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We take a close look at your toughest moments at work and turn the discomfort into advantage. Learn more at www.talentism.com
INTRO
Welcome to The Clarifier. In this episode, you get to meet Stef Sy.
I hire them to do something, they start doing it and then I start freaking out about them doing the thing I hired them to do!
After graduating from Stanford and spending time at Google, Stef founded Thinking Machines.
When her company grew to over 50 people, she hit a wall.
The complexity of scaling became very real.
Suddenly, she had to hire people to build processes to get things done reliably where before, she had used intuition and creativity. It was weird, threatening, and eventually… awesome.
And so where these people came in was to set up systems and structure where my cowboy ass just could not do it.
As Stef’s coach, I’ve watched her (as founder and CEO) grow this bootstrapped company from a small team of data scientists to a dominant AI and Data leader across SouthEast Asia.
I’m thrilled Stef will be sharing her founder journey today. Specifically, what it felt like when she discovered her superpower had become a liability,
And what she did when she realized scaling meant dealing with complexities she couldn’t handle alone.
Stef created Thinking Machines or TM to unlock the power of data.
She imagined a world where any employee, regardless of rank, could use data to make better decisions and she wanted to make better jobs for emerging tech talent in the Philippines. Something she just didn’t see happening in 2015.
She left Silicon Valley, went home to the Philippines, and got to work.
Stef Sy
Yeah, in the beginning we were so scrappy and everybody who came onboard was such a cool, unique, amazingly talented person. The very first person to join Thinking Machines, she was a journalist who had attended a workshop that I was giving which was a beginner’s “Learn How to Code” workshop. I had given everybody a lecture and then some exercises to work through, walking around the room figuring out like okay, what's everybody doing.
I just saw that even though she was a beginner in coding there was such strong clarity of thought in what she was trying to do that after the workshop, she came up to me asking for more resources on how to get better at coding and I said, “Hey do you want a job?” and thankfully she said yes. And we're still working together today. A lot of TM’s first employees, I met them through open source Python events. They were making really cool - you know we were showing each other - fun, small code projects, teaching each other, learning from each other and that was the first pool of people that I'd recruited from in Thinking Machines. So this was a small band of interesting nerds.
Stef wanted to create jobs that would allow these folks to flourish instead of mute their innovation and creativity.
Stef Sy
There are jobs where there's a ceiling to how much you can grow because the nature of the job puts you as a cog in a machine.
So for example, many outsourced jobs in the Philippines have very strict KPIs you have to hit. You do the job in a very, very specific way and you're replaceable. You're pretty instantly irreplaceable. Somebody else can be trained to do that job in a heartbeat. That's not the kind of job where somebody who has their own unique strengths and talents - that's not a job where they can figure out how they can excel.
In some ways, I actually think of myself as a gardener for a lot of the talent at TM. And TM showing other companies a vision of “what does excellence look like,” what can you take from our garden? How can you envision a garden kind of job instead of a cog kind of job? And build that idea of excellence and growth into your own organizations?
One of the reasons why I was able to talk people into joining in the first place - I started this company when I was 26 and looking back now I think, wow, it's a miracle that these people said yes to me when I said, “Would you please come work with me on this?” One of the reasons they did, is because I'm a pretty good data science teacher. I was pretty good at taking people, seeing what they could do, starting from there figuring out, “Here's what you need to learn.” Picking people who also knew how to learn, right? I think learning how to learn is a skill, almost the most important skill you'll have in life. So finding people with that drive, that growth mindset. The skill of learning how to learn and being able to see how they can fit together into a data science team with distinct skill sets, coach them, teach them, correct them directly and put us together, pointing our efforts towards really interesting problems that clients would bring to us. At that point in time, we were also very new to our clients. The pitch to them was, “Hey just give us 1 peso. You have to pay us.” That was the rule that we had set. “Please, you have to pay us something. But even if it's just 1 peso, give us a problem and we will try to solve it for you,” and that's how we were running. As, like a rock band for the first couple of years.
Angie
This idea of a rock band for an early stage company makes so much sense to me. A small group of people, making music, often chaotically, where each individual is unique and indispensable. I think right around this time you have an experience that's a pretty emotionally impactful one for you. Tell us what happened.
Stef Sy
Yeah, well, the first thing that happened is we got successful. And we started getting bigger and we started getting older. So four or five years into TM we were doing pretty well as a company, had a bunch more people on board but still had that rock band kind of vibe to us. And one of my colleagues who joined us - like this is the third person to join the team, somebody I worked with every single day - he came to me one day and said, “Hey, I want to build products. I love working with this team but I don't want to do consulting anymore.” And he had been, for the last six months, he'd been pretty open about wanting to explore that direction. And so for six months we were trying to figure out whether there is a space to build a product in the company. Is there a space for that to make sense given who TM is? And we were doing well as a consulting company and there wasn't a clear, shining B2B SaaS product that I could see in the stack of work you're doing. So I had to go back and tell him, “No dude, I don't think there's anything here for us to work on together.” And he then makes the very rational decision - communicated very kindly - that he was going to leave TM.
Stef Sy
And intellectually this was fine. This is so logical. It was so amazing to have this dude - this incredibly talented guy - give us like 5 years of his career, but emotionally it was horrible. It was horrible! Was the worst feeling in the world. I'm sitting there trying to process his resignation and the intellectual part of my brain's like, “Yeah, this makes sense. We've tried everything, this is correct.” But I went home and just like, lied down on the floor and had a total meltdown trying to process this. But if you're hearing this Steve, now you can know about this. We're still friends now. But I must say that was such a weird reaction for me to have about a colleague who's making a very kind, calm, rational decision and bringing it to me.
Angie
Ok, so I'm imagining you Stef on the floor of your room, devastated,by the experience of having one of your Day 1 team members - or just about Day 1 team members - make what you're calling a rational decision to move on to pursue the thing that he was passionate about that he couldn't do at Thinking Machines. What do you think you learned from this experience of watching - was it Steve? Steve, walk out the door.
Stef Sy
Oof. I mean, first I had to process that experience right? First of all, I was very confused by my reaction to that because the way I was feeling was completely not aligned with what I was thinking. And I think actually that was probably one of the first times you and I talked. And I was just like, “I don't get it! I don't get what's going on. I completely cannot understand why. Not why he's leaving, that was pretty rational, logical. Totally good reasons. Great notice and runway. He gave me everything I needed to make that transition smooth and successful. But what was I feeling? So first, figuring out what I was feeling. I had to learn that this is triggering something in me. 1, I need to figure out what it is and 2, as I started looking into replacing Steve, right? I realized that his role was completely individualized. There was no successor in place to step into his role. This was a very oddly shaped hole in our organization and there is no way I could hire somebody directly into that role. And I was looking at it and thinking, wow, we had crafted this job totally around him and you're now trying to replace, like a lead guitarist in a company but this is not a 5 person rock band anymore.
Stef Sy
This is like a really big orchestra. We were 50, 60, pushing 60 people at the time. We were going through, simultaneously, this transition into onboarding. Our Head of Operations was putting in place a lot of structure in our organization and I was not in a place where I could find another lead guitarist and put them in. Because that wasn't that wasn't the business anymore. I had to run a totally different kind of process. And understanding that that was the end of an era. And even realizing that that was an era to begin with, because I didn't know! Now I'm describing it to you as like, “Yeah it was a super cool rock band.” But when we were doing it I didn't know that it was a rock band.
Angie
There are so many powerful things in what you just said, I want to go slow for a minute and make sure I'm registering them as you share them. I actually remember - it was maybe about three years ago now, in December - it was a conversation we were having just before heading out for the holidays. I remember that emotion rising in you and you know I'm hearing you describe two moments of reckoning. Two different realizations and that first one was: there's a real emotional reason I started this company and it's not just to create a place where talented people can thrive but it's to create a place where I, Stef, can work with people for whom I have a deep affinity. Where I feel safe or I can solve problems in a way that feels invigorating and losing those people might actually be an important part of the process if I want to create a place where people can join and then move on and really relish the experience they've had and pass it on to others. But the “losing them” piece of it is going to feel devastating to me, like a part of my family is being ripped away.
Stef Sy
Right? It was crazy. I mean, I had described this garden that I wanted to create but it's not that I'm out of the garden, right? As I'm describing it you're thinking, okay there's a garden. But then there's a question of where am I in the garden? What is my emotional reason for forming a company? I wanted to be inside that garden. I didn't want to be inside the factory. I wanted not just to have a garden there but I wanted to be in that garden, like hands in the dirt working with really awesome people. Working with these very specific, brilliant weirdos at TM forever, question mark?!
That's when you know, when this guy left I was like, “Oh that's crazy!” Because for it to be a good ecosystem for people, it has to be a company that respects the fact that people move through different stages and cycles of life. It has to seed - you know the whole point of the garden is that it has to seed other gardens out there. People have to leave, people have come back. People leave and there's a whole rational reason why I wanted to design it that way. But emotionally I just really wanted to work with this core group of really awesome people forever. But that's not a company that's ah, that's not a company.
Angie
You know one of the reasons we use discovered evidence to understand ourselves better in the process of coaching is this idea of self-awareness and then ultimately, personal responsibility. By understanding our hidden motivations better, by understanding some of our blind spots better, we better see our actions in the context of those things and how sometimes the actions we take might undermine the ultimate goal we have. And so at the time, I knew your ultimate goal was to build a bigger and better TM but that if all you wanted to do was keep your beautiful weirdos around you, you were still going to build a rock band, not an orchestra. And a rock band can only get so big. You can only have one lead guitarist. You can only have one drummer, you can only have one lead singer and now all of a sudden -
Stef Sy
Right? There's no room to train multiple drummers. There's no room to train because you only have one drummer in a rock band. And I remember that was right after Thanksgiving I think, three years ago. And I think that was also the moment where I realized that I really needed to make an active choice to scale TM or not. I really needed to decide at that point. When you are growing a company and - knock on wood - I've been very lucky to not have a lot of VC money involved. And the investors I do have on board - with super supportive small friends and family round - they're very supportive and like, “Hey build something interesting in this world and do it your way!”
But I had a real choice in that moment: to keep the company as a rock band (and that filled a emotional need in me) or to really embrace that I had to transform if what I really wanted was to create this unique operating environment that would influence, not just the people who work directly in TM, but would be a cultural influence in our region that could impact a lot of people and a lot of companies, I would have to change.
So it's either the company changes or I change.
And it all came down to, “What am I really doing this for? Why am I really starting this company?” Because both of these things had a lot of truth, I mean, had ALL the truth in them.
Angie
Oof. Okay, so what's really resonant for me - I'm the lucky one here who gets to spend my days talking to founders - is this moment of realizing that there may be a conflict between the thing that makes you feel safe and fulfilled, happy on a day-to-day basis working with a small group of beautiful weirdos. And the thing that you believe is the ultimate fulfillment of your company's potential, which is this scaled, data science consultancy that creates better outcomes for companies and civil institutions in the Philippines because they can use their data better. They can make better informed decisions. They can become more meritocratic and also serve as a place that trains and then sends on the type of CTO level talent that's needed in the region, and probably underdeveloped in the region, and so here you have “What Stef Wants” and “What Stef is Great At” and here you have what the ultimate potential of this company is. And so how do you make sense of the difference between those two things?
Stef Sy
I think we were - I think you and I were talking about that for like two months actually. And I think that was really useful to have that understanding of what was on the table. Because I was talking to mentors, I was talking to friends, other startup founders and they all give advice from the perspective of, “Here's what I would do if I were in your shoes,” or, “Here's what I will recommend to you based on my understanding of what you want.”
What most people thought I wanted was, “Of course, you want to grow a huge company right? Like of course you want to go all the way, like try to go be a unicorn company, hire thousands of people.” A lot of that advice wasn't quite ringing true to me and finally, first understanding that there was like a choice to be made there between what kept me safe and happy on a day-to-day basis and what I really truly believe TM could be, that really helped me first sit down with myself and say, “Okay. Not what makes me safe and happy on a day-to-day basis. But what do I want in this world?” And it would have been valid - you know if somebody out there is facing the same choice - it is valid to say, “Hey actually I don't think I want to go through all this like pain and suffering to change and like, discomfort - like really extreme discomfort - to evolve.”
Because the process of evolution that I have been going through in the last three years has been painful, confusing, occasionally botched. But because I chose to do it and it was an active choice. It wasn't just like I just stepped into it by accident every moment of discomfort, I'm able to reframe it as, “Hey this is me learning and growing,” and I'm able to have a sense of humor about it I'm able to see how it helps me get to the person I want to be and get TM to the kind of company I think it can be.
And that's awesome. I mean, every action item that I've taken on since then you know could just be more described as more structured.
Stef Sy
Bringing on a VP of Operations, setting up a hiring process, setting up a promotion process, setting up guidelines for skills matrix, how we hire, how we train, how we systematize our approach towards solving client problems. And going through all of that to bring the company to, now like 200 people, while still retaining that like culture and spirit of it has been such a big - it's not over yet! I mean, I'm talking to you as somebody who's still in progress and the company is still in progress. But it was so important to recognize those motivations so that I could understand myself well enough to, not let go of them, but to understand when they served me and when they didn't.
Angie
Yeah, yeah, yeah, so I'm hearing that you kind of understood, left to your own devices, you might end up making the tradeoff in the other direction. “Let me just build the thing that feels safe that I feel a compulsion towards” versus, “Let me really anchor to my purpose for building this company and the ultimate potential that I think it can help to achieve.” And I'm hearing you say - I'm going to give a little voiceover for the part of the story that you just described - that you realized you couldn't leave yourself to your own devices so you talked about hiring a few different folks. Can you tell us who you hired and what exactly you were trying to do by bringing them on board?
Stef Sy
Yeah, so the very earliest hires of TM, I am not embarrassed to say, they were hired based on vibes! They were hired based on like, “Wow, that is a super cool piece of work. Would you like to come in and work together? And I'm sure you know, we will vibe and figure out how this is going to work.” The first real hire I made based on, “Hey the company needs something,” was a wonderful sales leader who built our selling organization. And that was really obvious to spot, right? It's like as a business I think we could be selling more, I'm not super strong at selling. Let me hire somebody to help me to build the business strategy. Someone with management consulting experience, somebody who knows how to structure and sell deals. Great! Brought that person on board. Fantastic. Then the trickier next hires were at senior leadership. People who I brought on to hire things that are a little less obviously needed. But I wasn't quite sure how to hire these people and so I got very lucky in a very strong Head of Delivery who joined our team, and a very strong Head of Operations. And the Head of Operations and I shared this manic insistence on talent development. Recognizing, spotting and cultivating talent but with very very different approaches towards it. She's one of the most systematic and policy driven-person I've ever met, with a memory like a steel trap! I cannot remember
if you ask me what our policy is on something on three different days I might give you three slightly different answers. And so where these people came in was to set up systems and structure where my cowboy ass just could not do it.
Angie
And so we have this term for stuff like this at Talentism that we use often which is “Design for People.”
So when you arrive at that moment when you realize that what your company needs in order to achieve its purpose in order to scale is not what you have to give. And, in fact, it might sit right in one of your blind spots, which your company needs right now. You can do one of two things. Well, you can do one of three things I guess. You can throw up your hands and say, “Well I guess I guess we're done. This is it.” You can practice the thing that your company needs, that you haven't had practice doing yet. Or you can hire, right?
You can design a system that relies on others, instead of on yourself, for that thing.
And what I'm hearing you say is when we got to the point where it was no longer sustainable to operate as a rock band - with individualized roles for brilliant weirdos - and when we needed to have a little bit more systemization in order to be able to hire at scale, to train talent at scale, to deliver on projects at scale, to sell and scale, I needed to hire other people who would be great at that thing.
So how did that go? Because I think you're describing a situation that so many first time founders find themselves in when they're starting to scale, which is I had to hire people who could do a job that I couldn't do, I didn't know what good look like, and when they got in the seat they started doing a bunch of stuff that really felt kind of challenging, maybe even threatening to me.
Stef Sy
Very threatening and it's crazy right? I hire them to do something, they start doing it and then I start freaking out about them doing the thing I hired them to do. Illogical, completely illogical. And I kind of want to point out also that I had a bit of insecurity from being so much younger than them. Also this is something that happens in startup world where you have this like young CEO with a good concept, hiring an experienced executive who's like 10 years older, seen a lot more and getting insecure about needing to prove - I wanted to prove that I could do the job. But I couldn't do the job! I hired them because I couldn't do the job but a piece of me was still pretty insecure about number one, proving to them that they had made a good choice to come work with me number two, freaking out in moments where they're doing the job I asked them to do.
For example, the VP of Ops trying to systematize our hiring process instead of Stef looking and saying, “Oh cool blog posts! Let me email the person who wrote the blog post, like hit them for coffee, see what they're doing.” She’s like, “Hey, why don't we have an application process?” where you look at one code sample, do some pairing, have a conversation. Set up a structure for what a panel interview looks like, how might we standardize interview questions?
So basically people are getting the same experience when you're working with us. Setting hiring targets. I was like, “Hiring targets?” The first time she ever brought that to me, you know the question of, “How many people do we want to hire this quarter?” And I was stunned. I was thinking, “What do you mean? How many cool people are out there who we can spot?!” A lot of these moments of chaos and friction between me and these executives I've hired, but also a lot of these moments of me learning from them and us all being very culturally aligned with each other. So starting with that sense of mission alignment, culture alignment and all these executives also had a little bit of weirdo in them. So we recognize that in each other. That was like a bit of a seed of trust. And needing to trust each other through this process. Also we were driving each other - I know I was driving our VP of Ops a little bit crazy and I still do - but learning how to trust her to run her process and her learning how and when to trust and deploy me, right? So that my strengths also still show up in this process. I'm going to tell just a quick story of how our VP of Ops was trying to systematize our hiring process and trying to systemize how we receive resumes.
Stef Sy
Process them, invite people to come to interviews, interview them. And one day I just got so paranoid, irritated - like, I don't know what was going through my head but I lost it. I went through the slush pile. I personally went through the email slush pile of resumes and I started picking up like, “What about this candidate? Have we thought about this one? Like yeah, their grades are crap but that shouldn't matter!” And completely undercutting her. Completely undercutting this process. Completely confusing. The hiring person who is trying to run this process. And I was worried. I was freaking out because I was so scared that we would end up hiring people who just looked good on paper that we would only interview people who looked good on the resumes. Because so many of TM's best employees, the best teammates to come join us, are outliers. Nonconformist people who got bad grades in college, somebody who dropped out of college, people who could do the work but who were under indexed, undervalued by most standard indicators. So I was so scared that now we are having a process. We're going to end up just like all those corporate companies. Who do things on a super strict process. And just thinking about that I got kind of worked up!
Angie
I can tell. Well, you know the way the brain works, when you're going back in time into a memory the brain doesn't know you're not there. So why don't you take a deep breath and come back to the present.
The thing I want to highlight is this is an absolutely common experience. I think you're describing what many founders - and often just sort of managers - are learning to delegate to other managers below them experience. Which is if I were doing it - I'm talking as you now, Stef - if I were doing it either it would go faster. It would go better in some way. I would be able to catch the exceptional people who don't meet the standard indicators, right? It would be more reliable. And this is the experience I think so many founders have when they say, “Okay. Instead of me being the doer, I want somebody else to be responsible.” And then they watch what happens and it doesn't look like they would have done it. And so we feel this Catch 22 of, “But if I do it, it won't scale and I won't be able to focus on my highest use as CEO. And I'll be stuck doing a bunch of the functions of the company that it's not sustainable for me to do anymore, right? So if I do it the way I want to, it's not going to scale or if I hand it to someone else. I have to learn to deal with the anxiety of it happening differently.” And I really want you to help us - you gave us some clues as to how you got comfortable with the approach that your VP of Ops was taking. I think one of the clues you gave us was there was a real sense of shared mission. And I think another one of the clues you gave us was from a culture perspective. You felt an alignment. Tell us more about how you got comfortable with your VP of Ops taking a very different approach to hiring and training than you would have.
Stef Sy
Yeah. I feel like it's such a common thing that happens. I don't know how - I think, I think she was actually the person who was brave enough to just see me going kind of psycho and call me out and say, “Hey you hired me to do the job. Why aren't you trusting me to do the job you hired me to do?” Instead of dealing with me on those specific peoples’ resumes, the thing that I was trying to pick a fight about. And so first starting from, just creating that space where we could step back and just have a very open vulnerable conversation with each other about what is the job that I hired her to do? Why did I believe she could do it? What did we both believe to be true to the spirit of hiring, growing talent, scaling and just having us sit down with each other and like reconfirm the fact that we're both completely aligned, completely mission aligned on developing talent and that we wanted to work with each other because we just saw we had different skills that we bring to the table.
First being able to spot what was happening, second being able to have a trust-building, vulnerable conversation about why we were both in this and what we saw in each other really got us to the place where we started talking about - we weren't calling it a design at that point but talking about how we saw the process running. How we would know if it was working or not, how I could still and should still be part of communicating culture to the team to make sure that they understand when they joined TM. Because I realized that it was quite important to me that they understood what culture they were signing up for. So I still do - until I think we were about 150 people - I was doing final interviews for everybody. Now what I am doing is when everybody starts, we do a culture onboarding in their first week of work where I really sit them down, talk to them about our formative stories. Because you know it's one thing to see your core values, but I think telling the story - story brings people along.
You know when you're reliving the story, you're almost like bringing people along with the story with you. And it's almost like fables, right? I actually think that core values or a company's cultural values are probably best expressed like fairy tales where you just tell the story. And they'll kind of get the nuance and the arc of that. And so building in that system for how and why we work together, how we recruit, how we hire. Where she deploys me - how I can see if it's working or not getting to that place where we're unlocking the system, that was super powerful and got us to this place where I don't freak out about the hiring pipeline anymore. But I will come to her quite often with ideas on, “Hey what if we do a coding boot camp event? Hey, what if we start giving away t-shirts at the bouldering spot near our office?” and we can have a fun talk about that.
Angie
So again I want to highlight just how frequently I hear this story and how common this experience is. Which is, in particular for founders who, in order to get their business from 0 to 1, to kind of give birth to this thing that didn't exist and now needs to exist through their own, you know, sweat and work and tears. They have been the one doing a lot of the stuff. And usually there's a particular spike that they brought to the table. Maybe it was business development and sales. Maybe it was building the product, visioning and building the product. Maybe it was hiring the talent, right? In your case hiring the talent was certainly part of it, and to transition that responsibility to somebody else can feel challenging, even threatening.
And I think what I'm hearing you say was a big part of your ability to transition was thinking about what was the responsibility? Why did you hire the person? What were the outcomes you were seeing through time and how did it make sense for you to be involved in the process? Both to evaluate how it was going but also to be used kind of as a cog - go back to that idea of cog job - kind of to be used as part of the machine to produce outcomes as part of the system. Was actually being run by the person you hired almost like they were your boss for this particular function or this area of responsibility.
Stef Sy
And I must say it's very nice to sometimes have somebody else be the boss. Just like, “Cool, just put that meeting on my calendar.” I know that I have a job to do. I'll do it. I'm part of the system. It's very nice to not have to actively think about every single thing that I do every day. So that's getting past Do and more into Design from that perspective. Um, actually it's nice to be part of the Do cycle because I love doing things. That's the whole - that's my whole motivation - for starting TM . I'm good at doing things - I'm good at doing a huge variety of things and then not being able to do everything was driving me totally insane.
Angie
I actually think that's a really important insight that we sometimes skip past, which is in giving up your legos as a founder if you do it in a way that doesn't actually allow you to scratch the itch of what's most satisfying to you, you're more likely to fail in giving up your legos. So if your VP of Ops hadn't found a way to let you still meet with candidates in a final round or meet with newbies in their orientation to talk about culture, I suspect without that outlet, without that ability to scratch your itch to be with your brand new, beautiful weirdos, you actually wouldn't be able to take the step back that was necessary for her to run the whole process. And so again, for other founders who are going through this really common transition, I think part of what made this recipe successful for Stef and her VP of Ops was not only blind trust - it wasn't blind trust - it was earned trust, it was cultural alignment, it was mission alignment but it was also finding ways that Stef could be involved that were productive, as judged by both parties.
Stef Sy
Even now it makes me sound a little bit like, you know, give the kid a toy. It is not that, right? The job that our VP of Ops asks me to do is like a difficult and important job. It's just that she can trigger it and it has a clear start and end and there's a very clear satisfaction that I get about doing that job, getting to the end, knowing it's done, moving on to the rest of my day and it's very - it lets me stay calm, I think. I think it helps me keep connected with the team. It's productive for them. It's both productive and emotionally satisfying for me. I think it's genuinely that no matter how busy I am, it's a big highlight of my week or of my month when I run the new culture onboarding and get people talking to me about what makes them unique, which values do they resonate with, and hearing their stories of their lives. That actually keeps me sane in many weeks.
Angie
You have heard Stef talk about Design a couple times now. At Talentism, we use that word to mean something very specific. It sits inside of our 4D framework. Those 4Ds are Do, Decide, Design and Decode.
Do: It’s what it sounds like. You are getting the work done yourself.
Decide: Also what it sounds like. You are deciding what other people should do and overseeing them as they do it.
Design: (this is where it gets tricky) You are thinking about how to enable others to get work done without your constant supervision. You are hiring people that think differently from you and helping them achieve their goals, without actually doing the work or telling them what to do.
Decode: Looking out to the market, the customers, the world and figuring out which insights are going to be game changing for your company.
Stef
I do want to highlight that Do and Decide are pretty easy, pretty straightforward to get to. You know you do something, you grow, you start thinking about, I make the decisions or I delegate different chunks to different people. I think that the part that has been incredibly hard for me has been thinking about design because that's a totally different muscle. That's a totally different muscle. It's not particularly intuitive. It's easy to say, “Oh let's think about your design in the system. How do we measure success?” But for um, for most people I think, myself included, it's actually a huge quantum leap to be simultaneously running a company and redesigning a company. As you're running and changing the way you think, a task comes in front of you. Most of the time the thing to do is you either do it or you say find somebody else like you do it.
It's very hard to step back from that problem because that problem is real, somebody is like, “This is a deal that could close. It's a hot lead off the press.” It's like a really tricky machine learning problem that's like just landed on your plate. It's trying to understand, “Do you have enough data to build this model?” It's trying to figure out if this person has an invoice that they haven't paid to you, what are you going to do about it?
And going from that problem which needs to be solved today to thinking about, “How does this problem - how is this immediate small thing a symptom of our system? How do we set up our system of work for building and deploying machine learning models into production? Or how do we think about our system of billing and invoicing clients? It's so hard to do that when immediately in front of you is a small screaming problem saying, “Solve me now please or this company might not make it to tomorrow!” So that's just like a really lived experience. Of pain and challenge. But it is possible I will have to say, it is quite possible.
Angie
So throughout this entire conversation stuff. I'm so grateful that you've been dropping breadcrumbs and giving juicy tidbits to listeners about what you've learned and how you would now share that as advice from your perspective.
Is there anything else that you would want to reflect on or share as a piece of advice or mentorship for other founders or or other managers who are scaling and facing similar challenges to yours and sort of going through their own journey of self-reflection and understanding their motivations and their blind spots?
Stef Sy
Yeah I mean um, as founders we're building dynamic systems. When we're doing our jobs well, problems don't go away, you just get new and different and hopefully more interesting and hard problems. There's no such thing as no problems. There's just low quality problems which you are solving the same problem over and over again and high quality problems which are new exciting and different problems you have to solve. The only common factor here is yourself, right? You are the only thing that holds true and constant throughout like this whole journey of starting a company, growing it, getting investors, maybe selling it, maybe taking it to IPO, maybe having to wind it down - what's the common factor here? You!
And me knowing myself more fully and knowing how likely I am to break things make them stronger just by my presence or absence. You know, sometimes I have to improve myself, sometimes I've to absent myself in the situation and put somebody else in there. Knowing those things about myself helps improve the odds of success for TM and for me. That means evolving. Evolution is so cool and powerful. I really think that if you as a founder can take your strengths because you have them like otherwise you wouldn't start a company - and take your superpower and recognize that at some points, if you are doing things well, your superpower will become a liability and at that point you have to evolve.
I had to redeploy my obsession with building teams and finding really cool people and constructing really unique roles for them. I had to find a way to evolve that and redeploy that into setting up great systems to bring in cool people, a culture that trains people into excellence in data. And then pointing this strength also at new things! I didn't realize it, but a lot of the things that made me good at talking to people and understanding where they could fit in our organization, also makes me good at talking to clients and figuring out what they need specifically for them. Not just what's a general best practice, but what does this person, this company need? How do I design something that's very uniquely for them? That's actually an evolution with the same roots as my original obsession with talent and that's awesome. I think that continuing to grow and evolve and chasing your obsession - making yourself a better person - no matter what happens to your company, I hope that that will give you a lot of satisfaction and happiness in life.
Angie
That was beautiful Stef. I want to put on a fortune cookie “When your superpower becomes a liability it's an opportunity to evolve.” I love it. Thank you so much for spending time with us and for sharing your journey.
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OUTRO
If you relate to anything Stef felt in this podcast, or the 4D model struck a chord with you, I invite you to have a chat with someone at Talentism.
Drop us a line at info@talentism.com and schedule a 30 min conversation with one of our coaches. We want to hear from you.
You can learn more about how we guide our clients at talentism.com where we share our insights from serving over 800 companies.
If you have a leader you’d like to see featured on this show, or a topic you’d like us to cover
Email me at angie@talentism.com
This episode was produced by John Hunter with story editing by Jessi Gormezano. Special thanks to Greg Kim, Rachel Kitto and Rocio Gonzalez.