The Identity Crisis Nobody's Naming, with Annie Tsai

Well, today, we're having all of those same conversations and more, but instead of shifting context from one meeting to another, because you're leaving one room and going to another room, we're just having all of those 9 or 12 or 20 conversations concurrently, and they never end. And so, that is, I think, a very real condition that executives and a lot of other ICs, I think, like skilled ICs in the workforce, are experiencing right now.

Welcome to Vlad on Leadership, interviews with technical leaders and operators about the leadership questions AI makes more difficult. I'm your host, Vlad Moskovski. I coach senior technical leaders and founders who are excellent at the job that's keeping them stuck. Hi, Annie. Welcome to the show.

Hey, thanks for having me.

I would love for the audience to learn a little bit more about who you are. So, so tell us a little bit, who is Annie Tsai?

Sure. I am a mother of 2 by day, and I also help run a software company called Interact where I am Chief Operating Officer. I also have a lot of interests where I spend a lot of my time. So for the last 8 years, I've helped grow an online community called Moms in Tech, where I also today am Chief Operating Officer of that organization, 19,000 operators and executive moms globally that have this really unique shared experience and dabble in a lot of other areas. I write a lot. I have a weekly column and a weekly newsletter called The Business Side of AI. And recently, I'm working on publishing my third book.

Amazing. What were your first 2?

The first one was in 2013, and that was a small business marketing guide for organizations that were really brick-and-mortar companies that were really just starting to realize the power of having an online presence. And then the second what is a financial literacy book focused on empowering parents to have these conversations around understanding how to save and invest and, you know, understand our global banking system and all the things that, you know, I probably never learned until I was well into my adulthood, but helping parents navigate those waters with their kids.

Amazing. I think I need that. And my wife for sure needs that. Very important topics. And you said that you run, you write a column on Business Insider. and AI. Do you have a premise or a theme or certain things that you are really wanting to share with that audience that maybe this audience would want to hear as well?

A lot of the premise or the thesis is really around the fact that we are in this really unique point in time where the disruption of a single technology is happening across all industries. You know, we've seen sort of technology disruption in manufacturing, we've seen technology disruption in education and in all sorts of other parts of the world and agriculture and industry. But now it's happening across all industries at the same time. And for, for people who have spent the last 10, 15, 20, 30 years of their building their careers under a premise that, you know, you could become an expert, a subject matter expert in something. And retire doing that thing if you wanted to. That premise is almost entirely disrupted now, right? That it's, it's almost untrue at this point. And so, I think for me, it was really about helping others understand what some of these underlying vectors were at play and how they could navigate learning new skills or evolving their skillset in order to really stay ahead of the curve a little bit. And then there was this other part of it, which was, okay, what am I learning that's really interesting in how I've had to evolve my role, which has completely changed over the last 2 or 3 years, and how can I empower more people to do the same, or, you know, at least find ways in which they can really take ownership of the opportunity because there is a lot of opportunity there, but in order to do that, you kind of also have to let go of a lot of things.

I want to hear more about that. So, you said that you've completely changed your role in the last few years. So, my first question is actually, What was it before? What is it now? And then I'll ask the letting go question because I'm really interested in that. And as you pointed out, people might have built their whole careers around something where AI can now do that thing better. I read a lot of stuff around product managers, and they pride themselves in writing product specs and various things that they do. Now AI can do all that stuff in a fraction of the time, so much better than they ever could. That's a real— that could really be very unsettling for people.

Yeah, I mean, I think largely the white-collar workforce is going through an identity crisis. Yeah, and I've been in the C-suite in various— running various functions and cross-functions for 15 years now, right, over 15 years. And that work largely was orchestrating work. It was guiding medium and large teams to execute strategy, but I was not doing a lot of that execution work. I was making sure that strategies were set. There was a lot of communication to make sure that teams were aligned, a lot of negotiation of resources, representing, you know, in conversations, the stakeholders that I was effectively representing to ensure that, you know, the ball wouldn't get dropped on a certain initiative, or to ensure that, you know, our priorities that we set at the beginning of year were being delivered with fidelity in all our decisions. And so it was really about being a connector and driving strategy. And over the last couple of years, it's really shifted a lot to this place where I am largely executing in concert with people that I'm guiding to deliver strategy. You know, we are building the strategy as an executive team, but at the same time, I'm able— I don't have to negotiate for resources You know, I am the resource, and I can be running 3 dozen tests simultaneously to see what's going to yield the best outcome, then implement it, you know?

Mm-hmm.

And so, we don't have to rely on technical resources in order to implement anything anymore, nearly anything. And that's created, I think, a real shift in both velocity, but also the the depth by which we can execute and breadth. That's been a good thing. On the flip side, I, the way I describe it to other people who don't live in my world in tech is, you know, we used to, as leaders, we used to go to, I don't know, 9 meetings back to back.

Mm-hmm.

And we would be running from one strategic initiative to another. And our job was to make sure that the trains were on the tracks, that something that, you know, in in executive committee we aligned on that was different, say we had to change a strategy, right, that that would get implemented all the way down the chain of command. And that was taxing because you were just running from meeting to meeting to meeting. There was a lot of context shifting there. Well, today we're having all of those same conversations and more, but instead of shifting context from one meeting to another because you're leaving one room and going to another room, We're just having all of those 9 or 12 or 20 conversations concurrently, and they never end. And so, that is, that is, I think, a very real condition that executives and a lot of other, you know, ICs, I think, like skilled ICs in the workforce are experiencing right now.

What does that shift do for your capacity for overload, for mental health, or for even focus?

I think it depends. For people who can sort of absorb the cognitive, the complexity of like, you know, that level of existence, I think it can be very empowering because for once, you know, the fact that they are, that they're constantly like jumping between topics or they don't, they don't have the ability to like long focus, you know, They're actually, they, they're actually at an advantage in this new world.

Those with ADHD will survive and thrive.

Thrive, really, right? But then at the same time, I think, um, even like for me, at some point I realized that I could only hold so much in my head. So I had to build a lot of systems around me to, to, to really hold information and like remind, build in like systematic reminders. So I stayed on track, um, because, you know, I'll have, I have over 20 strategic initiatives that are running concurrently right now across all of the different parts of my life. And there is no way I think that I could have continued to execute at this level with— without sort of some systems in place.

So, your solution was not even to personally expand your capacity in some fundamental way. It was actually to build lots of systems around you that allowed you to— it's sort of like you used to have 4 arms, now you grew 10 more. And in order to track them all, you need a system.

Yeah. And, and then I open sourced it and made it available to everyone and have been like giving people trainings. And the real— the thing is like, I think in AI, in the, in this sort of agentic AI world that we're in now, or the stage of AI that we're in now, a lot of companies are popping up as like application layers that are sitting on top of foundation models. And most of those companies are not gonna be around in the next 5 to 7 years because I think what people are gonna realize is that you can just build it yourself. Like, I could, I could have monetized the thing that I built, but I would rather, I think, more people not have the level of cognitive overload exhaustion than that they probably are experiencing and just ended up open sourcing, you know, some stuff.

Interesting. So, I mean, we can go down that track, but I wanna stay with what, what did you, what is, so what did you have to let go of in order to get to this place where you're at? And I get the sense that you're in a pretty healthy place. Like, you've, you've made your peace with what it is, your new role. You haven't, felt like it's happening to you. You've really jumped into it and made it yours and taken ownership of it. And that I think is amazing. And I think some people are there and some people are very much at the, oh my God, this is, this is happening. And I don't know what to do about that. So what have you had to let go in order to get here?

Yeah, I think, I think the number one thing that people are going to have the hardest time letting go of is the clout that comes with a title, the expectation of what you're due or how much time you've put in, because that's not going to matter anymore. It's what you're capable of doing and how fast you learn and how fast you're able to apply what you're learning to what you're doing in any part of your life.

Yeah.

That's really where it's going to matter. And so, nobody's really gonna be allowed to sit on their laurels anymore and enjoy the fruits of labor from 5 years ago, you know?

It sounds so, in some ways, existentially terrifying because what is expertise then if a college student can arrive and do your role with the support of some LLMs as good, if not better, than you can because they're more agile?

I think that there is still a place— there is a place for expertise and knowledge and institutions. Institutional knowledge. The question is really around whether or not you're able to leverage that knowledge in a way that other people cannot, right? So, a lot of people in, in like the creative world are talking about the differentiator between a new college grad and someone with 20 years of media production experience, that, that core differentiator is taste, right? That's not something that is built overnight. You might not know that a certain color palette is going to be better on an image because psychologically it hits differently, right, with a certain message. But someone with years of design experience will know that. And so over time, like, I think you could get closer with relying on an LLM for some of those recommendations. But there are things that I think someone with years of experience just knows. And I think part of the reason why I was able to accelerate as fast as I did in sort of this move from being, you know, like the orchestrator to like this much more hybrid space that we're living in now is because I had years of experience working with product teams. And so, I understood sort of some of the dynamics around infrastructure design and how you would architect, you know, databases and connect different things together. And so, I was able to call out the LLM when they doing it right, you know? And those things, I think, need to be learned with experience. And so, we hear a lot about like AI slop, and that's real because the people who have the ability to design it correctly the first time, to make sure the product spec is right, you know, it's— they have that sort of gut feeling about what a user experience should look like. Like, they can apply that knowledge and direct the LLM much faster and better than someone with no experience.

In a world where AI gives us more data than ever, the leaders who stand out are the ones who also listen to their body's intelligence. That's why I've created a free Somatic Intelligence Toolkit with practical exercises and use cases. Grab your free toolkit below. Now back to our conversation. And so it sounds like you were able to leverage these AI systems and build systems Because in a way, what I'm gathering from talking to you, Annie, and I already know this about you, is you're a very— it's like you combine this very logical perspective with a systems angle to it, right?

Yeah.

And I get the sense that you have some flexibility or resilience within you just based on who you are that has allowed you to quickly pivot when the technology was available. You saw the opportunity, and you were able to let go that operator, that coordinator, and move much more into the executor role.

Yes, I think that's true, but I think it came from a place where I had spent so many years designing and driving customer experience roles and functions, and really depending on our product and engineering teams to build, like, or evolve experiences for our customers. And, you know, when you're in a non-revenue generating part of the business for as long as, as some of these people and I have been in, the primary frustration for these leaders is that, you know, that if we were able to prioritize, you know, X, Y, and Z or whatever, right, we would reduce churn, which increases revenue, but you still need to jockey against these like quick new features and like, you know, in production and sales and all of that kind of thing. And so, I was just really excited that I no longer had to do that kind of stuff.

Mm-hmm.

And that was really what I was embracing. You know, it's like, this is our time. And so, it really felt like upside for me. I know most people don't see it that way. You know, copy editors, copywriters, I think for very good reasons, even though the quality is obviously not as great, you know, if you're only using AI for content creation and you're not training it properly, but, you know, they're obviously feeling a lot of strain around job stability there. I know designers are feeling a lot of strain with job stability. And so, there's— that's a very real thing, right? And so, like, getting out of the fear state and moving into the opportunity state, I think, is important work for— and the whole industry needs to go through it.

Yeah, I completely agree. And what's interesting is that as AI evolves, it will hit more and more of those industries. So, it's not just the copywriters, it's not just the designers or the engineers.

It's everyone.

Yeah, it's everyone, as you said, across industries. What is your greatest hope for people who are going through this identity crisis?

At the most meta level, I think American knowledge workers have taken this too far. They, like, what, what we do for work has been who we are for my entire life. And at the highest level, My hope is that this no longer is true, you know?

And what does that even mean? We don't even know, 'cause we've never seen it in our lifetime, right?

I've never seen it in my lifetime. I mean, there are, like, some people that I know that, like, say, oh, I— this is my work, and that does not define me. But that is very rare, you know? And I think that you can be great at your job and still not have that work define who you are as a person. I think that those can be different things also. And so, I think there's a lot of misunderstanding around when people say that, you know? So, I would love to see that for the American workforce. How we get there, I think, is going to take a lot of ups and downs.

You know, I was at a— I was in an event that I ran in San Francisco around this topic.

Yeah.

And the conversation turned to, if the doing is not as big or is not as connected and glued to your identity, then maybe there's a being. That, that comes more into the forefront.

Do you think that that's possible? Like, what do you think needs to happen? Because I mean, there are certain steps, right, that everybody goes through, sort of like the 10 steps or whatever. Like, have you—

Of loss, you mean?

Discreanted what those are?

The, the 10 steps of, of loss? Like, uh, I forget what— there, there's, there's a model for this, right? Like when you lose someone that you love, there's like the grieving process almost. Yeah, it's very interesting. I mean, I think about this all the time, and I talk to people, and I coach people who are engineers who are going through this, who used to love coding and no longer are doing that, who used to love deep diving into something for hours and hours, and now are context switching every 15 minutes between their gajillion agents.

Yeah.

And they're really mourning. Whether they know it or not, they're in the stage of having to let go of something.

I think that's real.

I think that's very real. And I think there is the productivity gain on the other side, the velocity that you spoke to. And for me, I'm not so fond of having answers to some of these highly complex societal almost shifts. For me, it's far more interesting to ask questions. So, it's like, what question would I ask myself if I was in an engineering position right now? And I think maybe the question that I might pose to myself, of many, one would be, what's the work that really fulfills me? Is it running a bunch of agents, or is it working on something really small that's defined? Is it maybe running experiments and seeing what works? So there's almost like a— we can focus on so many things in our work, in our life. And I think I'm a big fan of consciously designing your life.

Yeah.

For better or worse, many of us in the modern North America white-collar work, we're quite privileged. And so, I think it's a huge privilege to be able to say, what kind of life do I want and how do I get there?

You know, as I think about the moments where I'm happiest, it's always been— I was born to be an artist and then to get a paycheck, I went into tech, right? And so, in order to fulfill that part of my life, I paint murals at my kids' schools, these like big 25-foot murals. It's the best week of the year when I get to take a week off and paint for 40 hours, you know? We, I think it's really, you're right, that we need to find the time where we're able to recognize and sort of fill those buckets. Most people, I would guess, don't take the time to even think about what, like, what those buckets would be because we're just so busy with kids and with the grind and keeping up with everything that's coming at us.

Yeah, absolutely. I know that you've thought a lot about the parental perspective on this, so I wanna double-click to that because I think it's very interesting. You have little kids. I have a 2-and-a-half-year-old. So, you know, those of us who have little ones, or maybe even not so little teenagers, it's even more urgent to start to think about this. What are your thoughts about how parents should be thinking about all this disruption that's happening at the pace that it's happening?

Yeah, so I have a— my son's turning 13 tomorrow, and he, he asked me a couple months ago, he's like, what is Like, do you have any ideas to like what kind of jobs we're gonna have or, and what I should study in college? I'm like, I, first of all, I think you should study what you wanna study. And because if you pick something for the sake of a job, you're probably not gonna be as happy. The humanities are, I was an English major. And so those skills I think have followed me deep into the AI era, hopefully will continue to. On the job front, you know, like one, nobody knows what jobs have yet to be created. And this is true for every era of technology disruption, right? But two, it'll probably be some evolution of what is happening now because the problems still remain, right? The problems are never gonna go away. The, the, what changes is how those problems are solved. And so, just my, my goal of that conversation, I don't know if I ever got there with him, but it was, it was to get him to really kind of continue to embrace that, like, obsessed with the problems, like just being obsessed with thinking about making sure that the problems that you're focusing on are the right ones and, you know, contemplating and never being closed to how those problems can be solved because, you know, the tools that we have available to us to solve those problems are gonna be evolving forever. And that part is what changes jobs, but the problems don't necessarily change too much.

Mm-hmm.

That's how I talked about it to him. I think that even that was like a little too abstract. So I don't know, parenting is hard, guys. Yeah.

What was his reaction? Was he like, wow, that's too philosophical, mom?

Well, I'll tell you another story. So I was like playing solitaire just the other day and he comes in and he is like, oh, are you winning? And I was like, you know, winning is such like a human construct. And he goes, oh, and he just like turns around and walks away. So I think he's used to it by now with me.

Uh-huh. Yeah. It makes me, it makes me think about flexibility, actually, to be honest with you, because it's really easy for us to get comfortable with something. It's very difficult to look into the unknown and, and be okay with it and be comfortable and be excited about it.

It's true. And we, I think, let's see, it's 2026 now, right? And so we are about 50 to 80 years outside of the period of time where it was the nuclear family, where we— where everyone was told. And so, this is like our parents, right? They were told that you do your job well, you'll be able to live a comfortable life, buy a house, have 2 kids, buy a car, have a white picket fence. And this was, you know, the so-called American dream.

Mm-hmm.

And so, we are half a generation, if that, removed from that belief system. And I think it makes sense that we still think that if we work hard, we'll get our due, right? And we can do that one thing for the rest of our life. And so I do think that it'll take a little bit of time to sort of, like, pull ourselves out of that belief system. And AI is really smacking us with it every day.

We need a new belief system that's not the white picket fence, but something more modern.

Yeah, I don't know if anybody has really espoused that yet.

Creativity is the new white picket fence.

Like, you can build, you perfect future? Is that what you're thinking?

Well, just in all kinds of ways, right? I was just in San Francisco at an event, and someone says, hey, I've built this thing that I think solves this particular problem. I'm like, wow, that's really interesting. And I was like, are you— do you have a background in this? He's like, I've never built a software thing in my life, but I built this in 2 weeks. And so, the ability to create and build That's always been true in the physical world, right? Like, if someone wants to be an artist, they could watch some YouTube videos, grab a pen, and try stuff out, and they will create something.

Yeah.

Will it be museum quality? Probably not at first, but it's a possibility. That barrier of technology, of engineering, of coding used to block so many people. You can't just watch a YouTube video and code something, but now you can.

Some people talk about it as taste. I really think of it as like leaning into craft because you, no matter what it is that you're doing, you're building physical products or, you know, you're using AI-assisted coding or you're designing something to be built online or whatever it is, the evolution of your craft and your own expertise around that and how you apply your craft to the work product, that's really, I think, the special sauce that humans are bringing to this game, this particular game of AI disruption, because—

Everyone's gonna have the opportunity to be a craftsperson.

They can, and you can apply these skills to any part of life at this point. And that's the other really interesting thing, you know, is like I'm using AI-assisted coding for my personal life and for work. For Moms in Tech, you know, I just built out the new user portals, like, oh, let's make an online community replica this week, you know, that can take payments. And so, went ahead and built that. And anytime there's like sort of a problem that can be solved with technology in some way, it's about sort of taking all of the different parts of your world and pulling those skills out of your toolbox and then applying it. And that's all craft.

Mm-hmm. Mm-hmm. I like that. Crafts make— craft makes me think of 2 things, like being crafty, but also excellence.

Yeah.

You know, I think of that— I don't know why I have this image in my mind of someone in Japan who has been building—

Yes.

Little teapots or swords or whatever it is, and, and they have just deepened and deepened and deepened into their craft, uh, to the point where they make something that's so valuable, so unique, And so beautiful that anybody off the street, whether they know anything about that category or not, instantly is drawn to it.

Yeah, I love that. And I think with like this AI world that we're heading into, we, or that we're already in, that part of craft is really, I think, interesting for me because it goes back to like how I always described my work was I was the person that came in to solve problems. And it was always, like, something that was happening outside of my direct area of expertise. But because I had so many interests in other parts of the world, a lot of times the solution would come in from, you know, the art world, or music, or, you know, education, or whatever. And that is, I think, a part of crafting a solution that—

Mm-hmm.

That people without institutional knowledge, that people who only, say, have gone really, really deep in one area, right? Like, they're maybe going to be at less of an advantage of. And so, I'm actually really excited to see all of these non-technical, very sort of people of the world people that have welcomed experiencing life in different parts of the world, experiencing different cultures, you know, read all of the books, right? I'm excited for them to jump into this because I think that they're going to be building some really, really cool Yeah, I love that perspective.

Diversity of experience, diversity of culture, knowledge, thoughts, all now has a level playing field, and it will create something really different than just the tech bros.

Right, 100%, and we desperately need it.

Yeah, I absolutely agree. You know, there's something that I wanna explore with you, and this is almost like a subset of a skills set that I think is really important for AI use that I find in myself. And I think some people don't recognize that it's needed. And I call it metacognition or metathinking.

Oh, yes.

It's the thinking about the thinking. It's the, I want to design this, or this is the problem. Now, how can I think about that problem differently? And I think that that is really critical for good AI use. To go from beginner to intermediate to advanced, you have to utilize that.

Yeah, I completely agree. I think, you know, something that was interesting that happened on that front was I was supporting this Lovable She Builds event a couple months ago, and I would walk around, there were like 150 incredibly intelligent women, and some people brought their high school kids, and, you know, and a lot of people were opening up to use AI-assisted coding tools for the first time. And I think we've all been sort of trained that when we go into ChatGPT or Claude or Lovable or whatever, we just tell it what we want and then it builds that thing, but it always builds something crappy. And as I started talking to people, I would ask them, well, did you go into planning mode? Did you have a conversation? Did you really dive into problem identification and the various ways in which, you know, this problem could be approached? And the answer inevitably was that they had no idea what planning mode was.

Mm-hmm.

And, you know, just ties to your point on metacognition, which is, I think the most powerful tool of these foundational models is that you can have a deep conversation around what it is that you think you want and how to get to that point. But you kind of take like 5 steps back and you go from big to small. And AI can really help you think through all of the hundreds of ways that you can approach any certain problem. It can also help recognize that that's not the problem at all, right? By way of going through that process every single time, you get to a PRD, a requirements document, or a scope that's so much better than if you just said, give me this, that more often than not, it just builds it right the first time, probably way better than you ever would've thought of it.

Yep, absolutely. And what about being AI native? I mean, you are so clearly, I think last conversation we had, you were like, yeah, when even before Agentic was a thing, I was on board. I was running this and this and this. So, you're definitely at the forefront. I know that a lot of companies struggle to get people to move beyond ChatGPT. This is my question. Give me the answer.

Yeah, I think a lot of people are hiring for this question of AI native, but I don't think AI native is necessarily the right thing. I think you're looking for people that can be highly adaptive. And, you know, 'cause when you only hire for AI native, then you lose the part around context and craft and things like that, right?

Mm-hmm.

But if you can find people that are highly adaptive or find people within your organization that are highly adaptive and then empower them, create the systems that support change management. I mean, this, this directive around AI adoption is such, it's like at a core, a human condition of change Right? And that's not something you can slap licenses at and then make the problem go away. And this is the big failure, I think, of tech leaders and leaders across all companies today is that they're just, they're doing exactly that, right? And then they go ahead and lay off the leadership layer that is going to be needed to drive the human change management. And this is, I think, where some organizations are doing really well and where others, many others, are just failing miserably. AI-adapted is, is I think where companies are going to win. Taking people with the craft, finding the people that are really just curious, naturally curious, and going to jump in to solve problems, and giving them the ability and the systems and the support to drive change management internally.

I'm almost seeing like this really lovely formula, Annie, of what are the skills? What are the qualities? You need curiosity, you need adaptability, you need a craftsmanship mindset. And then what are the support resources around those qualities? And that's the system thinking, the metacognition, the ability to move from execution to planning, back to execution, back to planning.

Yeah, and I think from a leadership front too, something that's really important is, and some companies are better at this than others too, is creating space for tests that aren't always going to yield return right away. When you are on like a 30 or a 90-day business cycle and you have to show very immediate returns, it's almost necessary to make the test really small in order, and like very controlled, so, you know, the stakes are less high, and then roll it out more slowly within enterprises, because otherwise the expectations are just gonna be too unrealistic, because change management, human change management, takes time. That is not on a 30 or a 90-day schedule. And that is a huge disconnect between leaders and workforces.

I think right now, at its worst, what I see is leaders forcing people to use LLMs and AI tools as if, as long as my people use these tools, everything's gonna be great and we're gonna win.

Right. With no training.

Such an oversimplification, right?

No governance.

And I do think that the leaders themselves also need to model this. I have a great example of a client that I'm working with. Engineering, CTO, CEO are in a room together. Oh, the whole C-suite. They're having a meeting. They're talking about some sort of important client-facing dashboard that needs to be created. 15 or 20 minutes into the meeting, the CEO plugs in his laptop, says, are you trying to build something like this? Everyone's jaw drops.

I love it.

You know, they've just spent 20 minutes talking about it. He just built it.

We need to see more of that. You know, we need to see people who have, who are at the helm modeling what they both want to see, but also modeling what's possible. If we give people the support and the tools and the ability to grieve what they were doing before while embracing what's possible, I think a lot of people will be pleasantly surprised with the roles that they evolve into over the, these next couple years.

Thank you, Annie. This has been a pleasure.

Yes, same. It's been great.

Really appreciate it.