, it’s big work too. I think it could take years.

Jeremy Au: (20:54)

Years. I was like why am I angry at lunch today, but it’ll take few years will solve that. Rounding back, you mentioned about emotional suppression and the corollary that there’s avoidance and I think we see that a lot in the technology world that we’re both part of and every founder believes that they are here to change the world, make the world a better place, make this unicorn while the awkward reality which is like things are falling apart, firing people, not finding engineers, not sleeping enough and it’s not just the founders, there’s everyone else in the ecosystem. There’s one salient thread in places like Silicon Valley, Berkeley, where we put our heads down and do the deep work, but then also go to reflect on ourselves. That disparity is so large with inner peace and the “Ra ra, we’re going to go to the moon” mentality as opposed to the rest of the world where the contrast is tighter. How do you feel about that?

Karen Tay: (22:03)

That’s a really good question. I did notice that during my earlier years in the valley and there were times when I was sitting in a restaurant and the guy next to me would say – “I just went on my yoga retreat and now I’m feeling so stressed out".

People do look for meaning and significance and living a life aligned to their values but there’s still the reality of ‘the grind’ which still looks at you as a bit of a commodity like – “Let me invest in one hundred of you and hopefully one of you succeeds”.

What do you make of that tension yourself?

Jeremy Au: (22:43)

Oh…don’t we all wish we had the answers. I guess sometimes I think about it in a historical way because the Bay area was a very counter-cultural place and has that deep root of being in touch with yourself and I think there’s another culture altogether and I wouldn’t look at it as the same place, but more of a Venn diagram wherein you can have capitalism or venture economics, whatever you want to call it, technology, the future…and it’s all very Yin and Yang.

I think some of the people who do their best work are people who have done that self-work on themselves and are working in a place where they’re valued and so they go on to do tremendous things as a result because they have that multi levels of energy to pursue that which lets them carve out the time and resources to do the self-work as well. 

I was talking to someone recently and realized that you can’t have a world class executive coach because it’s expensive, but a world class executive coach can help you become world class and there’s that awkward dynamic where that Yin and Yang works really well once you get that flywheel going and that’s not accessible to most people.

Karen Tay: (24:04)

That’s interesting food for thought. I haven’t really thought too much about that mainly because tech talent has been scarce and there’s the ethos of valuing the individual contributor which makes startups thrive because of their flatness wherein everybody contributes and they really have to value the guy on the ground – the guy doing the user research, the guy testing the product. You shouldn’t see them as anything less than you. That’s bad for your business. I appreciate that about the Silicon Valley, coming from a more traditional Asian culture, Asian organization. The Singapore Public Service does value people a lot, but it’s ultimately a bureaucracy with some of the regular bureaucratic problems. So, when I work, when I work on attracting the world’s best tech talent to work on public problems, you run into this tension precisely. They’re very accustomed to places where the individual contributor can iterate quickly and can bring extreme value to the organization and argue directly with the CEO whereas sometimes you go into a bureaucracy, you’re like “What’s happening up there? Why does it take so long for me to get my budget? Why does this person and that person, all these people have to comment on what I do? The answer is obvious!” So, that is the big cultural gulf that I think I live between right now and I don’t think that a government necessarily should aim to be like a Silicon Valley company, but there’s so much to learn there about which parts of your organization you can release to some of these new modes of working.

Jeremy Au: (25:41)

There’s a lot of truth there and it’s interesting because you’ve been acting as that bridge and facilitator between government and technology; Singapore and Silicon Valley/the States and I think a lot of people like that role, right? Because they’re very bridge roles and it almost feels like people who do bridge roles tend to be undervalued by both sides. In the tech world, they view this people as public policy, your job is not to create value, your job is to preserve value by helping us to regulate or lobby or to interface with government and for the government, you’re helping us to attract, so on and so forth. Do you feel that?

Karen Tay: (26:26)

So, for Google public policy, they play more of an advocacy role, lobby governments to do a certain thing, take a policy position that’s beneficial to the business and that definitely falls under the product side of the house and engineering side of the house. You’re talking about that right?

Jeremy Au: (26:47)

Yeah, I think that’s one way to think about it.

Karen Tay: (26:49)

This is a really interesting thing about a country versus a company. In a company, certainly, your engineering and product side of the house should be out there making new things if not there’s nothing to talk about. Whereas, in a country, especially in a time like Covid, you look at things like how do you position Singapore to weather Covid well. The combination of policies, technology, and operations that are needed to do that, from contact tracing to swab testing to quarantining to what your quarantine policy should be to how do you reopen the economy, how do you keep hawkers afloat. Very much, the government plays that steering role and it needs to define the space that technology can contribute to and make it as conducive for super talented people to come in and help us solve it.

So, one thing I tried out last year was I launched a Covid volunteers effort for gov tech. It was really crazy. 700, 800 people signed up and I just met a bunch of them in the bay area last week because we were opening up here and they were like “Oh, guess what, we’re still working on the project now” and I was like “What? One year later”?

Well, certainly, not everybody who wanted to was matched because that’s inherently the problem with volunteers and those who were matched were matched for a long time and they told me that was most probably the most meaningful thing I did during Covid. So, I always see my role as creating these new commerce spaces where tech and government can come together at the level of problems and skills. I do see new value for both sides. These people will go on to think about “Okay, have you solved this problem; have you done that; have you thought of this thing?” And I think that is very much where the government needs to evolve and technology is actually very interested to solve because there are many, many talented people thinking “Well, I have these skills and my day job is not necessarily super, super meaningful, what can I do to benefit my fellow man?” I think that’s an existential question for most people in our jobs.

Then there’s working in the talent space specifically, there’s huge interest from the private sector as well because as a small country in Singapore we attract talent there and that’s why I took on an EDB role as well. You bring talent back is good for the whole system. They go into the government for a bit. They jump out. They work for a big tech company for a bit then they jump back in. We see that circulation happening a lot more. Recruiters in Singapore are hardly reaching out here. I did a study with LinkedIn and found that Singaporeans here get 3 LinkedIn pings every week if you are a software engineer, but none of them are from Singaporeans because the Singaporean side doesn’t know how to access this talent community at all. I think that’s also a very meaningful thing for Singapore. How do you start that flywheel of talent going back, circulating back out and things like that.

Jeremy Au: (29:47)

I remember as a volunteer during the pandemic, working on the giant Singapore Wiki on how to get out of X country and into Singapore. It was almost a hundred pages, I think. I’m still getting messages from people saying they read my document and got back to Singapore safe and sound.

Karen Tay: (30:11)

Thanks for doing that, but it’s not necessarily just tech, right? I mean, I would like to see the government just a lot more open to talent and people who have that civic-mindedness.

Jeremy Au: (30:20)

Yeah, and thank you for looping me in. I wouldn’t have been looped in if you hadn’t asked. So, this is an interesting dynamic here, right? We’re talking about the difference between corporations and countries. I remember this thing someone mentioned that the big difference between a corporation and a country is that a corporation can fire its customers and can fire its employees, but a country can not fire its citizens.

Karen Tay: (30:49)

Yeah, absolutely. Can Singapore be like Silicon Valley, no la, and we don’t even want to. Look at all the people who get priced out of the valley, that’s not possible for a country. People live here for a few years hoping to make money, not everybody does and then they retire in a low-cost area. I’ve had so many friends who have gone off because they couldn’t afford and the pace of life here. It’s just not possible for a whole country that looks after people from cradle to grave. At some point we all stop work and not everybody is interested in entrepreneurship for many different reasons. I think one big difference is that you look after someone for their life cycle and you can’t just look after the best. That’s the mandate of a country.

Jeremy Au: (31:31)

Yeah, the mandate of a country is to take care of everybody, every citizen and I also like the phrase that you said – from cradle to grave, because that is half the employee base or a certain employee, whoever they’re looking for the top 5% or the top 2% out of all the resumes they screen and that is well understood in the resume world, but what happens to the other 98%? Corporations don’t care about the rest they didn’t hire.

Then when you talk about customers, they only serve 1% to 5% market share for this situation and they don’t care about 95% of the market share and they don’t care about the other verticals.

Karen Tay: (32:06)

Companies are all about focus. Focus, focus, focus on which they call their specific archetype, let's not care about anyone else. Let's just focus on this archetype of employees. Governments are like "No, we have all these archetypes and guess what, we are responsible to all of them and that’s our job”.

Jeremy Au: (32:23)

It’s interesting because you’re one of the people I really respect. There’s that nuanced view of what the government is good at and what technology is good at and how we can work together. Do you ever feel like you end up having to defend the role of government in the private sector or, I guess, court of public opinion?

Karen Tay: (32:47)

It’s interesting, I live in the US now and lived in Singapore before and I will answer differently for both countries. I think definitely in the US, there’s more of a defensive role that the government plays. The entire US, the design of the US was to minimize federal government power except for very specific functions. That’s not to say that the federal government didn’t play a huge role in the Silicon Valley because Silicon Valley history is built upon things like NASA and defence. So, there’s still that, but generally, the government is trying to avoid it and think how to get around things. They hire lawyers and think how to get around this legislation rather than but for Singapore, it’s a totally different paradigm. The government is thinking this is going to happen blockchain innovation, cryptocurrency, autonomous vehicles, things that baffles other peoples’ minds and we need to get ahead of the game, what can we do to help you because we think we really want to build strong industries, good jobs for people. So, let’s work with the best innovators and try to create this new ground. I think that’s something the Singapore government is quite good at…relatively…and that’s also built on our history of being a small country with limited resources, let’s make ourselves a hub for all the good things and the government knows we have levers for that. So, when you go to Singapore, no one has to justify the role of the government. Of course you do want government approval. Not necessarily grants, but you do want a good relationship with the government. I think it’s a different paradigm altogether, one hundred percent.

Jeremy Au: (34:25)

That’s interesting because you’re talking about government in the States and then there’s government in Singapore. The other layer you’re talking about is the deep history and cultural ethos that’s just like there. Kinda looking towards the future, when an American thinks of Google, they are thinking of the same company as when a Singaporean thinks of Google. That’s an interesting dynamic where I think these big technology companies are the new wave of multinational corporations and I always remember this phrase of globalization, the flattening of borders, but a lot of globalization is actually just Americanization. So, a lot of things we talk about a globalized culture is pop music from Britney Spears. Now, it’s starting to be K-Pop and a little bit more stuff, but the dynamic is still globalization it means Americanization.

The view of government is very different in different countries, but the views of corporations are becoming more similar and aligned across different countries. What do you think are the responsibilities or stewardship that big tech companies, as they expand globally to countries like Singapore, Indonesia, Vietnam, and other countries, what would be your advice or recommendation on their stewardship?

Karen Tay: (35:59)

Yeah, I was just thinking of this whole issue of like YouTube, for example. How, even five years ago, they got away with the line – “We are a platform and not responsible for the content on our platform.” And Mark Zuckerberg in 2016 was like – “Oh, we have nothing to do with what happened in the election”.

That was something they really argued, like full on, back then and that has changed tremendously where in the past elections would be the place for public opinion about policy positions, now you see a total democratization to these platforms.

What gets boosted, what gets censored, what gets given the light of day?Those are questions that the tech companies are making based on incentives of how many clicks they’re getting. You’ve seen far too many instances where you can’t move fast enough and they have operational constraints as well in like taking down hate content meanwhile your platform might be used to propagate hate and murder. I think those are the fundamental dilemmas; what are you really optimizing for?

If you’re going to be optimizing for your business, but you have more influence over people’s minds than any government in the world. So, what is your responsibility now vis-à-vis governments. I think that is the central dilemmas for many of these media companies and I don’t think a defensive stance is sufficient because lives and communities are at stake, but then what’re your alternatives?

Governments tend to take a stand of let’s just fine you if you don’t do this fast enough, but does fining them do anything about the fundamental incentives, not really, but it’s better than not fining them. What is the alternative? What is the win-win? What you could call co-regulation where both are involved in this in a very dynamic and fast iterative way. What would that look like? Because the way that it is structured now is that Facebook has a policy and they hire billions of people to take down content but it’s not realistic because of how much content is uploaded every second. So, how do you align the incentives of governments and tech companies? That’s a really hard question because then it becomes whether the Facebook employees would agree with what a more authoritarian country would do in this case?

You need a new paradigm not just locking horns and avoiding each other, you get around my rules and I fine you repeatedly. If not, the central dilemma will never get solved.

Jeremy Au: (38:48)

Wow. You touched on a lot of things there. Not every society and not every government is the same and neither are we pretending that every platform will have the same challenges. Resource costs, dilemmas, interfacing with multiple governments across the world. I think, for me, what it reminds me of is that big tech companies are being very avoidant or passive aggressive, but how best to handle this conversation? For me, as someone who is a tech operator, I see the business rational of dodging the bullet a bit. If you’ve dodged it, why bring it up? You dodged it for ten years, that’s ten years of profit and you don’t have to step on anybody, right?

But, I think what you’re reminding me is that as a human being, our love for these platforms is saying something like we also believe in the health of society; we believe in being there and understand we have a role to provide jobs and profits, and we also care. I think everyone is trying to avoid saying that we care.

Karen Tay: (40:00)

I can see why it’s a big minefield to be honest and that is the inherent issue of global tech companies “Are you really going to do this with every single country?” And even countries that you philosophically disagree with on every level.

Jeremy Au: (40:16)

It’s like the same with the old multinational corporations like the oil and gas companies, they had different standards for every country they worked in. Employees were generally aligned and public was not as engaged to the same extent as they are today, I think, about where the oil and gas came from because it’s an invisible thing. Nowadays, it’s like this global content spread where everybody can see everything. I don’t know…the great convergence and dissonance of billions of people around the world trying to get on the same channel, and we can’t get on the same channel within the same country and we can’t get on the same channel across countries.

One thing that’s interesting about you Karen, is you are doing a lot of deep work with folks, you’ve often helped other people to be brave and step up to the challenges they are facing personally as well as team. I’m just curious, do you have any times when you had to choose to be brave and tackle something, a challenge of your own?

Karen Tay: (41:11)

I’ll tell you the most honest answer I have was to actually just take a break. That was one of the bravest things I did. When I burnt out, I took a break. My mind was spinning, how can I do this, it’s the middle of a pandemic, there’s so many people who have been making sure they’re fine and running the team, how can I do this. Sometimes the bravest thing to do is to step back from your productivity and value yourself.

I didn’t realize it at the time. At that time, I thought it was being selfish. At that time, I thought I was not being a good leader. After that, then I realized that it was the hardest thing to do for me, and I think you would empathize because it’s easy to build your identity on how much you contribute and what you do for other people and the underlying question is what am I if I am not doing all these things. That is sometimes the scariest question for any of us. Some people are forced to deal with it, whether due to health reasons or unfortunate circumstances, but I think most of us grapple with that at a deeper level.

When people say that I’m brave in whatever I’ve done, leading this and that thing, building this and that from scratch, but that was not as scary for me. None of that was as scary for me as taking a break when I really felt like I couldn’t go on. That was earlier this year. So, I’m back now, but that was scary.

Jeremy Au: (42:33)

Wow. Thanks for being so raw and honest about that. For those who are scared to take a break. How would you be present for them or how would you counsel them. Not about solving or what’s the best, most restorative ways to take a break, but how to face that fear and come to a decision that this is worth potentially taking a break for. How would you counsel them to understand that dynamic within themselves?

Karen Tay: (43:06)

I think I would ask them what’s your resistance and anxiety and give them a lot of space to unpack that and talk about it because even though we know we should, there are a ton of voices in our own heads that say no, no, no, no, I’m anxious about this and anxious about that and starting to disentangle that is important. Most importantly, with any decision, you don’t want to silence as many voices in your head saying this and that, and some people think that in order to come to a decision, I must silence all the other voices. That works some times, but on things that are really high-stakes to you, you don’t silence it, you give voice to it and you let that voice run its course and make its arguments, and that’s how you come to peace with any one decision. So, my first thing would be to let them air it out, what do you feel, what are you anxious about. Let’s start there and get empathy for them and realise that these are legitimate things, not just you being lazy or weak or unreliable, or all the things that you accuse yourself of, but these are real things. We’ve all been through a crazy year, some worse than others and whatever you’re going through is real. So, I think that would be the first thing. Obviously, all the other stuff comes later, but if you don’t give that person any of that space, you’ll just get stuck up here.

Jeremy Au: (44:29)

Wow, thanks so much, Karen. That was really good. Let me just wrap things up here, would like to summarise and paraphrase the top three themes. The first, of course, was thank you so much for sharing about how your passion for equity and people came about as a student, as someone who is a high performer, as a professional, and then talking a lot about why you care and how it takes different forms for different folks has been really interesting to hear from that perspective. 

The second was really about thank you so much for sharing about I think the interface between government and private sector, and between Singapore and Silicon Valley and I think it was interesting to go to that from a cultural perspective in terms of both an insider point of view as well as a compare and contrast perspective. Also talking about the roles and responsibilities that we have in terms of bridging and communicating and also being active participants in each other’s spaces

Karen Tay: (45:30)

Let’s get in to a defensive mode, create a new valley together, where are those places.

Jeremy Au: (45:34)

Exactly, and I think that’s a lovely phrase. How do you create a new valley together? This moves everything towards the future. That’s a beautiful phrase. And I think you were hinting at it for the first two thirds and we got into it more the last third of it. What I really love was the bravery to have stepped back from productivity when you need it and valuing yourself. That was just a beautiful phrase.

We talked about taking care of yourself, having energy levels, taking care of yourself, valuing yourself, and I think that’s a very, you could say, counter-cultural at a macro level but it’s also very counter intuitive for a lot of folks who have to grind, and I think we talked a little bit around it, around the dissonance between the reality that people are projecting versus the reality of the border we’re in today, both at the individual and the government level or societal level. So, we thank you for encouraging everybody to be mindful about their responsibility in stewardship of themselves as well so thank you so much, Karen.

Karen Tay: (46:29)

Yeah, great talking to you. I always enjoy your thoughtful questions.