You Are the Product: Managing Yourself as a Chief of Staff

0:09Tristan Lim: Hey there, it's Tristan again. Welcome back to another episode on the Chief of Staff Network podcast. As a little reminder, I'm a guest host on the pod and my day job is running Beyond Founders, where I help first time and veteran chiefs of staff to lead with clarity and avoid burnout. I'm based between Europe and Southeast Asia, and I've really, really been enjoying highlighting all the stories of operators from this part of the world. Now, for today, my guest is Brianne. Brianne has had a nonlinear path moving through Singapore's attorney general office and then actually going into oil and gas trading and eventually also running three of her own sustainability startups.

0:45Tristan Lim: She now works as a fractional chief of staff, deploying early into startups and then taking them from zero to around$1.5 million in revenue and then exiting. She works as a part-time operator, fixer, and systems builder. Ria talks openly about how her last startup ended and also how that experience became the reason she wants to learn from founders instead of being one. Now in this episode, we're going to get into a few things. Firstly, how her people before process philosophy works and why she always understands how people actually behave before designing systems for them. We'll also get into the whole chief of staff for hire or fractional chief of staff model, how she actually deploys into companies and how that whole rhythm actually works.

1:25Tristan Lim: We'll also then talk about one of the hottest topics in the chief of staff world, which is influencing without authority. And then we're going to get into building and merging markets, why one idea might raise$1 million in Asia, but$5 to$6 million in the West. We'll also talk about her take on never founding another startup again. And then we're going to hear her take on the whole generalist versus specialist question when it comes to being a chief of staff. All right, everyone. Step back and enjoy. Hey, Bri, welcome to the podcast. Super happy to have you here. Hey, Tristan. Nice to see you again.

1:58Tristan Lim: So we had met at the Chief of Staff Network event in Singapore, and that was in February? Yeah, I think that was January, February, earlier this year. Time flies when you're doing everything at once, I suppose. Thank you so much for making the time. I think for everyone listening, could you just give us some early context of who you are, what your background is, who is sitting with us today? So I've sort of taken a pretty meandering path to where I am today. Where today is, is I am the chief of staff for a startup at Series A. It's in the, I would say, the MedTech luxury wellness arena. They have a clinical device, but it also applies for where a lot of interest is nowadays, which is in recovery from sports and optimizing for athletic performance.

2:45What took me here was, I guess, like 15 years of understanding what you enjoy and what you're good at and finding a path between this Venn diagram where people pay you for it as well. I think that's taken me from public sector work. I used to work for the Attorney General in Singapore. So that was in knowledge management and in training and development. And that was what actually gave me a lot of, I think, systems thinking and understanding how to manage people first and then apply process later. And saw a lot of the, I guess, failures of technology. And I think that's what made me very interested to work in transformation.

3:26Throughout the next two jobs after that, which were more of jobs that I was headhunted for into business development for the oil and gas industry and services, I discovered also that I enjoyed a lot of the front-end revenue driving processes. So at the end of 2019, I think it was just before COVID, I decided to start my own business around that, primarily because it also coincided with my dog aging into his senior years. And I wanted to have more freedom to organize my life in a way that I could spend more time with him. And I haven't left that startup scene since. So 2020 and 2021 during COVID, I think, gave rise to a lot of what we now call the content creator or entrepreneurship community and economy.

4:13And I think that trend is set to continue. And I think it's actually much needed. It could be copium because for what we do, of course, it's good that more people are actually getting into entrepreneurship, creating new businesses where a lot of our skills are then applicable. Because not only do we have an understanding on the back end of what works in terms of systems, we also can understand all the important levers that drive a business. That's what I apply today as a chief of staff.

4:41Tristan Lim: One part you talked about was people before processes, something that you had learned. What do you mean by that? Well, I'm trying to be diplomatic. I think most people who work with governments understand that there is always a tension between what the top-down stakeholders need and what the ground-up stakeholders or how they execute. And I think that tension comes into two parts, which is the people in the process. So depending on how you apply your lens around that, it shapes how you navigate that tension for outcomes. So in my time, I think with institutions of any size and especially public sector, a lot of the top-down stakeholders determine the process because that's what looks for them.

5:26And they hardly consider, and I'm not saying that they should or should not consider, but they hardly consider what the executionary layer is on the ground. And I think one specific example where process came before people was when I was working for the public sector and there was an enterprise system that they had designed three years prior, I think, to my entry. So I happened to come in, fortunately for me, at the implementation stage and training people to use that system was incredibly difficult for a system that was meant to make things easier. It actually increased a lot more workload because the way it was designed, they understood the workflow process, but they didn't understand how humans behaved and how they worked.

6:11And I think that's the philosophy that I have today is that when you go into anything, and this is outside work as well, you have to understand how people already behave first before you try to do anything, whether is it navigate the relationship with them as friends, as workers, or let's say in the case of change management, to actually manage their behavior and then get them to deliver outcomes that you need?

6:34Tristan Lim: This is a thread, you know, people versus processes, which comes first and how to design for that. And the conversations I've been having with different chiefs of staff and also my own work, this is often a really, really big topic. I'd be really curious how your understanding of this tension has developed from kind of being in public sector, working in the energy sector as well, and then building your own companies and then now working as a chief of staff? How has the understanding of this topic grown? Well, I wish I had a very clear idea of how it's grown. I think what I can talk about is the sense of frustration when the tension exists and whether that frustration has been reduced or can be reduced over time.

7:18I think that's maybe the best way to put it. I think in the past, when you are in charge of driving outcomes in general, a lot of people tend to take a very logical approach where it's like, oh, this process makes sense. If it makes sense to me, why doesn't it make sense to other people? Because if you can convince them that it makes sense to them too, therefore they would do it. But that's not the case. And that frustration is something that you can work on because the frustration of navigating people or like having to put in the effort to convince them, persuade them, align them, that is always going to be there.

7:53So I think what I've learned is actually just to manage my own frustration and manage my own expectations. So knowing that I can manage my own frustration and understanding that I am capable in navigating that frustration gives me a lot more confidence in navigating the uncertainty of the frustration from other people and other roadblocks, I would say. One thing that I'll say is actually very interesting to look at this through. I'm currently reading this book called Hooked by Nir Eyal. I don't know if you've read it Tristan I think that this book should be actually one of those foundational books that everybody should read like if you ask me what would you give your child to read I mean how to win friends and influence people is great don't get me wrong but I think this is a much better book they should read this together when it comes to managing a product I think it makes a lot of sense to look at it through understanding people first how they function how they behave and then understanding if let's say your stakeholder wants this let's say not this level but let's say they want this result because i don't like a top-down approach let's say they want to reach b and right now you're at a so what does a now look like and then what do you need to get to b then make that loop again and say is that b realistic and if it's not realistic can we do somewhere in between can we get to like 10 15 and then how much resources how much navigation do we need and then move from there.

9:16And I think dicing up that frustration along with your sense of centeredness helps a lot.

9:21Tristan Lim: What about Hooked has been standing out? Like what are you taking from that book that makes you feel like it should be so fundamental? I think a lot of people talk about like organizational psychology and individual psychology. I have myself a very big personal interest in it. And I think what Hooked highlights very well is that framework to have when it comes to how do you get people to do something. We talk about behavioral change in psychology, but I think that book much more clearly and I would say very honestly boils it down to a few things. People don't change until they want to. And can they be helped there?

10:00Yes. Can you understand how to design the environment so that they get there completely? So I think that's what he elucidates pretty well in his book. We don't have you having to dive into probably like 10 ,000s of psychological studies and case studies.

10:14Tristan Lim: So he's just like, hey, by the way, this is the distillation and he's presenting it. Yeah, I think so. I don't know whether it's self-validation as well, because we all talk about how humans are very basic. At the end of the day, we haven't changed too much from our ancestors. We are motivated by a very few things, the same things that's motivated us for a few thousands of years. And who are we to argue with evolution, right? All you can do is design around that evolution. So yeah. I love that. Yeah. I want to pull this a bit into dynamics between principals and chief of staff, since a lot of our audience are either moving into the chief of staff role or currently a chief of staff or, you know, asking some questions around how to navigate that.

10:57Tristan Lim: A big one is obviously the principal and chief of staff relationship. So when it comes to managing this relationship, I know you have been in many, many seats from being a founder, also being a direct reporter, also being a chief of staff as well. What does a good relationship look like and what does a bad relationship look like when it comes to founder and chief of staff dynamics? I think it comes down to the same thing. When you look at your principal as a product, I think just to relate it back to what we're talking about, you need to understand what their core motivations are. You need to be able to very quickly learn what kind of person that they are and what kind of concepts and more importantly, the philosophies that they operate around.

11:38I think that's very important. What is a good relationship? I think overall from that is where your principles at least align. Or if they do not align, then again, the self-management part has to come in and you have to be okay with the fact that you will have to do things that are not in alignment with how you normally operate. So that's up to you to decide. And the power of agency helps a lot to determine the outcomes of their relationship, whether it's good or bad. But for me personally, a good relationship is where you have communications. Is it always easy? It's never easy. You should always assume that there will be miscommunication, but you should be able to trust that you can ask about that communication to get clarity and not assume intention.

12:22In Hook's book, and I think this is generally known model as well, there's a false behavioral model. And I can boil it down to two very simple parts of it first. There is intent and there is skill. You should always assume good intent with a principle that you are with, but assume that maybe it's a skills issue and communication is a skill that can be refined. So that I think for me works pretty well. That doesn't mean that you always think that they always have good intent. It's just sometimes that people don't understand that their motivations are not quite in line with their intent. That could be also true.

12:55So that's one. Two is where your principle also is investing similarly back on you, meaning that you're here to help them make their lives easier, but they also should not be acting in direct opposition to you. And so this is, I think, a layer on top of the communications is if you guys cannot safely communicate with each other, you will not be able to work together to drive the company. And I think that's probably the most important thing of all. And the other measure of things is, of course, if you do your job well and your relationship's good with your principal, then the outcomes within the culture of the company are very clear.

13:32Things move. People are generally feeling safe and satisfied. Are they happy? No, not necessarily. I think happiness is not necessary always. It's not achievable always. But are they satisfied with outcomes? And if you invested in their jobs, they feel like they can do their job, they can drive forward on the metrics that they need to drive forward. I think that's an important part of it. So probably these three.

13:54Tristan Lim: When it comes to, you know, another big topic that keeps on coming up for chiefs of staff is how to influence without necessarily having authority in many cases. You know, as a chief of staff, you have access to the deep dark secrets of the company because you have a full purview on what's going on in different areas and the permission to explore freely. but then the question is what do you do with that information and how do you create influence where you see that could be positive for the company without necessarily having the authority to do so i would be curious what you've seen worked so we'll come back to that if you could but i think in general my particular style is to again i have to qualify one thing i am a girl i mean i'm female so that this affects how i manage things because of how other people perceive me i generally like to do what apparently is called the Socratic Cushion.

14:48So I never quite reveal a lot of information. I always just go like, oh, do you think that's a good idea? Or I would say, oh, that sounds like a good idea, but do you think that this could happen? And then I just reflected back to them. Because I think there are a lot of assumptions here. Assuming that the team that you're working with are competent for what they were hired for, there has to be some level of trust that they know how to do their jobs. If not, then there's also another problem that we will have to deal with down the line. But when you actually allow them to just have a bouncing board or like a mirror to work through how they think, then you can see how the outcomes can be driven.

15:26And then from there, you can potentially navigate it a little bit to the left or right of where they're headed. And I think that's the best kind of influence is to allow people to challenge their own thinking and then to influence that without pushing i never think that you asking for anything is gonna end up you getting something you want that's just my approach yeah happy to share on

15:50Tristan Lim: my side i think what i have seen be effective and not effective what has been effective is definitely which is no surprise right but taking time to build a relationship with the people in your company, taking one-on-one time, obviously getting to know someone beyond the job that they're hired for, but like who are they as a human as a whole and being able to speak to those parts and empathize with those parts, have compassion for those parts, especially when moments are difficult. What I've seen as not really effective is, yeah, I think having high expectations can only succeed if the people who you're having high expectations to perform have number one ability to grow their capacity to do more, but also you're creating an environment where that capacity can also grow, meaning there's an appropriate amount of new responsibilities.

16:35Tristan Lim: And also there's a really, really a culture in the team that is supportive of one another, as opposed to siloing everyone and just expecting everyone to push in their own way solo. I think everything is better done as a team. So I think my answer is kind of like capacity and understanding your team's capacity and also helping them understand their capacity and then creating an environment where that capacity can grow. Yeah, that's probably really, really, really good point. Do you feel like that empathy could be a gap in certain teams because of the people that are leaving the teams? Where do you find those instances?

17:12Is it affected by the type of people that they hire? Or are there other factors at play?

17:17Tristan Lim: I firmly believe that all decisions and the culture of a company, it's downstream of obviously the people at the top, the leaders, including the blind spots. There's a great quote about culture. The real culture of a company is what happens when the boss isn't around or the bosses aren't around. What do people say? That is very much the culture. What are they saying? Are they nice things or not nice things? And that is very much the reality of things. There's always this tension when you're building a business. I don't think businesses are built for people, for humans. They're built for money and profit.

17:53Tristan Lim: I think you can have a humane experience along the way, but they're not built to help people thrive as humans. They'll build for a very specific purpose most of the time. And I think it can be difficult to kind of prioritize the human in the process because you might have investors that want their money. That's actually just fundamentally the system we're operating in. So sometimes the humanity bit can take a backseat is kind of what I've seen in my honest thoughts on that. Yeah, well, you took the words right out of my mouth because I was like, I think you've just described the global economy at scale.

18:23I think especially because, as you've mentioned, I had startups before and they were all in climate. And in that particular arena, I think that conflict, I think between we need to make money and the value is only determined by numbers and like dollars and cents, then humanity, as you've described, or like the human experience and everything else that cannot be boiled down to dollars and cents tends to fall by the wayside.

18:49Tristan Lim: And it's easy to justify that because we have numbers and hard figures to justify why it needs to fall to the side. We don't have time for this. you know we don't have time to invest in this anymore because easier for some than others yes exactly i feel like we're on the same page on a lot of things yeah pretty much i think because i think if you have grown up with a very empathetic view on people and you always put people first it's hard to not see it not being put first is it's a spectrum there's like people not being put first and then there's like you are here to extract all possible juice out of this human being so yeah so like for the most part i think both of us try to fall somewhere like a healthy balance between here rather than here but you're right like i definitely think that's why like when you say prince when you said principles earlier i meant it's a good point that it's about your principle but it's also about their principle their moral philosophy that's very important and i think sometimes picking someone to work with and this applies for life as well picking anybody that you want to interact with i think boils down a lot to this So yeah, driving that team culture from the get-go is important.

19:53Tristan Lim: How would you describe some of the principles that make you feel aligned when it comes to working with someone? Like what's important for you? This is across the board. I like it when people are aware of their own capacities. So bring it back to that point. This is more exemplified by when they say they will do something and then they mean it like their intent is there. but what they overestimate is your skill skill meaning not competency only but also time resources bandwidth mental bandwidth emotional bandwidth and i think to use that word because it's very cliched but i think self-awareness in that sense is very important are you born with it no but as you work with the team i think what's always good is that it's about learning about yourself as a teammate as well like do you understand your own capacity your own skills Do you understand and self-correct?

20:45And you need that feedback. You are the product. So you have to manage your own product here. And understand that when you commit to something, especially when there are dependencies on it within the team, how overestimating your ability to follow through is going to be impactful for everybody. I think that's one. So I evaluate when people are understanding of their own. If not, then they can self-correct in time. That's also very important. And I think probably being able to have a lot of compassion, I think, for other people. You can call it empathy. I think that's all within the same market.

21:20But I think when it comes to communicating, especially in teams that are nowadays pretty commonly multicultural, I think it boils down to having compassion that some people, this may not be their first language. English is not their first language. And if anything, you should be impressed that not being their first language yet, they can still function alongside you and do whatever you're doing or related to what you're doing. I think that's something that I value as well. That's what I would look for in the principle is that when you're hiring for people, it goes either way. We talk about the 996 culture.

21:54If you hire certain specific types of workers, for sure that they are more used to that culture so that there is a little bit less friction in managing expectations for us. but when they are not yet you need your talent then you need to take a different lens when it

22:09Tristan Lim: comes to managing that person and for those listening who do not know what the 996 culture is if i'm not mistaken it's nine to nine six days a week i think in the sf way you could say it's the hustle culture that makes sense yeah for sure but 996 is coming up from china yeah you're right i should have exemplified that sometimes you get trapped in the old little bubble of like people who only work in this kind of like hustle culture. And I forget to explain that some of these words are complete jargon to everybody else listening. In Germany, we go home at five. Well, not everyone. Many people do.

22:41Do you start work at like six or do you start work at like 10, like the French? You know, like nine.

22:48Tristan Lim: Definitely German culture. It depends on the startups, obviously. It really varies, but there's definitely a much stronger emphasis on I think having a work-life balance, especially in the summer. Yeah, it's very clear that particular difference between Americans and Europeans. I think now, especially during the World Cup, this is very, very apparent. How so were you noticing? Americans seem flabbergasted that Europeans can travel for a few weeks following the World Cup in the US because they only have, what, 14 days of animal leaving? It's true. It's been pretty funny. I won't say that it's a good thing or a bad thing.

23:19I think that's very contextual. But I think that whole balance to living to work and working to live is a very, very hard struggle. And then to run a company for a lot of the principles on top of that, it's always going to be a challenge for them. And I think that's why we have a job.

23:36Tristan Lim: Yeah. Since we're on the topic of, I guess, Europe, US and Asia, I thought it could be a good moment to also pick your brain around building a company in Southeast Asia or Asia, since you know a bit about that, versus kind of in the West and in SF or in Europe. But just setting that scene, I would love to hear your initial thoughts and what your experience has been like and also what you're noticing. Yeah, I think what's interesting now is that my principal is Brazilian. They have a company in SF. It's been very interesting working with her because she's probably the first Latin American principal I've worked with.

24:10One of my besties is Brazilian. But they're very different. Obviously, the first expectation I took from the principal was, let me just apply what experience I have with people from that culture and then adjust it along the way. And there are very specific instances, which I think economically you see this as well. So in Latin America, I think in general, they are generally a lot more relaxed. Not that they will not hustle, they will. But outside of that, there's a very different mentality where, do you know the story of Chicken Little?

24:40Tristan Lim: Remind me. So Chicken Little runs around and he's always expecting the sky to fall, right? And he behaves like it. He's like in this anxious, like anxiety loop. And he's just having knee-jerk reactions to everything. It's just stressful. right, for himself, for people around him. And so far, my experience with people who are from Latin America is not like that. Will they hustle? Hell yeah, they will. But outside of that, they're very, very chill when it comes to things. Like, not everything is an impending apocalypse. But this is also very similar with some of the people that I've worked with.

25:12They're not principals, but partners in Southeast Asia. They can be very, very chill. and I don't know whether this is like a result of it not being very metropolitan or not but all I have to compare is with Singapore and then with SF and LA in general do they act like they're a chicken little they're a little bit more that side it always feels like it's either going to end the world or not and I think talking about like work-life balance if you may not have the time for that balance sometimes you also don't have the cortisol for that balance and I think that's what it boils down to working with different cultures as well sometimes you just have to like take a tip from everybody that you're working with if you're very anxious and say is this going to kill the company in the next half an hour in the next two hours and then just get really granular with that and if it's not then just learn to chill but then on the other side of that flip pill it's like it may not seem like a problem now but if it's not a problem now it becomes a problem later and you learn later on that this should have been a problem now then you need to self-correct on that side and be a little bit more attentive and move a little bit faster.

26:19Primarily because there are some things, for example, fundraising, investor interests, hype. When it comes to getting a client's interest, acquire users, you need to really catch the moment. And sometimes you don't because it depends on your product. And understanding the value of your product also drives a lot of how you need to shape how you behave with your customers, behave with your users. And I think a lot of these things are all very, very much like nuanced when it comes to different cultures, when you are working with cross-border companies, when you're working with multicultural teams.

26:53So again, when it comes down to it, having that compassion or like curiosity, I think it's a better word here, that curiosity to understand people helps a lot.

27:03Tristan Lim: I love where you're landing on this because what it boils down to is curiosity and compassion. specifically if you're working with a team that is off a different culture or a principle that's off a different culture through having awareness you might notice your certain way of being may not be so conducive to like a smooth relationship even how you show up to a meeting how prepared you are how not prepared you are you know the things you talk about versus don't talk about but once you're able to tune in and actually have compassion that all things are done differently in different parts of the world makes sense but then having curiosity to kind of ask questions to see how it's difference, talk to other people, then again, come back to capacity, right?

27:40Tristan Lim: Then your capacity also grows because then you have the capacity to work with different types of people where it's no longer about that specific culture, but it's about just a different culture. And when you're working with different people, it requires maybe something different. I'm kind of curious about the working relationship, right? So I'm keeping in mind, choose staff who are listening, who also work with cross-cultural teams. This is a bit of a spicier question and you'd have to give like specific details but i'm just curious like you know when does it go wrong like when do things not go well and then how do we recover from those moments because i'm always interested in ruptures happen you know in relationships and working relationships everywhere but how do we repair just from the times that you and i have spoken i feel like these are things you think about and are very intentional about and i'd be curious how you navigate ruptures and relationships teams i think yes i am pretty intentional and i appreciate it you also highlight this because i think at the end of the day, there's work.

28:34And regardless of how the people behave during work, there are still people outside of work. And it's more so about myself that I think I want to appreciate the humanity in people, that there are people, whether you're good people or bad people, that's a separate thing. So I try to approach a lot of things with that mindset. There have been, of course, instances where you realize at some point, either I'm not adapting fast enough, and I'll always look back that first because we're meant to be the swiss knife right so as the swiss knife if you're not taking out the right tool or at some point you realize you don't have the right tool i think that's on you and through the journeys of you know having different principles then you realize where you are the same for a lot of things and in some cases you have to be like did i try hard enough to navigate to adapt and at some point you have to say let's just stop the pain for both sides and end this.

29:31But for the most part, I think, again, taking that whole point of this is not personal helps a lot. If let's say people will be people, there are a lot of, this is going to sound a bit, there's a lot of unhealed people around in the world and then that shows up, right? And I think that's why also in the more corporate world, trauma-informed organizational psychology is taking off so well. It's because they realize that a lot of people have a hard time, I think, separating their trauma from their work. We're human, right? Like I think we cannot really split our brain down into two boxes and just have one facade out there and not be affected by the other box.

30:09So by the time that those ruptures happen, you also kind of understand pretty well what that person's principles are about. And you should be able to have a very good estimate of what can you salvage from this and what can you not salvage? And then you can decide. And that's where the agency part comes in. You can decide whether you want to put in the resources or not to salvage that relationship or to salvage it so that at least you can get the company to a point where you're like, this is in accordance with my principles where I think I can contribute positively, not just to the principal, but to the team at large.

30:42If it is holding back the mission, then somebody else should be able to take over. And I think sometimes that repair is by leaving. It's like if you step on a shard of glass, I guess that's the best analogy that I have, but it's very small. You don't notice it yet. And then over time, it grinds into a bigger hole. At some point, your foot's going to notice. And then you're going to be like, can I continue walking? Sure. But do I want to? Maybe not. Right. And I think that's what it comes down to at some point, because you will realize that I think along the way that there are many, many kinds of people and you will not necessarily discover who someone really is until two to three, four months down the And this applies in general.

31:22I will say that what helps when I approach any kind of disrepair to go into things with the right energy is to always believe that people don't intend to be hurtful. That's one. And that gives you some understanding of how to navigate. Doesn't mean that you should ignore reality now. But if you thought that everybody was out to do you harm, I think that will affect how you work and that you bring your own trauma into your working relationship.

31:47Tristan Lim: Yeah, I'm thinking back to the intention versus skill part that you kind of shared in the beginning as well. One piece of advice, someone that I used to work with, he kind of imbued on me as I started in my role as a chief of staff. He planted that mental model in my mind. So I also was just more aware when it came to intention versus skill. As you said, skills are learnable, actually. All skills are learnable. That's why it's called a skill. and sometimes the intention can be clear, but the execution is maybe not the best. Yeah, that sounds like a very good mentor for you. I think that sounds like you were very fortunate to have someone to share that framework with you as a starting framework at least.

32:27Tristan Lim: Yeah, he also wrote this really great article about joining hyper-growth startups. I was more like a brain dump on his thoughts on it and it was very, very useful. I think this is definitely like a very good starting point for like if you ever want to talk to your audience for example, or even for the rest of us, the differences between somebody who is used to working at that scale, it could be very different. I think that will influence a lot of these things as well. Some of these frameworks are meant more for a different pace. Yeah, you're totally right. Come back to what you said about the Swiss Army knife, right?

33:03Tristan Lim: Sometimes you actually just don't have the tool you need. Maybe you need like a little scissors, but your Swiss Army knife isn't enough little scissors. And it's actually what you need because different organizations go at different speeds and, you know, being hyper growth versus not like it's versus being bootstrapped. So it's a different situation. Yeah. And some people have only a hammer. So they think every problem needs. So there is that. Yeah, there's that for sure. I want to talk to you about your journey from moving from being a founder to kind of becoming a chief of staff. One of the reasons I'm interested in this topic is because we had recently shared an article with the community about life after being a chief of staff.

33:43Tristan Lim: This is something I had written and also taken inspiration from different interviews that I did with other chiefs of staff. And after sharing this article on our newsletter and also our blog, a lot of people reached out to me and they reached out kind of highlighting certain parts of the article and just also wanted to share a bit about their journey of like the questions they're asking themselves, you know, after being a chief of staff. So I'd be curious about your journey from now going into the chief of staff world after being a founder? And also, how do you think about full-time versus part-time, like the configuration of working as a chief of staff as well?

34:18What I want to highlight is a couple of things because I don't know where a lot of people come from into the chief of staff role. One of my primary motivations, you know that Venn diagram that I was referring to? So things that you enjoy, things that you're good at, things that somebody will pay you for. So it was actually through my startup founder journey that I realized that I don't think I have yet what I needed in terms of skills, or if you say capacity, if you will, to accomplish the things that I said I wanted to. And that is what made me take a step back from that. Because with my last startup, what the clearest understanding to me is what I learned.

34:56And we talked about some of this today. I think what life is like after Chief of Startup, maybe I go back into a startup founder. I don't know. It seems unlikely at this point but i've learned to never say never right now i always said i would never do something like higher odds and here i am so i think the chief of staff role allows you to learn from people whom you might want to be like i think that's what's very important when i left my last startup i was like i know startups fail knowing it and living through it is two different things and what i think made me one like actually take a pause and like really need to spend some time with myself to understand if I wanted to do it again or could do it again to be more precise was all the partners that I had let down so like I will delve a little bit into what my startup did just to give context I think everybody's more or less familiar with Kickstarter as a platform so it kind of was like that, but only focused on climate projects where people could then fractionally lend money out to projects like that to finance them to get to where they need and then allow them to create a natural asset that could then be fractionalized back to the original lenders.

36:09So I involved a lot of companies who were also startups and SMEs themselves. A lot of them, I would say, classified in the real world as like not-for-profit or more philanthropic. So it's a balance of being for profit and then not so much for profit. And a lot of them, because of my previous volunteering work in climate for the last 10 years before that, gave me a lot of trust. So that platform was meant to enable them to be able to progress away from always having to rely on philanthropic capital and progress more towards a for-profit because that's the only way that it can be somewhat sustainable.

36:45or at least lean more on the non-profit side as in they can make running costs make sense right and then not always have to be living from hand to mouth as it were and when i had to exit that startup one was because i didn't navigate my own team's relationships well so that was lesson number one and two i did not handle i think the offboarding of those products well because i was exited from my startup not voluntarily and while i actually reached out to a lot of the projects to explain to them what's going on. I do not blame them for being like, oh man, that sort of feeling. Because I think over the year that we were together, like we spent all of us a lot of time in making sure that things move forward because they also needed that light at the end of the tunnel.

37:30And so I do not want to repeat that experience again. I don't like letting people, especially people who need it down. So chief of staff was a way to actually then for me also learn from people to understand further, what did I do wrong? What can I do better? And then my job is very much in that sense, or that role is very much in that sense, an extension of myself. I don't know how true this is for most people. We always say that we should separate our jobs from our identity, which is true. But I like that my role is part of my identity. But that's my choice, right? And so when I'm in the chief of staff role, it's very important for me that I'm also learning from whom I'm with as a principal and with the team that I'm with.

38:09So what life looks like after that, I think will be a combination of my learnings from being a startup founder and then what I learned from other startup founders who are, I would say, more successful than I am in many respects, but also taking into account a lot of very different experiences as startup founders and then taking that and then moving on to the next thing. Hopefully, of course, it ends up being retired somewhere. I think earlier rather than later will be nice so that I can actually spend all my time working on things that are meaningful for the world and for myself. But I think for the most part, that's what the startup founder part was, was a process of understanding whether you were or not the best that you could be.

38:51Tristan Lim: Thanks for going through that and sharing with us. One of the parts of the article that was highlighted by a few people was something we had written about how, you know, being a chief of staff, you are constantly of service to your principal and to the company as an extension. And you get really good at doing that, right? The better you are at being of service, doing interim roles, seeing the blind spots, stepping in for your principal, being a great sparring partner, being this mirror to them, to the company, you know, completely just being of service, right? And the question is what happens when you put that same amount of care and attention and presence, but you reflect it back to yourself as opposed to a team, you know?

39:36Tristan Lim: So let's say after finishing, you know, working as a chief or something, Oh, you put that same care and attention on what do I need? What do I actually really want? You know? And that seemed to stand out in the article and several people wrote to me that that stood up because they're like, I have no idea. It was like, it was the answer that quite a few people realized you know not that it's a bad or good answer but it's just a reflection like hey actually i don't know what i want yeah i don't know to them to think about it i guess no space maybe right well i guess this kind of relates to what you wanted to touch on was that i guess being fractional is where it's at in a way if you structure it for what you need again haven't read the article so maybe you would have to like tldr it for me like how you pour back and do yourself because i think this is where the fractional bit comes up right there is a line somewhere where you go like okay that's where this ends and then on this other side of whatever else is not chief of staff is when i refill my own cup yeah i mean currently i spend my time doing more less like 50 fractional chief of staff work and 50 coaching and for me this is like a perfect balance because the chief of staff work it really really like scratches my itch of wanting to support in building companies and then the coaching bit is scratching the very strong edge to also just be very present with someone on a journey where they are currently then helping her sort of bring the human through that process well i'm in bali so there's not much i can say i mean i think what really helps support myself is like i have things that i don't compromise on so like getting like my daily sunlight and stuff like that and when i'm with my dog and that also helps i will agree like i think what i've also noticed with people who are either founders or chief of staffs for the most part that i've met at least mine is i know because i'm adhd so it scratches an itch because i like to solve problems you know it's like going to a spanish restaurant and ordering tapas there's always a bunch of different problems to solve within a company so like because you have so many cross functions you get to like have a little peek at everything and so that's great and then the other side of things what really helps me feel like things are worth it so i think balance changes from product to project and from day to day but what i feel helps me fill my cup and sometimes that fractional may not be very clearly defined and say like i dedicated supposedly 20 hours of my week this week maybe now it's 24 28 30 hours you know depends is knowing that i'm working for something that I think will make an impact for what I believe in.

42:06I think that's the same thing that drives most startup founders. In the past, when I was a founder, it was all climate related because I generally am very much a tree hugger. So that satisfies that part. And because of that, because of my principles, a lot of what I'm willing to dedicate is worth it. And nowadays, because I've pivoted slightly, I would say to more like human health rather than planetary health, which I think is interlinked, obviously. It also drives me a lot. And that in itself, knowing every day when I wake up that I am doing something that I believe in, actually gives the baseline.

42:40So I also make sure, of course, that I don't go over and say like, I'm going to work 996. But if I have to, it's very few days. But those days still when I get out and I know that I'm contributing to this mission, I think is what fills my cup. What I have noticed outside of the startup arena or even like a series B, series C onwards. It's in general, a lot of people, I think you've highlighted it very well, that they haven't had space to do that. I don't know for a lot of people outside of like my immediate, like say in Singapore or people that I've met in the US, but a large part of us are probably told like, this is sort of the pathway for life.

43:20You go to school, go to work. And there's some formula of vision of success. And then from there, when you reach that nobody talks about what's after and i have a lot of friends who have been in corporate all their lives and they've reached that point now right that inflection point where they're like now what's next like i've studied i've gotten a job i got married i had kids now what i mean the job will always have to be done for another two decades or so three decades or so but what now is it just the same growing for them every day and i think that's the same inflection point that a lot of these people may be responding to is that they've never sat down with themselves at all whatever they're doing and been like is this what i wanted to do now and now that i have now time to think about it because things are coming easy right either they have like their fire plan in place or like they go do the job it's very easy for them to do the human brain requires drive it requires purpose it requires something for them to achieve and this is very well studied in psychology as well we can attain a lot of things but we will never really truly be content if we're happy because we need something to chase we need something to attain and so i think when people get to this point is when they call it like the quarter life crisis or midlife crisis whichever way you want to put it but i think that's what people will have to sit down with themselves and understand who am i because it is still tied to the identity and what do i want to do next it doesn't matter if your role now is called chief of staff or it's called executive assistant or if it's called business development specialist whatever it is you will reach an inflection point so i think that's kind of where maybe a lot of people are responding to you from

44:55Tristan Lim: that state of flux one thing i talked about in this article was about i find that people in the chief of staff role or adjacent roles one of the things we are developing by being in the role and if we continue doing the job it's actually having agency and how having generally a higher sense of agency because in order for you to be good at your job, you need to figure things out. And when you're getting good at figuring things out, you're getting good at being resourceful and trying to solve problems in different ways. And I think that's having agency. It's like, where do you put your high agency-ness after life and after being a chief of staff?

45:35Tristan Lim: And you can either turn that inwards towards maybe you build your own thing, whether that's a fractional chief of staff business, whether that's, you know, building a different type of company, or there's also trying to work for a different principle and kind of going back into the chief of staff world. So my take is that as a chief of staff, that's actually what you're building. You're actually building your capacity to do maybe things you didn't expect because you're thrown into unpredictable situation quite often. And your ability to learn and grow is actually perhaps, maybe not always, but perhaps higher than people in other roles where the roles are very clearly defined.

46:11Tristan Lim: As we all know, the chief of staff role is so, it can be so ambiguous at times because it's depending on what the company needs and, you know, how well defined the role is at different times. And yeah, I think that well-defined part is where it's shaky. Yeah. And that's so synonymous, right? Every single person who's ever been a chief of staff has had to wrestle with like the role being unclear at some point or another. I really do think that the more we can kind of tune into that part and realize that that is actually a learning that we are going through as being chiefs of stuff. As we kind of come to the bookend of our time today, I wanted to also ask you a bit more like rapid fire, like hot takes on certain things.

46:50Tristan Lim: So one question is, as a generalist that can sort of deploy everywhere versus a specialist that goes deep into one thing, if you had to pick one side for someone starting out today, what would you advice and why? I actually highly advocate not getting there first and then taking two steps back and really sitting down and writing down and being very honest with yourself. What do you like to do? And then there's the like to do, there's the I really don't like to do. And then in between, what are you willing to do for the right price? And then go from there. Because I think this comes back to that whole journey that we talked about from where I come from.

47:32It spans a lot of very different things. It was all like a process of discovery about yourself. If you had asked me when I was in legal, oh, do you think you'd be good at sales or business development? I'd be like, you're crazy. I couldn't imagine. So at least at this point, to take a snapshot, I think that's what you need to do is to have regular snapshots and understand what gives you joy, what doesn't give you joy, what are you good at, get to that Venn diagram and then go. Because for me, I've been very generalist. I would say like I have gotten much more like down that T bar in a lot of things.

48:06Will I ever be able to do digital marketing? Sure, I guess. I have a conversant understanding enough, obviously, to manage a team. But if you ask me to really understand a lot of things, I will need time to do it. It's that middle section of the spectrum. Is it worth it for the price? And that price for me is time. It's not where I can apply my skills the best nowadays so i don't and i think this is that conversation that you need to have yourself then decide if you're willing for that trade-off to if you're a generalist and the trade-off is that if one day you wanted to become i don't know like a digital marketing specialist that might not be the best way but if you tell yourself that to get to the digital marketing specialist point maybe you want to start working with your general skills for a company that does digital marketing so that you can eventually get there the trade-off that you You invest your time and it's worth it.

48:56Go for it. And I think there are a lot of people, as I've observed, and maybe it's also like a pre-selection because I read a lot of stuff online on Twitter and we're exposed to a lot of very brilliant people and Substack and a few other places. But it seems like there are a lot of people who are polymath. So they can be both generalist as well as deeply, deeply specialist in a lot of areas. But that's not the general population, I think. I could be wrong. and whether or not you are part of that population is something to consider as well you have to understand it's good to look up for these people and i do a lot because i'm like one day i hope to be like to my maximum capacity right or to train for that capacity but if you are not like them then you need to also regulate yourself and understand that you're not going to put yourself down this deep dark hole of like well i guess i can't do anything you know so i think that's maybe where a lot of the self-reckoning has to come in first before they even make a decision

49:54Tristan Lim: of whether they want to be like a generalist or a specialist. But currently for myself, I am getting a little bit more like, I guess, structured training, I would say, alerting when it comes to actually being a product manager. Not so much that I want to be one, but I think that the principles and the lens to which becoming a more trained or structured learning with being a PM helps a lot with a lot of areas. And that's why I was also at that book. And so I don't think I'll ever be a product manager per se. Have I interviewed for such roles before? Yes, because I'm very curious about certain products and how they affect and impact people's lives.

50:32And it is in a way, a lot of transferable skills. I mean, you've worked with PMs before, so I think there's a lot of similarities in between, but I will never say never, meaning that one day I might end up becoming one. I don't know. One other thing I would add back to your article is that for those people who are asking what's life after Chihua stuff one very good takeaway I can share is like isn't it exciting that you have that space now to explore?

50:56Tristan Lim: For sure. The sky's the limit. I think that's completely true and it's like how to make use of that space. How to just explore, you know in whatever direction it can be as well. I definitely think so. So I hope that answers the question and I wish I could have an easy formula for people. yeah if only the word is an easy one but i think that's the journey right not to sound completely cliche but the journey versus the destination it's always about the journey and along the way like you just need to know whether there are things that can bring you joy whether it is like uh working out or in some cases some days you just have to have a cookie and carry on yeah yeah all right is there anything else you want to share before we wrap up today no but thank you very much for the conversation i hope that this is helpful for your audience as well.

51:41And of course, like if there's anybody who wishes to speak about that whole journey, of course, you can always reach out.

51:46Tristan Lim: Thank you so much, Brie.