Richard Baker

Richard Baker, VP of Product Design at PandaDoc, discovered early in his career that simplicity can often be the best policy in all aspects of life.

From building the first enterprise UX team at General Electric to leading design teams at OpenGov and PandaDoc, Richard Baker has found an essential common denominator: we're all humans. And his care-driven approach to management has made all the difference.

About the Guest

Richard Baker is a seasoned design leader committed to growing design and innovation teams' influence, scale, and output to improve business results and the customers' experience. He fuses strategy, design, and technology to help teams solve difficult problems. He has 15+ years of experience in helping enterprise organizations amplify the impact of design in their business, products, and culture.

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Alison Dean (00:09):

This is the Breakthrough Podcast, an ongoing series where we interview game changing leaders in technology, business, government, and entertainment about their experiences and perspectives in life and leadership, learn about their latest breakthroughs and hopefully inspire you to have some of your own. Welcome to the Breakthrough, I'm Alison Dean, and today we are talking with Richard Baker, currently VP of Product Design at PandaDoc. PandaDoc's mission is to help organizations eliminate workflow inefficiencies, and I say amen to that. Richard sent me this quote from Winston Churchill, "To improve is to change, to be perfect is to change often," which is quite deep. Hello, Richard.

Richard Baker (00:55):

Hi Alison.

Alison Dean (00:56):

So I want to know what that quote means to you.

Richard Baker (00:59):

Yeah, well one of those things in life is that things are always changing whether you like it or not. And usually, you get the most frustrated when change is thrust on you, right? And so that's a good quote just to kind of remember around perspective, and just kind of thinking through every shift, every problem, every change is always a growth opportunity. So it's just a good reminder to keep growing, and if you stay still too long, then trouble is afoot.

Alison Dean (01:27):

I love that. I actually was tempted to put that into Slack today for my team. Because I was like, "This is a really good nugget to just think about." All right, so I want to know, what is the first breakthrough that you remember that set you on your career path?

Richard Baker (01:40):

Yeah, so I was a designer at GE. I was a individual contributor and I was supporting about 20ish software products at the time, so that's not sustainable. And so it was generally just whoever screams the loudest, and do a little work here, do a little here, do a little here, and that kind of stuff. And so, I started talking to my boss about, "Hey, we should get more designers and we should scale up." And he's like, "All right, well write something up." I was like, "What do you mean write something up?" And so I started doing that and dug into it and he is like, "Great, now go pitch it to an executive." I was like, "Wait, what?" So he kind of coached me through this process and I ended up pitching that to the CTO and just the idea that we should have a UX team. And so he said, "Okay."

Richard Baker (02:31):

So just from there on, just started growing the team slowly and shifted into a player coach, and then grew, and grew and grew. And so ended up that team grew to about 30. Wow. We had a ton of fun over the six or seven years, but that was very interesting, just this concept of like, "Ph, you want to change something? Well then write it down and go talk to people." I just thought I was supposed to just tell someone else and then they would fix it. And so just this idea of like, well, if you see a problem, go fix it. Just this idea of fixing and kind of self-sustaining, almost. Just solving problems. I think that was a great lesson and it's helped me quite a bit through my career.

Alison Dean (03:09):

Mm-hmm. I can reflect on similar situations myself; write it down and see what happens. Okay. So given your background in the public sector, including roles with the city of Jacksonville and OpenGov, what intrigued you about making the move to PandaDoc?

Richard Baker (03:25):

Well, I'm always careful when I think about my career, I like to kind of design it, like you would design anything else. I was at the city, I loved doing government, I loved seeing the impact. And then when I left GE, I mainly left GE because I didn't want to be the train guy. And then when I was at OpenGov, I didn't want to be the government guy. It was just an opportunity to explore a new market, a new area at PandaDoc, it's still B2B software, but it's still a little bit more consumer driven, and so it's a larger scale; we have 40,000 plus customers. And so it was just a fun opportunity. Plus, I'm a big document nerd. I don't know what it is, but documents, templates, note systems, note software, all that kind of stuff. I'm just a big old nerd for it. And so when I started using their product, I was like, "Ph, this is really interesting." And then someone demoed how they use it and I was blown away. It was insane. So from then on, I was pretty excited about it.

Alison Dean (04:31):

I love that. And then what would surprise people about PandaDoc? Like me, for instance, anything that would surprise me about PandaDoc?

Richard Baker (04:38):

I think, so this is something that was very surprising to me. The co-founders are originally from Belarus, and so they're really big in the tech space there. But what really surprised me is the company has a lot of folks in Belarus, Ukraine, Poland, that area. And then, when the war broke out, they moved a lot of people. They relocated them all, so anyone they could, they just relocated. So finding all that out after I joined was really interesting because the team grew, they probably doubled within the past year. The design team probably doubled within the past year. Beginning of this year, they just finished a giant rollout of brand new interface and some great amazing features. And then, they've been kind of just doing a ton of work over the past year, and they've done all this work in the middle of a war.

Richard Baker (05:31):

And I just find that amazing, the perseverance and the focus of just building quality products, delivering user value. They're really passionate about building and solving this problem around document management for users, and just overall meeting user needs. They're super passionate about it. And seeing all the stuff they've done in the past year in the middle of a war, I was like, "I don't think I could do that. I don't know if I would be focused when I got evacuation and maybe bombs going off." I don't know. That was very inspiring to me just to see the progress during all that time.

Alison Dean (06:07):

Yeah, the focus on the people, right? So it sounds like they emphasize and care for their team.

Richard Baker (06:12):

They do, yeah, quite a bit. It's a very great organization. The vibe, the culture there is very refreshing. So it's a great place.

Alison Dean (06:20):

It's always good when you can describe your workplace as a refreshing place to be. I like that.

Richard Baker (06:23):


Alison Dean (06:25):

Okay. Do you have a morning routine?

Richard Baker (06:28):

With the new role, I have a new morning routine. I used to have a little bit of a different routine, but most of my team is in Eastern Europe, so I've shifted. I typically like to start my day early. I like to get up around 6:00, and then in my office around 6:30 and kind of focus on deep work for at least an hour or two before I do anything else. So I've shifted that. So now all my calls start at 6:30, so I'm deep in the workday at 6:30 in the morning, and then I kind of go till lunch, maybe a late lunch, and then have a pretty decent size lunch, just like time-wise to just breathe. And then the afternoon is kind of just focus time.

Richard Baker (07:08):

So it's a different cycle for me, but what that's allowed me to do is have a lot more face time with my team and have a lot of time, especially as I'm getting to know everybody, and learning all the styles and reading a ton of documentation, all that kind of stuff. So that's given me two, three more hours a day of chatting with my team and getting to know them and working with them. And then the afternoon I can have-

Alison Dean (07:29):

Focus time. Yeah.

Richard Baker (07:30):

That's been a big shift, because previously I worked with a lot of West Coast folks, so I would still get morning time, but I'd have a much larger block of focus time. So flipping that, I'm still getting used to.

Alison Dean (07:40):

It takes time, yeah. When you've been doing something for so long in one way, change is change, right?

Richard Baker (07:47):

That's what Winston Churchill says, right? You think about change.

Alison Dean (07:50):

Flex those muscles. Okay, so I appreciated one of your tweets that mentioned public speaking. You said, "A few things will terrify you as well as public speaking. You'll use all that nervous, scared, and panicked energy to prepare, become an expert on your topic, and simultaneously help your audience grow." So in all the ways that you've helped your audience grow, how has public speaking helped you grow?

Richard Baker (08:14):

Yeah, boy, I do hate public speaking. It's just that over preparation. So at GE, we were reworking kind of how design team worked, how we did innovation, kind of new product introductions, all that kind of stuff. And we kind of worked on a system that worked really well, how we could go from innovation, and discovery and then easily dovetail into traditional agile design work. And it worked out really well. At the time, I saw some conferences, and I knew some of the coordinators, and so I submitted the talk and it was just one of those things of we did some stuff, submitted it, out of mind, I moved on with my life. And then all of a sudden they emailed and they're like, "Hey, we would like you to do this." And so now all of a sudden you got to turn it into a talk. It went from one paragraph to a 45 minute talk now.

Richard Baker (09:01):

And so, just preparing and making sure that you don't sound like an idiot, that helps stretch your own models and your own understanding. And then, actually preparing for that, I was able to refine and rework some of the things that we were doing internally and improve some things because of that over preparation. And then again, this goal of not wanting to sound like an idiot, I shared the talk with other people and got their perspectives and they're like, "Hey, maybe you should do this?" And I was like, oh, that's a good idea. And we implemented that again at GE, and tweaked it and iterated. So I find a lot of designers fall into that category of they like to be over prepared. They want to be the expert on whatever it is, especially when they get up in front of a lot of people and pretend to be the expert.

Richard Baker (09:48):

So yeah, that's really helped me just in terms of refining our approach there. But then also, as you move up in your career, it's a lot of public speaking, essentially. And sometimes you're prepared for it, sometimes you're not. And there's been a lot of times where I'll get on and accompany all-hands and it's like, "Ph, we're going to talk about this, talk about this. And oh, by the way, Richard's here. Why don't you tell us a few words? Explain this thing." And I'm like, "Okay." So just being prepared and being able to talk through those things, it's a good skill to have. And I think that's one of those things that no matter what your job is, if you're technical or not technical, if you're growing into individual contributorship, or leadership or any of that kind of stuff, solid public speaking is really going to help you just get your points and your thoughts across.

Alison Dean (10:36):

Okay. So do you have a number one tip? So if someone's embarking on their public speaking journey, is the number one tip to be over prepared, or would you say it's something else?

Richard Baker (10:45):

Number one tip, if this is a prepared talk, then you got to record yourself, and go over it over, and over and over it. Because after I wrote my talk, I'm like, "Okay, this is good." And then I do the little voice app on the iPhone and start recording myself. And then I'm like, "I would never say that."-

Richard Baker (11:03):

On the iPhone and start recording myself. And then I'm like, I would never say that, I might type that, but I would never say that. And then I type out words that I can't actually pronounce, I just fumble over. And so it's like, well, we're going to have to change that word. So that would be the big thing is after you write down all your thoughts, you got to say it out loud because I bet a lot of people are the same way. That they write in one voice and then they speak in another.

Alison Dean (11:25):

That's a great tip. All right, continuing our tradition of past guest questions. This week's Breakthrough Club question is from Kieve Huffman, who is CEO and founder at Engager Brands. He asks you, how has creating strong design teams changed in our post pandemic world?

Richard Baker (11:54):

This is a good one. So we used to be able to get in the same room and see each other, confirm everybody has legs and a torso and like, oh, you're a real person. That kind of ceremony is really important when you're doing design. One, it's going to build culture, but then two, we get in a room and we scribble on post-it notes and draw on whiteboards, and there's this creation aspect to the way that we work. And that ultimately builds trust amongst designers because in design teams, it's one of the few roles that part of your job is to criticize other people's work. Not many jobs you say that, but as a designer, that is part of the critique process. You do need to do that to have a healthy team. And so you have to have trust to be able to have that good critique process and to build the trust you need to have real relationships.

Richard Baker (12:42):

And so it used to be a lot easier. You get in a room, you know each other at a personal level, and then you do workshops and you just kind of grow together as a team. And that cohesiveness happens. And now it's digital. I mean, I still haven't met most of my team and it'll probably be a while until I can meet them in person. And so you have to really be diligent. You have to be thoughtful around what kind of exercises you're going to do, how the team is going to come together, what kind of outcomes you want from these specific meetings, or whatever that collaboration piece is. Because if you just get all on the same Zoom call and then you talk for 30 minutes, everyone's going to be muted. They're going to have their video off, they're going to be scrolling their phone. It's just a mess.

Richard Baker (13:22):

So you got to really be a little bit more focused when you craft that experience. And then you got to think about how is it going to be approached, how are people going to react? And then whatever it is, whatever you would normally do in person, you have to double it. So as a team, if you might do two team builders a quarter, great, now you got to do four. It's just as a rule of thumb, you just double it. And you got to have that time together, but it can't just be wasted time, it's got to be very structured. Because no magic is going to happen anymore. The magic is about being in person. And so now, when you're digital, you can't rely on that magic, so you got to create your own magic.

Alison Dean (13:58):

That's another bumper sticker. You have to create your own magic. I like that. Okay, so another one of your recent tweets reads, "Before digging into your design system, ask yourself what problems does the company want the design system to solve?" To piggyback on that, designing UX are important elements of any digital transformation. So I'm curious through your own design lens, what does transformation mean to you?

Richard Baker (14:26):

Transformation's a tricky one because everybody has their own thinking, their own style of that. So anything beyond iteration, I think of transformation. And so usually my rule of thumb is transformations require more change management than the actual transformation. It's all about managing that rollout and the change because people don't like it, it could be great, it could be the best thing ever, but nobody's going to like it because it's change. And so when I think about transformation, I think extra work, because it's all about change management process. And really making sure that it's well received, people understand it, it's simple enough to be understood, all that kind of stuff. At OpenGov, we dealt with that a lot because a lot of our bread and butter was helping governments that were paper-based and leading them into a digital process. And helping them rethink staffing models, and software, and hardware, and how offices work, and all that kind of stuff. Yeah, it's a lot to it.

Richard Baker (15:32):

In fact, when the pandemic first hit, we had a workshop. We were going to be in a customer's office, and then all of a sudden everybody went on lockdown, and so we called them and said, "Hey, you know what? No problem. We're going to do the workshop. It's going to be great. We can still support this, and here's what we just got to get. Everybody will just dial in on Zoom, and everyone will have laptops, we'll do a Mural board, and the whole thing." And they're like, "Great." Except for, nobody has laptops and most of us, it was a rural community. And so most of us have satellite internet and can't do video Zoom calls. And we're like, oh, okay. That I just remember, in terms of the stumbling blocks of transformation. When you go from paper to digital or in-person to digital, those pieces that you don't think about, it's just kind of a given, but all of a sudden you hit them and that is where the details really shine through in any kind of transformation work.

Alison Dean (16:32):

What do you think the most important element of change management is?

Richard Baker (16:36):

Simplicity. So everything has to be simple. If there's like 18 bullet points and 30 different steps, stop, just go back, do over, get it down to 3, and then roll it out. It's got to be super simple, because so much about change management is really just a systemized version of the telephone game. You're going to tell these people what's changed, and then they're going to tell other people, and they're going to tell other people. And then five people down, they're just going to get a note that says, "Oh, by the way, we don't use paper anymore. Do whatever you want." That's why simplicity is so key.

Alison Dean (17:13):

I think too, it's really important for there to be the right executive sponsor to sort of mandate specific things because I think if it doesn't happen at the right level, there's no hope for it. I think if there's one person at the top that's like, "And this will be the way." Then at least everything, to your point about simplicity, then all that stuff actually can take proper effect. And I've heard so many stories on this front where it's like, "The CFO didn't send that email or the CEO didn't send that email." And everyone was just rejecting things. And it's like, ugh, after all that work. Okay, so you just revealed a project, but I'm curious, is there a project that comes to mind for you as being the most memorable and why? And is that the same project that you would consider the most difficult and why? Or are there projects in those two buckets? Memorable and difficult.

Richard Baker (18:04):

Okay, I'm going to stretch the term project a little bit.

Alison Dean (18:07):


Richard Baker (18:08):

So at OpenGov, the mission was around leading transformation and really helping governments become accountable and efficient. And that took on a whole new meaning as soon as COVID hit and pandemic happened. And then that really just kind of made the mission real in so many different ways and for so many people. And so the work that we did there, we helped countless offices open up again. And they were still in lockdown and you couldn't do any building permits, you couldn't do inspections, you couldn't do any licensing because you had to go there and do a paper form and then people had to process it and everything was closed. So helping so many governments open back up and have software that supported that process, but then at the same time just made it 10 times better and had huge benefits for the citizens. That I think was really inspiring.

Richard Baker (19:08):

And the people that we worked with, citizens and the actual government employees alike, they were so thankful. They were so excited. Every little change, every time we call for a research call or just want to get feedback, oh, they're just so excited to hear from us. And they love being part of that process. And I think that was very exciting, very rewarding just to be part of that shift. And so much of it has stayed, and it's not like, oh, we all get together. We do this thing, and now the world's opened back up and so now we're back to the old processes. No, no, no. All that stayed. And so now all of a sudden people can get their building permits done, click of a button, and so everything has just been made better through that process. Just to be through that process, and see that happen, and see so many people excited for that shift was just super exciting.

Alison Dean (20:00):

I love that. That also in the difficult category as well?

Richard Baker (20:02):

Yeah, there were some difficulties. There were some difficulties. I won't name specific projects. But at GE, GE Transportation at the time, it's now been merged with another company, but at the time a lot of what they did was build software for the rail industry, a lot of freight rail and other things. And so we were really heavy on research because at the end of the day, if you do it wrong, if you build the software wrong, if it's not usable, people could die. That was a reminder, and everything was safety first for us. And so that got a little daunting at first because you meet all these experts and they've been in the rail industry for 50 years and you're learning all the process and you're starting to make changes or make proposals for software that may just be paper.

Richard Baker (20:49):

And so when you start talking and interviewing people and there's so many ways people can die, that was daunting. So I don't know if it was difficult, but it certainly stayed in our minds of like, "Hey, this is the reason why we do research. This is the reason why we want to do things right, and we test, and we validate, and all that kind of stuff. All the great pieces of the traditional design process. But it really came down to safety first." And especially when you're changing, you're redesigning an industry. And everybody that you talk to, "Oh, we've done it this way for decades. My father did it this way when he was in this job, and now I do it this way when I'm in this job." And then now you're like, "Great. Do it this way." And they're like, "Hmm." So there's some friction that happens. That also made things a little difficult, but at the end it also made it the most rewarding.

Alison Dean (21:37):

And also probably exciting.

Richard Baker (21:39):

Yeah. Once you kind of see some of that progress, it was very great.

Alison Dean (21:42):

And also you can see how it's impacting these people that have been sort of leveraging old systems or things that have been set in stone for a certain period of time. It's refreshing almost to see how those things are adopted when you yourself were sort of behind all of that happening. But I would agree, I think anytime you introduce life or death situations, I guess-

Alison Dean (22:03):

I think anytime you introduce life or death situations, I guess, this is a difficult challenge to be accepted. Yeah, for sure.

Alison Dean (22:09):

Okay, so we're going to do something I like to call the break on through the rounds, since it's our halftime show break. So basically quickfire rounds. Okay. iPhone or Android?

Richard Baker (22:28):


Alison Dean (22:28):

Twitter, Instagram, or TikTok?

Richard Baker (22:30):


Alison Dean (22:31):

I kind of knew you were going to say that. Favorite color?

Richard Baker (22:34):

Right now, blue.

Alison Dean (22:36):

Morning or night?

Richard Baker (22:38):


Alison Dean (22:39):

I kind of knew you were going to say that too. Superman or Batman? Neither. You're like me. Favorite place to travel?

Richard Baker (22:48):

Somewhere beachy. Anywhere Beachy.

Alison Dean (22:51):

Anywhere. Okay. Favorite book?

Richard Baker (22:55):

Oh, man. I really like things I can learn from, so not fiction. If it's going to teach me something, I would say that I used to read encyclopedias. I thought that was real fun when I was younger and then I graduated to manuals. I would say, of all time, The History of Graphic Design. Maybe. That might be my favorite of all time book.

Alison Dean (23:19):

I love that.

Richard Baker (23:19):

Super boring.

Alison Dean (23:20):

No, I love that. Okay, A historical figure that you'd like to have coffee with?

Richard Baker (23:26):

Ooh, let's see. And now I can't think of his name. The guy who designed the IBM logo. Famous graphic designer.

Alison Dean (23:33):

Oh, I feel like I defer to you for that stuff.

Richard Baker (23:36):

I should know it. He's in the book.

Alison Dean (23:38):

All right. That guy. This is where everyone's going to comment now and be like, "Don't you realize?" If you had one superpower, what would it be?

Richard Baker (23:45):

Invisibility maybe.

Alison Dean (23:47):

Ooh. Okay. All right. That's mysterious. Last TV show you binged.

Richard Baker (23:53):

So I don't like new shows. I only shows I've already seen.

Alison Dean (23:55):


Richard Baker (23:56):

Just finished Mad About You.

Alison Dean (24:00):

Oh, that's a good one.

Richard Baker (24:00):

Yeah, I don't like new stuff.

Alison Dean (24:02):

I like that.

Richard Baker (24:02):

I don't have the patience to pay attention.

Alison Dean (24:04):

Right. You're like, oh, that's a familiar... Familiar voices. I like that. Favorite song on the radio right now?

Richard Baker (24:10):

I don't listen to the radio. I couldn't tell you.

Alison Dean (24:11):

Favorite song in general.

Richard Baker (24:13):

The ones without lyrics. Is that a good one?

Alison Dean (24:17):

Like Jazz, blues?

Richard Baker (24:17):

Yes. Just background music while I do other things.

Alison Dean (24:19):

I like it. Focus time. Favorite movie?

Richard Baker (24:22):

Oh, this is bad. Groundhogs Day. I like that one.

Alison Dean (24:25):

Okay. Favorite Candy?

Richard Baker (24:27):


Alison Dean (24:28):

Favorite podcast?

Richard Baker (24:30):

Should I say this one?

Alison Dean (24:31):

No, you don't need to. No, it's okay.

Richard Baker (24:33):

I've just recently been listening to Dana Carvey and David Spade, and they're interviewing old SNL guests. It's been very interesting.

Alison Dean (24:44):

That's cool. I need to check that one out. I like it. Okay, last one. Typewriter or word processor?

Richard Baker (24:52):

I'm going to say typewriter.

Alison Dean (24:55):

You know that that one was specifically for you. Speaking of typewriters, since I know you're a fan, I would love your thoughts on the impact that they have had on tech and why they are still relevant.

Richard Baker (25:10):

Oh yeah. Okay. Typewriters are great.

Richard Baker (25:13):

So impact, they changed a lot of the ways that we type. So our keyboard comes from typewriters, and really a typewriter is just a small printing press. So it's in that whole realm. They let us mass produce the written language and write to people in a great way and faster, express our own thoughts. I mean, it definitely is transformational. The best fact is that the QWERTY keyboard comes from typewriters because they want to slow you down. Because specifically this typewriter here in my background, the Underwood, it's got this bowl of letters and they're flying. And if you type too fast, then they start hitting each other. And so they had to redesign the letters so that you would slow down and you wouldn't put too much strain on the keyboard. And so now you think about, man, every single device has the QWERTY layout on it almost from your phone to the ATM sometimes. And I mean, it's everywhere.

Alison Dean (26:08):

Tell me about thank you notes.

Richard Baker (26:11):

Oh yeah. Okay. So I do have two typewriters and I like to write thank you notes on them. I think it's a little bit more deliberate. And handwritten notes is nice, but a typewritten note, it stands out even more. And one of the things that I'm trying to do, I'm going to start doing in January, is I want to start, at least once a month, hopefully a little bit more, actually writing thank you notes to either mentors or people on my team, or whatever it is, specifically on my typewriter because then I can combine those two things. But there's so many people that I have worked with in the past or I am working with now that have had such a great impact on either me as a human or me and my career. And so I want to let those folks know either good things that they're doing or the impact that they've had on me. Yeah. So I'll be using my typewriter for that. I got special thank you notes just for this, so I can feed it in the little typewriter and everything. So yeah.

Alison Dean (27:09):

I love that. Okay, so you harmoniously segued me into the next question, which is, what is the most impactful lesson that you've learned from a mentor, and who was it? And why was it so impactful?

Richard Baker (27:21):

A CTO at GE, he mentioned this several times, not to have any surprises. Leaders in general, they don't like surprises. And so that's really stuck with me because I like to do that. I would create a document or a vision, and all this kind of stuff, and I'd be all perfect, and then I'd unveil it to them like, here it is. And he's just like, "No, this doesn't make sense." And it's all great relevant feedback, but it's just in general, no surprises. And that's really worked well for me, especially when doing important presentations or working with other leaders in other orgs. They should kind of already know, if something's amiss, they should know that. So no surprises has always been kind of a mantra when I'm working with folks. If there's something that I was like, "Ooh, that's a doozy, I need to let them know ahead of time so they can have time to process and plan."

Richard Baker (28:15):

And if you're doing it with other people, if you're presenting in a group setting, then they're aware of their expression when they hear that meaty update or something like that. But that served me well, and that's something I always think about. It's just no surprises.

Alison Dean (28:28):

Is that the number one lesson that you want to pass on to your mentees? No surprises? Or is there something else that you want to pass on?

Richard Baker (28:36):

No, I would say it's caring. You got to care about your team, you got to care about the work that you're doing. And I think this is also now easier to lose sight of in the digital world, in the social media world, and the Zoom world, is that you got to really care. The people that you're working with are humans. And so you need to really remember that and care about them as a human. And so when I'm working with my team or I'm building the team, and establishing those relationships, that's one of those things I always come back to is you got to remember everybody's a human. There's a certain human level that you want to connect first and then you can go to business. But if it's so transactional and so dry, then later on when you do have a conversation that is very transactional or it could be a tough conversation, then that personal connection is going to really matter so that everybody understands the tone or why you had to say something or this kind of feedback or something like that.

Richard Baker (29:38):

So I think that's super important, is just care about the people that you're working with, and then that's going to also lead you to care about the work that you're doing, and making sure that you show up and you enjoy it and you have fun with it.

Alison Dean (29:50):

You've said this, which I love, "Good team culture doesn't happen by accident. It must be curated and designed just like a user's experience." So to that end, and I guess to your points on caring, what other monumentally big leadership lessons have you learned that you're taking into your current teams?

Richard Baker (30:10):

I would say another thing that's really important is a sense of purpose. Everybody gets projects they don't like, but it's important to connect the reason, like the purpose.

Alison Dean (30:21):


Richard Baker (30:22):

This is happening because, or I need you to do this because. I think that's important. And as I've started building more teams and then during COVID times and the remote times where it's so easy to get burned out and attrition's at an all time high, and then just overall dissatisfaction is at all time high, that's really resonated with me is just making sure that everybody knows that, hey, this project that you're working on, it may be super boring. You might just not enjoy it and that's okay, but let me explain why it's really important and how it's going to matter to the business and how it's going to matter to our users. And able to connect the dots is at least enough to be like, oh, okay, well I get it. I'm not going to enjoy it, but I get it. And they're going to work through it and then the work's going to be better. So that's a really important one that I've been thinking about.

Richard Baker (31:12):

Design culture is the big one. The culture on the team in general, being diligent around how everybody works together, how everybody collaborates, that's really key.

Richard Baker (31:21):

And being specific around collaboration. It's really easy to get busy. And I did it today. Let's see, right now I have 22 Slack messages I have not responded to. And I know they're there and I have to talk to these people, but today, coming back from a holiday, heads down, just worked on this thing I needed to clear out.

Richard Baker (31:40):

And so it's really easy to, especially in the digital world, to just heads down and focus and just knock something out. But collaboration is really important because it makes your work better, but also it breaks down all those silos that you have so often, especially in tech companies. Marketing does this and product does this, and design does this. And so that's another thing that I've been really thinking about a lot is just this collaboration by design and making sure that we have the right moments to collaborate and to work on those silos, and to make sure that everybody's seeing each other and they understand what we're doing. That's been really important too.

Alison Dean (32:16):

Is there a recipe for that, you think, within organizations? The cross-departmental collaboration and where those things can intersect?

Richard Baker (32:24):

It's hard to say a recipe. You can look for hotspots. You can look for either hot or cold spots. Like friction I would say is a hotspot. Maybe no friction or no collaboration at all might be the cold spot, but you can look for those, or just dissatisfaction. But it's one of those things, you got to talk to a lot of folks and just really observe what's going on, what's not. And then when you hear, "Oh, well we can't do this because product isn't going to let us do it." And then you're like, "Oh, okay, well now we got a silo. Now we got something that we might need to work through where there might be a misunderstanding."

Richard Baker (32:57):

So I don't know so much about a recipe, but it's really just about listening and it's kind of like active listening, kind of hear the meaning in between the words, and then starting to think through what couldn't break some of that down. I think that's probably the biggest thing is, you just got to pay attention.

Alison Dean (33:14):

Yeah. I think, though, to your point from earlier, talking about writing things down and sort of the impact that you can have, so it's how listening and identifying these things, and then perhaps being that change maker, even though you might not think that that's the role that you've signed up for. It's interesting when you have that perspective, when you're understanding, especially coming into a new org, that that could be one of your designated responsibilities, even if you didn't think it was.

Richard Baker (33:43):


Alison Dean (33:46):

Okay. So as we know, you're in the midst of a new role at a new company, in a new industry. So what projects, initiatives, projects, are especially interesting to you as you continue in your career?

Richard Baker (34:00):

I do love team building, and so I'm focused on that right now as I come into a brand new team, and just looking at what's working, what's not, how do we tweak things, how do we build the trust? It's almost like trying to elevate the EQ level of the team. And so just looking at those kind of exercises, and that's what I've been working on right now. It is certainly a passion of mine, is having good healthy teams. Because ultimately a healthy team is going to have healthy work, it's going to have good quality work. And so I think that's a good place to start. That's a big area.

Richard Baker (34:35):

And then the other area, fortunately I get to really nerd out on document creation and management. I have strong opinions. Every time I'm using certain tools that I won't name, I'm like, "Oh, why doesn't this work? The button should be right here." And so now I can go through that and learn our product super deep, and when I come across some of those frustration points, I just write it down.

Alison Dean (34:57):


Richard Baker (34:58):

It's like, "Oh, I know who I'm going to talk to about this." That's been fun, just learning the space, learning the industry, learning our product, and really getting deep into it. It's been a fascinating journey.

Alison Dean (35:09):

As it relates to remote team building, is there some specific modules that you employ or anything that, specifically, you think works really well in a remote team environment?

Richard Baker (35:23):

FaceTime is a big one. We need to see each other's eyeballs. That's what I tell my team. It's like, "I need to see your eyeballs." That's what's important. It's in a variety of different ways. So I think about, one, it's around how we collaborate as a team, and then also how we collaborate with our partners. It's about how we do our critiques, how we talk to each other, how we have those conversations. And we need to also make sure that we have a space or an outlet for just goofing off. It can't just be business all the time. We got to have a Slack channel or something where we can just post nonsense, get it out of our head. And now everybody is stuck with that image in their head, not just me. It's like those kind of things.

Richard Baker (35:59):

And then growth. Growth is a big one, because we can get so bogged down in work. Any time you check something off your to-do list, there's going to be five more things to get in there. Backlogs are bigger than ever. And so we have to carve out the time to stretch each other, and stretch the team, and build up our skills and kind of sharpen the knives, so to say. That's a really big important one.

Richard Baker (36:23):

So it's kind of just process, but then it's also skill and growth, and making sure that everyone has time to invest in themselves and invest in the team. I've found that just making sure that we have that time to do things as a group, but then also individually, starts to create that shared connection, creates that trust. Shared team trust is huge. I mean, you cannot have a functional team without trust, especially in the design industry, because a lot of our job, we're just supposed to be critiquing other people's work, right? We're paid to tell you why your design is not good. A little drastic, but in general, that's what it's about.

Richard Baker (36:59):

So yeah, if you don't have trust, then I'm going to think that you just hate my design because you hate me as a person. Never about me being a bad designer. I would never be a bad designer, come on. So I think trust is really important.

Alison Dean (37:10):

Yeah, I would agree with you. Okay. What future innovations are you excited about? Could be personally or professionally. And what do you think is the next frontier, innovation-wise?

Richard Baker (37:21):

There's been a lot of this AI-powered writing, like GPT-3-powered, there's like, and there's Jasper, and all these different things out there. And then on top of that, you have Grammarly and all these other tools that will either suggest content for you or rewrite your content. And I find that whole space fascinating, and it is pretty relevant to PandaDoc and just document management in general.

Richard Baker (37:47):

I find that space very interesting. Not interesting enough where I'm going to go code and figure stuff out, but I love using all these different tools, and seeing what they're doing, and how much better it is than just six months ago. And some of the things are wild, like you can go in there and say, "Oh, I want to do a blog post on woodworking. Go." And then it writes this whole blog post with childhood memories and origin stories, and it all fits together. And you're like, "Man, that's wild."

Richard Baker (38:16):

So that whole frontier is interesting. Right now, it's mostly around marketing, and I think it's going to be really interesting when that meets the enterprise. That'll be exciting. I've been keeping up with that, playing with the tools. I'm excited to see where that goes. And then the extension of that is imagery, where you can just describe an image and AI will just generate it for you. That's fascinating. Mostly scary, but also fascinating.

Alison Dean (38:41):

I'm with you. Okay. We talked about an early breakthrough. What about a recent breakthrough that you've had?

Richard Baker (38:50):

I've been thinking through what kind of leader I am and I want to be, and I've been working with a coach to help me think through, just in general, become a better leader and just some of those exercises. And I think understanding my strengths and weaknesses, and then also being okay with certain weaknesses that can stay weaknesses, and then certain strengths I just want to double down on. I think that's been a personal breakthrough for me, and just kind of being okay with that balance or maybe that imbalance, and then knowing what areas I want to work on and knowing what areas I'm okay just to be bad at. It's like, you know what? That's going to be okay. And just move on, yeah.

Alison Dean (39:31):

Because we can't be perfect in everything, right?

Richard Baker (39:32):

I guess not.

Alison Dean (39:33):

Or I guess if we all aspire for the Winston Churchill, sort of, mentality of just continue changing and ultimately, you might arrive at some level of perfection. Okay. Is there anything I didn't ask you that I should have?

Richard Baker (39:48):

I think you did a great job. I think you covered quite a bit. You even fit my typewriters in there, and so I can't complain about that.

Alison Dean (39:56):

All right. Well, great. I mean, I don't use that as an opportunity to just get compliments, but I do appreciate it. That question came up because I think one of the first guests that we had, I think they brought it up to me. Like after, "Oh, you could have asked me this." And I was like, "Oh, that's actually a really interesting thing, as I kind of continue on with this, to just punctuate things with that question." So anyway, that's the background story of why I've now inserted that one as the final question, because we want to make sure that you get the full experience.

Richard Baker (40:30):

Right, and I'll give you a tip.

Alison Dean (40:33):


Richard Baker (40:34):

You can start asking that question in normal life situations. So for example, if you're signing up for cable. You know, you move to a new area, you want cable, and then you're asking all the programs and all that kind of stuff. If you throw that in there, because I ask that question all the time, and I ask that question and they're like, "Oh, well, most people ask about the discounts if you can combine." And I was like, "Oh, well, I'm going to ask that question now." And then boom, half price, it was magic. Apply that to every step of your life.

Alison Dean (41:02):

Everything, I know. You never know what you're going to get with that sort of approach. I totally agree. Well, it was fabulous having you on The Breakthrough. I thank you, Richard, and hopefully we will have another chat soon.

Richard Baker (41:15):

Yeah, for sure. This was great. I appreciate it.

Alison Dean (41:17):

Awesome. Thank you for tuning into this episode of The Breakthrough. Be sure to subscribe on your favorite platform, and follow us on Twitter and Instagram at Breakthrough Pod. I'm your host, Alison Dean. Until next time.

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