Giant Robots Smashing Into Other Giant Robots

392: Better Together with New CEO of thoughtbot, Diana Bald

May 13th, 2021

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.

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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 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

CHAD: Awesome. You can subscribe to the show and find notes for this episode at If you have questions or comments, email us at 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

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