The Exchanges

Q For listeners who maybe aren't familiar with you and your career, could you just kind of briefly walk us through your journey in design and then a little bit about what you're up to these days?

A Okay, so let's see, I am a first generation immigrant to the United States, and so with Asian parents, there were really only three options that I had for a career. From like the time I was six years old, I was told I could either be a doctor, a lawyer, or an engineer. Nothing else was really in the realm of possibilities. Unfortunately, you know, I was really scared of blood, so I couldn't be a doctor. And I only liked reading fiction growing up. So I was like, could never really be a lawyer. So I was always like, okay, quite this engineering thing. But actually it was during middle school and high school that I discovered what I love to do is drawing and in particular digital art. And the reason for that is because I actually have very shaky hands. And so whenever I draw a line, it never looks good. I have to erase it, start over, you know? And so by the time the The art was done. It was like a mess. It was like, here's like, 20,000 eraser marks. But when I discovered MS Paint, and I kid you not, that was my very first design application. I was like, oh my gosh, I can draw a line. And even if it looks crummy, which it always does, because you have to use a mouse in those early days, I can just control Z, go Zegui, and just keep trying over and over again. No one ever has to know how often I, I tried to get to this to be what I wanted. And so MS Paint became PaintShop Pro, and…

AI assessment note: “when I discovered MS Paint, and I kid you not, that was my very first”

Q the reason we are chatting again three years later is, uh, you're re-releasing your incredible book, The Making of a Manager. I've got it right here. Uh, you've sold a bazillion copies. It's been on every list that I've seen. Uh, you're releasing paperback version. You're adding some chapters. I guess, first of all, just how do you feel on the, reflecting back on the, the success of this book?

A It honestly went beyond my expectations. So I'm super happy with it. My big motivation to write it was, I think largely because I felt if I had to write this thing, I was likely going to become a better manager. And that was actually a huge part of it. Um, because thinking about and writing something, you know, I've been blogging for a long time. And I know that part of my process is when I really sit down to try and put down everything I feel and write letters to myself, it really helps me. And so That was honestly a huge motivation. I hope that it would go out there and it would sell some books. I was thinking about that maybe for people who grew up in companies like mine, like Facebook, you know, high scale Silicon Valley, it, it might resonate. I couldn't have expected that it would have much wider reach than that. And, um, and that's been really awesome. And just how many people will tell me things like, I thought I was the only one who felt this way, but this book made me realize that Hey, these are very normal feelings. And that's certainly how I felt just stumbling through and feeling like an imposter for so many years. And so I'm, it really is very gratifying to hear that from readers.

AI assessment note: “It honestly went beyond my expectations. So I'm super happy with it.”

Q would we let that tell us what to do? And to your point, it's not gonna tell you what to do. It'll tell you where opportunities arise. Let me take us back to the management chat and maybe just let me ask something broad. What, what do you feel is the biggest change in the role and day-to-day work and life over manager these days with the rise of AI?

A I think that managing change, it's always been manager's job to manage change. And there's always the chaos of what's going on. I just think the rate of change is accelerating. And then we've seen that over the last couple of decades. And so I find that there's just a great deal, more uncertainty that people have about things like we all, you know, where are they going to be in two years from now? I don't know who, who really knows. Right. You know, are we gonna have AGI in five years? That kind of changes a lot about the landscape, not to mention, I think there's quite a lot of fear that many organizations are feeling. You know, it's like if my career has always been in design and now these tools are getting better and better at what I'm doing, then holy shit, what happens to my career and my future? And do I need to pivot? Do I need to learn different things? And so It's this change. It's this feeling of uncertainty. And I think a lot of times managers have to deal with that in addition to what you were saying before, which is they also have to learn these new skills, which is managing AI and managing kind of like these more powerful tools in their arsenal of trying to get things done. So that is very different. I think then maybe, you know, 10, 2030 years ago. Um, and so I think that the skills that become more important are obviously Communication, feedback, compassion, but…

AI assessment note: “It's this feeling of uncertainty. And I think a lot of times managers have to deal”

Q to be really helpful to you. So thanks for getting into all the detail there. Last question for founders or even PMs. A lot of them are struggling to hire designers. There's just like such a shortage of great designers. Do you have any advice? I know, I don't know if there's an answer to this, but do you have any advice for founders or PMs trying to hire designers?

A Yeah, this is, I mean, it is definitely, I mean, for hiring anyone, right? Even engineers too. It's all of us are looking for really great talent and there is a shortage. So for designers, this is what I often advise for founders. So the first thing is that, you know, designers want to work with people who, who care about design, right? They don't want to be like, Hey, you know, you're going to toss me some spec and then I have to like come up with a thing and then I toss it over the engineer. So the first thing you could do is demonstrate a commitment to design, you know? Make yourself out to be someone who cares about design. Again, not cause you just need to fill a box. Cause like everyone says you need a designer for your company to like, you know, get that team, but because you truly care about it and that already puts you far ahead of the pack, right? And so what are some ways that you can demonstrate your commitment to design? Well, the first is, even if you don't have a full-time designer, are you committed? Are you working with like a, a good agency or some, you know, are you able to like, if you have venture capital funding and you know, you're thinking about what to invest in, Are you working with someone on a contract basis on an age, you know, just to build a really wonderful marketing site or to, you know, focus on even the V one of your product being something th…

AI assessment note: “So the first thing you could do is demonstrate a commitment to design”

Q I, that's what I wanted to remember. On the, on the writing, something I wanted to ask about is you've, you've kind of slowed down for good reason. You have a startup to run, and you've started doing more tweeting than, uh, newslettering and blogging. How do you think about that? Just like, is that intentional? How do you think about, I don't know, Twitter versus newsletters and other things?

A Yeah, it was very much, you know, this is a, another New Year's resolution that came up later. Right. And one of the things that, you know, I recognize myself about myself is like, I kind of have a tendency to ramble, you know, and I've gotten this feedback as well in three sixties where I'm not always the clearest communicator. I can be a pretty good storyteller. And I am clear in writing often than I am in person, but this was another area that I wanted to get better at, right? I wanted to get better at in the moment, communicating more clearly and being just a little bit sharper, a little bit crisper in the points that I had to make. And I remember, you know, I worked with a number of colleagues who were just so good at this, right? There will be some really complex topic, this big product thing that we're trying to figure out. And in the moment, you know, they would go and they would say, okay, I see. This is what the problem is. The problem is one, blah, blah, blah, blah, blah. Two, blah, blah, blah. Three, like, right. And everybody like, yeah, you know, that's amazing. Like, you know, that's so crystal clear. Like this huge thing, we're all talking past each other now became boiled to something so sharp and so beautiful, right? And I always had so much respect and admiration for the people who could do that. And that wasn't me, but I was like, okay, well, as, as anything…

AI assessment note: “Yeah, it was very much, you know, this is a, another New Year's resolution”