Why the Chief of Staff Should Own AI Adoption, with Zen Foo

0:09Hey there, it's Tristan. Welcome back to another episode of the podcast. I'm a guest host here, and my day job is running beyond founders, where I offer coaching and advisory for chiefs of staff and founders. My singular goal is to help them lead with more clarity and intention every single day. I'm currently based between Europe and Southeast Asia, and I really love highlighting the stories of operators from all over Southeast Asia. Now for today's conversation, I have had the pleasure to interview Zen Fu. Zen is the Chief of Staff at Aspire, the YC-backed series C finance company out of Singapore, where he's also been the key person driving AI adoption for the entire company.

0:46In this episode, we'll be talking about why the Chief of Staff role is the best positioned person in the company to lead AI enablement and the three stages that Zen sees companies we've been through from hype to chaos to eventually governance when it comes to ai adoption secondly we'll be talking about magic moments or how getting one person to the aha moment there's more for adoption than anything else does thirdly we'll be talking about balancing likability and respect and also being of service to others versus being of service to yourself and also how to protect your principal's trust when the hard calls come we end by having a really candid reflection on what the Chief of Staff role really teaches us.

1:26Things like better judgment, deeper empathy, and being more comfortable in our own skin. Like most of the incredible guests I've had on the pod, Zen is sharp and refreshingly honest about all the difficult parts about being a Chief of Staff. Let's get into it. Hey Zen, welcome to the podcast. Good to be here. You and I met a couple months ago, right, in Singapore at our last Chief of Staff Network meetup. Is that right? I think it was two months ago, three months ago. we went to this like bar and it was really awesome just meeting like other chief of staffs you brought really good energy i remember you saying how the unenough of these events and like man i'm excited to just meet all these people and learn from all the other chiefs of staff definitely man i think it's one of these things right where i think chief of staff is such an interesting role and persona slash character that to be honest i don't meet many people who are on the same wavelength i mean you meet a lot of people in the same ballpark but not necessarily that same wavelength.

2:22And it's one of those things, right? When you meet your tribe, your fellow people, it's just very exciting to be around like-minded people, I suppose. Yeah. For everyone listening, do you want to give us some context? Like who are you? What have you been up to? Tell us a bit about yourself. So I'm Zen, of course. I grew up in Malaysia. I think I was the age of 17. I moved to the UK where I did my studies there. And I went to a university called the London School of Economics, where everyone goes to become an investment banker. And I think I've always been the sort of person where I've always been a bit of a dreamer.

2:57Ever since I was a kid, I've always hated being normal. I've always hated following the crowd. And I think I've always been this sort of very enthusiastic dreamer type personality where as a kid, I was like, oh, I want to go and join a company that helps me change the world, for example. But I went to LSE because it was the best school for economics. And I'm also very competitive, ambitious, if you will. I really loved economics as a subject. So I decided to go to LSE. And unfortunately, LSE really fell into this trap where everyone at LSE sort of placed a lot of value in the jobs that you get or like a summer internship, for example, I was very focused on that.

3:35And it was really quite a, I wouldn't call it toxic, but it was definitely not a great environment to be in. I always felt very out of my skin because every time I met someone, I wouldn't be talking about, oh, what are you thinking about your life or what are you doing this summer or what makes you an interesting human being? But a lot of the conversations are centered around things like, okay, what summer internship do you have, right? Is it JP Morgan or Morgan Stanley? And if you're neither one of these two, then you're a loser, right? So it was a very weird environment to be as someone in my early twenties back then.

4:02I ended up, you know, selling my soul and got a job in finance in London. My first job was at Hitch's BC. Was it one of those two? No, it wasn't. Unfortunately, It really wasn't because I was like, what is Morgan Stanley, right? So I was sort of randomly applying for jobs back then. Somehow I lucked out and got a job at Hitches VC, which was great, by the way. And I really enjoyed my time there. I've started my career in trading, actually. So I used to be a financial markets trader back in the day. I used to trade treasury bonds, FX swaps, interest rate swaps, really macro stuff. And honestly, from an intellectual point of view, incredibly exciting, incredibly stimulating.

4:37again just from that intellectual point of view very very fast paced super high pressure the pay was great as well but i ended up hating it because i was sort of doing the same sort of thing every single day right and i used to tell my wife like every day i go into the office i feel like this movie brownhawk day where you just repeat that loop every single day i was at hsbc for about four years and realized like it doesn't matter how much money folks pay me i want to do something like meaningful with my life i want to do something that i would be proud of you know telling people I was doing, I want to go out there and change the world, which I've always wanted to do since I was young.

5:09So basically before the money got too good, I quit my job and decided to join tech. Why tech? Because tech then and even now always represents, I suppose, the frontier of what we're doing, what humans are trying to do. So tech was really exciting to me back then. I joined a company called Monzo, which was my dream company back in the day. Monzo, for those who don't know, is a digital bank, very similar to Revolut actually. They're huge in London. and they have a really great branding and presence as well. Everyone knows Monzu as sort of this nice guy bank. And I really liked the values they had as well.

5:41And so I was really lucky, managed to get a role there ever since I haven't really looked back from tech. And I think Monzu was a really pivotal moment for me as well, because I learned that I didn't really enjoy finance and stuff, but what I really enjoyed was generalist problem solving. I really enjoyed tackling different problems from first principles, building stuff. And I think since that moment, I've been very intentional in my career to position myself as such and only take roles, which would allow me to sort of further myself in that direction, which I guess is sort of culminated in this chief of staff role, because I see the chief of staff role as a sort of ultimate generalist who gets to be part of big conversations with the exec team, but also get your hands dirty, solving problems.

6:24And yeah, thinking really the ultimate sort of first principles builder type persona, which I love. What about being a generalist is really exciting for you? I'll be super honest. I'm just someone who gets bored like really easily. That is not an uncommon answer that we always get. You like dipping your hands in everything and just like tinkering. I do. And I think I also have a lot of, it's going to sound like super self-indulgent, but I think a lot of intellectual curiosity as well. And I'm sure a lot of chief of staff is totally the same thing, right? I think when we do things, when we learn things, we aren't doing or learning things for the sake of doing it, but we genuinely are interested in understanding the why, right?

7:01Like why? I was the kid who asked like why, like for everything, right? I asked why to the nth degree, and I think it's carried over into my adulthood. But yeah, I think the chief of staff is an amazing role because asking why and digging deep and really understanding things and then going out to build solutions is really bread and butter of our role. And I guess it's kind of a good thread that was already, you know, when you're doing the cycle of working in hsbc you're doing that for four years day after day year after year and at some point you also began to ask yourself like why why am i doing this i'll be super honest i was actually really worried that my brain was like i was losing iq points basically by the same thing we're talking about just the same processes and just repeating or correct yes the same traits the same sort of processes the exact conversations every single day and i think there's a certain like malleability with your brain, right?

7:48If you don't allow your brain to be malleable or expand, I always fear you lose some form of intelligence or creativity. Again, I think that generalist sort of chief of staff role really allows you to be thinking about different things every single day, which is awesome. Tell us a bit about the transition into becoming a chief of staff and what was it like to have your first role? I've really loved it. And I think I've always been sort of doing a chief of staff type work without the official title. Going into this chief of staff role officially has been really awesome for me as a person and also for my career.

8:19I think just having that official stamp of approval and almost that credibility to act as that person, you know, to really embrace that role has been awesome. I'm someone who loves not only just getting into weeds of things and solving problems and thinking about things from first principles, but I think I'm genuinely someone who also really enjoys navigating an organization, managing different stakeholders, having to adapt like communication styles. And I've always really enjoyed all this sort of stuff. I think the chief of staff has just allowed me to fully embrace that and have that as my part and parcel of my everyday, right?

8:52One thing I've found significantly different, which I love as well, is in previous roles, I've never necessarily been a very senior person. But I feel like chief of staff, I think I'm always a very opinionated person with strong convictions. So if you ask any of my friends, my friends will tell you Zen is that super annoying guy who has to have a say about everything. The great thing about the chief of staff role is, I joke of course, right? But I think the great thing about the chief of staff role is that you really have the opportunity to think about very difficult problems that your company is facing and have your opinion heard.

9:24And honestly, as you build that credibility as well, you start building a sense of what good looks like, whether or not this decision makes sense or not. And as you build that credibility, as more and more of your decisions actually convert into real operational reality, it's definitely a good feeling. And it's definitely helped me, I guess, have better judgment in general, right? Overall in my personal life as well, to be very honest. Can you say more on that part? I think a lot of the role of ChicoSaf is not only just doing stuff, but also just being this person that people go to for trusted advice almost, right?

9:57And as you build that credibility, as you build that confidence, more and more people will start defaulting you for, hey, what should we defaulting to you as the go-to person to ask for, hey, what should we do in this situation? Here are the facts. Here's the situation. I think obviously this can be something that comes naturally to you, but obviously it's something that I've trained over the last couple of years at Aspire as well, right? The more and more decisions I've had to make, you know, you start seeing what sort of repercussions happen. And I think genuinely what makes a good chief of staff is effectively someone who's got good judgment and can communicate that and can make sure like whatever is discussed is actually carried forward and follows through.

10:33That is very much part of the job. And I think that's genuinely also translated a lot into my personal life, right? In the sense that I have a lot more confidence now in terms of what a good decision might look like. You know, even if it's really silly things like how should we plan our trip, right? There's obviously an optimal way you can plan a trip to hit whatever criteria that you want. Maybe, you know, maybe I want to go and visit place A and place C, but place A and place B are like really near each other. So we should like, you know, spend a whole day in this area. It's silly stuff like this, right?

11:00Yeah, for sure. For sure. Yeah. But I genuinely feel that difference, or at least that confidence in my daily life. I'm giggling because it resonates so much. I think that there's perhaps more thoroughness in how to think about things. So as you said, also in the everyday life, how to research something, but also how to take decisions. Because at some point, you need to make a decision. As we all know, being the chief of software, because you have so many different stakeholders, and at some point, you need to make a decision and you need to stand by it and somehow also be flexible with how that might be received.

11:29Could you tell us a bit about, as you've been a chief of staff at Aspire, what are some of the developmental edges that you've encountered for yourself? You know, we talk about growing. When we grow, we're pushing the envelope in some ways, right? In some parts of how we operate. Tell us a bit about what that's been like at Aspire for you. I think a lot of the work that I've done at Aspire, besides everything we just discussed, has really been about, well, when I first joined, a lot of it was transforming our company, our tech team at least, into a well-oiled engine. And so a lot of the work that I was doing was around building out our operational processes, building out an engine that basically worked very seamlessly, right?

12:10Processes, planning, for example. And a lot of what I was doing early on was just sort of building out even like automations, structure, governance, making sure stuff was always kept neat and tidy, for example. We're talking like linear tickets or we're talking like Notion, like what we're talking about here. Exactly. Simple stuff like that. One of the first things I did, super simple, was our product roadmap was kept in Excel, right? Which is insane because we have like, I don't know, 30, 40 columns and like 200, 2000 rows. And like some internet built some macro that you had to press the macro and then your ticket would, I mean, like didn't make any sense, right?

12:47So simple stuff, just having like foresight and just the understanding of the tools available to us and saying, hey guys, like Jira exists for a reason. Our engineering team are using Jira. Why on earth aren't our product tickets in Jira, right? It's just simple stuff like that, building processes around that, making sure people actually follow the rules. But most importantly as well, a lot of the role is making sure the lives of your stakeholders are made as easy as possible. Because what you'll learn is that no one will buy into... You can have this grand vision, this great BCG type slide and vision and strategy, but no one is going to buy unless it's easier for them.

13:20It's easy for them to do it, right? So a lot of what I was doing was also just listening to the complaints of, for example, are productive and trying to build solutions that help them. I'm picking up on the thread, which is being great at listening, asking why, which is like such a common thread. And then the agency, right? Like how do you then have the agency and learn how to, I guess, like wield the power with responsibility and kind of go in the organization to kind of also impact change. What has it been like for you? Just the last question on, I guess, in this specific, like your time at Aspire, what was it like to see yourself grow in the role over time, starting from day one and then over time kind of growing and seeing yourself take on more?

14:01When I got this role, I mean, I was really excited, but also really nervous because I think chief of staff can mean a lot of things in a lot of different companies. I mean, honestly, in some companies, you could also just be this glorified admin person. That being said, now, when I look back on my journey at Aspire, I can safely say that this role was everything I'd hoped it would be and maybe even more, I think. And I feel extremely fortunate and privileged to have had the opportunity to be doing this role with the people that I service. And yeah, and all I can say is I think I've come a long way from my starting point.

14:33I think hopefully a bit more polished today, hopefully making better judgment decisions, but also from a technical perspective, very into AI, for example, nowadays, you know, I'm building with AI and again, all this stuff I would definitely not have been able to do outside of this current role I'm doing now. That's a good segue into the next part. In the last conversation you and I had, he talks about how the chief of staff is probably the best position role in the company to run AI enablement and to kind of be the torchbearer or like the lead when it comes to actually bringing the company into this new age.

15:07Tell us why, like what's the thinking behind that and what are you seeing? I bring three points. I think the first point is that I think even before we talk about enabling the company, we need to talk about the personas who would enable themselves naturally. People are so often busy with their own work, you know, doing their VAU that they don't even have the time to learn how to use all these AI tools. I think someone like the Chief of Soft or Chief of Soft Persona is very much naturally incentivized to learn about AI because Chief of Soft are like masters of context switching, right? And they would have to like build a slide deck today.

15:38They would have to build some sort of product strategy tomorrow. They would have to manage their linear tickets some other day. They'd build some automation for their team because like some product managers are happy with some workflow. And because you're spread across so many, doing so many different things and you're context switching in terms of like your brain, but also what you're doing. AI is just the natural default thing that I go to now to manage all my work. I haven't opened any Word documents or Excel documents or PowerPoint, like whatever in the last six months, because I just work out of my cloud.

16:06This cloud does everything for me. Cloud maintains that context for me as well. So I think first point is like the CUS is just naturally incentivized as opposed to use AI to learn about AI in the first place. And then the second thing I would say is that AI enablement itself is a very, very cross-functional sort of thing. We have to build a lot of infrastructure. And when I say infrastructure, I mean, maybe more of like governance or policy, or just even how to think and use stuff, right? All these different tools that are available to us. For example, example, when we talk about AI, we talk about things like AI workflows or agents or skills or artifacts, right?

16:42And a lot of this could be team-centric domain knowledge, but a lot of this stuff as well would sit across the entire org. Now, who owns that, for example? Who would own like an org-wide skill? Like let's say we have like some sort of aspire tone of voice skill, right? Where whenever we use a skill, we write copy and follow a certain, you know, maybe that's a bad example because that probably actually would submit marketing. But, you know, surely you can think of skills that would sit across the entire org right and who's managing that who's navigating that who's driving that who's actually pushing that it would need to be someone who has oversight of an entire org which could be someone like the ceo or coo who are often a bit far removed or like someone like the chief of staff right who would be able to have that visibility across the org and the third part is i think the hardest part actually is not so much thinking about what solutions to build right but it's actually empowering people or enabling people like we've discussed before.

17:34Getting people to buy in is actually the hardest part. Getting people to actually adopt and to use this new technology is actually the hardest part. And I would say a lot of my job is actually teaching people why they should use AI, how they should use AI, what is the first pilot sort of program they could build with AI. And again, I think Achi Wasab is very well positioned there because I've had my fingers in so many different pots. I understand the problem statement of the operations team, or at least one problem statement of the operations team. I understand one problem statement of the legal team, the marketing team, et cetera.

18:05And because I understand enough about AI, but I also understand enough about, you know, the individual problems of different teams, I have enough expertise to go and sit with them and say, hey, you know, we talked a lot about AI, but here's actually a pilot thing. You could build an agent, you could build to manage operations tickets, for example, right? Which is actually what I did, right? I sat with the team, I diagnosed the entire workflow and I said, hey, we could actually just automate this whole thing with agents. Let me sit down with one person in your team, build these agents out, but then also empower this person to then take over, get them excited, and they can manage all your agents moving forward, right?

18:39Something like that is how I sort of did it. I think for all the chiefs of staff that are listening, that are having major FOMO, you know, the classic thing about being chief of staff is that you need to balance being super stuck in the weeds, but also having the bird's eye view and kind of maintaining both that context, right? For all the chiefs of staff that are too busy being stuck in the weeds that do not have the capacity to kind of zoom out. How would you say they could get started with kind of zooming out and, you know, getting started with using AI to help them get out of the weeds as well?

19:13My answer, maybe a bit controversial. I would say naturally using AI would help your daily problem statement already. In my head, most chief of staffs would benefit, you know, just from using AI. But maybe a more tangible answer is you just have to put in the hours, I think, right? If you don't have time to experiment, think of it as an investment. If you understand how you use all these tools, I guarantee you, your life would be so much easier in three months, right? It'll be so much easier, so much more efficient. You just have to put in the hours and find a way to block it out. So for example, when I started doing all this stuff, I basically made the decision to say, I'll spend the next one month really learning this stuff.

19:51I'm super busy at work, but I blocked out two hours every night to learn how to use this stuff. And I actually started by asking Claude to generate a 30-day program for me. to learn how to use AI from zero, how to build my first agent, basically. And basically, just allow yourself to go down the rabbit hole. Because if you're not tinkering with this stuff, you're not learning. You have to have hands-on. You have to be building stuff. You have to be tinkering with this stuff. Everyone is really on their own journey. I think it's very intimidating. But trust me, to those listening, it's so much easier than you think, especially with Claude, with Codex.

20:21You can literally ask the agents now to teach you how to do stuff, and they would pour you. So it's not as hard as people think it is. I think what you're saying is quite important like the meta thing of like hey can you teach me how to use you most people would default to okay this is a tool for me to do that task but a lot of people wouldn't say hey this can be a tool to teach me how to use the tool it is both the instruction manual and also the actual tool that can you know help me have massive leverage over whatever I need to get done can you give us more examples actually of I know you spent a lot of time and despite being like the AI enablement lead.

20:59Can you give us more examples of how you were helping the different teams, like from the small experiments to the bigger ones? And give us some insight on how that process was like. So I think the first thing obviously we did, right, was to consciously just say, look, we're going to give everyone Claude regardless of the budget. So we make Claude available to everyone, you know, please use it. Then I think there's a lot of like other philosophies, around how to actually approach AI enablement across companies. But I think the way that most modern tech companies are now sort of looking at it is to let stuff happen a bit organically.

21:34What we've noticed is that it doesn't matter how many workshops or even KPIs or metrics you put together. Even if you have a heavy hand and say, your team must use X number of tokens, it will be able to count the number of tokens, will track the number of tokens. All this stuff doesn't work if people aren't excited about AI. and getting people excited about AI is actually, in my opinion, the most important battle to be fought. Because if you get people excited about AI, things will naturally follow. It's not going to be everyone. But what I've noticed in Aspire is that at least 10 % to 20 % of people are genuinely excited to be building with AI.

22:10Some of these guys are off by their own. They are super hardcore. We've got non-engineers who are building code every single day, building apps, building tools. All that is just naturally happening by itself now. The mission statement is, how do we get people to be in a place of excitement first and then start doing all those things by themselves? We do very, very simple things. We started with very, very simple things by just even having stuff like AI demo days, for example. So we gave cloud to everyone. And then we started doing things like AI demo days where people would have the opportunity to present things they've built.

22:40We did a lot of AI workshops to start off with just to give everyone that baseline level of understanding of how to use AI. One thing we found was helpful is we curated workshops to be very specific to functions. So for example, we would have a very specific Claude 101 workshop for our product team. The backbone of all these workshops will always be the same. We always cover the same things like artifacts, like skills, like connectors here, all the basic things, blah, blah, blah. But getting people to have that magic moment is again, the most important thing, right? Getting people to that aha moment is so important.

23:12And the only way you'll get people to experience that magic moment is if you show them something or get them to build something that resonates with what they do every day. And so, for example, when I ran my product 101 cloud workshop, I came in with a bunch of skills that say, hey, use a skill to one-shot writing your spec. No longer do you need to manually write your specs. No longer do you need to check what the engineering specifications are for specs. No longer do you need to think about your 100-inch cases. I wrote you this skill that you just plug in, you just tell it what you want to do, give it some sources, and it gives you this engineering-grade spec, wonderful.

23:44Stuff like that. Here are some artifacts, blah, blah, blah. And so we've replicated that sort of model across different functions, which has worked very well, number one. But number two, I think it's also not about just getting workshops right, but you have to also have local champions almost. I'm just one person, and even a small team of us couldn't do enough. But instead of giving people fish, really important to teach people how to fish and get them to be excited to then teach their own team how to fish as well. We also run this AI champions program at Aspire, where we have identified people who are excited about AI.

24:15But more specifically, we're trying to identify at least one champion in each team. And then what my job then becomes is, okay, how do I empower these champions with more advanced techniques like cloud code or building workflows, building agents, etc.? Get them excited, sit with them, work with them, pilot stuff with them, get them to build their first agent or whatever. And then once they've gotten to that stage, I just need them to be honest with you. And they are now evangelizing AI within their teams. They're building solutions within their teams. And I don't do much. They come for me for advice sometimes.

24:44But a lot of these guys are super AI-pilled already and are doing amazing jobs in their own teams. So that's kind of how we've progressed, I guess, over time. And now we're really getting into a stage where we're trying to democratize vibe coding for the entire company. Because we get more and more individuals in the company who are building code, even though they're non-technical. And building code is actually the easy part, right? Because Cloud Code just builds amazing code now. The hard part is actually the plumbing and the infra behind it, right? So how do you scaffold a code repo, for example?

25:12which GitHub repos do I put my project in? How do I deploy my projects in a safe manner? How do I spin up a backend database, right? All this stuff typically requires like a DevOps team or infra engineers. We're trying to build solutions that just make it as easy as possible for the entire team to one-shot deploy apps and stuff. So yeah, that's sort of the journey that we've taken, which has been really, really cool to see and to be a part of. It's change management, right? It's like transformation. It's like enabling transformation within the team. I really love the phrase you use of magic moments as well.

25:43On the micro level, it's with every experience, you have these magic moments that kind of turn the experience from being very flat into something quite special. Magic is just a transformation, right? Transforming from one state to another. First on the small level, but then when you have enough of those small scale magic moments, obviously on the bigger when you zoom out, you notice that, oh, okay, a whole company is like AI native to some degree. Yeah, I mean, that's such a nice way of putting it, to be very honest. I like that, you know, micro magic moments, you know, a hole becomes a giant magic moment.

26:14That's a good way to put it. If we had a time machine, I guess, and we could go back to before we were using so much AI, Metaspire, and compare it to right now. You know, in these movies, when you kind of go back in time, it's the version of the time travel where you're like, there's a version of you in the past, so it's not you. So you're like walking me through what it was like back then and what it's like now. Like describe the difference in how the company operates and what are you seeing? I mean, back in the day, it was people are super manual still. I mean, people are still literally writing documents in Word.

26:46People are not thinking about maintaining knowledge bases, again, which is super important for AI. People are still thinking in terms of raw output versus in terms of systems and loops, which again, I wouldn't say everyone is thinking about that as fire, but it's for sure every single day, I see more and more and more people getting converted to the other side. I think one amazing thing as well, like I said before, and I've said this a few times now, but for me, the most telling indicator, I suppose, that we are truly becoming an AI native company is that we're getting so many non-engineers and not just junior mid-level people.

27:21We're getting some really senior people as well, building amazing workflows, automations, dashboards, fully functioning apps. I mean, I wish I could show you some of the stuff that our team has been building, Like even like our really senior guys, we have like VP level folks who are building a cloud code, like beautiful enterprise grade software. Right. Like I could literally sell some of the stuff that we've built, like a full SaaS company. Basically, it's pretty exciting, pretty amazing. And when a company has momentum, I guess, how do we integrate all that into a cohesive same direction momentum?

27:56You know what I mean? It's again, a great question. And to be honest, we're also not super there yet. And I think a lot of companies would tell you very similar things. I think we're at this stage where it's a bit of beautiful chaos and we're just letting it happen. We are starting to think about things like governance, for example. So now we're starting to think about, okay, how are we actually tracking every single AI project in Aspire? Because we have no idea what people are building. How do you put the right frameworks there? And to your point, how do we start setting the right KPIs to ensure that people are actually directionally building with AI, whether it's actually building apps or even just using AI to improve things like workflows, automations, et cetera, what is the right structure to do that?

28:36Because you don't want to be over punishing as well, right? Because then it becomes this whole game that people are trying to play. Like, oh, I have to build one AI app per quarter. Does it make much sense? So to be very honest, we're still figuring it out. I would still say we're not like super there. We're just starting to think about these things, but I would say we're fully in that sort of excited hype mode where again a bit of unstructured chaos at the moment yeah and when you zoom out and kind of see these different stages as someone who's you know responsible for ai enablement i'm thinking of the other chiefs of staff listening who let's say want to start kind of replicating maybe some things that you've done could you help me like recap the different stages roughly that you see when it comes to this role i would say like that's the early stage where it's just like getting people to adopt trying to get people excited i'll say like the hype stage, which is just getting people excited to even understand what AI does and getting a couple of power users up and running.

29:27There are these champions, like I said, right? And really forming a core. Here are the five people in my company who really know AI, and we stopped using them as leverage to build excitement, to build enablement, to look hype around the company. Then you move into this middle stage, which is probably where we are now at Aspire. I would call this AI native or close to being AI native in the sense that people are defaulting to AI. Most people default to AI. I mean, I walk around the office, most people are just using their cloud. People are thinking about knowledge bases. People are thinking about connectors.

29:56People are talking about agents and workflows. Again, our power users from earlier, I've all graduated to super, super power users. Again, all these non-engineering guys building a cloud code, building apps, et cetera. There's a lot of excitement. There's a lot of building. There's a lot of usage of AI. But like I said, it's all a bit unstructured. It's all a bit chaotic. tickets, how to really keep tabs of what people are doing. Then I think we enter the final era where everything is a lot more structured, right? And right now it's a lot of bottoms up, but I think the final stage is you have to have that top down, which is again, a layer of governance and tracking, right?

30:27How do we actually measure things like ROI, right? For AI, an insanely difficult problem statement, but I'm sure some companies have cracked it. Who is setting AI KPIs, right? For the teams or how are they being set, right? Are Are there even AI KPIs? And it has to be more than just like how much tokens you're using. How are we actually converting AI into tangible business outcomes and how are we measuring these things? Another really cool problem statement is how are we having more single sources of truth? For example, again, like everyone is building code by themselves in their own repos today.

30:59People are deploying skills all over the place. But if you look at some really pilled up companies like Ramp, for example, in the US, they have built custom marketplaces for their apps they have built custom marketplaces for their skills they have like ramp dojo or something where anyone in the company can upload a skill into this marketplace that is shared by the whole company they even have ramp glass which is like their own internal version of clawed code but ramp glass if i understand correctly has like graft knowledge of their entire knowledge base it also like understands their design language really well like whenever you deploy an app or whatever it goes i guess straight into the marketplace.

31:33I'm not entirely sure, to be honest, what RampGlass does. But again, my understanding is it's a centralized Ramp version of Claude or Claudecote, basically, that anyone wants to build anything that goes through RampGlass. I think that's a sort of like super mature stage that I think Aspire we're now thinking about. But yeah, obviously not there yet. As you're talking about companies eventually moving from, let's say, not using AI at all, to having some adopters, to it being a known and really exciting skill that everyone's using, to then being, okay, company level, we have a RAM glass, if that's what RAM glass is.

32:06Everything that is outputted from the company goes through a filter or goes through a transformation process that it cohesively both represents our identity, but also, I guess, like it's cohesive because it's centralized. It's like eventually RAM's AI, eventually Aspire's AI, eventually YC's AI, which I know they already have something. But then if that's the micro level, which is companies, using mod a bit more, we have like state level, like maybe territories within the country and then you have country level and then now when I think now when I think about like the bigger picture right I mean that's the goal it's for every single country to actually have their own super intelligence that is a great thought to be honest yeah I obviously haven't given it more thought than just my own company but that is a really interesting thought you know the more conversations I have with chiefs of staff I feel like I'm gathering a lot of the common traits that I notice just by speaking to people who've been doing this role for a while.

32:58And one thing you and I have spoken about is this tendency, because I know I have this for myself, the tendency for people pleasing. And I remember when I, you know, had my first chief of staff role, how much I wanted to prove myself and how little I understood how to have strong boundaries. And for me, you know what that causes actually a burnout at the end of that stent as a chief of staff. But I wanted to pick your brain a bit about this because because it is something quite common in terms of this people-pleasing attribute. And also, I know a lot of chiefs of staff struggle with how to navigate that.

33:32So I'd love to kind of get your thoughts on that. To be super honest, I also haven't quite figured it out. And like you say, I think it's interesting, right? It's interesting that when you say it like that, that most chief of staffs naturally are sort of these people-pleasers. I wonder why, right? And I guess it's because you have to be good at navigating so many different kinds of personalities. So I think a cornerstone of being a chief of staff as well is just like the ability to be liked or respected, which I guess comes with that people-pleasing tendency. The honest truth is I haven't quite figured it out.

34:00I mean, I am someone who feels guilty for not taking on more work, which is a terrible, terrible trait to have, but it's true. I'm someone who, and I'm sure most CUSs will say the same, but I'm someone who looks for ownership, right? I'm not someone who would say, you know, oh, this isn't my remit and I want to do it. I'm someone who's, oh my God, there's a problem over there. like let me go and fix it right and i think most cheapest stuff relate to that personally i've never been very good at saying no you know when i do say no it's often at a point where i've reached like this limit and that limit is basically i open my calendar and like every single hour is blocked out for the next five days i'm like i don't even have time to lose the bathroom some days and then i break and then i sit down with my manager and i would obviously very rationally go through okay these are all the things that i played like there's no way i'm delivering like a whole bunch of all these projects well let's either take some stuff off or just accept that i'm going to deliver a bunch of b minuses and if you're okay with that then that's fine and to be honest with you it normally is the latter like what someone ends up saying it's like you know what that's fine just keep doing what you're doing i'll accept that you'll deliver it a bit of a lower grade but that's fine but then again that's also terrible for all these high achieving achiever stuff so we hate delivering b minuses right we love delivering a pluses and And the fact that we're delivering 10 B-minuses instead of like 3A-pluses just really aggravates me as well.

35:19And then we go on this whole cycle. Oh, I'm not good enough. Like, I didn't like the fact that I'm not delivering good work. Yeah, this is the sort of, you know, vicious cycle that I find myself in quite a fair bit. In my work as a coach, this is actually one of the topics that I am working through with several chiefs of staff. How to be okay with doing less and saying no to things. and oftentimes like what's been really interesting is that what comes up is the work we do and the time we spend at work is just like one expression of how we spend our time right we also spend our time playing many other roles wearing many other hats in life but in the work identifying the work sphere like this comes up what i've noticed is in working through this with several chiefs of staff they also notice how this outside of work is also an issue like saying no to certain things or trying to have boundaries.

36:06So it then becomes a glimpse into like, okay, this is just one aspect of life we're showing up. But maybe it's just something we have to be comfortable with and just accept that this is part of who we are, right? I mean, this is the reason why we've gotten, I guess, where we are in life, which is great. It's just another cost that we have to pay, I suppose. I think there's something also in like, you know, what you had said about, you know, being liked and in order to get buy-in from so many different types of stakeholders, you need to kind of be able to work with people. And what I mean by work with people is like understand and have compassion for people's experiences, especially in the company context.

36:44So remember what you were saying about getting by on AI enablement. It's like making it so tasty that people want a piece of this and people have different taste profiles, right? Depending on what department you're leading or in. I think there's something in there because we have the ability or we're more geared towards words, being able to be compassionate for some different types of people. Like there's something in there of like, the more we listen, the more we try to understand, the more we'll also have this sort of like energy exchange that happens. I really like that. And I think you really hit the nail on the head, right?

37:15I think there are many things that make good to yourself, right? But I think another cornerstone, as you say, is really like relative empathy and compassion in the sense that you're able to understand or put yourself in the shoes of the person opposite you, how they work, what they might be going through, whether they're a senior person or a junior person, which then affects the way that you speak to them, the way that you interact with them, the sort of questions you ask, sort of things that you are trying to drive through. So I think it's a really interesting, but very true point that you made.

37:44What do you think about respect versus likeability? Can you be respected, but not necessarily liked? And can you be liked, but not so respected? Definitely. I try and balance that as well. Again, I think it's also a very fine line to balance. And again, I'm not the expert at doing it. But for me, I think I adjust how I behave and how I speak my tonality, depending on the context of the situation, right? Basically that, I mean, I can be very hard, but I need to be, I would say my default person is quite affable. You know, I try and like put on that likability sort of factor, like non-aggression, right?

38:18That's my default. But again, I can be aggressive, right? And I can be very firm. And again, I think one great thing about chiefs of staff is that they are also very convicted people, right? And I think another defining characteristic is they want to do things for the right reason. They're not people who follow the crowd or want to get something off their plate just because it's the easy path. I think we typically would choose the hard path if it's the right path, right? I think that really defines this as well. And I think what that leads to is like, look, if there's a situation where you don't agree with something being done or you notice like someone is trying to be taken advantage of your affable sort of character converts into this person of conviction right and look i put my foot down when i need to put my foot down i protect the right people when i need to protect the right people and i think people will respect you more for that but again it's knowing the time and place i think it was just that skill that people like us need to master again that is another thing that i'm noticing in these conversations it's like how to balance being responsible to your principal versus being responsible to the company.

39:19How to navigate those hard calls where, you know, let's say you get a piece of really critical information from, well, a very common one. Common one is, you know, that we're going to lay off X number of people in the company. You have that info. Some of your closest friends are people in the company who will be laid off. And I've been in that situation. I know many of the chiefs of staff that have been in that situation. How do you think about this? How do you navigate situations like those when it's kind of tough. That's a tough one. Again, it's hard to give you any sort of playbook because I think it's so contextual, right?

39:50It's so different with every situation. And again, I think I don't really have a playbook for myself either. I think it's just what my gut feels at the time is the right thing to do. I mean, in the situation you described, like anything with to do with confidential information, I think actually like the primitive that you should always operate on regardless of whatever's happening, right? It's not to lose the trust of your principal or not to lose the confidence of your principal, right? So if it's something to do with like discreet information, you shouldn't be sharing. I definitely wouldn't share, you know, any of that.

40:16Right. But then again, like, I think you can still put your company first over your principal in some situations without losing the trust of your principal. Right. But again, it really is a function of what the situation is, how you manage it and how upfront you are with your principal, but there have definitely been times where I've pushed back to my principal and saying, look, I don't think what you're doing here is the right thing to do because of X, Y, Z reasons. These are how people on the ground are going to be affected. Have you thought about that? But end of the day, I'm not going to go behind his back and say, look, if this is your final call, it's your final call.

40:46But this is my opinion, right? And I don't agree with it. That point of not losing the trust of your principal is, yeah, I think you hit the nail on the end, that one, because our responsibility is to enable the decision-making and scale the decision-making of whoever our principal is, whether that's a CEO, anyone else in the team. And yeah, obviously that trust is super critical, which also makes it even more important to work with principals that you believe in and that you have a good chemistry with and that you would want to be in this situation with. Exactly. In an article that we recently wrote in the Chief of Staff Network blog, there's this line that says, as a chief of staff, we're always of service to others.

41:26But what happens when we try to be of service to ourselves? I'm wondering for you, you know, how has that looked when you give me the example of like your calendar being back to back to back to back, being off service to everyone else? How do you think about and how do you balance also kind of being off service to yourself? So the way I think about the role is that on a micro level, I think it's very hard to be off service to yourself, especially again, with that sort of personality that comes in, right? Someone who is looking for ownership, someone who's a people pleaser, someone who just finds it hard to say no.

41:55But the way I find this role or how I've served myself in this role anyway is more on that macro level. And for me, I think chief of staff has been the greatest job I've ever done because just the amount of exposure that I've gotten across the company. I think it gives you so much confidence in terms of judgment. It gives you so much visibility. It really teaches you how to speak with execs and people, but also people on the ground alike. And the way that I've seen this chief of staff role has really been the ultimate internship always. You know, it's like really understanding how a series C scale up works from ground up, every single aspect, every single facet of it.

42:31And I've very intentionally gone into the role, trying to understand all these different moving parts as well as I can to figure out which moving part interests me the most. And I think it's a very, very privileged role because no other role will let you have so much exposure, so much agency over what you want to do as well. I mean, a lot of the things that I do most of the time, also just self-driven as well, It's like, hey, I think I want to fix this. Let me go and do this. I'll spend the next quarter building this out. And I think that has been a great service to myself because I think I've come out of this role, again, with all the good things I mentioned earlier, I've come up with a much more confident, competent person, but I've also discovered what I really enjoy.

43:08And in my case, it has been AI. And I've really had the opportunity to almost carve out this AI role for myself to figure out what I actually want to do, how I want to build it. And again, very fortunate for the company and my principal for trusting me and just giving me the space to figure things out by myself. That's how I see it, serving myself, I suppose. The environment in which we operate in as the chief of staff, it really matters. Because if we have that space and we have that trust and we have the support, also in US dollars kind of support, in the monies, which is also very important, right?

43:47But I think if our team and the principal that we work with is willing to invest also in our own development, both in cash, but also time and space, meaning blocking out certain times to do some programs, to maybe have some mentorship, maybe to do crash courses. I think that can make all the difference because then, as you said, apart from being of service to others, we're also in an environment that allows us to grow on the things that we care about. And it's amazing for you to have that setup where you also are trusted enough actually to be able to carve out your own thing and also have the trust to bring the company into the next phase.

44:26Okay, I wanted to also ask you about your work experience working in Europe or in the UK versus working in Asia. The reason why I'm asking this one is because we have a growing audience based in Southeast Asia or different parts of Asia. Most of our audience is normally based in Europe and the US, but we are starting to interview and get more people listening in from the side of the world. Do you think you could just share briefly some of the things that you notice working in the UK with English teams versus working in Singapore? So for this question, I might not be the best data point. Again, because the company that I work for in Singapore, Aspire, I think we're very European by heritage.

45:02All our C-suite are, you know, sort of from Europe. And we are very, very, I would say liberal, right? In our company's policies and our culture. But that being said, I could definitely provide more of a generalist view, again, from what I've observed. And from what I've observed, you know, I think working in Singapore, the culture tends to be a lot more aggressive, especially if you're working for one of the more, how should I put it, one of the more Chinese owned companies, right? I'm talking about the Airwallexes, for example. They can be very, very aggressive. I think in Europe, especially in the tech startup scene, there's a lot of emphasis on not only just getting the job done, but also a lot of emphasis on being a human being, which is great, which I really love.

45:43And I think I aspire, you know, incorporates those values quite a fair bit. I wouldn't say to the extremes of the companies I've worked for in the UK, for example, Lonzo, which is very, very big on being a good human being. In fact, even more so, right, than getting the job done sometimes, I feel. from my sort of viewpoint from the companies that i've observed here in singapore very aggressive and a lot of emphasis on kpis basically so it's almost like everyone's just wearing a mask and you are just the kpi that you own people can view that as a bit of a toxic environment but it does get the job done so see it as how you these one of the most common things is like well if there's not making any money we're not gonna have a job right so it's like how do you have the balance of for sure you know being treated as human i think sometimes you do need to make sure people own the metrics that they're actually responsible for for sure it's a bit of a balance always yeah but i say this is very only true for like the sort of very local or very asian companies with a lot of asian heritage or chinese heritage for our listeners in europe and the u.s who don't have much context on like chinese companies or chinese heritage companies like when you talk about aggressive like what does that look like i think there's a lot less and again this is just purely from what i hear i've never actually worked in one of these well actually i have but that's for another time i think there's a lot more directness here in singapore right there really is a lot less of beating around the bush or scotting other with the niceties i remember when i'm in europe like it's very classic british behavior to like sort of tiptoe around the problem but very eloquently deliver the message you want to deliver without flipping off the guy right here it's a bit different here like they can be very very direct basically and there's no sort of manners of politeness sometimes if the guy is in a bad mood he'll just sort of shoot you in public but again i think it's also just a reflection of the sort of environment that folks are brought up in as well right in the uk manners and politeness is very integral to that society whereas in in china or you know in certain asian countries it can be very different right people have been brought up from day one to just do what needs to be done to get the job done right and there's no sort of tiptoeing around the problem.

47:53Yeah, I think there's also this other element of, in Chinese culture, like I went to Chinese school growing up in Malaysia, inherently like power structures, like whoever has more power, in this case, if you're in a company, your boss has more power than you, they have the right to treat you in a worse way, essentially, because you don't know any better, is the thinking. And that means, you know, hanging out to dry in front of the whole company. That's one way to also do that. it's just a different way of operating, I think. I think as I speak to more people who are chiefs of staff operators who are based in Southeast Asia, I'm also just trying to get more of this conversation going to also see, you know, other people's experiences, but also share a bit with our US friends and European friends, like how things are different, you know.

48:37Zen, last question for you, man. You talked a bit about how the world has shaped you, and I know we touched on this in the beginning of the call. In this next phase of life for you, like, I'm mostly curious, how do you think about the chief of staff role for you and what are some things that are staying with you in terms of how you look forward in life as well? I feel the chief of staff role is never really meant to be a permanent one. Like I said before, I think this is ultimate sort of learning two, two, three years of learning, and then you could figure out what you want to do, what niche you want to specialize in, in terms of your career.

49:05But similarly, I think it also applies very much to my personal life, right? I think the chief of staff role, and I mentioned this before, I touched on this before, has been, I would say definitely more transformative professionally, but also transformative personally as well. And I think despite my next role, probably not being another chief of staff role. Again, I think I take a lot of things away from this role. Again, most importantly, I think it's trusting my own judgment a lot better, right? Trusting that I can make sound judgment, that whatever decisions that I'm making is probably not too far from, or is in the ballpark of the right quadrant of being the right one, at least, right?

49:40It's directionally going to be a decent decision. And another key thing that I've definitely learned, and I will definitely take forward is very much that human aspect as well. You brought this up and I wholeheartedly agree, right? But I think a lot of our role is that sort of empathy and understanding the person opposite you, right? Being able to adapt to get to the person opposite you. And I think inherently all of us have this skill, but I guess, you know, being in this chief of staff, I've just had to really like dial it up to a 10. And I'm a lot more thoughtful around working conversation, like working in the conversation nowadays, you know?

50:14Again, thoughtful in the sense like, okay, I'm having this conversation. What is this outcome that I want to achieve? Do I go on the charm offensive or am I going to show a bit of steely conviction? I think before I was a lot more laissez-faire with the way that I approach conversations. So I came across not as self-aware as I'd hoped to be, but definitely taking that away from my chief of staff experience. And I think last but not least is actually just honestly, just being a lot more comfortable in my own skin. And I think I get this from meeting more and more people in this role. I mean, in the Chief of Staff role, I meet a lot of really interesting people that I love talking to.

50:49I get a lot of energy from talking to people. But I think also in the past, right, I've never quite liked some aspects of myself. For example, I'm terrible at directions, right? I don't know why. I can't find my way around a map or directionally. I'm super clumsy sometimes as well. And I think it's someone who's always been a bit anxious and high-performing. All these small things really bug you. And why am I like this? Like, why am I not good at driving? For example, it's just, you know, but I guess all these insecurities before I just accept as who I am. It's again, because I meet more and more like super interesting people who are, you know, have their own little quirks and uniqueness.

51:25I think ultimately this role has taught me that to be super cheesy, but it's true. I think our shortcomings are what makes it special and different and unique, right? You know, the chief of staff role is this ultimate for me anyway, this ultimate sort of, you know, you are who you are, be confident in who you are and no chief of staff role is different, but they're all awesome people in their own way. And yeah, I think that's what I will take with me from this role. I think that's also a perfect way for us to wrap up this episode. Zen, thank you so much for your time. It's been such a pleasure, man.

51:55My pleasure. I mean, this was really fun. Thanks a lot for doing this. Hello, this is Scott Amento closing out today's episode. Thanks again to Zen, Chief of Staff at Aspire for joining us and to our Singapore chapter lead, Tristan Lim, for leading the conversation. A few things from this one that stayed with me. One was the three-stage AI adoption arc from hype to native to governed. Two was the point that getting people to their magic moment is the real work of enablement. And lastly, is Zen's framing of the chief of staff as the person in the company best positioned to own AI transformation because no one else has the cross-functional context to actually pull it off.

52:31We're seeing more and more of these stories emerge and it's great to hear it firsthand. If this conversation resonated, and especially if you're somewhere in Asia doing this work, we'd love to have you in the community. Chief of Staff are building at the highest levels across 25 plus cities and the Singapore chapter is one of the fastest growing. Links to get involved are in the show notes below. And if you're exploring the Chief of Staff path or working towards landing your first role, our Chief of Staff Launchpad course is the best program to give you the skills, frameworks and network to get there with confidence.

53:02Links are also in the show notes below. Thanks for listening and we'll see you next week. Bye.