1. Podcasts
  2. The Chief of Staff Podcast
  3. Speaking Directly When No One Else Will with KJ of Bifrost AI
The Chief of Staff Podcast

2 Sep 2026 · 1h · 25 chapters

Episode artwork

Speaking Directly When No One Else Will with KJ of Bifrost AI

In short

KJ (Head of Strategy & Operations at Bifrost, Singapore) discusses how to speak compassionately yet directly and bluntly, how the chief of staff role is misunderstood in Southeast Asia, and how he uses AI daily for strategy, go-to-market, and decision-making. He also explains physical AI and Bifrost’s approach to bridging simulation and reality for autonomous systems.

Guest backgrounds

KJ has 6 years in chief of staff/CEO’s office roles across two startups. Previously at Parenting (Parent Inc), he worked in the CEO’s office during a Series B to Series D run, including M&A and investor/board work; the business reached ~30M users, ~300 people, and operated across seven countries. He joined Bifrost pre-seed (<10 people) and has helped grow it through seed to scaling, focusing on AI/computer vision model training for robotics, defense, and space.

Key claims

Compassion is “table stakes” for respectful bluntness. Chief of staff is a founder-extension Swiss-army-knife role, not an EA/L&D catch-all. AI should keep a human in the loop for accuracy.

Notable examples

He describes an 8-round, 8-week hiring process. For conferences, he uses speech-to-text (Whisperflow) to convert spoken prospect conversations into structured notes and update a prospect sheet; he also uses AI for investor updates, GTM research, and internal dashboards. He contrasts APAC diligence (numbers/process-heavy) with Western “product-first” conversations and faster deal speed.

Written by AI. May contain mistakes.

Chapters

1:56

KJ's Background and Journey to Chief of Staff

KJ shares his experiences leading to his chief of staff role and insights into the startup journey.

“Tristan, good to meet you and very happy to be here.”
3:23

Understanding the CEO's Office Role

KJ discusses the dynamics of working in a CEO's office and the importance of various skills.

“So I had worked in commodity trading, but I'd worked a lot in corporate finance, private equity, as well as investment banking, always focused on technology.”
5:35

Transition from Parenting to Bifrost

KJ explains his transition from Parenting to Bifrost and the experiences gained.

“large institutions to some of the best VC funds.”
8:17

What is Physical AI?

KJ defines physical AI and explains its relevance in technology and robotics.

“What did it feel like kind of coming to that, you know, from the world you were in before?”
10:09

Bifrost's Journey and Product Evolution

KJ shares insights into Bifrost's growth, product focus, and the broader implications of physical AI.

“You start learning about what the founder cares about, how they think, what are their instincts, when linear thinking enables them and when non-linear thinking enables them.”
14:00

Understanding Physical AI

Learn about the concept of physical AI and its applications in various fields.

“That is quite literally lines of code eventually resulting in a physical manipulation in the world.”
15:10

KJ's Journey at Bifrost

Discover KJ's experience in the hiring process and role as Chief of Staff at Bifrost.

“When you met, I guess, the two founders, is it correct that they were already looking for chief of staff or did that role sort of get co-created?”
16:30

Growth and Evolution of Bifrost

Explore the growth trajectory of Bifrost from pre-seed to Series A and its evolving operations.

“And you've been at Bifrost for four years.”
18:43

Chief of Staff Responsibilities

KJ outlines the key responsibilities and challenges faced in the Chief of Staff role.

“Now that the product is more mature as a company, we've come further along.”
21:04

Balancing Structured and Unstructured Work

Learn how KJ manages structured processes while accommodating unstructured tasks.

“We have a fair amount of things that the processes are mature enough that they can kind of run, and we know how to manage it.”
Show all 25 chapters
24:05

Leveraging AI in Strategy

Discover how KJ uses AI to enhance productivity and decision-making in strategy.

“even though you may not be able to make that meeting.”
27:36

Practical AI Applications

Gain insights into practical applications of AI in various functional areas at Bifrost.

“Everyone has their own preferred stack of when to use GPD, when to use Clawed or when to use something else.”
28:01

Organizational Tools and Strategies

Learn about the importance of setting up high context and various tools in strategic roles.

“Setting up artifacts and organizational skills is pretty useful as well.”
30:21

Speech to Text and Note Taking

Discover how speech to text technology can enhance productivity and note-taking efficiency.

“Something I initially wasn't used to was using speech to text.”
33:23

AI as a Co-Analyst in Strategy

Explore the role of AI in financial modeling and strategic decision-making.

“There's like a few small ones here and there as well, just for completeness.”
36:19

The Role of Chief of Staff in Different Regions

Understand the differences in the chief of staff role across cultures and regions.

“All of them are like isomers or isotopes, very similar to each other.”
39:47

Investor Perspectives: East vs West

Analyze how VC-backed companies in APAC differ from those in the West regarding investor expectations.

“Large corporations are starting to use that position as well.”
42:04

Differences Between Eastern and Western Investment Approaches

Learn about the contrasting dynamics between venture capital in the East and West.

“So it's also likely to use it to solve its current problems.”
45:33

The Unique Role of a Chief of Staff

Explore the distinctive challenges and learning experiences of being a chief of staff.

“Could you give us a bit more on the learning side?”
49:56

The Importance of Direct Communication

Understand the necessity of speaking directly with founders and the impact it has.

“It forces you to expand and it forces you to communicate.”
54:38

Building Relationships Through Compassion and Agency

Discover the balance of compassion and agency in a chief of staff role.

“So perhaps even having those conversations proactively as a chief of staff to a principal can help reveal the state of the relationship.”
56:00

The Importance of Regular Updates in Roles

Learn why it's crucial to regularly revisit and update workplace protocols.

“of time, whether you're already in a role or seeking one.”
56:30

Impact of Chief of Staff Role on Personal Identity

Explore how being a chief of staff can lead to identity challenges outside of work.

“As we wrap up, I would love to ask you one last question around being a chief of staff.”
57:38

Navigating Context Switching

Understand the benefits and downsides of context switching in both work and personal life.

“one is I have mixed feelings about context switching because in my personal life now, I would say I do feel a lot more productive because you can see that you can do 10 things in a day.”
58:46

Growth Through Honest Communication

Discover how the role of chief of staff fosters personal growth and better communication skills.

“You get better at realizing that not everything is a debate or you don't have to win every argument.”
A man walking through an airport, asking his phone a question

Ask about this episode

Get the gist, explore an idea or ask about something said.

Claude

On The Chief of Staff Podcast, what are the key points of this episode?

Searching your listening

Transcript

Automatic transcript. May contain errors.

0:09Tristan Lim: Hey, it's Tristan. Welcome back to the Chief of Staff Network podcast. As a quick 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 to avoid burnout. Currently based between Europe and Southeast Asia, and I've really been enjoying highlighting stories from operators from this part of the world. Today's guest is KJ. KJ is the head of strategy and operations at Bifrost here in Singapore. He spent the last six years in the chief of staff role and also around CEO's office roles across two different startups.

0:39Tristan Lim: First at the Parenting, where he sat in the CEO's office through a series B to series D run, and now at Bifrost, where he joined as a pre-seed chief of staff, and he's been helping grow the team. Bifrost is a physical AI company working across maritime robotics, defense, and space. KJ came into all of this from a finance and consulting background. Maybe a lot of you can relate to that. And he's very, very clear about the moment that changed him when the decision stopped being for clients and started being for his own company. In this episode, we'll be talking about why he thinks compassion is table stakes and the real underrated skill in speaking respectfully, directly, and bluntly all at the same time.

1:19Tristan Lim: Plus, he'll give us a bit of insight into what it's like to go through eight rounds over eight weeks and how that was really important for him to land this job. We'll also be talking about why the chief of staff role is still very misunderstood here in Southeast Asia and how the East and West differs, especially when it comes to investing. We'll talk a bit about the process analysis and how that differs, but also how they think about product first and also think of products afterwards. We'll also be talking about how KJ is using AI on a day-to-day basis from speech to text at conferences to go-to-market research and why keeping a human in the loop is still the way to go.

1:52Tristan Lim: All right, everyone, sit back and enjoy. KJ, welcome to the podcast. Tristan, good to meet you and very happy to be here. Thanks for having me. Thank you for being here, man. We are sitting at the Bifrost office in Singapore. Which part of Singapore are we? We're around Maxwell, where everyone likes to eat Tanjung Paga, which is most likely what the neighborhood is. The food court, right? The Maxwell food court. It is tasty. I guess for everyone listening, could you give us some context on who you are and what are you currently working on? So I'm KJ, Head of Strategy and Operations at Bifrost.

2:28I've been in the Chief of Staff related position and the CEO's office position for the past six years across two startups. So I've seen the journey from the growth stage to late stage, as well as the really early stage to the scale up stage. So that includes journeys zero to one, 1 to 10, 10 to 100. Currently, I'm focused on, at Bifrost, artificial intelligence, computer vision model training, focused on robotics, fixing the gap between simulation, evaluation, and reality, as well as helping autonomous systems train better models for a whole host of industries.

3:04Tristan Lim: Tell us a bit about how you got into the chief of staff role specifically and how that sort of unfolded. So it makes a lot more sense in hindsight, but I guess that's how it goes. So my early experiences were deeply rooted in finance and consulting. Within finance, I had the experience of focusing on a bunch of differently important buckets that came out to be useful. So I had worked in commodity trading, but I'd worked a lot in corporate finance, private equity, as well as investment banking, always focused on technology. So these early experiences helped me get a very strong sense of how investors invested in technology companies, how technology companies raise money and how they grew organically and inorganically.

3:42And that was something which was very important to me. I was always interested eventually in becoming some form of technology operator, even though academically and professionally, I was interested in finance. But this really gave me that motivation that, okay, this makes a lot of sense. And I then went on to work in consulting, which was focused a lot on energy. It was focused on transition, working with large enterprises, large energy companies globally. And that gave me a very strong strategic lens. And I had this mixed bag of experiences. And at that point of time, I was really itching to do something different, take all of these experiences and move in to a startup.

4:20And that's when I ended up moving into the Parent Inc about six years ago, which is where I would say my current journey truly started. I moved into the CEO's office six years ago, it was 2020, and the CEO's office term was just starting to get a little more popular globally, where founders realized the need to arm themselves with team members that came with these experiences in finance and consulting, but who were not strangers to the world of technology, even native to the world of startups. They knew what was up, they were wired in. They had a sense of how things were to grow, what the monetization challenges are, what the product requires, as well as how to work with investors and take care of future capital needs of the company, scaling needs of the company.

5:01You always needed that. There was almost a global collective moment of cognizance where this position suddenly became important. And I guess I was part of that wave where I got my break into the industry. So the parenting was very interesting. It was focused on Southeast Asia. It was one of the largest platforms focused on parents, children, education, direct-to-consumer brands, anything and everything that you need in that part of your life. They were number one in the region and they were backed by some of the strongest investors in APAC that came from Singapore, Japan, Korea, right from like large institutions to some of the best VC funds.

5:39And those were like very interesting two years where we went from series B to series D. We acquired Line Messenger's Vietnam business. The business witnessed tremendous growth. We had 30 million users. We were 300 people. We were split across seven countries. A whole new direct-to-consumer arm was born out of this, focused on products from mom and baby. The platform really, really improved in its features and subscription, its insights and reports, as well as the advertising arm of the business that was focused on large FMCG players. All of those things were truly humming along really well. I, as part of the CEO's office, going to see this firsthand, where we got to look at M &A, We got to look at fundraisers, investor relations, board meetings, as well as many other projects of trying and testing how to build new businesses, new ideas, scoping out opportunities for organic as well as inorganic growth, testing out new business ideas on the application, on education businesses, considering many other angles of improvement internally as well as internal projects.

6:38So it was a very, very interesting role where I got to work with an amazing founder, a top brass of C-suite executives and amazing colleagues. It was a great learning experience. And that's how I got into the CorpDev CEO's office type of role.

6:53Tristan Lim: Forever understanding, what is CorpDev? There's many ways to define it. Typically, it is a skill set which is born out of finance, but is molded by business. For example, some CorpDev folks may focus a lot on acquisitions. Some of them may focus on raising funding. A lot of them are focused on strategic partnerships. You may also focus on internal restructuring. If you're a very big business, many different business units. My role at that point of time for a series D startup had elements of all four, where we could look at smaller companies that would have been a great sum of the parts for us.

7:26We were looking at opportunities to raise capital for ideas that we had forward. We were looking to build out many new different businesses that we'd already started out on. At the same time, we were looking on how we could improve internal efficiencies and build partnerships. I would say that was the broad definition of corporate development. In some places, it's more focused on M &A. In some organizations, it's more focused on partnerships. And sometimes it can be just purely financial in nature. In my case, it was a mix of all of them.

7:52Tristan Lim: You know, for a lot of people listening, they might be new to the role, the chief of staff role, or considering it, or, you know, obviously experienced in the role as well. I always find it really enlightening almost to like hear about people's first roles in the CEO's office because just because they may differ a lot from experience to experience. So I'd be curious what your experience was like setting up the CEO's office, as you said, or being responsible, sorry, for the CEO's office at the Parent Inc. What did it feel like kind of coming to that, you know, from the world you were in before?

8:21Tristan Lim: How did you navigate that? I think that's a great question. For myself, I would say it was a very interesting change because when you come purely out of a services background where you're focused on, let's say, finance and consulting, the prime beneficiary is someone else. But when you take all of those skill sets and start working for a founder, there's an internal change that happens where you start realizing all of these decisions are for your own organization. And that changes absolutely everything because now there's an element of risk. There's a greater sense of accountability. And to be honest, the consequences are a lot more serious, both in terms of upside as well as downside.

8:57And getting used to that is very different. You start caring about things very differently. You don't just obsess over how well a slide is formatted, but you care a lot about how someone is treated. You start caring a lot about conflict resolution. You start thinking more long-term than in basis of short-term projects. You start thinking in terms of timelines instead of transactions. A lot changes. You also have to learn how to work with larger teams, all of whom may have very different levels and different culture, which is very different from when you're working, let's say, in finance or consulting, where teams tend to be smaller, more concentrated, and everyone's average level is very close to the same.

9:36When you move into an operating environment, different teams have different skills. We optimize for different things. And the CEO's office needs to know how to work with all of them. There's huge room for personal growth in terms of building, I would say, some form of pendulum for EQ, where you know where to swing with which team and how to work with whom. I think that was a big challenge. But I think once you overcome that, it becomes exciting because then you start realizing how to get things done at scale. So I would say it's not just the technicals, it's also the soft skills. Learning how to work with the founder, I would say is of course the number one in all of this.

10:09You start learning about what the founder cares about, how they think, what are their instincts, when linear thinking enables them and when non-linear thinking enables them. That is something which is very hard to wrap your head around. And you only realize in hindsight that, okay, you know what, this is why the founder is the founder because they have an instinct. And that instinct is not something that's in a textbook. And you start developing that muscle where you start appreciating that. So I would say those are like the first one or two main things that really stay with you and then they become part of you.

10:36And then that changes you.

10:37Tristan Lim: It's almost expanding your awareness through that expansion awareness. You know, obviously it can be challenging because you're taking in the same information, but then processing it in a deeper way, perhaps, and seeing that they can have bigger consequences. And then it's like, what do you do with that? Yeah, absolutely. Tell us a bit about what happened after parenting. How did that move into Bifrost happen? So after two years of the parenting, it was a great experience. I learned a lot. I'm very grateful for the team. It really helped shape me in terms of getting multifaceted, learning how to balance operation strategy as well as finance, working with large and small teams, being able to context switch, chuggle and truly function as a Swiss army knife.

11:16I was at that point of time itching to move on to my next challenge. I definitely wanted to do something that was more early stage. Seeing a series B to series D journey turn out successfully early on is a huge gift. It was earned, but it was also a positive event that happened, right? It gives you the confidence to go and try something new. And at that point of time, this was a world which was before Chad GPT. It was late 2021, early 2022. And this was a time when I was really interested in software anyway, but I started getting into AI in a big way. There was a lot of learning that was going on on the sidelines through things that were my own personal interests in cryptocurrencies, in fintech, in robotics.

11:57And that's when I started to realize that, OK, I need to start taking artificial intelligence more seriously. Five years ago, the world was a very different place. The whole world felt like AI businesses were just like these science projects, which you did for fun, and they weren't ever actually become tech startups. That was just, I would say, a bias or a broadly felt sentiment about the industry five or six years ago. The reason I say this is that was a time when I had made up my mind that, you know what, I want to go and be part of this. It's good to experience something more technical, and it's definitely good to experience early stages.

12:28At that time, one of Bifrost's investors introduced me to the founders because they felt that we would be a right match for each other. Bifrost was founded by two very, very bright and talented technical founders. They were looking for a chief of staff at the time, someone who could come and compliment them, who understood what the journey was about, and who also brought mutually exclusive skill set to the table, but with a very similar mentality. And that's the journey at which I joined. So when I joined Bifrost, we were at the pre-seed stage. We were about less than 10 people at that point of time.

12:59And that's when I joined them. It's been four years since, and we've seen a lot happen. We've grown. We've been focused globally. The product has evolved a lot. The space has moved from obscurity into mainstream public consciousness. Physical AI has started to become a term that is more broadly understood.

13:18Tristan Lim: Tell us a bit more about physical AI. What is physical AI? I think the simplest way to explain that is the whole swing between software and hardware that eventually ends up interacting with the world. Autonomous systems that interact with the physical world is the simplest way to explain physical AI. Take a robot, for example. It may take years to build in perfecting exactly what the vision language action models need to be, what the hardware needs to be, what the component needs to be. Hours of teleoperation, training, slams, everything goes into it. in just making one simple demo, which is in a basket with balls of many colors, pick out the one white ball that exists.

13:58And there's an actual robotic arm that goes in there and lifts it up for you. That is quite literally lines of code eventually resulting in a physical manipulation in the world. Simply put, that's physical AI.

14:10Tristan Lim: So physical AI is the outcome of the hand choosing the right ball to pick up. It's the whole process. Where we see this in everyday life is self-driving cars. a bunch of sensors detection. We see it in defense. We see it in robotics, industrial robotics. And now what we see on the internet is the chatter more along, let's say, humanoids or various different types of robots, factory robots, robotic arms. That's just one vertical of physical AI. But broadly, where artificial intelligence interacts and impacts the actual physical world is physical AI, treated as a broad term. In this process, we've seen that happen.

14:43So Bifrost was founded as computer vision model training software, right from synthetic data to robotics, evaluation software, all of those environments where you can compare policies, you can compare benchmarks. That's what the past four-year journey has been like, focusing on a more technical product, a more technical team, a lot of the clientele emerging out of more developed markets like the US, Singapore, Japan, and beyond. It's been a very interesting journey being chief of staff.

15:10Tristan Lim: When you met, I guess, the two founders, is it correct that they were already looking for chief of staff or did that role sort of get co-created? They had been looking. I was introduced to them and I became part of that process. The interesting part was this I learned much later, but many different profiles and many different people were considered for the position. I went through about eight rounds over eight weeks before we both shook hands and we felt that we were right for each other. Eight rounds over eight weeks, so one round a week. We saw each other every week for two months. And I just think to the founder's credit, it was a very mature and very wise way of hiring for it because they tested for pretty much everything.

15:46We tested technicals, tested soft skills. We tested situations. We had some rounds where we just spoke about industry, where we just looked at how wired and we each were. We had various different encounters. I don't know what the others went through, but I can speak of my experience. I do think it was very interesting because this is a position where you work intimately, you work closely. There's going to be a lot of agreement as well as a lot of disagreement. And it has to be done respectfully, knowing that the company has to be kept first. It's not personal. What I can completely agree with now is a chief of staff is a very delicate position to hire for.

16:21I guess to some extent that does result either in more rounds or more touch points or just a more holistic process in who you choose to bring into the organization.

16:30Tristan Lim: And you've been at Bifrost for four years. How has it been in the company and how have you sort of grown as well? So to contextualize, I joined Bifrost in the pre-seed stage. And in four years, we've gone from pre-seed to seed to series A and now scaling beyond. In this time, we've seen a huge uptick in the number of customers we work with, the countries we operate in, the size of our team. And the company and the product has evolved a lot as well over time. We've worked with various different verticals. We've worked in maritime, aerial, robotics, space, earth observation, and beyond. It's definitely been a journey where there's a very high slope and you really have to keep up a strong learning curve.

17:09So the way I started as chief of staff was to immediately bring some form and structure and to complement the founders and to help the company get off the ground. The first thing to do was to bring my immediate skill sets into the organization, which is to come in and own a few verticals, working closely with other colleagues and the founders. The first one would be finance, for example, from board meetings, investor relations, investor updates, investor management, fundraising. That would be a very strong number one. A very strong number two would be just general strategy and operations, which are how we can build more structure on working with customers, perhaps potentially right countries for us to expand into.

17:46Customers need to work with internal processes. And a good number three would be building out the team. We need to go in. What are the positions that we need? Where do we need them? What's the level of seniority that we need? Key hires. How do we make that happen? And having that built in-house is very important instead of just outsourcing that. And in addition to that, there's a bunch of other operation matters which can be very head-off but are very important. Sometimes it's growth marketing, sometimes it's events, conferences, working with governments, exploring non-diudative forms of financing, anything else that Bifrost can do, being recognized, speaking, many other opportunities.

18:21So the early days of Chief of Staff involved a lot of that. And as time passed, they all started to centralize and get stronger and stronger. Over time, I moved on from the chief of staff role and moved into the role of strategy and operations. In many ways, it is an elevated version of what I was doing before, but it also comes with stronger responsibilities and focus areas, especially on number one, which is go-to-market. Now that the product is more mature as a company, we've come further along. We have a better idea of what our target markets and target verticals are. We focus on building a lot of repeatable processes and going deeper into those spaces.

18:55So go-to-market focuses on a bunch of that. internationally as well as through verticals. And then, of course, there's the corporate development side of things, which is how can you build stronger partnerships with industry, whether it's building partnerships with regulators, whether it's building partnerships with large enterprises in target verticals like robotics, industrials, research, academia, artificial intelligence, or defense. Those are two broad things that start to take up more of the mindshare. Of course, in addition to focusing on all the other matters that I've spoken about, which could be finance, hiring, operations, or just overall strategy and growth.

19:30Tristan Lim: How do you manage all that? You know, you listed, I think, a lot of things. You know what? I'll tell you when I find out. I have to be honest here. The best way to explain it, in my opinion, is half of it is an absolute process. And the other half of it really depends on what's important at that point of time. So there's structure and there's unstructured, just like data. Certain aspects move in a very easy cadence. So the core syncs, finance syncs, hiring syncs, strategy syncs, pipeline syncs, sales syncs, they're all scheduled. They're all structured. They move like clockwork. They happen every week.

20:06They happen every two weeks or they happen every month or every quarter. Each of them has their own cadence. They have their own life. They have their own processes, their own softwares, their own pre-reads, and their own actions right after. In addition to that, there are things that may suddenly become important. Certain opportunities may show up. There may be a conference that's very important. There may be a customer that's very important. We may have to go raise a round of funding. We may have to go and build out the team and expand in a certain way. We may have to consider getting more word out there.

20:34We may have to experiment a little bit with our social media, with our outbound, with making videos or product demos. A lot of those priorities can be event-driven. They can be focused on time. They can be focused on where the macros are at that moment, where the industry's at the moment, or where the company's at the moment. So to close it, I would say half of it is absolute process, which must work like clockwork, because that's what runs like the spine of the company. But the rest of it is a little more reactive and opportunistic based on when it needs to happen.

21:03Tristan Lim: I'm sure most users of this thing can probably resonate with that. We have a fair amount of things that the processes are mature enough that they can kind of run, and we know how to manage it. but then we have to edge well i don't have educations but like less structured work things that happen now i have to throw this question at you because it's a question pretty much everyone listening will wonder when the thing that's unstructured takes a really big chunk of time and then eats into the structured stuff what do you do and how do you pick up on all the stuff that you've classed one if a conference happens it takes a whole week because that's what's needed but you miss like three sync meetings for sales go to market and whatever else How do you keep up with the backlog in your company?

21:45Tristan Lim: How do you manage that? Things have changed a lot on our end. Number one is we've been very used to working internationally from day one. We've been used to working across time zones, across regions from day one. And that's why even if we're at conferences in a different country, we have a pretty strong site on when our meetings are. We really run by our calendar. I'd frankly be handicapped without it. It is in many ways the living, breathing pulse and cadence maintenance of Bifrost. So if we have a conference, for example, beginning of the week, if there are certain meetings that you just can't take because it's either clashing with the conference or clashing with your evening gala or clashing with like side events that you're attending off of the conference, just highlight up front that, hey, listen, I don't think I can make this meeting.

22:29What do you need from me ahead of time? Or if I can't make it, I'm just going to share my points async up front so that you know what I would have said at that meeting. So that way, even though you're not present on that call, the information that was needed from you, the decision that had to be made, happened anyway. So that's number one. I would say number two sometimes is just making it very clear that you won't be able to join, but following up right after. And the meetings which are very important that relate to the conference, perhaps you can go ahead with them. Like, for example, if you're at a conference which we're trying to generate sales, it makes a lot of sense to join the weekly pipeline meeting.

23:00Or at least drop notes around it because, you know, there's a lot to be shared there. Over time, I think the founders are a great example of this and the rest of the company has learned from them is how to use AI to make sure that, you know, you can be a little more productive, put your points together and just really improve and streamline communications ahead of time, even if you can't make it. because I would say in any organization, which is similar to our scale, where the founders, I would say, are probably like the busiest. And then of course, like your functional heads and your team leads and chief of staff are like that number two layer, right?

23:32Who tend to be like the second busiest. The amount of decisions they have to make and the amount of communications they need to do on a daily basis is truly an order of magnitude higher. At the same time, the face time they have to spend with customers or conferences, for example, is again, very similar. So if you have those routines and agents set up, which can have pre-reads ready for you, which operate a clockwork, their dispatch, their schedule. It can really, really help optimize and take away that thought fatigue. And that helps you be present in person somewhere else, but also be more intentional about your virtual presence, even though you may not be able to make that meeting.

24:07Tristan Lim: Tell us a bit about you as head of strategy. How are you using AI in your role currently? And how has that evolved over the last couple of months? I'd say the usual bits, which almost everyone can guess, is the initial rewards are improvement in productivity, improvement in coordination, improvement in centralization. And as a result of that, you can be more present, you can be more timely, you can make decisions faster, and you can get a lot of tasks scheduled. You can extrapolate away a lot of autonomous, mundane tasks and just have them prepared. And that really saves a lot of bandwidth. So I think the number one thing to do is to go and identify what's repeatable, what's repeatable with low context, what's repeatable with high context.

24:50And then you just structure that away. And you can use whatever personal agents that you're using, but you can use that to really automate things. A good example of this is take investor updates, for example. If there are some parts of it that are consistent, you know where it needs to pull from instead of doing it manually. Similarly, if there has to be a motion of go-to-market towards a certain vertical, you know what the existing materials are like. You know what your existing dashboards or like at the same time, a good directional sense of what type of customers we're going for. All of that really helps get off the ground.

25:22If you want to use AI to get a version one to mock a certain industry. At the same time, you have a good example of what type of candidate you're looking for. It really helps identify certain markers that you care about as well. Right? So I would say those are like some of the immediate gains that come where you're just spending a lot of time doing repeatable tasks. That's number one, where it helps you free up that time. But number two is where it actually helps you make better decisions. So I can give you a good example of this. Let's say you're focusing on go-to-market. And this is very important.

25:54If you start looking at the more technical industries, if you look at unmanned surface vessels, you look at maritime, where you look at robotics, you're really looking at certain frontier labs that are working on a certain problem statement. They have certain markers, they have certain characteristics, they may have raised a certain amount of money, They may be backed by a certain type of investor, or they have certain types of functions in their team, say perception, for example. These are companies that we think we could work with. We could add value in any shape or form. It could be a research collaboration.

26:23It could be a potential customer. It could just be a partnership. But doing that again and again for various industries is very time consuming. It's a misconception that AI can do perfect research for you. It can really help you boil it down, but it still requires manual intervention. It does a decent job of data enrichment once you've actually got it out there and you need it to, let's say, go and start prospecting, it can do a better job. So I would say those are some good unlocks. But another big unlock, which I'll conclude with, is just the ability to build internal tools. It's so much easier now to build nicer looking dashboards on top of what were previously just numerical concrete jungle Excel files.

27:01And that makes it a lot easier for another internal user who may be non-native to that field, for example. So a finance dashboard for non-finance people, for example. A GTM dashboard for non-GTM people. A product roadmap dashboard for non-product people. All of which is very important in an organization because you work with everyone else. Those are some of the quick gains. So you get away with repetition. You get better at depth and research. At the same time, you have better dashboards, which make you work more easily. So I would say those are like the first three low-hanging fruit when you start using AI, especially on the strategy and upside of things.

27:36Tristan Lim: I guess if you drill down a bit more, like practically, whether it's Clawed or ChatGPT, are we talking like just setting up a project with the custom instructions and whenever you do research, you go into that project or how are you going about that? Clawed is definitely very useful. Everyone has their own preferred stack of when to use GPD, when to use Clawed or when to use something else. For us, I think core work is useful. Code is useful. Scheduling and dispatching is useful. Setting up artifacts and organizational skills is pretty useful as well. We've also got many different teams. Each of them work very differently.

28:10And we use a bunch of different tools. I would say that setting up high context is extremely important. And that's what makes the biggest difference for us.

28:19Tristan Lim: I can imagine you as the head of strategy, if you're supporting on creating the board deck or investor updates, obviously having the same shared context would help a ton. To be honest, financials, you always do need a human in the loop. You don't want to report any wrong figures. You don't want to make mistakes. You don't want to get other things wrong, like variance or your calculations. But when you really need to crunch a lot of data in a short period of time, that's when you start realizing a lot of benefits. I'm speaking purely on the strategy side. There's many different ways in which this unlocks value, especially on the product side or any other side.

28:52Like if you're trying to work on the code base, you have code. if you're trying to work on mock-ups, you've designed, you've so many different things that you can use. I'm speaking purely for my functional areas and I'm trying to speak more on like what's top of mind for me right now. I would say using it for go-to-market is definitely one of the big ones because in our industry, and especially if you're building artificial intelligence software that can be used for robotics or computer vision, your end customers are folks who may be using it to aid their R &D. They may be using it to aid their product development.

29:22They may be using it because it's less costly than collecting real data. They may be using it because it'll help them build something that'll improve revenue. Either way, broadly, you're selling into one function, but they may have a different end goal. That means you naturally have longer sales cycles compared to other businesses. You really need to be very tactical in who you engage with, whether it's a partnership, a research collaboration, or let's say a paid engagement. And precision and go-to-market is very important. So you need to plow the field, but you can't spray and pray. So human intelligence really helps you.

29:54But when you want to really go through like thousands of companies in a certain place and you want to contextualize everything you've learned and boil that down to, let's say, 20 very, very high signal opportunities that make sense for us to go for, I think that's where the X factor comes in, where it really helps you 10X. That's what I'm currently obsessing over. So there's a lot of good tools out there to play with. The whole game has changed, whether it's CRMs or data enrichment. I think that is definitely one of the more important aspects.

30:20Tristan Lim: Can you go a bit deeper in how are you setting things up? Like what is your stack? Something I initially wasn't used to was using speech to text. Initially, I felt it was just non-native. I either enjoyed typing or enjoyed the sound of my keyboard, whatever it was. But once you get over it and you start using speech to text solutions, like I like using Whisperflow. It's a pretty good one. You realize it's such a big hack. What I'm about to tell you next is actually pretty useful. Speech to text helps you take note pretty quickly. And you can throw it in there. You can throw it into your cloud.

30:50You can throw it into your agents. And it can go and summarize all of those notes properly, format them and throw it in the exact right places. So I'll give you a very good example of this. I was at a conference and the whole point of this is go to market. We're meeting many different prospects in the maritime space. We're chatting with them. We're meeting about 30 to 40 different companies over a span of three days. This is not a situation where you're in a meeting or where you have a live note taker. It's also impolite to just be taking notes on your phone or to have like a recorder on because you're not a journalist.

31:21You can't be like taking notes on your diary either because you're walking around, you're getting pulled into side chats and coffees and you're having meals and dealers and galas and all sorts of stuff. But you need to remember who you spoke with. If you have their card, what you spoke to them about, what the notes were, what the next steps were. Sometimes the person in the company you want to meet is not the person you're talking to. They'll introduce you to someone. That's a lot of context. And I tried this and this is amazing. After every person I spoke to, I just used Visperflow and I just spoke everything that happened and it converted into notes for me pretty easily.

31:53And at the end of the day, I basically had spent no time taking notes, but because I used speech to text, I had absolutely everything summarized at the end of the day. Took all of that, threw it into one document, put that into Claude and it straight away had a complete note for me because it looked at my prospect sheet that I was using before the meeting and went in through all of this in there. So I didn't have to spend any time figuring out what were the actions or the next steps for any of them. At the same time, I also just took pictures of every card and threw it into Claude and it extracted all of their emails for me and went and updated on the exact same sheet.

32:23So this is a good example of you're on the move. You don't have too much time, but you can use speech to text, Claude routines to take all of this data and go summarize it. And it keeps updating that dashboard in real time. So I think that was a massive unlock from like a go to market point of view.

32:40Tristan Lim: On Whisperflow, do you say who you talk to? Hey, I just met John from XY. That's what you're talking about. That's what you actually say in Whisperflow so that it knows the context of who you met. Correct. So speak clearly, speak politely. I just spoke to X company, Y person. Here's where I learned. Fit, not a fit. Next steps. They might introduce you to so-and-so person. They're working on this. Could be interesting. And you just throw in all those important keywords then neutrally and it picks it up. It's very good across accents to understand what you're saying and it turned into notes. And you just summarize all of that at the end of the day.

33:12This goes into Cloud and then Cloud knows where to put it. So I think this is just a good example of using it in a situation where you're genuinely strapped on time, but you need to remember everything. And a second brain that functions alongside you truly helps. There's like a few small ones here and there as well, just for completeness. I mean, I'm sure everyone listening has their own routines and their own ways of using it for their own problems. But if you're in an industry which is hot right now and you're subscribed to the newsletters, your inbox is exploding every morning and you can't simply keep up with everything going on.

33:43Especially if you're in artificial intelligence, you have different newsletters focusing on AI, you have newsletters focusing on IPOs and liquidity, you have those focusing on new product launches, robotics, deals, everything. And it's very hard to keep track of. Just simply getting in there to summarizing it, connecting everything makes a huge difference. The second one, which is more interesting is any form of analysis. And I think that's why it's very important to figure out which version you must use of whatever AI enabler tool that you're using. because sometimes, let's say if you're building a financial model, there are better ways to analyze things.

34:15There are better ways to find mistakes. There are ways to find bugs. There are ways to find mistakes in your projections. You can ask it to poke holes. You can ask it to test. And I think that's very important. It becomes a co-analyst companion for you, for your models, which is very good, but you're using it for internal analysis, you're using it for benchmarking, you're using it to calculate margins, or if you're using it to go out and raise, all of that is very important. This has reached a point yet, like recently news broke out, No names, but there was a company where they ran an entire fundraising process purely using an AI chatbot, which answered all the questions on the data room because it knew everything that was going on inside the data room, right?

34:53It was very familiar with all the models, all the assumptions, the mechanics, growth levers, decks, absolutely everything. And that's perhaps what's next or where we're headed, right? So that's just an example of what happens when you start using this on steroids.

35:03Tristan Lim: as a lot of the, I guess what I like to call like translation work, so to say, gets to be done much better than humans can do. Over time, where jobs are left for operators and choose to start actual building. I think we can take a step back here, right? If you look at a lot of deals and a lot of investments, a lot of time spent on going through building a thesis, going to the numbers, building confidence and comfort around the economics of it, the legality of it, the mechanics of it is great, but it can be done in lesser time. And that's if all the information is just organized in a certain manner, retrievable immediately, and it's quick.

35:43The humans involved in the deal get more time to build trust, get to know one another, figure out how they're going to work with each other and spend more time talking about product. Because that's what builds a lot of conviction. You get a lot more time to test the product, to do product demos, get a sense of where going. And you can do so much more in the same amount of time instead of just riffing off one model forever. Eventually, we would expect to reach that point. Of course, models are complex. You can use AI as a companion to debug them and test them and find errors in them. But moving forward, we are looking at a time when you can have this kind of assistance.

36:18Tristan Lim: So we've been talking a bit about AI at work. One of the questions I love to ask the tutor staff that I interview on the podcast is what is it like to basically be a chief of staff in this part of the world a lot of the people i speak to are based in southeast asia a lot of audience listening uh based in the u.s or in europe could you give us a bit of an idea of what is it like building in i know it's a u.s based company but you know being here in singapore with the team versus other teams and other cultures that you've worked in i think i'd like to start by prefacing what was i would say common in both my roles, as well as what was different at the parenting and at Bifrost in both places, CEO's office, founder's office, chief of staff, head of strategy and operations.

37:03All of them are like isomers or isotopes, very similar to each other. But the most important thing in both is they're modeled after the founder's office, CEO's office, and chief of staff roles that are popular to see in the United States. I think that is the core in both of them. They're both designed for the person to come in and operate like a Swiss army knife, bring in at least one or two strong areas of functional competence, which the company needs at that stage, the founder needs at that time, and is idiosyncratic to the person coming in. And operate as an extension of them, operate as a force multiplier.

37:42And of course, move like a free radical where you're required. That's common in both of them. So I would say in terms of my role structure, it's similar to what you would see in the US or Europe. In terms of where I'm stationed, yes, I'm based in Singapore. At the Parent Inc., my work was more focused on Southeast Asia based out of Singapore. At Bifrost, I'm based out of Singapore, but it's more focused a lot on the US and territories beyond as well, whether that is Japan, the UK, EU, et cetera. I would say I've seen the two regional experiences. In terms of my perspectives on it, I would say in the US and Europe, it's understood more commonly as a position that adds to the C-suite bench.

38:24It bolsters it. It has an ownership. It has a risk associated with it. And it can operate on specific tasks or special projects. In Southeast Asia, more broadly speaking, I've seen instances where a lot of others try to do that. But a lot of times I've noticed the chief of staff term is not fully understood or understood as it should be. Some examples of that, in my opinion, are sometimes it's just used as a catch-all term. A certain company may have X, Y, and Z vacancies that may not typically sit together. They just package it into a chief of staff role and open that role up. Unlikely to work well because it may not attract the right kind of candidate or fill that gap for you.

39:06A lot of organizations, instead of just opening up a general manager position, will open up a chief of staff position because it sounds nicer. And I think that just sometimes may send the wrong signal. Some folks also totally misinterpret the situation. They think it's like a purely human capital or a L &D position or like a talent position.

39:24Tristan Lim: Like a chief of staff. Exactly. Quite literally, right? Some folks think about it more like an elevated EA, which is definitely not what it is. So there have been a lot of misunderstandings around the position in this part of the world, in my opinion. I would say majority of them don't get it right. A minority of them do get it right. In Southeast Asia, another interesting thing I've noticed is the chief of staff position has started to go beyond just startups. Large corporations are starting to use that position as well. So you start seeing people who are general managers of a certain principle, who's essentially a business unit leader within a large organization.

40:01That's interesting. I would say that's happening in other parts as well, but that's a bit unique. Why do you think that happens? I'm not sure, to be honest. I think the scope is a bit broader and it makes sense because a lot of these business units are getting pretty large for just that one BU unit to manage. Southeast Asia is not just seven different countries, it's seven different currencies, seven different tax codes, compliance codes, seven different teams. There's a lot to take care of. And I think it really helps to have a chief of staff who can work with you. Perhaps that might be one reason.

40:31APAC is also a region where the profit pools are really, really growing for a lot of industries, especially FMCG, financial services, technology. Those two factors together might really align to warrant that position in there. But yeah, I would say the best place where you see these differences is when you go for an event. You go to an event in Singapore or Southeast Asia that's focused on chief of staffs, and you realize you meet many different kinds of people. The variance is very high. Other parts of the world, you end up meeting more people who are more similar to you. You end up meeting a lot of startup chief of staffs and you start talking about like, oh, what is it like when you were at this stage versus what is it like when you were at that stage?

41:06You live in the same realm. But here you end up meeting folks who are totally different things to optimize for because they may not come from startups. So I'd say that's interesting. You get a more diverse profile of chiefs of staff in this part of the world.

41:19Tristan Lim: I think what you're saying about seven different countries, seven different currencies, seven different actually cultures as well. It's so true. I think the role of a chief of staff, especially in this region, it can be such a high leverage role, especially if you then have chiefs of staff who are familiar with working in different countries, understand different cultures, like that becomes a really, really crazy unlock. Yeah. I'll say one more. The industry in this part of the world is still moving towards a level of majority, which the US, which Europe, which India and China are already operating at.

41:55I think this is also a part of that, right? Where the industry at a slightly lower level of maturity is starting to adopt to a position that originated from more mature markets. So it's also likely to use it to solve its current problems. And that's probably another reason why you might see many different types of chief of staff in this part of the world.

42:12Tristan Lim: Tell us a bit about what it's like to also be in a VC-backed company that's in different stages, obviously, but also from the perspective of one that is backed with investors from the West versus the East. That's interesting. You know, I feel like in my experiences that I've already outlined, a lot of the APAC investors compared to the investors in the US were a little more interested in the numbers, the process, more analysis heavy. Due diligences could be more detailed, a little more academic in nature, and a lot more dense sometimes. There is a focus on relationships. There's a lot more meetings.

42:47Juxtapose that with what we're seeing in the West, where we're having a more product first conversation. There's a lot of learning. There's a lot of sharing. There's a lot of sense in, okay, where's the product at? What does it actually do? What is it making possible? It was previously impossible. How is this going to work? A more broad sense of, okay, is this the right time? Has the time arrived? What's worked? What's not worked? And then moves into the similar things of like, okay, what the numbers may be, what the analysis may be, what the diligence may be. There's definitely a difference in speed at which the transactions move.

43:16There is more of a comfort in taking contrarian bets in the West, which becomes a little more obvious over time and eventually comes to this part of the world as well. So those are some differences. I would say power dynamic is another different one. The level of friendliness between operators and non-operators is different to see. I think in comparison, the US and Europe, you tend to see a lot of ex-operators, a lot of XPMs, a lot of ex-software engineers become investors. So they've built something in the past. They have a sense. They do understand where the company might be. They may have a good sense of what is the right question to ask at this point of time and just, I guess, culturally a bit more friendly barriers are down.

43:55There's a lot of capital. And then there's also a lot of good founders and a lot of good companies. So, you know, there's not necessarily one being more scarce than the other, but in a lot of emerging markets, we tend to notice in venture industries, which are like one to two decades old, where you have a lot of non-operators being the venture capitalists. They may come from a background in finance or consulting or corporates. They haven't necessarily worked at a startup or built a product before. And they're the ones gatekeeping the capital and talking to the people who are actually building things.

44:22There may be an imbalance between the amount of capital available and the amount of good ideas available. That may make the relationship sometimes feel a little more formal, a little more transactional. And after a few meetings, you then achieve that level of warmth. Okay, you know what? We get each other. So you do tend to see this. It may be culturally linked as well. Certain investors from certain countries can be a little more textbook. They can be a little more cookie cutter. Sometimes they may freestyle a little more. At the same time, if you look at stages, at the early stages, people tend to care a little less about the numbers.

44:51They care more about what is the founder market fit? Do you have the right team to go with? Are you at the right time? Is this the right product? Do you have the right monetization? How much do you need? So the pre-series A stage or the series A stage or the pre-seed stage, you can tend to really have those elements. But if I tap into my previous experiences, we were looking at like series B to D, it's a lot more strategic in nature, which is you start looking at, okay, how does this dollar get magnified? Where does it get spent? What business unit does it go to? How are your margins improving?

45:17How is your revenue improving? What are your metrics like, right? So it's a lot more about the numbers. It's a lot more about returns. It's a lot more about value. So definitely east or west, early stage or late stage, there are differences in terms of what becomes more important where. So I think being able to see it all has definitely been a gift.

45:36Tristan Lim: Could you give us a bit more on the learning side? What has it been like for you as a chief of staff, you know, being the CEO's office? What are the growth moments for you that you've experienced that kind of stick with you? This is a non-standard profession. I think I should start with that. There aren't a lot of people doing this. And if you ever look at yourself in life and you look at most of your friends or your colleagues or peers, you're going to realize you're the minority because there are very few other people like you doing this. Most people you know are not doing this. As a result of that, your learning experiences are very different.

46:07I think the number one point is we don't work with a regular boss or a regular manager. We work with someone who owns the damn thing and build it. They operate differently. They care differently. Their feedback is different. Their priorities are different. They also swing very differently. And I think that is a huge change from working with, let's say, just another manager who's just a version of you, but five years older. Someone operating with that level of skin in the game, getting used to working with them and understanding what moves the needle, what's important, how you can be the antithesis of them when required, as well as how you can be exactly them when required.

46:41I think that is, on a philosophical level, one of the biggest learning moments. Because it rubs off on you. You get much better. You start operating one level above, let's say, employee mentality. You start operating like an operator. You start caring more. You start realizing everything is your problem. And you need to build this eventual unspoken chemistry of when you need to be where the founders can't and when you must be where they are. And I think that is number one. Everything else stems out of that.

47:08Tristan Lim: Yeah, I fully agree. I think in the previous conversation I had with another chief of staff, it was very much around this, actually, like this being at the center of it. When are you mimicking or being a body double versus when are you actually thinking completely the opposite because that's what's needed? What is doing that well versus not doing it well? I'll be honest. I think a lot of times I've done it well, and I think a lot of times I've not done it well. And that is the norm. At least in my observation, founders are some of the hardest people to work with, but all some of the best people to work with because the amount they change year and year, that delta is not normal.

47:44It's very, very different. There's a layer of opportunism, mission, vision, existentialism, being in the right place at the right time to build everything, thinking about the organization, what are we going to do this year? Every January, you realize that they show up with a different energy and you see that energy float and move and remold itself mid-year and then really push towards the finish line, right? And you look at that with every founder, regardless of stage or sector or region. Being around that forces you to get on with it. I think the most important thing I do is I like to ask point blank, which is what has changed and what are our priorities right now on a quarterly basis.

48:20Whether you want to do it before a board meeting or is it in a one-on-one standup or a core sync is different. But I think it's very important to make sure you're aligned because the year may have begun with everyone thinking X is the goal. Three months have passed and you think X is the goal, let's see with the stuff, but in the founder's mind, instinctively, it might have changed to why, but you've probably not had an explicit conversation about it. And you start realizing over time that things are starting to feel different. And I think that's when having that conversation is important. It helps.

48:46Mistakes are part of the process. Agree to disagree is part of the process, but I think getting aligned is very, very critical. So I think that's one. That results in a chain of other events, which is realizing what's super important and why. If we are looking to hire a certain kind of position, what is a core skill that they must all have? Is it perception engineering that is very important? Is it a forward deployed skill set that's very important? If we're looking for a certain type of investor to raise our next round, what's important? Is it their nativity towards our vertical? Should they have done more deals in this space?

49:15Are they the kind of person whose main value to us is capital or relationships or guidance or introductions? As well as strategy, which is what are the verticals you want to focus on? What's the way to do it? Do we want to take an approach which is more outbound focused, more inbound focused, more warm referral focused, whether you want to do more conferences, do you want to start spending on marketing or not? All of those things require that constant alignment. And you grow through all of that because you get the freedom to work on many different things. So you also realize yourself what you're good at and not good at.

49:43You get a sense of what to delegate and what not to. And it really pushes you, you know, really go and get better. So you make mistakes, you be scrappy, you use AI where you have to get feedback when you need to, and you get on with it. So overall, it really expands you. It forces you to expand and it forces you to communicate. And I think both of those are essential in being able to operate at this level.

50:04Tristan Lim: The last conversations I've been having, a reflection that has come out of those conversations with other chief of staff, and I'm curious to hear your thoughts on this, is the two essential skills that a good chief of staff has. One is being high agency, being able to take something and run with it and figure it out, like figure it out ability. And the second one, which I truly believe is extremely important, is having high compassion, being able to understand in this case, what the founders or the principles that you work with, having compassion for these struggles, like what are they going through in order to translate that back into what should you do versus not do?

50:43Tristan Lim: What do you think about that? In my two stints of doing this, I've encountered each of those being valued by the founders that I worked for. I would say at the parenting, one of the things that the founder emphasized at that point of time was high compassion. At Bifrost, one of the things that have constantly been emphasized, high agency. So do I agree with that? Yes. Have I experienced both of them? Yes. Have I seen them both cared about at different stages? Yeah, I agree. I have a slightly different take on this, which is high agency is very important. Compassion is table stakes. But this is something that I personally value is being able to speak respectfully, directly and bluntly all at the same time is something that I think is very important.

51:27I think this boils down to what kind of chief of staff you are. If you're the person who has been brought in there to operate as an extension, as a thought partner, as a sounding board, who can look at the upside and the downside, who can really just lay it out on the table and just make life easier for the founders by either watching their six or going and analyzing things or just taking that one step forward or breaking it down and just having the courage to maybe share some hard truths once in a while or feedback. As long as it's constructive, respectful, and in the interest of the company and all our performance, I think it helps.

51:58But if you're the kind of chief of staff who's in a position where you're not really there to be a thought partner, all you got to do is execute because the decision has been made. Or if that's not necessarily the culture, then it's very, very different to be that way. But even then, I think you need to take the courage to do that if you truly want to fly. And if you're a founder's office, Shiva Staff, then I think this is definitely worth the risk. Because more often than not, at least in my experience, I have at least accepted that if spoken politely and respectfully, even if you're disagreeing or if it's a hard truth, founders actually appreciate that.

52:28Because a lot of times, they may not get that unless it's from like a well-wisher, like a really early stage angel who loved them, you may not always get it. And a good example is, let's say, if it's from employees or prospects or prospective investors or whatever, even if someone wants to reject you for not investing in you, you'll end up getting a slightly generic reason why someone didn't join the company, you might end up getting a slightly generic reason. You may look for polls inside once in a while or even have like a brainstorming session, but sometimes people do hesitate to share how they feel.

52:57And you know a lot of other positions in the company have the privilege of not speaking directly. But I think if you're a chief of staff or in a related position, I think it is your responsibility to try to speak directly, especially when no one else does. If you think that there is something that needs to be said, which the founders might be blindsided about. So I think that is an underrated skill because it's unpopular. It may not be very nice, but it's essential. And I think having a chat with your founders that, listen, if I ever disagree with you, what's the best way for me to do it. That really gives you the platform to do that while still maintaining that relationship.

53:35I would say if I could add a third, I would add this. But I also feel this is probably a subset somewhere of compassion because you're not here to like necessarily offend your founder or your colleagues. You're just here to be able to look at one of the truths without having a personal stake in it.

53:51Tristan Lim: That's wonderful. And I love this because it also helps through trying to have the conversation with your founder of like, as you said, what is the best way to share my disagreement or my opinion, it will also help reveal the nature of the relationship the founder wants to have with the Achiever staff. Because as we know, there are many cases where companies may hire, put a job ad out for Achiever staff, write out all the right things. But when it comes to bringing that person and actually working with them, as we know, it's really tough. Being a founder, you're building this company and to really let someone else into the process and to trust them and to hear feedback that maybe you don't want to hear because you've worked your ass off to get to this point.

54:32Tristan Lim: It's one thing saying you want it. It's another thing actually receiving that and like being okay with that and going through your own arc. So perhaps even having those conversations proactively as a chief of staff to a principal can help reveal the state of the relationship. And then it can perhaps also be a seed for a conversation that can be had of like, hey, do we want to continue in this way? Or do you want me to basically give you feedback openly? And in what way can I do that? or is this actually a relationship where you just want me to execute on the things that you say? Yeah, I totally agree.

55:02When I reflect, I think one of the best things that happened was that we did go through eight rounds because this was one of the things that we could speak about, which is that how do we disagree?

55:10Tristan Lim: Would that just come up organically or was that intentionally? It was. I remember like the CEO asked me a very important question, which is what is kindness to you, right? And I think that was in my round three. And that's not a question I'd ever been asked in any role that I'd ever interviewed for. And I think that speaks to your point that you're realizing that high compassion is very important. Of course, the other rounds also focused on high agency, but we did focus on situations. We focused on what are you going to do if X happens? What are you going to do if Y happens? What are you going to do if Z happens?

55:40How do we disagree? How do we make a decision if we simply cannot agree? What is more important to you? Is it X or is it Y? And I think all of those things really help you build warmth towards one another, especially over eight rounds. So I think it did play its part in some way or another. I won't say that this is a foolproof process, but it is good to have that chat at some point of time, whether you're already in a role or seeking one. It's the kind of thing which always needs a refresh.

56:08Tristan Lim: Yeah, absolutely. The company evolves, people change, we're all different versions of ourselves. And it's like a system update. You got to do it regularly. I actually couldn't agree more. That's a great reminder, actually. I guess, you know, if you're a chief of staff and you're listening, how incredible, right? to be proactive about wanting to actually have those conversations and to revisit protocol in any ways, like what works well for you now has a change from before. It's a really good one. As we wrap up, I would love to ask you one last question around being a chief of staff. How has that impacted you outside of work?

56:39In a lot of ways, you know, I think I've done it long enough now to maybe see some impacts on me. I think outside of work, in some ways, it does give me an identity crisis. Because unless I'm speaking to someone else that is either an entrepreneur or part of a CEO's office or a chief of staff, most people do not understand what I do nor do they relate to it. And that's because for most of them, the level of agency is not the same. The level of urgency may not be the same. The interpersonal nature of the relationships at work may not be the same. And the context switching demanded on a daily basis with depth and range may not be the same.

57:19That's just not something which resonates. So it can be isolated. You may not necessarily be able to talk with your friends or family in a manner which is linearly understandable to them about what you do at work or just generally what the rules of the game are. So you only end up finding residents in others who do something similar. I think that's a big one. The second one is I have mixed feelings about context switching because in my personal life now, I would say I do feel a lot more productive because you can see that you can do 10 things in a day. So that's amazing. You get better at multitasking.

57:51You get better at operationalizing things or optimizing things or setting reminders or using your calendar or like, you know, getting bills paid in a certain manner. You really get better at adulting when you start mixing some of those things. But I also feel like the downside of context switching is attention. If you want to sit and do one thing for a long period of time without any distractions, without your phone pinging or you using an agent or you pressing a run, I think that is some sort of cost of being chronically online or just constantly switching across different things. So I think those are the two big ones, to be very honest with you.

58:28But broadly speaking, it makes you more functional and it rounds you well. You do develop a presence. You can hold a lot of different rooms. You get to move around a lot and connect with a lot of different people, but you learn a lot about yourself because you find yourselves in situations you usually wouldn't if you were just doing one thing, right? So you get better at disagreeing with people. You get better at giving feedback. You get better at realizing that not everything is a debate or you don't have to win every argument. You're just trying to communicate honestly sometimes, but it's a lot of accepting hard truths about oneself and then just moving on and getting better.

59:01So accepting iteration as a form of life is tough, but it's worth it.

59:05Tristan Lim: I think that's a wonderful note to end on. Thank you so much, KJ. Appreciate you, man. Thanks, Tristan. Thanks for having me.

59:30And by the way!

From the publisher

Guest: Kartikeya Jaiswal ( https://www.linkedin.com/in/kjaivc/ ) (KJ), Head of Strategy and Operations, Bifrost AI Host: Tristan Lim ( https://www.linkedin.com/in/tristan-lim-709527a2/ ), Chief of Staff Network Fellow and founder at Beyond Founders Epi...

More from The Chief of Staff Podcast

All episodes