328 - Christy Lake (CAO, Twilio) on designing for a future nobody can see

0:00Christy Lake: You get a company that's got a headline, oh, you know, we're taking out 40 % of our workforce and we're doing this. And you're like, gosh, what do they know that we don't yet have clarity on? And we kind of came up with this three horizon view. The first horizon is like the actions that we're taking in the here and now that we feel very confident that we need to do to enable us for whatever's coming ahead. The kind of second horizon are bets that we're going to place and where we think things are going. It's kind of your 12-month zone where we are starting to have a little bit more clarity. And then we just parked a whole bunch of stuff in Horizon 3 that were these like really interesting, really provocative ideas or articles or things that are being researched that were like, we don't see an application in the near term.

0:50Christy Lake: And that's a little too futuristic for it, but we're watching it. We're going to watch the space and see what becomes of that thing. You're listening to the Modern People Leader Podcast, where we go behind the scenes with today's top HR leaders and work experts. We talk to them about how they've gotten to where they're at, what they do every day, and what they see coming next for the future of work. Hope you enjoy.

1:17Chrissy, this is our eighth recording in the last like 11 days. And so, yeah, this is like a little recording marathon that we've been on, but we're so happy to have you here. How's your week going?

1:31Christy Lake: It's great to be here. It's been a very good and active and busy week, but so far so good. Love to hear that. Daniel, I was literally taking a drink of coffee as you said that. I was like, man, I'm like powering through. It's been a lot of podcasting. Yeah. What a great way to end our week, y 'all. Right. This is my second of last meeting, so it's going to be strong. Nice. Well, Well, Christy, we start every episode the exact same way. And that's with something that we call good news stories. So we all go around and share something. Could be personal, could be work-related, just whatever's coming to mind for you.

2:06Christy Lake: Well, I have two children. Both of them started back to school this week. But I launched my oldest child into high school. So we have entered a whole new chapter of education and independence and experiences. And so it's been really great to see that launch. And Steven, both of your daughters are in high school now? Or was Cora in high school last year as well? Yeah, no, Cora's a freshman. So I have a junior and almost eight-month-old boy. And so I'm experiencing the extremes right now. But honestly, it's really beautiful. like teenage daughters, like seeing them with my son. It's like walking to the room.

2:54I'm like, what is happening? Like, this is just, you know, it's different. And even experiencing it is like different, but it's amazing. So the, yeah, Cora just started and she loves it. Her schedule, she goes to an all girls school. I got the full debrief. And if I can take the mic, I'll give my good news is the girls with two teenagers like smooth transition is important and I reminded the girls last night I have them Thursdays and every other weekend so I just saw them last night for the first time this week and I was like yeah like a couple years like there were it was like two months of like I can't believe that these are the people I have to have lunch with kind of conversations and they were like what are you talking about so smooth transition whether they remember the pain or not I'll take the smooth transition and I've got a weekend of soccer ahead I've got my oldest daughter plays for a national club team and they have a big tournament in college station so fun times for me watching soccer yeah yeah fun drive but I like the one-on-one time at this stage in their lives like that's it's a fun fun thing I'll take the soccer mom duties for sure.

4:13Soccer dad duties. And on that note, like, you know, this is, this is my third time, like solo dadding for a weekend. Christy, I have a 15 month old and my wife is on a bachelorette party this weekend. She left yesterday. And so night one out of three check and it went really well. And I think I'm going to take her to, we have this beautiful wildflower center here in Austin. I think it's called like the Lady Bird Johnson Wildflower Center. So I'm going to take her there tomorrow morning, I think. And then there's this place called the Thinkery that's like this interactive museum for kids. And I think the plan is to take her there at some point this weekend.

4:56So we've got a full agenda and I get solo Lena time for 72 hours, which I'm looking forward to enjoy and so christy walk us through the story i mean you have some pretty impressive companies on your resume now you're at twilio as the chief administrative officer give us like the origin story tell us how you ended up where you're at you know we hear all kinds of stories in the podcast and i'll never forget the story that was told about a mexico beach fmla backfire One of their employees was out on approved medical leave and then somebody spots them on Instagram. Feet up on the beach looking a little too okay for someone supposedly recovering.

5:40So cue the call from the CEO wanting to pull their leave and all of the panic that followed. But here's the thing. There's actual legal precedent that says a photo isn't proof of anything. You can't just yank somebody's protected leave because of how a vacation pic looks. You need real evidence. And that's a trap a lot of HR teams fall into. Making a compliance call based on gut instinct instead of actually knowing the law. And that's exactly the gap 650 has built to close. 650 helps teams manage compliance across the full lifecycle, from handbooks and policies to agreements, legal updates, and research.

6:16And their AI-powered research center gives you a way to ask employment law questions in plain English so you can better understand what applies and where. Because compliance calls shouldn't be made on gut instinct. they should be grounded in real legal clarity. For those of you that want to learn more about 650, go to the link in the show notes and let them know we sent you.

6:35Christy Lake: Well, I'll try to give you the short version. I was a math major for a number of years. In college, I switched to being a poli-sci major because I thought I wanted to be an attorney. And I graduated and took a job as a recruiter. And so, you know, that is the storied career of how everybody gets started in HR. It's like, we didn't really know what we wanted to do. There were a variety of different things. I started in this role and I was like, gosh, I really love the business of people. I have always enjoyed that moment of connection when you feel like you've given someone something to think about or a piece of advice, or maybe gave them the ability to have a different perspective on something.

7:13Christy Lake: And so that was my first foray. I spent kind of the first five years of my career across two different consulting firms in campus recruiting capacity, moved to Home Depot for five years, had a bunch of different jobs, recruiting, did a chief of staff, did an M &A role, moved to HP for eight plus years, and similarly had a bunch of different roles, talent roles, M &A integration, took my first HRBP role. And I guess I would say from that point forward, they've just been HR business partner roles of increasing size and scale and capacity. So I spent time at Medallia, Box, and now Twilio for the last six plus years.

7:51Christy Lake: Last year, I started leading the legal team, which is when my title transitioned to CAO, which is sort of an amorphous title, which means I think you own more than a few things. So now I lead the people and legal team together, which is to say two separate organizations that I lead in parallel. And it's just been a ton of fun learning, growing, seeing new things, experiencing the different, the business from different perspectives. Just curious, from what I've heard, I've never sat in a chief of staff role or an M &A role, but from what I've heard, those are both very challenging roles. When you think back to those times, like which would you say was more challenging for you?

8:37Christy Lake: In different ways, they were both incredibly challenging. The chief of staff role, in the context that I did it. Basically, it was a highly developmental role where our CHRO had you as a ride along. And so I attended every meeting that he was in with the exception of like one-on-ones with the CEO, various board sessions and other one-on-ones, but actually quite a number of those one-on-ones I would be involved in if they were talking org design. So it really gave me the opportunity to be in that kind of right-hand seat, to understand the breadth and complexity of business that he was engaged in, to see his decision-making process, how he engaged in different sessions, the way that he operated, so data-driven.

9:23Christy Lake: But in that way, it was grueling. It was a retail business at Home Depot, which is where that role was. We had six days a week that were basically scheduled. It was your five business days and then a half day on Saturday, 7.30 to 12.30. We were in the office conducting meetings like nobody's business. And so it was just physically grueling, but so impactful. One of the best roles I've ever had, hands down. My wife is a chief of staff at a 12 ,000 employee company for a C-level executive. And it's just fascinating like that role and what the the skills required to be an effective chief of staff it blows my mind and she's amazing at it um the so twilio i i i know i founded a company that had um mobile capabilities and so and we use twilio as part of our solution as an extension of our solution.

10:23And so I know very well what y 'all do. But when someone asks, what business are you in? How do you explain to them the core business?

10:32Christy Lake: Yeah. Well, once I get over the fact that we're not truly a real estate company, I explain to them, I mean, there are probably two different use cases that are more easily understood because it isn't household brand. I think if you're a developer, if you're anyone that started a business and you have customers, people are more familiar with Twilio, but one of the easiest use cases is like when you log into your bank or any other more secure app or website, often they have two-factor authentication enabled and you will get a code on your phone that gives you the number that you need to access your account.

11:12Christy Lake: We enable your bank or whatever that company is to get that code to you in a very secure and efficient manner because we have built all the API pipes to the different carriers. And while it seems simple to just get a text message, there is a mountain of complexity from compliance and regulatory. There is a ton of complexity behind the scenes that we abstract for customers to allow them, to allow companies to communicate directly with their end customer. Another use case that I reference, I have a Rivian and Rivian is one of our customers. They are using us to handle all of their kind of final mile customer communication and engagement.

11:54Christy Lake: And so in a highly contextualized way, when I open my Rivian app, it understands who I am, all the experiences that we've had between company and customer. It has all that context so that when I need something, they already know I got new tires a month ago. I was in for some battery service thing, you know, six months ago, and they have all of that history. And in one place can tie together our phone calls, our text messages, the chats that we've had on the app. And it's like, we're just picking up. And so providing really a delightful customer experience using our full platform to enable these like highly contextualized engagements that I can now have with Rivian where I don't feel like just another number.

12:36Christy Lake: I'm like, oh, I'm Christy, your customer, and you know everything that we've done together. So that is another use case that's maybe a little bit more understandable about how Twilio kind of powers those interactions. That's a great example. And my dream car is a Rivian. My wife probably wouldn't like to hear that. She works at Toyota, but I would love to have a Rivian one day. So before we get into some of the planned topics, I've been asking this question to every people leader that I talked to over the last probably a month or so, I've had about like 11, 12 of these like off the record conversations and the responses have been so good.

13:14And so bear with me and hopefully this is okay. But what would you say is the hardest thing on your plate right now as a chief administrative officer?

13:23Christy Lake: Well, I mean, there are a variety of things in the broader capacity that are interesting. I would say a lot of it boils down to AI, which is, I imagine, the answer or some flavor of the answer that you get from everyone. It is, look, work has changed and evolved. I've been at it for decades now, and we've been through seasons and cycles and new technology has come in that's changed the way that we work and new leadership philosophies, new even office ideas. Gosh, when I started, I was in a brown cubicle somewhere, and then it was open floor plan and, you know, all these sort of changes to the way that people have worked.

14:01Christy Lake: Nothing has been more transformational or I imagine will be more transformational than the introduction of AI to the way that we work. And I think the hardest thing about it is like, A, just navigating the here and now. Like, models are changing and updating every single day. The way that you even AI effectively changes every single day. And so it's not like, oh, I learned, I'm just going to say like Microsoft Word, you know, because that was a big deal when it came out. Like you learn it once. Yeah, they make improvements. They'll happen with some cadence, but it's like on the margin. Once you figured out how to work in a cloud native way, like it's kind of intuitive.

14:42Christy Lake: AI is so dramatically different. The capabilities are evolving so dramatically. So So there's the upskilling, there's the security aspect of it, there's the data and governance aspect to it. So all of that is incredibly challenging in the here and now. But I think the thing that is even harder is trying to be as smart as you can about designing for the predictions of like, where is this thing taking us? And that is where I think like zero of us have a crystal ball. We're all prognosticating what do we think is next? How do we position our function, our company, our people to be successful in whatever that new model is?

15:29Christy Lake: How do we actually do the change management and kind of start to design the from to? And I just think that crystal ball feature has never been more opaque or maybe more challenging than previous times of change or cycles of change that at least I've lived through. I'm just curious.

15:52Prior cycles, it felt like there was a playbook that was developed pretty quickly because we're already a few years into this and it doesn't seem like there's a clear playbook. And that seems different to this cycle than prior cycles. As a consultant, I know the consulting world is usually part of identification, ideation, formulation of the playbook. And then it's applied. That knowledge is shared and learned and then boom. It doesn't feel like that's what this market is like to me. I'm just curious what your thoughts are.

16:32Christy Lake: Totally true. True. I mean, you have, I think when you think about previous cycles, you would see the evolution of some new technology. You'd get your big, you know, system integrator consultancies out there that would start to develop their playbooks. And you have this sort of predictable three to five year window of change when you have your early movers, your late adopters, whatever. But they're like, great, we can go run this play. Small, medium, you know, enterprise size businesses, choose your own adventure. I've never seen a disruptive technology that comes with so much uncertainty, the pace of change, so that like the second you had whatever the playbook is, it's like out of date.

17:17Christy Lake: And candidly, I'm just going to use the word fear. I don't know what else to attach to it. Not only like at the base level job loss, like and relevancy, like am I still relevant? Is what I do still going to be needed tomorrow? like that's some pretty core fear that is very understandable and very human but you have it all the way to like the will this destroy humanity you know you've got like climate political but also like i don't know are the robots going to launch the missiles like it is nothing that I've seen has come with this large an aperture of change, uncertainty, pace, and risk. And, you know, I'm sure like there's a spectrum of all of that, but like, I don't, I'm not familiar with anything that's been bundled that way.

18:07Christy Lake: Have you seen anything like that? No, we haven't. And, and you mentioned, this is hard for several reasons. You mentioned security, upskilling, and then you said the prediction piece is the hardest piece of all of that. Are there, as the chief administrative officer, are you being asked to make some predictions about what work is going to look like or just where all of this is going and then what the strategy should be? What are some of the predictions that you feel like you're being asked to make? I feel like I just set myself up for that question. Darn it. But no, I mean, no one is like holding my feet to the fire and saying, where is this going?

18:48Christy Lake: That said, as a functional leader, like I and my team, we have a responsibility to help to the best of our ability guide the company through this. And that does mean having some forethought and foresight, if we can, to point us in a direction. And so a couple of years ago, we invested in building a skills infrastructure. because it was like, you know, roles as we think of them today, their componentry is skills. We've got to kind of get this level of fidelity if we're going to work in a more agile and dynamic way in the future. And so there's some bets that we've placed in terms of like getting the organization ready, thinking about the tasks that make up roles.

19:34Christy Lake: And if some of those tasks start getting, automated or can be managed through AI more efficiently? How do we think about reassembling the work that is left for the humans? Having a perspective on where we need and want and will demand humans in the loop and where human judgment is a premium and kind of designing with that as a principle so that we're not moving too quickly to automate or otherwise AI-ify bodies of work that we think will be incredibly important for us to have that human judgment. So your question was, am I being asked to make predictions? No, no one's asking me for like a hard line in the sand, but I do think it is my and others responsibility working in partnership with our enterprise technology organization, working in partnership with our security organization, our privacy organization to really have a point of view for the business as to how quickly we want to change.

20:31Christy Lake: What are some of those design principles that we have and what is the future that we're working towards. I mean, here's what I'll say. We went through a cycle of honestly, just inundation with everything, all the headlines that were being written and all of that kind of FOMO inspiring, you know, you get a company that's got a headline, oh, you know, we're taking out 40 % of our workforce and we're doing this. And you're like, gosh, you know, what do they know that we don't yet have clarity on? And we kind of came up with this like three horizon view. The first horizon is like the actions that we're taking in the here and now that we feel very confident that we need to do to enable us for whatever's coming ahead.

21:11Christy Lake: The kind of second horizon are bets that we're going to place and where we think things are going. It's kind of your 12 month zone where we are starting to have a little bit more clarity. And then we just parked a whole bunch of stuff in horizon three that were these like really interesting, really provocative ideas or articles or things that are being researched that were like, we don't see an application in the near term. And that's a little too futuristic for it, but we're watching it. We're going to watch the space and see, you know, what becomes of that thing. And so we it gave us some comfort to be working in this three horizon view because it was like, I found that mostly what we were hung up in is the stuff that was in horizon three.

21:58Christy Lake: That's so futuristic. You're like, I don't even know what to do with it. And it's like, great, we're going to park it there. We're going to watch it. So that's kind of how we're approaching it. It's so having this real kind of mind's eye kind of weak. And what I mean by that is I started a new job and I'm head of revenue. So I've like been in HR or adjacent to HR for, well, my entire career since 2000. So 26 years, 25 and a half years to HR and now in a revenue focused role at an AI music software company. And we were, you know, we are building for the future and And it is so interesting to see how the team is growing and to see what we're able to accomplish.

22:51The level of efficiency is absolutely insane. Like this is my first week. And yesterday I vibe coded. The last phase was like re-skinning it with our branding, our CRM, our first CRM. And I have a clear view on pipeline. I've got like all the activities, which isn't enough. I need to have more. Now I need to start driving activities. But like all of this is like I just did, you know, it's like Friday of my first week and I've already got the CRM in place. So it's kind of mind boggling to me. And I as much as I'm like rooted in this world, I also my mind is kind of has a also is also rooted in the traditional world.

23:34And I asked my co-founders like, you know, a question about org design and like, what does the org design look like going, you know, from here? And they looked at me and they were like, is that even relevant now? Like, it's certainly so different to what it was before. Can we use the same language and have like that kind of conversation yet? And I understood exactly what they meant. And so I just, you know, when we think about like org design, you know, I've got to imagine that that's something that CHROs and I'm asking you because in the CAO role, you have like a unique vantage point. And so like, what does that look like?

24:16And I am very much rooted already in dimension two that you described, or at least I'm trending that way, because I feel like I get surprised that we're still having conversations in LinkedIn, that headcount is at risk here. And to me, it's like what people are saying no longer matters. Yes, there is going to be an impact. If you've done any work in this, you know that. And so I know that's a lot that I threw at you, Chrissy. I'm sorry, it's Friday and I probably drank too much coffee, but like, what are your thoughts on org design and how are you grappling with it? How do you look at it? I know you don't have the answers, but just how do you start to examine that problem?

24:56Christy Lake: Yeah. Well, I mean, what's interesting about your experience as contrasted with where I'm sitting today is you're in a startup. I won't make any assumptions about how large that startup is, but it sounds like it's very small, very small, less than 10 people. Right. So, you know, there's been much written about the billion dollar company with one engineer and with vibe coding and some of the amazing tools that are available now, like is a billion possible? I don't know. Why not? Like anything's possible, but you are starting in an AI first low human sort of way. So you're not redesigning. You're just starting in a modern way.

25:32Christy Lake: And every headcount that you add will be very judicious, very intentional, and will fill some human need or some perspective or set of experience that you may not have, or you would like to be directive on the way that you're building from zero to whatever you become. We are not there. We are starting with an install base of people and roles and customers and systems. And so the transformational work will look very different than the AI first work that you can just from zero to whatever. I think it was Goldman that did some work on the task construct of work. And so you imagine for every role, you are doing myriad numbers of different tasks that have different skills associated with them, but you could deconstruct a role into a set of tasks.

26:23Christy Lake: Their analysis suggested that 25 % of all tasks will be AI-able in the future, if that's a verb. And so what you're left with is it won't be uniformly distributed, but for the sake of this conversation, let's assume it's uniformly distributed. all of your people now have 75 of their role that in some way they need to engage with but a quarter of it has just pieced out so do you leave people at three quarters capacity no like you probably have to do org design to say okay if all these tasks just went away we have all these humans do we need all these humans do we need less of these humans is there new work that has come in that's filling that 25 % bucket?

27:04Christy Lake: Do we need to reorganize some of these tasks and some of these teams? When you get down to it, there's a ton of OD and OE work that will be required for ongoing concerns that have those install bases of systems, of tools, of people that have to go through this change. And then you hit the thing that I think will be the most, is the most challenging, which is always, you know, any consultancy would say change most often fails in the human behavior realm because we are creatures of habit. We have ways of doing things. For God's sake, my tabs are left to right at the top of my screen and some of my team bring their tabs top to bottom.

27:47Christy Lake: And I'm just like, I don't know if that's for me, right? Like, do I need to make that change? Is it going to make my life better? I'm just going to live with my tabs at the top. it's a stupid, silly example, but like magnify that across all the different generations that are at work. The human nature of change is the hardest final mile. And so you're going to have a lot of companies that are not going immediately to the I'm vibe coding my CRM because I've got this behemoth CRM with all of my proprietary customer data with our business workflows that have been coded into it, you know, that it's just going to take a minute.

28:22Christy Lake: And then you got to get all the people to change too. So just to continue this thread and going back to like your three horizon view. So you have horizon two, which are the big bets and horizon three, which are some of the provocative ideas. Are you able to share any examples from either of those buckets? And I, I realized like, this is probably all like very in the work. So yeah. What can you share? and if it's an example related to people and the work you're doing on the people side, then even better. When I think about our recent humans times machines conversations that we're having with CHROs, there's one theme that keeps coming up.

29:02The vision is clear, the pressure is real, but the roadmap is a little bit less clear. It's one thing to talk about the future of work. It's another to sit down with your CEO and say, here's how work, the workforce, and our organization really need to change. But I get it. There are a lot of difficult questions that you need to answer. Like, what work should we redesign? How will AI reshape roles and careers? What kind of organization do we need to move faster? And these are exactly the questions explored in Deloitte's latest Human Capital Trends Report. There's some interesting findings in there.

29:39The report shows that we're no longer balancing tensions. We're at a tipping point. The report brings together insights from thousands of leaders and explores how organizations can build a human edge. It's about moving beyond simply having humans and machines to creating a system where their capabilities multiply. It looks at how companies are redesigning work for this new future, how to shift from a mindset of cost efficiency to want to value creation, and how to move from static plans to dynamic orchestration of talent and technology. In other words, it helps turn big future of work conversations into practical leadership questions for a world that won't sit still.

30:18If you're thinking about how your organization evolves in the age of AI, go check it out. It's a great read. I read it a couple of times. So if you want to learn more, you can find the link in the show notes.

30:29Christy Lake: Yeah, I mean, Horizon One, we have the most certainty about, which is this like skills-based infrastructure, enabling systems and tools on top of that. and starting to do some of the work analysis to understand how jobs will be impacted and kind of tying that to the skills and how those will be impacted. I think Horizon 2 and the things that we're like working on now, like we have, we've done a lot of, I was like, it's not agentic yet because you can't action on it, but we've done a lot of the AI infrastructure for like some of the transactional work that we're doing in the people team. And we're looking at a lot of AI that's embedded in the tools that we're using.

31:11Christy Lake: So not uniquely things that we'll build. But there is a lot of, there's a lot of thinking on like the employee experience and the UX. Like increasingly, I don't think people are really going to be interested in doing like better search, you know, with all of your internal systems. People want one prompt box that has all the connectors to the data sitting behind it, that you can just go action. And if you can put a Gentic on top of that to take independent actions for you, like even better. And so I think that's the space that we're doing exploration on. We're not yet there, but we've got some POCs going on, you know, some of the agentic work and I think are trying to hardwire as much AI-ification of the transactional work.

31:55Christy Lake: Horizon 3, we don't have anything going on just in full candor. That's like the space that we're watching for like the research that's being done and the theories that other people have and like kind of watching to see where things might go. but not any investments that we're placing in that. I think connectivity is going to be like the, a major, major area of focus for the EX. I just like in the way that I work, there's so much connectedness. My cloud is like literally connected to everything. And it's like, because of that I'm able to do so, so much. And yeah, switching that to going back, going to a world where like, I can barely I'm using cope, my company's using copilot and barely, you know, barely connecting to anything.

32:50Like, I think that's a real EVP differentiator, like, easy way to just make it lovable to come work, work with you. And so I think that that's that super, super smart. You know, when you think about like when you look into the future do you have any any hypotheses in terms of and all the the demographic you know the demographics of the workplace when you consider that do you have any other beliefs like things that are going to be really really important for the employee experience

33:24Christy Lake: i think you're right that people do want things to be modern and smart and easy and approachable you know do i have any predictions i think ux is definitely at a premium people aren't interested sort of the headless app is the way of the future people aren't interested in having all their real estate taken by 27 different unique siloed things that they need to get their work done that is true i think the thing that i hope that people will pay attention to is not moving so fast to the agentic and the outsourced that they're losing visibility or focus on where the human in the loop matters. And I'm certain it's the seat that I sit in where I do think a lot about people and capability and organizational capability, but I just think it's sexy to look at, you know, what do we not have to do anymore, But it's just as important to think about what do you want your people to do?

34:32Christy Lake: And what are some of those critical skills that are going to be required? And how do we make sure that we're nurturing those and not losing sight to them? Because everybody's, you know, going to be in their sort of one prompt box, just working away happily. And on a similar note, we've talked a lot about the future and some predictions and where this is all going. What do you think is not going to change specific to the employee experience? What's going to be more important than ever? it's a great question i think i think people still have core human needs to be seen to be recognized to be thanked to feel like they have a relationship with the people that they work with like what i do and how i get my work done should be frictionless and high impact but to the extent that I'm not that one engineer working solo, like I still care that I'm working with humans and would like to be valued for the contributions and my intellect and the things that, you know, that I can bring to our work.

35:46Christy Lake: And so I still believe that there is criticality around, you know, they used to be called soft skills. Now I don't, now they're being called power skills is the new one that I heard of, but like that being effective as a human still matters a lot. And so as I was like preparing for this, one of the topics that, that I saw come up again and again in the prep notes is remote first. And, you know, I want to talk a little bit about that because we, Daniel, having launched a podcast literally during the pandemic, you know, we know we've had a few conversations and quite honestly like there was then the narrative and conversation flipped and then we never had that conversation and which was good I needed just some time away from it but the it's come back up a couple times in the last like month and I realized like you know I miss this topic there are a lot of big bets and hypotheses you know thinking about like trying to figure out where everything was going.

36:57Like we were in this, it's kind of a bizarro world because we were in this situation, you know, not so long ago in a completely different context in terms of like, you know, do we need to be physically co-located to do good work? And I think there are, there are pretty varying views today. And so I'm curious like where you have ended up, or I guess some of the hypotheses that you had and, you know, what you've learned and kind of where y 'all are at. So yeah, tell us a little bit about that.

37:29Christy Lake: So I joined Twilio in early April of 2020. People had just been sent home a couple of weeks prior and we were in the thick of trying to navigate remote and it wasn't an option. Those days it was just everybody was remote. But as the year went on, it became more of an option. And that's when the RTO conversation started heating up. So we, I think it was in 21. We never called people back and we finally affirmed our remote first posture. I want to say it was in 21 and we've stayed the course and it was controversial is not the right word, but not necessarily the normative decision at the time, because you had lots of companies that were like, you know, it's gotta be five days a week and we're losing the hallway productivity and whatever it may be.

38:17Christy Lake: And as I said then, and I'll continue to say, different companies are optimizing for different things and they have different designs. And so whatever works for you is great. But at the time that we made the decision, we decided to be data-driven. And we also set down a list of design principles that we were kind of working against. So from a data perspective, only 15 % of our teams were co-located, meaning that if 100 % of you were going into an office, only 15 % of you were going into the same office. Otherwise, you were going into an office to jump on Zoom to talk to your teams globally. And so this notion that there was this like team level productivity was sort of busted when we looked at the data and we were like, in fact, we're already working in a distributed way.

39:07Christy Lake: Now, do we think there's benefit to being in an office, even if it's not your team members? and is that benefit outweighing the challenges or downside? And then we referred to these design principles. And number one was you can be effective from anywhere that you are. That impact matters more than like in-person presence. That we would be a net talent winner because we could hire talent from anywhere. and we would have access to talent pools that otherwise wouldn't be available to us if they were just proximal to the offices that we had at the time. And collectively that led us to make the decision that we were gonna stay remote first.

39:51Christy Lake: And along with that, we took a decision that we would keep one core office per region where we could host teams, do offsites, whatever, have our meetings, but that we would offload all of our other offices. And over the course of years, we have done that and kind of burned down our real estate. And the money that we saved from that real estate, we intentionally put into T &E so that we could support team offsites. Because one of the other things that we anchored on is that connection matters. That trust is non-negotiable in an environment where you're remote first. And that we believe some in-person experiences, team building, relationship building, shared experience is one of the best ways to support and nurture having a high trust environment.

40:40Christy Lake: And so we made all of those investments. We have stayed the course and it has really proven to be a success story for us. We absolutely have been able to invite and retain talent to our company that would not have been available to us if location had been a thing. We were a net winner when others were calling people back because we had lots of people that came to us and were like, we're not going back. Like we're coming to Twilio. And so the talent has been incredible. We've seen engagement up into the right, like every single quarter retention is growing alongside tenure is growing. And so we've really been able to, I think, have a recipe that has worked for us.

41:29Christy Lake: Now, I say that not to be preachy, but those were the decisions that we took. Those were the principles that we designed around. And it has proven to be successful for us. Not every company can do that. We don't operate labs. We don't have requirements for various in-person things. So the nature of our business allowed for it in a way that it may not be for others. I'll never forget, me and Steven were in New York maybe a year and a half ago. Could have been a little bit longer. And we met up for coffee with Annie Dean, who at the time was head of Team Anywhere. I could be getting that wrong. Head of Team Anywhere at Atlassian.

42:08And she kind of blew our minds. And she had this really strong hypothesis that remote first companies were going to be the leading AI-first types of companies as well because there are cultures of documentation. All the note takers are in every meeting and the more things that you have documented, the more you can feed back into the system and create this org brain of sorts. Part of that equation that we didn't talk about at the time is the talent. Not only can you tap into the technology better, but you're going to be able to recruit the best AI talent or just the best people in the industry.

42:49And so fast forward to today, and I imagine, you know, Twilio and the other remote first companies are probably a little bit ahead on the AI front. But now what we're starting to hear, and this is more so from like, I mean, we don't have like hard data on this, but this is what I'm hearing from my friends that work at these types of companies, and from some people leaders is that now that there's like this, I don't know, like this AI burnout of sorts, like people are burnt out at work. And if they're in like this remote first environment where they're now being asked to do more than ever. So like they've been able to eliminate the 25 % of admin work, but now they're operating at like 125 % capacity because they have all of this technology at their hands.

43:39And because their company is set up in a way that allows them to do that, they're now just feeling, yeah, they're exhausted and they're like tired of hearing about AI. Does any of this resonate? I know I'm kind of rambling here, but is this something that you're hearing either from your employee base or from other people leaders that you talk to?

44:00Christy Lake: Yeah, it does. And I mean, I think there are a couple of things to unpack in there, which is, you know, when you think about the burnout that people had during COVID, it was a whole bunch of things that were compounding at the same time. Like maybe you had a family at home and you had to figure out the homeschooling thing for your kids. Like, seriously, that's a full time job. Now you're all in the same space. Jesus, God, I loved you six hours a day, not 18 hours a day. You know, like you just had all these things. Plus you had the fear, the health concerns, like, you know, there were very real things that people were dealing with.

44:37Christy Lake: At the same time, they were dealing with this new way of working that I'm used to being in person meetings. And that takes a different type of energy to read the room and observe the signals and participate in the conversation. And now I'm staring at the screen and the blue light and whatever all day long. And my God, is this exhausting? and it's really not filling my cup in the way that like having a laugh with a co-worker used to before now I'm just meeting to meeting to meeting there's no water cooler time so you had a whole bunch of stuff going on there right like that was a super stressful time then it feels like we kind of settled into this well this is just how we work and like if you didn't get yanked around you know I moved across the country now they want me back in Seattle like whatever like you know if you navigated that period of time, like you just are in this norm.

45:23Christy Lake: You have another massive disruption that's happening with AI now. And to the best of companies' abilities with upskilling and with rolling out programs and rolling out tooling and policies that govern what you can and can't do and yada, yada, yada, you have another of these super disruptive cycles. And going back to the top of the call, when we talked about like, you know, why is this period so different? it also comes with the by the way you might not be relevant tomorrow if you don't figure this out by the way even if you do figure it out you still might not be relevant because your job's gone by the way like they're building a data center in your backyard like how do you feel about that you know like who knows like people are just dealing with so much but if i just localize it to work i do think this notion of like you know everyone in some level being told if you're not upskilling, the person that knows the things is going to come take your job.

46:17Christy Lake: And by the way, like, we're only going to offer you probably like, you know, 15 % of what you need to know in an organized way with training. The rest of it you're doing on your nights and weekends and you're upskilling yourself. I mean, I think that's the reality. I literally just had dinner with a friend last night who was talking about her company. And she's like, I'm leading a team of 120 people that I'm responsible for getting up to speed on the new ways of working. And no one's telling me how to do it. So I'm trying to navigate the change for myself, but also lead the change for my team.

46:52Christy Lake: And it is truly her nights and weekends that she's just trying to like make herself as smart as she can. So she can be as relevant as she can. I feel like that's what's happening at an individual level across every company. That's my unofficial hypothesis. I love the hypothesis. I agree with so many elements of it. I think to further complicate it, it's like there's whatever the, I'm going to sound really old and probably early Texan, the old Storman, Foreman, Norman, like that, the change curve of teams, I forget what that's called. but I feel like there's something like an AI version of that and where they're like these off there is no norming you're constantly because it's like the second you figured it out there's a new way and there's a new way and there's a new way so you you never get out of it yeah well that I love that connection you probably just explained that and in my head I'm like trying to connect these dots because that's so true and you there's like a surge and exhaustion and then like a rest period and then a surge and an exhaustion and i think the other another dimension of this that i don't know if i this came up in conversation probably on the pod that the the number for those that are like actively adopting AI, the number of like menial tasks that we used to deal with is going away.

48:27So like, there's no more like hiding behind a spreadsheet or just like, you know, getting comfort go nerding out on a spreadsheet anymore. Because like, guess what, guess who's better at spreadsheets, apparently Claude, right. And so now it's just like complex task after complex task after complex task. And it's like, when is this ever, is, is this ever going to end? And I think it's that like lack of norming that is kind of feeding this loop of like never ending, like, and I could see how for some that turns into like perpetual doom. It's like, oh no, like it's just a spiral that keeps going.

49:03Christy Lake: And you're, when you're always being reset to learning a new thing, you never get to enjoy that period of, you know, what would be called mastery. Like, oh, I've got this. It's like all of a sudden, oh, no, but I don't got this because there's a whole new way. There's no mastery. Yeah. Right. So you're just, yeah, you're in a change loop. Well, Chris, thank you so much for going with us on this journey today and letting us completely hijack the conversation. We are getting to the end of it. I want to make sure we get you out here on time. And we have a couple of traditions left. So the first one is rapid fire questions.

49:42Same set of questions that we ask every guest. And question one is, what's one piece of advice that you'd give to somebody that's in HR and just starting their career?

49:54Christy Lake: Gosh, I mean, probably what I would have said 12 months ago is no longer relevant. But what do I think is still relevant for people starting their career? One, I would say go broad. Like the more well-roundedness and breadth you have to your experience and your exposure, the bigger your aperture can be, the better business executive you will become. So I think context is always incredibly important. And so I would say rotate around to get as many experiences as you can. always say yes to sort of ancillary opportunities to dig into different things. And if I could do like advice part two, I would say everyone in every function is a technologist now.

50:38Christy Lake: And so you no longer can just be a practitioner where you know sort of a functional craft. We are all technologists. And so while you are going broad, be very curious and very adaptable to whatever the tools in tech are because it's just the one prompt window now. So you've got to be good at it. Got to be good. You got to be good. Next question. If your team gave you a superpower nickname, what would it be? I mean, I have no idea, but I think because I have a few areas that I look after now, I'll go with Captain Cross Functional. Oh, I like that. Oh, that is really good. Next question. What's a strategy or practice from another company that you would love to steal?

51:29Christy Lake: I don't want to give you a non-answer, but what I believe to be true is that you can learn from all different companies, all different industries, all different sizes. I think there are practices and approaches that you can learn from any of them. But what I also know to be true is every company is different. Every culture is different. And so what works for one may not work for another. So I think maybe just be a student and be like an observer of lots of different companies. But I can't say there's like one thing that I'm like, man, I wish we had that thing because it probably wouldn't work here.

52:06Christy Lake: Not because we're like super special, but just because, you know, every company is unique. I feel like once you have that consultant mindset, I relate to that as a fellow consultant, former consultant. And last question, you know, we've been so fortunate. Daniel and I have been doing this for years. We've had so many like insane guests on the show, many of which because of this question, the last one, who should we have on the show next? Like if there's a HR voice that you think an innovator out there in the job, like who deserves a spotlight? Well, I did not do my homework to see all of your past guests.

52:42Christy Lake: So I apologize if this is redundant. And actually, I've never met her, but Avani at Atlassian. You mentioned Annie earlier. I was in a forum where she presented some of the work that they've done. I think Atlassian has always been a company that's been on the front end of work and doing a lot of research and investing in teams that are thinking deeply about how work is evolving. And so they have often been a company that we look at to just understand where are they looking? How are they thinking about things? And so I imagine that would be an interesting conversation if you haven't already spoken to her.

53:16We've had Annie on and we've also had Molly Sands, but we've never had Avani. So we would we would love to have them. Final tradition is one word or phrase close. So whatever, you know, whatever is is swirling in your in your mind as we close this out. And it could be anything.

53:34Christy Lake: Something that I say regularly, it's a core belief of mine. everything good is downstream of curiosity. Like if you start with curiosity, it will lead you to discovery, awareness, insight, perspective. But if you are not a naturally curious person, it's really darn hard. You're going to have to force yourself to go through learning cycles. And so I think just adopting a practice of curiosity is beneficial in so many different ways. So that's something I find myself saying a lot. I don't have a word or few, but I have a feeling that it's going to be hard for me to work after this. Such a perfect way to end the week is my phrase, Daniel.

54:21What do you have? I'm going to say Horizon 3. I really want to know what the research is saying. I should probably be more tapped into that. And I don't even know, where are you looking? Guys, did y 'all see that? I forget some big company announced. Was it that the singularity had had, that has been achieved. It was like, God, the payments, the payments company. Oh my God.

54:48Christy Lake: Stripe. Yeah. In there, like an investor memo. Yeah. Check that out. So not to me, that's the horizon three stuff. They're like, I have no, they're like, we strongly believe that singularity was achieved in like in Jan. man. Check it out. It's wild. But to me, that's the horizon three stuff. But. Wow. Well, that's a good way to end the episode. Chrissy, thank you so much. That was amazing. We would love to have you back in the future and hope you have a great weekend. Pleasure. You as well. Good luck on the pitch this weekend. Thank you. Bye. Thanks for tuning in to another episode of the Modern People Leader.

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