Giant Robots Smashing Into Other Giant Robots

Chad and Lindsey take listeners behind the scenes and go deep into the nitty-gritty of recent thoughtbot company changes driven by the pandemic and the organization's need (and desire!) to go fully remote – all while reaffirming and revisiting the organization's values, mission, and purpose as part of the process. Become a Sponsor of Giant Robots! Transcript: CHAD PYTEL: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel. LINDSEY CHRISTENSEN: And I'm your other host, Lindsey Christensen. And we're back. Thanks for tuning in. CHAD: We've missed you. LINDSEY: Yes. We’ve been kind of busy. CHAD: We've been busy, and we knew we were going to take a break after the last season. We didn't necessarily know for quite how long, and then a whole bunch of stuff happened, which we're going to tell you about today. From the last episode, you heard about the change to the thoughtbot CEO, and we alluded to some changes that we've made to the company. And we're going to talk about those today. LINDSEY: Yeah. And in true thoughtbot Giant Robots fashion, we’ll go behind the scenes and give you the nitty-gritty of why things happened and how it's going because it's all really interesting. CHAD: Yeah. I think on the surface, it's really easy to think about how maybe these changes have been entirely driven by the need to go remote or the desire to go remote. And the reality was that's an important part of it, but it really was so much more than that. Some of these changes that we've made are ones we've been talking about for a long time. And it wasn't until almost a year of operating in a different way that we said, “We need to make some of these changes in order to accommodate remote and working from anywhere.” And we fell back on a lot of other problems we needed to solve along the way. LINDSEY: So we actually decided to break out remote work into its own episode, which will be the next episode. And I'm sure it's going to come up today, but it's a whole other area of changes and focus, whereas some of the reorg changes that we just underwent solved a lot or are trying to solve a number of challenges that we've been working on over the years. So I guess to start off, before we reorganized, how did we function? And that was largely geographically based. CHAD: Yeah. And the geographic basis means that we had a studio in a city, and in that studio, we offered the complete thoughtbot services. And that was driven by this idea back in 2012 when we started to expand. Prior to that, we really held the company to less than 30 people. And we were primarily a group of people all in one location working together, and we were all of what thoughtbot was. And we really liked that. We liked the structure. But people wanted to move and live somewhere else. And our purpose is that we believe that there's a better way to work. And we want to share it with as many people as possible, although we've revised that purpose now as part of this process. And so I really remember the day we were having a company meeting, and someone stood up and said, “If we really believe we have a better way to work, why are we not trying to bring it to more people? Why are we losing these great team members only because they want to live somewhere else?” But we also really liked the small, close-knit team of people who worked closely together on client work. We had done some client projects that were split across teams and across time zones and that kind of stuff. And it just didn't feel as good as we wanted it to feel, especially because it was hybrid. And so we said, “We know exactly what a great thoughtbot looks like. Instead of trying to expand what that great thoughtbot looks like, let's try to replicate it instead.” And so when someone wanted to move to a new city, we said, “That’s great.” We looked at the market in the city that they were moving to and said, “Let's grow another thoughtbot around them and use that as the starting point for a new thoughtbot studio that would be a full design and development team that offers and works with all the different kinds of clients that we work with.” And that was the model which brought us to being in six cities in the UK and in the U.S. and about 100 people working with a whole bunch of clients every year across those. But for the individual person working at thoughtbot, individual designer or developer, it felt very much like thoughtbot had always felt, which was you were working with a team of three or four other people directly on that client. Oftentimes, the client would be in the same city as you. And when we could meet face-to-face with people, they'd be working in our office, and we'd be working really closely with them. LINDSEY: Another interesting element of that structure was the marketing, and community was also very locally based, so engaging in and hosting local meetups. Actually, all of our offices -- We had offices, first of all, in amazing locations in all of these tech hub cities, and all the offices additionally had space for specifically events and community type of activities. And we thought a lot about nurturing local community, creating local partnerships. Obviously, we're thinking a lot about the hiring pool, and nurturing potential future hires in those cities as well. CHAD: Yeah, and that's what we had done in Boston where we got started, and it's very fulfilling to be part of your local community. And we wanted to embrace that as we grew. And for a good while, it worked pretty well. We were certainly able to grow quickly once we decided to do it. A lot of people who listened to the podcast a long time will recognize that we actually at one point had ten cities, some of which were pretty established and other ones which we were expanding into. And we learned a lot along the way about how much harder it is to build a local business than we originally were anticipating it would be. One of the things that we learned, and I've talked about this on the podcast in the past, is that with our reputation in the design and development community, we could often go into a major city and have a great first year because there was a lot of pent up demand for people who wanted to work with us, work at the company and as our clients. And that really led us astray in the beginning because we would go into -- We were expanding in three or four cities in the same year, and they were all super successful. So we were hiring teams to do all the work that we had. What we weren't doing was all the legwork we needed to do to build a sustainable local business. And so after the first batch of clients or the first batch and a half of clients we were done working with, we didn't have a sustainable pipeline of new local clients coming in. And so we learned a lot about how much we actually need to do when going into a new city to not only have that great first year but to have a great fifth year. And so we had a few failures where we had to close some studios just because we couldn't afford to operate them profitably, and that was pretty painful. I forget the episode numbers where we talked about it in the past, but we have. You can go back and listen to it. We can link them in the show notes. LINDSEY: In addition to having the designers and the developers in the local studios, at least in recent years, we also had the structure that each city studio had a managing director. And a lot of those managing directors actually came from design and development themselves, but they were in charge of everything local including, and especially the sale, so finding new clients, onboarding them, the actual profitability of their studio, hiring. And again, as you mentioned, that was across all kinds of clients, all kinds of projects, but primarily locally based. CHAD: And once we realized what it was going to take to build local businesses and make them successful, we refined that managing director position a lot. It wasn't one that we necessarily had in every studio, and so adding it or, in some cases, making the difficult decision to swap out the person in that with someone. Now that we understood what was necessary, making sure that someone in that position actually wanted that job and could do it. And that has been the journey we've been on; I would say for the past three or four years of making those changes, figuring it out so that when it was working well, each of the studios could work really well. And we've made a lot of progress with that. But one of the problems we had, so we have all the individual studios, and then we have the corporate-level people which are myself and you, marketing people, operations supporting all of the studios. And one of the things that we've struggled with over the years is being consistently profitable as we've grown or primarily operating break-even, which historically we were very comfortable doing because the whole leadership and shareholder of thoughtbot and ownership all worked here. We care a lot about paying people as much as we can possibly do and having the greatest benefits we possibly can while staying sustainable. And so it wasn't an issue. We're not running the company to generate lots of profits that then go to some investors or shareholders. So operating breakeven wasn't historically a problem, where it started to become a problem is as we grew and grew, the numbers became large enough that when things didn't go like we were expecting and we were managing to break even, then we would be very unprofitable very quickly if something didn't go the way that we were expecting, and it started to put the company at risk. So we started to focus more on profitability. And one of the things that was hurting profitability is that we were maintaining these small teams with offices, and just the overhead of a small team across many different geographies added overhead, which made it harder to be profitable because we needed to do everything in each individual location. LINDSEY: Right. So now, really getting into those big challenges that were pressuring us to rethink how we operate, profitability and margin was a big one, which once you look at the breakdown in the numbers, the overhead of having the different studios was one. I think that also bleeds into the MDs have really challenging positions. They're responsible for a lot: they're responsible for the happiness and fulfillment of their teams; they're doing business development; they're doing client management; they're in charge of their entire revenue sheet. So that was another area that I think over time, we were consistently looking at; how do we improve this role? How do we make it so that folks can be successful here? CHAD: Well, you can imagine, too, that designers and developers at thoughtbot we were seeing a similar thing, which is in a lot of ways, thoughtbot is modeled around me and other early developers. And I would often tell people I really like a lot of variety. I like to be working on one client and have huge scaling problems and challenges that we’re working at and growing their business to a whole nother level. And I like rotating off of that. And I then like working with a startup where we’re building the first version of the product. And for some people, no doubt that is exciting and challenging but worth it. And same thing on the sales side for managing directors, like being able to know how to effectively communicate and sell to the needs of each of those different kinds of projects. It's totally doable, but it adds to a lot of effort and angst being spent on just always trying to do everything, both on the development side and the managing director side, and it's hard. And that was one of the challenges that we were hearing either explicitly, or in a lot of cases, I don't think people realized it was happening. Everyone at thoughtbot is amazing and is great and very high execution level and all that stuff. And when you start getting challenges or feedback about poor performance from a great performer, you start to question why is that? What's going on? And it's an unrealistic expectation to have someone work in as part of a large enterprise for six months and then next week have them working on a brand new startup MVP that's got to go to production in six weeks and necessarily expect them to on a dime be able to change their approach to managing that product and making sure that it's successful. And like you said, we want to put people in a position where they can be as successful as possible in everything that they do and having good people spin their wheels even if it's not a performance problem -- if there's a level of interest or excitement for one kind of client over another, we have a system of collecting feedback about what you want to work on and rating the incoming projects. But the primary determinator for what project you work on was which one was starting at the time your other project was ending; that was the primary determiner. So people effectively had no choice about the kind of project that they would work on. And that was a common complaint that we heard from people is that lack of control. LINDSEY: And even though it wasn't supposed to happen, I think people did have reputations for a specialty, and the managing directors or whoever was staffing a project would seek out certain folks for certain projects. So even though we'd like to think of everyone as being able to handle any kind of project, and at a basic level, they could for sure, people with specialties were sought out for things. So that was already happening organically. CHAD: And related but even going deeper on it, when we're maintaining small groups of people that are a complete replica of everything that is thoughtbot, and it's a group of 9 to 25 people, that ability to specialize or to have a career path that extends -- The company you're a part of feels like a 20-person company, and in a 20-person company, there's naturally not going to be tons of room for a big career ladder and lots of advancement or specialization. You will trend towards having a team of people that are more generalized and less hierarchical. LINDSEY: Were there any other big challenges that come to mind for you when we were going into, like, let's revisit how we're structured? CHAD: Well, there was one that touched on all of what we just talked about, and that was design and thoughtbot. And this is one thing that's super interesting. And I think I've talked about it on the show before. But we started from day one as a design and development company. We've always done design, and we've always had people on staff that did it. And one of the things that happened, though, is being the first consulting company in the world to switch to Ruby on Rails and being a big contributor to that community, and building a reputation through our open-source and through our blog and everything on the development side, that part of the business has grown. The development team is much larger than the design team. And a lot of people in the world view thoughtbot as oh, they're a Rails development company and really it wasn’t -- What we've always talked about is Rails is in service of the products that we want to design and build and creating great products. And so design has consistently been a challenge over the years as the reputation there isn't as big as on the development side. And so what we saw in the individual studios were each individual studio needed to have a certain number of designers in order to feel like it had a design team and to be able to service the work that it did have locally and a management structure within that team that made sense. It had all those problems that we've just talked about. It was difficult to be profitable. It was difficult to have enough locals work for the two or three designers that were in a studio. And that specialization for what they would do and the kinds of projects that they would work on didn't always match the actual work that we had in a particular city at a time. And so because we were organizing the work that we did geographically, it wasn't uncommon for a designer to not have client work to do and that hurt the design team because we were attracting these great designers. And people are at thoughtbot because they want to build great products; they want to do great work, and then they join the team, and they're not doing it. And so design turnover has been much higher than other parts of the company for that and other related reasons. LINDSEY: Okay. So I have a question for you because you and Diana started on this process before I was involved. So for you, when did reorganization first start? CHAD: Well, as I alluded to at the top of the show, we had been talking about these kinds of things for a while. And I think you were part of most of those discussions as part of the management team where it'd be like, oh, should we break out design? And there wasn't really this clear -- Our strategy for the last many years has been strong local studios bound together by a common purpose and values. And we were feeling pretty good about that strategy. So these problems would crop up, and we would evaluate them in the context of that strategy and say, “No, we're reaffirming our strategy.” So it wasn't until having gone through 2020 and looking towards what 2021 was going to be like and saying, “We've got all these things that could be better. But one thing we know that needs to change is we can't go through another year of everyone planning for all of this to be temporary and to be back to the way that we were before.” We had already been breaking down the geographic barriers of studios because many projects were being staffed across offices at a much higher level than ever was before. And we had given everybody the thumbs up to move wherever they wanted, and we were going to support it. And we had about 20 people move from places where we had a studio to places where we didn't. And so it was really that that crystallized the need to -- I didn't know exactly what we were going to do going into it, but this feeling we need to do something because we can't stay in this limbo state for another year, which is what we were predicting in terms of how long we were going to be in the current operating mode. And even when it does come back, we now have 20+ people who don't live where we have offices anymore. So we can't go through this next period of time expecting things to just go back to the way that they were. So that was when we knew that we were going to do it. So I guess that was at the end of November or the beginning of December of 2020. LINDSEY: It was exciting to have this push to do it. As you mentioned, we talked about different options before. Like Joe had come up with, I remember, a really clever squad-based team proposal. We’d thrown around, “Should we do an industry-based team structure?” But I think what was really missing was a push, a driver, you know, you have to. Because it was “Everything else is kind of working okay the way it is. What if this is a big mistake?” And so we wouldn't move forward. So we had these major drivers to decide on something and then went into what I think is a really successful and fascinating series of brainstorming and iteration sessions pretty quickly as a leadership team to hone in on what we've ended up rolling out. CHAD: And I think one of the things that I appreciated, and it was Diana who did this, was saying, “Let's make sure we reaffirm or revisit our values and purpose as part of this process.” And when you have a company that is driven by values and purpose, it's important when you're making big decisions to revisit them so that they're helping guide what you actually do so that you don't get off track. And we anticipated that the change was going to be big enough that maybe even the value -- We need to be open to the possibility that the value or the purpose would change or should change in the process or had already changed and we hadn't reflected them. And so that was a part of it, like expecting to go into it doing that. And then we can't have a...or maybe we could, but we decided it wasn't realistic to have a 100-person meeting. So again, for a lot of the things we do at thoughtbot, we treat thoughtbot like a product in and of itself. And we use the tools and techniques as designers and developers on that product itself. And so we did survey the team to get their thoughts around purpose and values and around what it had been like to work remotely and just a few questions in general about how they felt about projects and work and that kind of thing. And then, we took that information that we had gathered from the team into the design thinking and brainstorming sessions with the leadership team, which was the managing directors across all the studios and the design and development directors, and then the corporate leadership. LINDSEY: And I'd say at the forefront of these exercises and decisions was how do we ensure thoughtboters are fulfilled? And also, how do we provide the most value to clients, and where those things intersect, how could we potentially reorganize ourselves? And these sessions are some of my favorite things to do, even though they can be maybe stressful times that are driving these exercises. But doing these kinds of really open brainstorming and design thinking exercises, problem-solving with our team, which is full of the smartest, most thoughtful, kindest people, I find incredibly fulfilling and really drive amazing outcomes. And I’m kind of sappy, I guess here. But I start to feel like, oh my gosh, I know why our clients love working with these folks. It's a really powerful exercise, and you come up with really amazing ideas and outcomes. CHAD: Yeah. I had a thought as you were saying that, though, that I agree, but I think you could do exactly the same thing but not be committed to actually making a change. If you were just doing it, it would drive me crazy. [chuckles] And I think that that's an important component is that we went into it saying something is going to change; we don't know what it is. We define problems, and then we come up with solutions to those problems, and we are going to make a change. And that was the difference between the previous we're all sort of venting or trying to do it in a leadership meeting. And I think off-sites and brainstorming sessions and that kind of thing get a bad rap, but when they're actually necessary and when they're done well, and when you have a group of people that are committed to improvement and actually making a change, they can be really great. LINDSEY: Yeah. And I think you all had set out a goal. You and Diana had set a goal schedule of how this would work, which is coming up with ideas as an extended leadership team which is maybe like 18 people. And doing that, we booked a half-day, maybe a bit more; obviously, this is all virtual. And we'd have different sessions where we were breaking out into smaller groups of maybe five people randomized each time and working through a specific challenge or coming up with a specific proposal, then reconvening as the extended leadership team and running through those proposals. So that would be the first individual day. And then you and Diana went off with those proposals and ideas to make some executive decisions around what you thought made sense and then re-proposed to the extended leadership team for feedback and iteration with the goal that every week we're getting closer to the final, final thing that we're going to roll out to the team. And also, by the way, how do we roll that out? CHAD: I'm curious from your perspective how that worked because we didn't go into the process expecting it to work that way. Well, I guess we did. When Diana and I were planning it, though, we initially started from a different place, and then we realized this is going to be too difficult for a group to converge on, and it probably does need us to go and force a convergence basically and then go back and make a proposal. But I'm curious what you think about that. LINDSEY: Oh, I think you absolutely have to do that. CHAD: [chuckles] Okay. LINDSEY: And that's the way I operate, too, even from a marketing perspective, is to take input and ideas and see what folks think. But at the end of the day, you can't make a group decision; someone has to make an executive decision based on what they've heard. So I thought that worked well. Plus, I was in the group that came up with the idea for the reorg we chose. I don't want to brag about it, but it was a great decision. CHAD: [laughs] LINDSEY: So yeah, I guess getting into what that actually was, what we ended up deciding and have moved forward with was breaking out the teams, so keeping a team-based structure but no longer geographically-based but actually each team based on the types of clients and client projects that they're providing services for. And obviously, those services are tailored to the type of client projects. CHAD: Shall we go through them? [chuckles] LINDSEY: Yeah, we should go through them. CHAD: [chuckles] Okay. LINDSEY: So the naming came after the fact, but we also had a lot of fun with branding and naming these teams and went all-in on the rocket theme, as you'll hear. So we've got four main service teams. The first one deals with the earliest stage products kind of pre-product so validating ideas, and that is thoughtbot Ignite. The next team deals with more MVP, V1 but not really a quick project, like longer MVP types of projects, and that is thoughtbot Lift Off. The third team deals with more established companies and teams who are elevating their product and teams to the next level that's thoughtbot Boost. And then finally, we've introduced more DevOps and maintenance services under thoughtbot Mission Control, and they also manage our PR reviews as a service, reviews by thoughtbot. So that's the quick overview of the four teams you've got Ignite, Lift Off, Boost, and Mission Control. CHAD: And the interesting thing about the team structure and what each team was going to focus on is that once we made the decision that this was -- there wasn't really a lot of question around what those teams would be. We knew these different project types existed. It was something that we have documented, and it's in our marketing. We have positioning statements already. A lot of these client types were already created. We have an internal consulting class that people take, about 20 people a quarter take it. And it goes over the different kinds of clients that we work with and the different needs that they have and how to work with them. And it was split along these lines. Now there were some small details on the edges to be worked out, but what was difficult was making the decision to do this. Once we made the decision to do it, what those teams would be was pretty clear. LINDSEY: Obviously, I love it. From a marketing perspective, breaking out these different types of clients makes so much sense. You're talking to them about different sets of needs, goals, pain points, so there's great focus and clarity there. And then that trickles to everyone's job. The managing directors now are responsible for one of these service-based teams. The designers and developers themselves are specializing and really enjoy that type of work. And in the breakout group during these brainstorming sessions that I was in, I remember when we were starting from this place of anything goes, I was asking the directors in my group, “What do you think makes our team fulfilled? Are they more interested in a specific industry? Are they more interested in a specific technology? Are they more interested in a type of client?” And the directors in my group all said, “I really think it is the type of project that provides fulfillment in different ways for different folks.” So we took that as a starting point, and then it was, “Okay, well, what are those different types of clients if we could put them into four or five buckets?” CHAD: And Ignite and Lift Off are really interesting to me because it's a good example of where the lines can be effectively drawn. So you alluded to it already, Ignite is for the earliest of products and teams where the idea hasn't even been validated yet, and they need our help determining whether it even makes sense to proceed at all. And then when we do validate it, the size of what we're building and the speed at which we're going to be able to get to market falls under 12 weeks. It will typically fall in the 8 to 10-week range where we've gone from that concept that we validated to a launch product in the hands of users. And they’re ruthlessly prioritized. They're usually pretty straightforward, both on the tech side but also in what we need to build. And I think one mistake we've made in the past is taking large finance and healthcare companies and these large companies that we also work with and trying to do the same thing that we do for those Ignite clients for them and ending up in a place where maybe we haven't done as good a job, or the project doesn't go as well because we're trying to squeeze it into a place where it doesn't fit. And that's what Lift Off is; it’s creating a space where it fits, realizing that a client who comes to us with this massive need it's not massive because they're doing too much. It's massive because they have a big problem that they want to solve, usually for a business that already exists, and it's a new product within that business. Maybe they've even already validated it. And the integrations that it's going to have, the systems it needs to talk to, the level of scale that it's going to have is different than is going to be possible in 8 to 12 weeks. And when we try to squeeze it in there, it's not going to be successful. So Lift-Off is giving a space for those projects to thrive in a way. And I also think it's one of those things where it's going to have an impact on our sales too because what would happen previously is that one of those clients might come to us and we're furiously trying to squeeze it down. And how a client perceives that is potentially like, “Oh, they don't know how to do what we need them to do, or they don't want to do it. Or they think our idea is bad because they're saying we need to validate it, and we've already validated it. We have an existing business that we're building this off of,” or something like that. And it causes us to lose that work, which we would otherwise love to have. And now a client like that comes and is talking to a managing director who gets the needs of that kind of project and a team of people that are going to work on it that understand that there's a process to run through and it's going to take six months or a year. We're going to launch along the way, and then we're going to continue to grow the product from there. It's just a different feeling all around, which I think is going to have a positive impact on our ability to actually grow those parts of the business. LINDSEY: And Lift Off by nature of working on those health, tech, and financial products is also dealing with highly regulated spaces, which is another reason why those projects are necessarily longer and more complex and lend themselves well to someone who's dealt with it before. CHAD: Right. Another thing, and we touched on this a little bit earlier with Boost, is a big part of our business historically is that those clients that have built-in Rails along the way, they've built a super successful business. They're scaling a lot. They're growing their team. They need technical leadership, experience mentorship, and those projects tend to be very development-heavy as well. Like, we have clients where we have four or five developers working with them and no designers, and it caused the design and the development team to be very lopsided. But we really liked that work, and it's very valuable to clients. And so same thing with Boost, Boost instead of that being something which is pushed off into the back where like, oh, well, it's not the project-based integrated team of designers and developers launching a new product, and so it's not our ideal work. It gives a space where that can be our ideal work, and the kinds of people who want to work on those kinds of projects with that level of experience and need feel like they are able to do that on a team that is focused on that. And that team doesn't necessarily need to have a design team that works or looks the same as every other place at thoughtbot. And it creates a place which can focus on what it needs to do in the best way possible that is the most fulfilling to the team and success for the customers. And it looks different than thoughtbot has historically looked, and that's okay. Because actually, when you pick it apart, it's not that different; it’s just taking the 20% of all of the thoughtbot studios where the 20% felt like something that wasn't quite right and putting it all together to make 100% of something that feels right. LINDSEY: And from the design perspective, Boost design is a lot around optimizing what already is in place or helping take care of design debt that's been neglected, making sure design and development are talking to each other and thinking about those processes to make them talk to each other better. Whereas Lift Off and Ignite are more introducing design or design processes or design frameworks like putting your design system together or thinking about your accessibility processes, those kinds of activities. And then Mission Control is probably the newest to thoughtbot in terms of services that we're offering clients. CHAD: And within Mission Control, there are two big areas that are different, so the first is maintenance. So we historically have been project-based at thoughtbot. And what that would mean is that well, it doesn't necessarily mean -- So historically, project-based plus everyone working on one project at a time, I think the combination of those two things meant that what we mostly did was we help people set up their own team of people who are going to take over from what we had done after we launched the first version of the product and level it up from there. And most of our clients got to the point where the goal was to become self-sufficient. And we also would meet people who had already built something and were just looking for our expertise to help take care of it but not necessarily have enough work for someone full-time. And for both of those clients, we didn't really have a solution for them. And so that's where the maintenance team in Mission Control comes into play because it's a team of people who have opted into splitting their time across multiple clients. The contracts are different where they're paying a monthly recurring maintenance fee for us to take care of certain things every month: security upgrades, patches, small bug fixes, and features. Maybe they even have a team on staff where they're doing the majority of the development work, but they just want our support in helping things go well. And also, you mentioned the pull request review service that's within Mission Control as well where we have a separate service where you can sign up, and you just request a pull request review from thoughtbot, and then one of our team members goes on and gives you feedback on that pull request. So that's one part of what's happening in Mission Control is that maintenance work. And then the other is DevOps, and infrastructure is an area where the majority of projects that we worked on across all of thoughtbot were deployed to Heroku or the teams had their own DevOps and infrastructure people and creating a specialization of that for a handful of projects for an individual studio that has that need, over the course of a year, never made sense. But once we started to do it and we took a more global view to it and said, “Across all of our clients, what is the need either met or unmet and what might we be able to do? And where is the interest of our team?” It became clear we could offer -- like, our clients need us to do this sometimes. And for the clients who need us to do it, we want to be there for them. We want to do it. And creating a team of people that is global, that can do it across time zones 24/7 is also one of the needs of the clients, and having that team span those geographies is one way we've been able to do that when historically we would have shied away from that. LINDSEY: And speaking of the team's interest in different areas, different services for the rollout of this new organization, we, by and large, had folks opt in to what they wanted to do even as far as the managing directors picking what team that they were going to head up. CHAD: So we said, “These are what the teams are going to be,” and we did a company-wide presentation. And then, we asked people to submit their first and second choice. And then we made the decision around which of the managing directors were going to do what and then we announced that to everybody. Am I saying this the right way? Did we announce the managing directors before we asked everybody or just before the deadline was up? LINDSEY: I think it was trickled in. At first, it was “What team do you want to be on?” But then, as that's going on behind the scenes, you and Diana are having discussions with the managing directors around where they want to be. And then, as that information became available, you shared that with the team also to help with decisions, same with the design and development directors. I think it was announced the design and development directors chose the teams they wanted to be on and lead. And then, once that was finalized, that was also shared with the team as they're voting on where they want to head. CHAD: And the majority of people got their first choice and the majority of people the person who was their manager also chose a similar choice. And so there was a lot of change but not too much churn, I guess is the way I would put it. We were able to do it in a way which I think people felt like they had a choice. And I think going into it; people were afraid of that like okay, am I going to make a choice here and then end up on a team of people I've never worked with before? That was not the case. Now there's certainly a big blending of the teams, particularly Boston and New York were the biggest studios. And so they make up the majority of the people in each of the Boost and Lift Off. But people are working with people that they have worked with before. LINDSEY: And it turns out the people they didn't work with before are also awesome, also, very cool. CHAD: [chuckles] So much effort over the years spent -- that strategy of replicating what was great about thoughtbot into other geographies is true. And so the standards that we had for hiring, and the kinds of people we hire, and the screening for values fit, and all that stuff led us to a place where everyone at thoughtbot is great. And so I wasn't really concerned about that, but other people may have been because there's always a fear of the unknown. LINDSEY: Yeah, definitely. I'm trying to think if there were other rollout things that might be interesting. CHAD: Well, one of the interesting things it's a little in the details. On the surface, that is the team, and those are the services we offer. But we also needed to contend with the fact that we are in the U.S. and the UK, and we didn't really feel like it makes sense to have those teams span 10+ time zones, that that would be too far of a stretch. And it would affect people's fulfillment on the team as well as the services we are able to deliver. So these services that we offer are actually fulfilled by two…do we have a word for it? [chuckles] LINDSEY: Geographies? CHAD: Geographies, yeah, I guess. LINDSEY: There are two geographies that we ended up naming Launchpad 1 and Launchpad 2, because rockets. CHAD: So Launchpad 1 is all of the Americas, and Launchpad 2 is Europe, Middle East, and Africa. And so they provide all of those services in those places. But they have teams that are formed across the whole geographic region. And then eventually, if all goes well, we'll have Launchpad 3, and that'll be [chuckles] the other side of the world. LINDSEY: I've got the icon ready and waiting. So I guess timing-wise, this all happened...rollout was by the beginning of the year, right? January? CHAD: Yeah. One of the things is more people took more time off between the December Holidays and New Year's and everything than they have ever done before, and we needed it. Everyone needed it. So we weren't able to finalize what team everyone was on and have a conversation about that with everybody before they saw it in a message somewhere, which we really wanted to do. So we ended up not being able to finish all of that before the end of the year. And so it rolled into the first couple of weeks of January as people came back, and we were able to talk to them. And then I think we made the internally public announcements about all the teams that everyone was going to be on, and we did a formal kickoff. What was it? January 8th or something like that. LINDSEY: Yeah. And I think that's actually a really good point to bring up is the communication to the individuals. It was important for them to hear it one-on-one from their manager before anything was announced more broadly and then to transition to their team if their manager was changing, which in a lot of cases, it didn't, but sometimes it did. Having one-on-one-on-one transition meetings to really ease that move was also important to not make this really abrupt and unnecessarily stressful in a time that is already very stressful for reasons we know. CHAD: And even if someone's direct manager wasn't changing, it was very likely that their director would change. And so, in those cases, we still did a one-on-one-on-one, but it was with the new director sitting in as well as a skip-level one-on-one on-one. And we did it quickly, but it was important to make it happen quickly. LINDSEY: And it was also important to not abruptly change on the clients because obviously, we weren't doing a full stop of client work just because we're doing some reshuffling internally. So that was phased, and we didn't even really make it a big deal to the clients because that probably would have just added confusion as we were making these changes. CHAD: Yeah, definitely. And we made the decision that we weren't going to just arbitrarily say, “This person is now on this team; therefore, they have to leave this project,” so we made that decision. And we have as natural points in the project for a rotation to happen. People will move to a project; if there's a mismatch between the project that they're on and the team that they're on, they'll move at a natural point. But the reality was that a lot of people also chose -- It's not like we have 57 different project types; we have three. And so a lot of people were already working on the project type that they chose just because the odds were good that they were. There's been very little customer-facing impact to it. So it's early days. It's March now, so it's been a couple of months. But how do you think it's going, or where do you think the growing pains are? LINDSEY: Good question. I think there's been more of a smooth transition than there have been growing pains, first of all, which has been nice. I think folks have been pleasantly surprised by really enjoying their new teams and new team members. I think growing pains-wise, on the operations side, obviously we've had to...I think we’re still in the process of figuring out how to best pipe certain kinds of inquiries into the right team and managing director. Sometimes it's a no-brainer. They're like, “I need to validate this idea.” It's like boom, “You're off to Dawn for Ignite, and you’re going to have a conversation there.” But if they come in and they say, “I'm working on an MVP, and we don't know if that MVP is one of the really fast ones or one of the more complex ones,” then it's like, okay, is this going to Dawn or Emily? CHAD: And we historically didn't need to have any handoffs because one person was able…one person and team; it was based on geography. So we knew exactly who was going to be having that conversation with them. So operationally, it's actually one thing we didn't touch. So no one was let go in this big reorg. There was a position for everyone, I guess, if they wanted it. But one area we haven't touched on is anyone who was local, who was in a support role moved up into the corporate level in a support or operations role. And there weren't that many of those people, but the office manager in Boston is now full-time in people operations. And the office manager in New York City is now the operations manager for the whole team, the whole company. Kelly, who was doing business development just in Boston, is now helping across all of thoughtbot, which is really good at using her skill set across the whole company. I think that that's good. And now, like you said, figuring out how to support everyone across the teams is a little bit of whether it be the operations manager figuring out how to get people computers when we hire new people to like what you were saying around inquiries coming in and making sure that they're sent to the right person. The thing that has made it more challenging for me is that just a confluence of events at the time where we were making some of these changes. And now it has made my involvement different than I was originally expecting them to be. I expected to be a little bit more involved in certain things, but because I've been pulled into several important client projects and was working on client work at the time that then expanded very rapidly, it's been challenging for me to manage the workload. But in some ways, there's a bright side to it, which is it's giving other people the space to operate without me, which I think can be good because I'm very confident in what everyone's bringing to the table. And when you go through a big period of change like this, if everyone was deferring to what I thought as the founder or looking for me for answers or permission to do something, I think that we would suffer for it. And so being forced in a way to not be available for everything that's going on is a way for people to have more ownership over it and not be relying on me, and I know that they can do it. LINDSEY: Cool. CHAD: So we never said what the new purpose was. So maybe we'll just talk a little bit about that, and then we'll use that as a wrapping up point. LINDSEY: Sounds good. CHAD: So I mentioned earlier our purpose had been we believe that there's a better way to work. There's always a better way to work, and we want to find it and share it with as many people as possible. We had written down that purpose several years ago, like a decade ago, I think. And I believe a good purpose describes what is the underlying motivation for the company and the people at it. And when we did that survey of people, a few of the questions we asked touched on it. And it wasn't that surprising to me about -- one of the threads in that was this idea of positive contributions to the world, making sure that the things that we work on and do have positive contributions to the world and that being a motivating factor. Like, that's part of what makes the team tick and what they want to be doing and are fulfilled by and that kind of thing. And so we incorporated that into the purpose. And so we adjusted the wording a little bit to make that incorporation, but we ended up that we believe that it's always possible to continuously learn and improve the way people work while building higher quality products that make positive contributions to the world. This resonated with me in a way that -- it's a little bit more wordy, and that's not why it resonates with me. [chuckles] Specifically, our previous purpose of we believe that there's always a better way to work and we want to find it and share it with as many people as possible lacked one thing that I think a good purpose can incorporate, which is what is a clear idea of what the alternative is like, what you're fighting against, or what you're trying to improve. It's there in the previous purpose. So, in theory, there maybe are people out there who believe that there's not always a better way to work that they've achieved it or something like that or that they have particular practices which aren't great. But it's not explicit or really even implicit in the purpose. And the new purpose we believe that it's possible to continuously learn and improve the way people work while building higher quality products and make positive contributions to the world. You can point to someone who might believe the opposite of that, that you can't build higher quality products that make positive contributions to the world while also continuously learning and improving the way that you work and everything, that to build higher quality products or make positive contributions to the world, you might need to compromise on the values of continuous improvement and learning. And our new purpose makes a statement that you don't need to compromise in order to achieve that result, and I like that about it. LINDSEY: I really like the addition of talking about the kinds of positive products because I think once you know thoughtbot at all, you know that that's underlying the purpose but take out the guesswork, just tell the folks. All right. Well, I think that's a good place to stop. I'm glad we didn't even go into the remote because there's obviously a lot to talk about. CHAD: Yeah. So we'll talk about that next time? LINDSEY: Yeah. We're going to talk about what changes we've made in going completely remote and what that looks like, what we think it looks like for the future. CHAD: Cool. LINDSEY: So you can subscribe to the show and find notes for this episode at giantrobots.fm CHAD: If you have questions or comments, and we'd love to hear them, email us at hosts@giantrobots.fm, or you can find me on Twitter @cpytel. LINDSEY: And you can find me on Twitter @Lindsey3D. This podcast is brought to you by thoughtbot. CHAD: It's good to be back. Thanks for listening and see you next time. LINDSEY: It's so good to be back. Stay tuned. This podcast was brought to you by thoughtbot. Thoughtbot is your expert design and development partner. Let's make your product and team a success. Support Giant Robots Smashing Into Other Giant Robots

Chad is joined by Diana Bald, the new CEO of thoughtbot, to discuss her background, the organizational changes to the leadership of the company, and the reasoning behind them. Diana on Twitter Become a Sponsor of Giant Robots! Transcript: CHAD PYTEL: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel. And today, I'm joined by the new CEO of thoughtbot, Diana Bald. Thanks for joining me, Diana. DIANA BALD: Hi, Chad. This is so fun. This is so exciting. I've only done one podcast before this, so I'm excited. CHAD: Well, don't worry. You can still be CEO of thoughtbot even if you're not a podcaster. [laughter] DIANA: Okay, that's great to know. CHAD: So it's been several months now. So I want to go back and talk about how we arrived here. But I'm curious, how are you feeling now? What does it feel like? DIANA: It feels great. I think I'm getting more and more comfortable every day, which is amazing. And I think the year has gotten off to a great start, so that's helping me feel more comfortable as well. So far, so good. CHAD: So for folks who are listening, I'm sure they're wondering who are you? [chuckles] Let's give the audience a little peek into your background and how you arrived at thoughtbot, and the role you originally had. DIANA: Great. How far back do you want me to go? CHAD: As far as back as you're comfortable. DIANA: Okay. I actually was really interested in technology at a younger age. I put myself through undergrad and grad school while I was doing tech roles. I trained lawyers on how to move from the analog world into the digital world. That was one of my very first jobs at a law firm. And then, shortly after that, I did webmaster work when I was putting myself through MBA school. It was a very different world than it is now. This is way back when the internet was really just kicking off; it was 1998 to 2001, around that time. When I graduated from MBA school, I was recruited into Univision into their leadership pipeline, which was very much focused on business development. But my very first project there was web integration, integrating the univision.com with their TV and radio. That was when I started to move away from technology. I was there for ten years. I had a variety of different roles, a really fun job. I got to experience a lot of different roles, lived in a lot of different cities. I spent a lot of time in Philadelphia, where I actually launched a television station in Spanish, which was really fun. And then I came to New York. After Univision, I spent four years in the advertising and marketing world. I spent two years with IPG at ID Media, which was a direct marketing agency. And then two years at MDC Partners at an agency called TargetCast, which later became Assembly, which was more media buying and planning. And then, when I left there, I went to Liberty Mutual for three years. And at Liberty Mutual, I fell back in love with technology. I missed it. I was doing a lot of strategic partnership opportunities with really interesting companies that were doing brand new business models and disrupting insurance, and there was a lot of exposure to telematics and IoT. And it was just calling me back, and I was like, I got to get back to tech. And somehow, I don't recall exactly how, but I found you. You and I chatted, and then I fell in love with thoughtbot [chuckles], and then after that, the rest is history. CHAD: You joined us as the Managing Director of the New York City studio. I want to say that was a position we were advertising for, and you applied to it. DIANA: Yeah. CHAD: And one of the things that really stood out when I first met you and as we've got to know each other and work together is the variety of experience that you had because I've only ever done what I do, which has its own strengths. So the fact that I started freelancing web design and development in high school and have continued to do that now for 25 years is a strength, but it's also, aside from the jobs I had as a dishwasher or the checkout person at the grocery store, this is literally all I've done. And the variety of experience you have not only helps thoughtbot be better, but I also think it positions you well for our business. In consulting, you need to be unflappable in a lot of circumstances, and I think you're good at that. You're good at maintaining an even keel and talking with customers and dealing with difficult situations and that kind of thing. DIANA: In some ways, I'm envious that you have been able to stick with development the entire time; that’s really, really cool. But in other ways, I can see what you're talking about because I do feel like I have had a variety of roles and seen a lot of different situations. And every one of these situations has had their challenges. And they've all been generalist roles where I've dealt with clients, and then those clients had challenges in their respective industries. So I've really learned a lot about keeping things in perspective, if you will, more so than people who are in a role for a particular time and see that aspect of it. I'm seeing things from a bird's eye view much more often because maybe I've seen the situation in the past only it was in this industry, or I've seen this situation in the past, but it had these characters. And it's like I can carry that knowledge over to thoughtbot, which has been really helpful. CHAD: So the managing director role, I think I've described it on the show before, and it’s sort of the CEO of the individual studio. That’s the way that it works. You oversaw the individual studio, and you were responsible for business development and the whole P&L of the studio, the whole business. Going back to first joining thoughtbot, what was a surprise to you? DIANA: How comfortable I felt. [chuckles] I felt like, oh, I'm home. I felt like, oh, there you are. I've been looking for you all my life kind of feeling. I don't know how to explain it. It just felt really good. Like, okay, these are problems. I like these problems. Or this is really joyful. I felt like I was actually in my element for probably the first time in my career, although I've had some jobs where I felt pretty much in my comfort zone, but thoughtbot took it to a totally new level. And I don't know if it's thoughtbot, or the role, or the combination of the two, or maybe it's me where I am now in my life and just having had all these different jobs and experiences. Maybe it's all the above. CHAD: One of the interesting things that's been a journey for thoughtbot not only just with you but with several people is up until a few years ago, we hadn't, aside from some office managers or people operations, we hadn't had people in direct client-facing roles who are not designers and developers. And it comes from a place of fear and skepticism about that, historically for us, for me personally. And I don't think I was wrong per se; I was just misguided. And I've learned over the years that when you're afraid of something, there can be some truth in what you're afraid of, but you should let that fear guide you into making good decisions and not let it hold you back from doing anything. And that's what we were doing: we were so afraid of what adding non-designers and developers to the consulting side of the business would mean for us as designers and developers that we didn't do it at all, instead of trying to find people who would be a great fit, who would be great advocates for us, a great fit for the company. And once we figured out the recipe for doing that, I feel like not only did it make thoughtbot better and stronger on the business side, but it made thoughtbot better overall. One of the things we strive for is an inclusive, diverse environment, and that doesn't just mean the obvious things. It also means having different perspectives and experiences that a group can bring to the table that makes the results better and more enjoyable, and more fulfilling to work in. And I think that you've been successful in bringing that to the company, and it felt good and not only you but the other people that we've added in the managing director roles. And that kind of thing that brings that different experience and different skill sets to the table has made thoughtbot better, I think. So, thank you. DIANA: Thank you for letting us bring it to the table; not every place lets us do that. But you've set up a culture, to your credit, that I think brings the best out in people. And I think you've enabled that to happen, so thank you right back. [chuckles] CHAD: There's another angle to that, which has been on my mind, which is what we were doing in the past was basically forcing designers and developers to do some of those things and potentially setting them up to fail because it wasn't a strength, or it wasn't an area that they were actually interested in. They were just doing it out of love for thoughtbot or wanting to see us succeed. When you put people in a position where they're going to struggle or where they're going to not succeed, that's doing nobody a favor as well. And so that's in part been on my mind because as we've been reorganizing the company and everything, I think that's part of the lens at which we're looking at it: what can we do to make things easier to make us more successful as a team and as individuals in our day-to-day work, too? DIANA: I think that there's a lot there. I feel like in every designer; there is a business person because they're breaking things down. They're deconstructing constantly, and they're asking tons of questions that business people just naturally ask. And then developers are super creative, and they're problem solvers, and they do the same thing. I feel like it's a combination of art and science. Everybody's got their science part of it, the developers, designers, even people like me with a business development background. But then when you do enough of that thing, and you're meshed with the people who bring a complementary skill, then you're able to do the art side of it together that you wouldn't get solo, for instance. If you just put a bunch of business development people in a room together, it's very different than when you mix them up with a designer who brings that side of thinking and a developer who brings their thinking. I think together we're better than siloed. CHAD: So when it came to the actual transition and having you step into the role of CEO and move into the COO role, and I want to be relatively honest that it wasn't some grand plan that I executed over a period of a long time. And if that had been the case, I think we would have gone about it a little bit differently and certainly with more transparency for the rest of the thoughtbot team. For the listeners, the path there was that Matt Jankowski, a long-time COO and member of the leadership team at thoughtbot, was getting ready to move on. And that wasn't the only thing that was changing. Obviously, 2020 was a big year; it was a difficult year. And so the combination of all of those things and me looking at what does the leadership team at thoughtbot look like going forward? Who is going to fill Matt's responsibilities? That kind of thing, and really breaking down those roles and responsibilities and coming to the conclusion that the CEO role and particularly business development are inherently coupled at the company right now and that we have a lot of things we need to do in front of us and who is the best person to be able to do that? And feeling like it might not be me. And the things that I was going to be taking over from Matt operationally were in and of themselves a significant area. I love thoughtbot. I love helping it work better and being close to the client work. And now that we've built an incredible team of managing directors, that was another thing that was on my mind that I've built that team. I'm really proud of that team, and it's an awesome team. But who's going to be the better mentor and leader for that team going forward now that we've got a team of experienced people who are slightly different than just designers and developers and who have different needs and jobs? And again, the best person for that might not be me. And so those were all the thoughts that were going through my head. And then things came together really quickly. DIANA: Yeah, they sure did. [laughter] They sure did turn around and come together really quickly. First, I have a lot of admiration for you, in particular, like the way that you're able to take a step back and look at things objectively and not let ego get in the way of things because that's a big deal. Not everybody is able to do that, Chad. And I've worked at a lot of places, as we talked about, and I've seen ego get in the way. And I've seen ego get in the way in a bad way. It's not always a friend. Sometimes it could be a friend, sometimes it's a very powerful friend to have, but sometimes ego can hurt. And so there's a lot of wisdom to that. And in terms of the speed at which things came together, yes, I agree; I think that's a reflection of the times we're living in. We're in a time where things can change on a dime, and we just have to be able to pivot and be able to reassess the landscape, see what we have to do, make the necessary modifications and then go. And I'm really proud of both of us and the team of the managing directors and everyone at thoughtbot for our ability to quickly adjust and do what we had to do during the really crazy year that 2020 was. CHAD: I spent the majority of 2020 in intense survival mode. And so it wasn't until we were through that period that I realized how much it had affected me, whether it be in burnout ways but also in terms of realizing that we were going to survive. At the end of March, early April, it was the most difficult time. We saw a good portion of our business…new projects were starting, people doing new things. At the end of March, early April, a lot of that new stuff got completely put on hold as the whole world recalibrated. And so we saw a significant decrease in revenue in those months, and we didn't know where it was going to go. So we were very proactive about redoing our numbers and making sure that we weren't going to go out of business and didn't go out of business. And once we were able to do that and to stabilize things, we still needed to spend a significant amount of effort for the rest of the year, working really hard to make sure that we made things less bad. And that was pretty difficult. But my main point or my takeaway from the year and part of what has led to this transition is the realization that I don't really have any plans to go anywhere per se, but rather than be like, oh, I need to keep my position forever, it's more we're coming up on the 20-year mark of thoughtbot. When we came up on the 10-year mark of thoughtbot, we asked ourselves the question, “Okay, it's ten years. We're not really going anywhere. What do the next ten years look like?” And so, as we continue to move forward as a company, I think the horizon tends to expand. And it's like, okay, we're coming up on 20 years. What do the next 20 years look like? So, I don't really have any plans to go anywhere, but am I going to be doing this and the same thing in the same way for another 20 years? Probably not. [laughs] I'll be getting close to retirement age. So I always have come to work every day, just trying to create the place that I want to work, doing the kinds of things that I want to do. And I think that motivates everyone at thoughtbot. That's how we all come to work every day. And I think it's one of the things that leads to that culture that we have. And I think this transition has been part of that expanding horizon part of thinking about being a resilient company that is going to last for a long time. DIANA: Yeah, absolutely. I think that's one of the things I love most about thoughtbot is just that we're intentional and that we do want to make this a place that people want to work at. CHAD: So we asked for questions from the audience, and one of the gists of the episode was what was the actual way that we communicated this change to the company? DIANA: So I think we went about it in multiple ways. You notified people in the early stages. And then, we also went about a transition period, which was like the second phase of it. I think you can speak best to the first phase. CHAD: Yeah, one of the first things I did was once the decision was made; I met one-on-one with the rest of the C-level team and looped them in on it. And then I think the next thing was crafting a company-wide message that went out to the whole company. I'm not sure if there was much in between those two things. DIANA: Yeah, I think that's what it was. CHAD: Now, one of the interesting things, as I was saying earlier, is that part of the change that was happening at the same time was Matt transitioning out of the company. And so I think in some ways that made the whole thing a little bit more understandable for people. There was change already happening, and they were together. I think in retrospect, in other ways, or at least one thing I wanted to make sure people understood, is that the COO role and the CEO role going forward aren't necessarily the same as what they were in the past. And so even though Matt was leaving and I was taking on that title, that doesn't necessarily mean I was just going to be doing everything that he did in the same way that he did it. And the same is true for you in the CEO role. DIANA: Yeah, we bring our own personalities and our own strengths to the roles. We give each other room to do that. I know that you like to be involved in the development. You like to be involved in sales as well. It's important that things change, that things don't stay the same. I think it's important to evolve and to bring in different viewpoints and change the roles a little bit if we need to, which I think we've done and we're doing. CHAD: And so someone asked, “Were people surprised?” I think people were very surprised, don't you? DIANA: [chuckles] Yeah, I think so. I think I was surprised, [laughter] starting with me. Yeah, everybody was. But it's understandable; you’re the founder. And I think change does bring an element of surprise in and of itself. CHAD: Yeah, I think we got to that place very quickly. But in retrospect, knowing where we ended up, I could have envisioned more proactively saying, “This is a transition,” not even necessarily with you specifically just like “maybe next year I won't be CEO,” like giving people some clue that a transition of some kind might be coming. But I didn't know myself, and so it wasn't really practical to give people. But I think in retrospect, it would have been nice to make it more clear that that's the kind of thing that might be on the table. DIANA: I also feel, though, that there is an element like we were speaking about earlier that sometimes things change and they change quickly, and we can see more of that happening in the future. I don't think that's going to stop. I think that actually might increase to some extent. So it's great if we have an advance notice of things, but sometimes there isn't the room or the opportunity to do so. CHAD: So then you moved into the role. We had a transition period. What was that like for you? DIANA: It was interesting because I thought, well, let me bring things that I always wanted my CEOs to do but never did. And let me not do things that I saw my CEOs doing that I didn't like. [chuckles] Let me start there. And one of the things that I really enjoy, and I think it's part of the culture here, is just being a little goofy and a little silly and just having that freedom. And I actually think that that makes for a better, healthier environment. And I guess I wished my prior CEOs were a little bit less uptight, maybe, if you will, a little bit more goofy, a little bit more fun. And so I think bringing that even more because you already bring that but really doing it together. [chuckles] CHAD: Well, I have to be honest, I used to be a lot more goofy than even I am now. And I've just been worn down over the years [laughter], which is why part of this is just making sure that things stay fresh, too. But yes, I really appreciate that. DIANA: And also another thing that I would think is really important to me is that voices be heard. It's all a collaboration, right? Because I've worked at some big companies, I would say a lot, but not all of them have been big companies, and it's been very top-down, and it shouldn't be that way, even in big companies. I think that it should be a dialogue. You put something out there, but you also have to hear the feedback. That feedback loop is really important. And you might miss something really, really big if you don't have that feedback loop. And I really enjoy that we are doing that here. We have our director sessions where we break out into teams, and people come up with ideas, and they share those ideas. And we take that in, and we synthesize it, and we say, “Yes, that's valid. Don't agree with that. Definitely agree with that.” We're able to have that dialogue that I think serves us really, really well, which is another thing that I'm really enjoying about my new role and working with you in this capacity. It’s great. CHAD: I have a couple of things that surprised me, and I'm curious what surprised you. But the first is that I knew that things were going to have to change. There were too many pent-up questions at thoughtbot. It was too obvious that the pandemic was going to last a lot more longer, but I didn't know what any of those things were. I just had a sense that they were going to change. And so the process of navigating that change with you and not being the one who is CEO while that's happening has been really positive for me and surprising. What's been surprising for you? DIANA: Very few things surprise me if I'm honest. [laughs] I feel like with time, with so many experiences people have, things get less and less surprising the more time we're on this planet. I don't feel that surprised about things. I actually have gotten to a point in my life where I'm seeing things as opportunities (and you and I have talked about this a lot) and leaning into those challenges and turning them into what's the silver lining here? Can we find the silver lining, and how do we pull that silver lining out and actually turn that into something really strong? I'm doing that more and more. And I feel like the pandemic has actually really called that out and made that a strength in a way which is ironic, but it's actually been really a very useful skill. CHAD: So the other thing that's been surprising or unexpected, once the transition was over, some things happened that pulled me into client work much more than I was originally expecting. And that's been really interesting because I feel like it's both good and bad. There are things that I would historically be involved in, and even in my new role, I should be, and I just can't be. So all of you are left to do things without me, but there was never any doubt in my mind that you'd be able to handle it or that the team would be able to handle it. But I think it's actually been an interesting thing to have those two things coincide. We've got these transitions going on, and we've got the reorganization, and suddenly, I'm a lot less available than I have been in the past. So that's been something that's been unexpected that we've had to deal with. DIANA: I think one of the things that's helped me deal with that is that you've been working on some very important projects for the world, and that really do help humanity. And I just think that that's been one thing I keep thinking about: Chad’s doing really important stuff right now. So I think that's been a good thing to keep in mind as well. And then there's another side to it, too, where it's like a parent analogy. Even though I'm not a parent, I have young people in my life. You leave them alone sometimes, and sometimes they'll surprise you, and they'll actually be able to take care of themselves. And they're able to actually do more than you thought they would because you left them alone and it’s like, let's see what they do. And then they actually do something really cool. Some of that has played into this, too, which is interesting. CHAD: Well, from my perspective, it's almost the opposite of what one might think, which is I never had any trust issues. And I always believe in the thoughtbot team to be able to do things. But oftentimes, I feel like I'm being asked for permission or being checked in with just because I'm the founder and that kind of thing. And so I actually think it's been healthy to be not available and be pretty explicit about that because then it means that I'm not being an artificial gatekeeper for people and things. DIANA: And it also strengthens the decision-making, I think, because people get to practice that without you and not become dependent on you solving the problem for them, for instance. That's another healthy side to that. CHAD: So in upcoming episodes, we're going to talk about the reorg, and a big part of that is going remote. We don't need to dig too much into it now, but through the lens of becoming CEO through that transition, that has been entirely remote. For me, as CEO, I was traveling to each of the studios meeting people in person once a month. How has it been going through this transition, becoming more embedded into the rest of the company at different levels and that kind of thing and having it be entirely remote? DIANA: It's got its pros and cons. In some ways, we've been able to move really quickly on some things. We've also been able to bring perspectives that maybe we wouldn't have thought about before. On the other hand, I really enjoy getting out and seeing people in person, and I feel like there's a chemistry that's developed when you're able to go to lunch together or just have coffee together. And I’m missing that side of it and looking forward to the day when we can do that safely, especially the folks in London; getting a chance to do that with them would be terrific. But I think as with anything, it's got its pros and cons associated with it. We’re trying to lean into the pros as much as possible because this won't always be the case. There will be a time when we all come together. And we might as well just make the most of this time that we're apart to move as quickly as we can, learn as much as we can, and take those learnings so that when we are in person, and we do connect that we can then explore other advantages that that brings us. CHAD: So when it comes to working from anywhere, which we're specifically not saying that we're an entirely remote company; it’s just that we are now working from anywhere going forward. And that was an intentional choice. But that's been an interesting transition; I think because previously, our whole strategy as a company was local studios working with local clients with a local team. Our culture was built up around our physical places of work. So my question for you as the CEO of thoughtbot is how do you maintain that culture, or how do you change it to not lose what people think makes thoughtbot great along the way? DIANA: I think we're in the process of discovering that right now. And we are learning things that work and things that don't work. And I don't have an answer. I can only speak to things that we're trying to do. I have noticed there have been a lot of people who have left and gone to different parts of the country, or some have even left the country. And I think that was really surprising. I wasn't expecting people to move to some of the places that they've moved. But knowing that they have an increased comfort level in their lives because they're closer to their families or they're doing things that they need to do right now in certain locations that are not where they started gives me a sense of reassurance that this was the right decision because we're giving people that space, that ability to do that. And some people really did need to move to different locations and deal with certain things. And then just giving that extra flexibility that’s honestly practical, it's just practicality. I feel like all we've done is introduced the element of this is just a practical application of life. Like, if you need to take your kids to school or if you need to go to the doctor, go to the doctor, it's okay. If you need to run an errand, go ahead and do that. You don't have to be tied to a desk in one location all day long. It's healthier if you do what you have to do and then get back to work when you're ready. And then we've had a lot of issues that have impacted society in general that have affected thoughtbot overall, like the things that happened with George Floyd and some of the things we're hearing about recently in Atlanta, killings in Atlanta. Sometimes people just need to take a moment and process all that and see how do we make this world a better place and how do we bring our best selves to thoughtbot? And in our new remote structure, we're giving that, not that we didn't do it before, but it's just giving that extra space that it's okay, it's safe. It's safe to do that. Take the time you need and the place that you need, if it's closer to your families, do that. I feel like that's been a very practical thing that we've done. There's a sense of loss because I miss all the New Yorkers. [chuckles] I’d see them often, and everybody would get together on Fridays and have lunch together, and there's a sense of that loss. Seeing our Slack channel go away was sort of sad in a way, but then happy in other ways. But that's true with everything that changes. With everything that changes, there's a beginning and an end; there’s a transition. And we're going through that. I'm looking forward to the days that we can bring people together, maybe in an in-person summit. I think that's going to be fantastic. It's going to be so much fun. But right now, the summit that we had virtually was a blast, and everybody was virtual, and folks had a really good time. So it's just we're finding that right balance. We're testing and trying things. I hope people feel they can bring ideas to us, and we can implement different tactics, tricks, cultures, all that is work in process. CHAD: I think we're in for an interesting time over the next year because part of why we had offices before was that highly collaborative environment with not only the thoughtbot team but with the clients that we work with and whether that would have been in their office or in ours. And when that was completely off the table, there was no discussion. We didn't need to be in person with someone. The team wasn't going to be based in New York because you're in New York, those kinds of things. And so the pandemic was the kick in the pants we needed. And since clients were also entirely remote, it just wasn't an issue. It'll be interesting over the next year as we navigate being able to be in person again staffing projects remotely, having teams be distributed, that kind of thing. It will be fine. If we didn't think it would be fine, we wouldn't have done what we did, but just because it will end up okay doesn't mean that it won't be a little bit of a challenge or interesting. DIANA: Absolutely, yes, I agree. I think we may even be more experimental and traveling to different cities where the client is, for example, together as a group, which we really didn't do much of in the past. We've talked about having things like pop-up offices, which is something we will experiment with. So there's some experimentation to happen. I know we're going to make mistakes. But I know we're also going to do some stuff that's going to be really, really great, too. We have to try it, though. We won't learn until we try it and lean into what works. Let's do more of the stuff that's working. CHAD: Yeah. And the other thing, and I think we communicated this to the team, which is like, this is what we're doing today. It's going to be iterative. And one of the things people need to keep in mind is that we spend a lot of money on offices. And so once we remove that, that money can be put to completely different things whether it be getting together in person more often, or it be other benefits or just operating more profitably so that we're all working a little less stressed. There are all these things that are going to come out of it. And that doesn't even necessarily mean that three years from now, we won't have small offices in some places that look very different than what the previous thoughtbot offices look like. But the best way forward, we felt, was to completely wipe the slate clean and rebuild what it means to be at thoughtbot and how we're working both financially but also from making this new structure work really well perspective. DIANA: Yes, exactly. CHAD: So, any parting words of wisdom or thoughts? DIANA: Yeah. You made this really comfortable for me. I was completely out of my comfort zone, but I think you made me feel comfortable in having a podcast conversation. So thank you for that. It was a lot of fun. CHAD: If people want to get in touch with you, ask you questions, follow along with you, where is the best place for them to do that? DIANA: Email is great. Also, I am getting more active on Twitter now. It's something I'm having to do, but you can also find me on Twitter @dianabald, first name, last name. And my email is dianabald@thoughtbot.com. CHAD: Awesome. You can subscribe to the show and find notes for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. You can find me on Twitter @cpytel and Lindsey on Twitter @Lindsey3D. This podcast is brought to you by thoughtbot and produced and edited by Thom Obarski. Thanks for listening as always, and see you next time This podcast was brought to you by thoughtbot. thoughtbot is your expert design and development partner. Let's make your product and team a success.Special Guest: Diana Bald.Support Giant Robots Smashing Into Other Giant Robots

Chad and Lindsey talk with Courtney & Tye Caldwell, Co-founders of ShearShare, discussing culture-fit with new hires, incorporating values into brand-thinking, fostering relationships, and planning for 2021. Please take a minute to help guide our next season with your thoughtful feedback on our Giant Robots listener survey. Thanks! This episode is sponsored by HelloFresh Enter code ROBOTS80 to get a total of $80 off, including free shipping! ShearShare ShearShare on Instagram Become a Sponsor of Giant Robots!Special Guest: ShearShare.Sponsored By:HelloFresh : Get a total of $80 off, including free shipping! Promo Code: ROBOTS80Support Giant Robots Smashing Into Other Giant Robots

Chad and Lindsey talk with Alasdair McLean-Foreman, CEO & Founder of Teikametrics, discussing the intermingling importance of mission, vision, and values. Please take a minute to help guide our next season with your thoughtful feedback on our Giant Robots listener survey. Thanks! Teikametrics Blitzscaling- Reid Hoffman Jeff Weiner - CS183 at Stanford Dunbar's number Previous Netflix Culture Deck Alasdair on LinkedIn Become a Sponsor of Giant Robots!Special Guest: Teikametrics.Support Giant Robots Smashing Into Other Giant Robots

Chad and Lindsey are joined by Michael Sheeley, founder & CEO of Nurse-1-1, to discuss crafting values with purpose, living those values in the product's messaging & marketing, choosing not to publicly publish them, and what the landscape of healthcare looks like going into 2021. Please take a minute to help guide our next season with your thoughtful feedback on our Giant Robots listener survey. Thanks! This episode is sponsored by HelloFresh Enter code ROBOTS90 to get a total of $90 off, including free shipping! Nurse-1-1 Michael on Twitter Nurse-1-1 on Instagram Become a Sponsor of Giant Robots!Special Guest: Nurse-1-1.Sponsored By:HelloFresh : Get a total of $90 off, including free shipping! Promo Code: ROBOTS90Support Giant Robots Smashing Into Other Giant Robots

Chad and Lindsey discuss the history of values at thoughtbot and how they served as a key differentiator in the early days of the company, and navigating the tricky waters of when client values don't align. Please take a minute to help guide our next season with your thoughtful feedback on our Giant Robots listener survey. Thanks! The thoughtbot Founders' story on Giant Robots thoughtbot Purpose Statement AgencyU Become a Sponsor of Giant Robots!Support Giant Robots Smashing Into Other Giant Robots

Chad and Lindsey talk with Courtney & Tye Caldwell, Co-founders of ShearShare, about their early days of in-person marketing, the importance of naming, consistent messaging, and the effects of hiring a head of growth. ShearShare Mentored by Failure- Tye Caldwell ShearShare on TikTok ShearShare secures $2.3M in seed funding Google's Black Founders' Fund ShearShare on Instagram Become a Sponsor of Giant Robots!Special Guest: ShearShare.Support Giant Robots Smashing Into Other Giant Robots

Chad and Lindsey talk with Alasdair McLean-Foreman, CEO & Founder of Teikametrics, discussing the day-one origins of marketing there, building your reputation through content marketing, and the efficacy of various content channels. This episode is brought to you by Teamistry. Discover stories of teams who work together in new and unexpected ways to achieve remarkable things, on the Teamistry podcast Teikametrics Stats & Trends From Prime Day 2020 Webinar "How to Make Podcasting Work for You"- Lindsey @ Startup Boston Flywheel 2.0- Early Access List Teikametrics Acquires Adjusti.co Nikola admits prototype was rolling downhill in promotional video Alasdair on LinkedIn Become a Sponsor of Giant Robots!Special Guest: Teikametrics.Sponsored By:Teamistry: Discover stories of teams who work together in new and unexpected ways to achieve remarkable things, on the Teamistry podcastSupport Giant Robots Smashing Into Other Giant Robots

Chad and Lindsey are joined by Michael Sheeley, founder & CEO of Nurse-1-1, to discuss the blurry line between marketing, research, & product, committing to branding, acquisition costs, SEO & content marketing, helping to power a new provider platform, and hiring a head of marketing. Nurse-1-1 Nurse-1-1 Healthtech Blog Utilization Management White Paper Well At Home Michael on Twitter Nurse-1-1 on Instagram Become a Sponsor of Giant Robots!Special Guest: Nurse-1-1.Support Giant Robots Smashing Into Other Giant Robots

Chad and Lindsey discuss 'what's in a name' when it comes to branding, where (and where not) to start when you first begin your marketing efforts, and staying engaged with your customers. This episode is brought to you by: Teamistry- Discover stories of teams who work together in new and unexpected ways to achieve remarkable things, on the Teamistry podcast Hover: 10% discount on all new purchases! SWOT analysis Being Human in the Absence of Humans- Remote Teams Workshop Become a Sponsor of Giant Robots!Sponsored By:Teamistry: Discover stories of teams who work together in new and unexpected ways to achieve remarkable things, on the Teamistry podcastHover: 10% discount on all new purchasesSupport Giant Robots Smashing Into Other Giant Robots