 So over the next about three hours, I have the privilege of getting to interview a whole bunch of folks so we're gonna do a series of 30-minute interviews and Every one of them is unscripted every one of them is unprepped meaning they don't know the questions I'm gonna ask If you saw inside the actors studio ever right with Jonathan Lipton and the stack of blue index cards with the What was your fourth grade teachers? Actually they say like tell me who mr. Johnson is right and then they're like oh my god. That was my fourth grade teacher and I Didn't do that much research, right? So I just want to set the stage, right drive the bar low for expectation But it should be a lot of fun and And so we're gonna get started and we're gonna start with Ashley So if you missed it Ashley already spoke here at work camp a cookie But now you get the redux right you get the opportunity to come back and hear some more and Ashley I want to start by asking you You have a design role at automatic, right a company that has been known for a very long time as being engineering centric and You're doing something that is an engineering centric per se But really is helping the organization move forward and think about how it addresses the millions of people that interacts with What's the hardest part about your job? Well, I think the hardest part About it really is kind of what John was speaking to a little bit earlier like getting on the same page about like the audiences that were We're reaching right what the what the challenges are what they're really particular in different needs are so that they become more human and we can develop and design to actually meet their needs It's challenging especially when we I think the the traditional way of Of working was kind of assuming that our end customers or users have similar needs to our own and so kind of We discovering what the actual And use cases are where we're tripping them up both in like communications and how we're marketing Our products as well as and how we're we're building them and adjusting them over time It's just a big learning curve for us that is like a collaborative effort to get through When the in the software world right where this notion of oh, I'm just scratching my own itch Right which leaves to people looking really rashy But also the the consequences you do presume that well everybody ages in the same place I age and that's not reality Right, so instead of going from the inside out and telling the world here's what we think is a better move Right, you're really trying to bring it from the outside in right. This is what people Need is what they're struggling with is what they want and bring it in How receptive have you found the organization the people you're working with which isn't really an automatic issue? It's just a general issue, right? It's a very human issue Yeah, how hard is it to help people get out of their own shoes put themselves outside and figure out? Okay, what do what do other people need you know it actually hasn't been That hard though. It's it's like the practice of doing it and making it like a ritual that everybody does enough, right? because I Think easy for John to get some great case studies traveling around talking to small business users and saying what their Needs are and like connecting it to a product for people to see See the need there, but making that like an actual it's like an actual habit of ours to each speak to our end customers and break our In some ways personas can be bad, right? If you get too locked into like one idea of what that customer looks like to break those ideas down continually And to reshape the stereotypes So there's there's a lot of initial buy-in It's more like how do we get that practice in place where that becomes something that we do together regularly and Like the listening and the discovery That you kind of saw and John slides just a little while ago that that becomes part of What we do in the development process and the design process and that is connected to our support teams So that we've got like a full cycle of support in that like cross organizational focus on on this So it's really just getting that practice like anything, right? You're like, you know You practice to get that big music role like it takes Building up the muscle kind of breaking it down and making it Just a part of the reality that happens over time But I've been really impressed with the initial interest and buy-in and the support that we've gotten from like heads of each of our divisions and products on such a kind of radical change of thinking Yeah, you don't ever hear anyone complain when you first initiate the whole We should ask what end users want or what they struggle with like nobody goes. No, I don't want to talk to them It's just that practice part right putting in place now. You did a lot of work before automatic with the White House a Place that I would presume also was spending a lot of time Matching up both internal initiative and policy and everything else you're doing with the outside world right and bring that in Did you guys develop certain practices on how to listen to people or how to collect that information? That is applicable broader than to just when you're at the White House Yeah, I mean there's some ways and surprisingly the government gets it right There are some parts of policy development where it's natural to draft it and then you're legally required to have Like conversational periods where you get comments and you collect comments Like that's an amazing practice that could be applied to our like design and development processes That it doesn't really happen right now I wouldn't limit it to just like that certain point like your initial round or like version one of something But it's so excellent to be in a situation where we have that like infrastructure in place with policy I learned a lot from our legal counsel at the White House Like to my surprise But one of the big things that I learned is like the how important precedent is for me getting anything done at the White House I had looked for any precedent of what's been done before and use that as a case for building up where we needed to go in the future and That policy precedent was a really big one for us to start to experiment and figure out how we could do it on the design and development side as well We'll listen to Our constituents when it comes to policy development like why wouldn't we when we're building the sites that communicate that policy to them So yeah, I think there's there's a certain amount of like practice, it's almost like liturgical at the White House with like policy development that like can be integrated into private sector processes and Even just I'd say it was less of like a culture initiative In the White House like building up that side was a little bit harder So it's been good to see that that's There's always some cultural change that needs to happen, but that's not our number one struggle in automatic right now In wordpress.com One of the things that happens when you build the platform for all the people that wanted to comment on policy and petitions and everything else and Anytime you create that that window where you have to listen to people, right? You also get to listen to the minority voice Right. It's not just the overwhelming majority that's speaking all the time There's that notion of listening for something you weren't expecting something that was different or a voice that was Representing an entire community that you weren't really paying attention to You you are a champion for inclusion Focused on diversity. How important are developing those disciplines around listening for inclusion? I mean It's essential. It's like the base foundation for it because you don't know what you don't know So you've got to discover and find out and create space for that and like Trying to make it as democratic and as open as possible is certainly a challenge for like you're kind of Alluding to we the people or petitions platform that we built It took a lot of discovery to figure out like what's the right threshold for a petition to become Publicly visible right like you don't want as soon as it gets created for it to be publicly visible like lots of spammy stuff Really bad quality But you don't want it to be so high that somebody with like a limited social network Can't like get it to the point where more people can see it and sign on so like figuring out like where that balance is that That folks who may be a little bit more disenfranchised have a chance of actually getting their voice and their perspective in front of the White House And then in you know technical side things like At first everybody had to make an account in order to even sign a petition Which is I mean you've got there's a lot of trust involved I don't want my email at the White House platform, right? Yeah, you know and like can you imagine if you know before dreamers you have folks who are like brought here and they're not like as young kids like not Sure like what their status is for citizenship and wanting to have a real dialogue and that sort of thing and being like Like is this gonna get me? Like kicked out of the country and trying to open a dialogue on this very same issue So one of our big changes there and just lowering the bar to entry And like making things more inclusive was to just take out the process for signatures You still needed to create an account to Author a petition but in order to sign a petition like to not have to Like create an account So there's so many different ways that applies but in fact here question Yeah, I think it's like the base foundation this kind of listening and being really intentional about Like allowing everybody to share so that you're not like listening but You know with people to people who just are on the same wavelength or have the same audio frequency as you because they have access to the technology and they're already paying attention to the You know WordPress community forums or something that's a very specific group Well, that's that's one of the challenges we have in the WordPress ecosystem, right? Because we talk about there's all the people that are using WordPress, right? They can't spell it with a capital P, but they can actually you know submit a blog post somewhere They have the people who know there's a capital P they go to word camps. That's a smaller group of people But that's still a larger group Then you have the people who contribute code to it right much smaller community capital C Right, those are people that that have Yeah, hyper and gate and part of the dynamic is we tell the whole world, right? It's open source anybody can contribute, right? But then they submit a Ticket somewhere like hey, this didn't work and Someone goes and changes the status to won't fix which is painful for me, right? I mean, it's my only like someone at once asked what would you change if you could change anything I'm like just that phrase to like looking at this and maybe we'll think about it later would still feel better than Won't fix right like you just rejected me as a person and not my submission, right? But you have this dynamic of If I just read somewhere someone submitted to get two years go by nothing happens, right? Then someone else who's in the hyper-engaged community looks at it and goes oh, we got fix this right away, right? And then it gets fixed and you feel gosh, I'm kind of happy that the thing got fixed but I'm also being told indirectly that Me reporting it wasn't worth you know the whoever this person was right wasn't worthy enough to report it Only a big name got to right and so the inclusivity that we want even in the contribution right or their little forms on some word camps that say Do you have you contributed wordpress, right? What does that mean right like did I donate did I show up and put food on the table? Did I run the meetup? Did I speak or is it in terminology? It's well you wrote code So then all the other people are disenfranchised and you're like ah So part of the figuring out of inclusivity in the wordpress community is figure out one of the on ramps right? How do we develop on ramps for people who are all senior developers? Yeah, and we all need we need that to grow the ecosystem in the community further, right? It's not going to grow if we keep kind of our own closed bubble of people who can contribute easily It's going to grow when we like enfranchise others to contribute in a like regular way with the technology They already have available There's go I think there's probably always going to be a little bit of a learning curve But how can you like lessen that and make it something that's um, that's manageable and like show the benefits of it? It's a really good challenge. So we need to we the people for we the For we the wordpress. You can right like I mean there's no reason like like can people email Their ideas and it goes it still goes to I think you just finished at John at 9ceves.com, right? We just send everything to John Yeah, but that we have to have to find the way it's right to drive inclusivity When you decided to come to automatic, I mean obviously you had you were doing a lot of amazing things incredible things What made you say I want to join automatic and work with wordpress a few things. So I mean Lots of great conversations with John I was like, what's out of that? Oh, I know wordpress. It's not a medic I was one of those you can judge me. It's okay But you know based on the time there's kind of a growing recognition for me of the importance of tech Communities in a really broad sense and Like in franchising empowering democratizing so that more people could share their their voice and perspective To go against the closed garden ecosystem that was leading towards You know fake news and influencing elections So like all of that had You know a huge part to do with it We need people sharing their their voices and engaging in real dialogues with one another In areas that they don't Agree, I couldn't guarantee it was happy that we the people lasted a little bit longer than our administration was one of our goals We can't guarantee that that's gonna happen when the administration changes. We need to build up these types of tools and the awareness and Like the passion for that type of dialogue and conversation in the much broader community and a change happens from a community first way So as our administration split up as we had to we had no Opportunity to stay on and try to influence the person in charge now But as we kind of rolled out I think If you could connect the dots you could see that there's actually a lot of commonality and where people For the Obama administration ended up President Obama opened up the foundation instead of just being like a library where people could go it is community Organizing it's empowering people Really to to help grow their communities to get others to participate in civic dialogues that affect Policy we're just you know in their local neighborhood or in a much broader sense So we need to do that across industry and I think I can't deny the power of wordpress. What are we at? 29% of oh my gosh, like that's a huge opportunity that we have that we shouldn't take for granted That's awesome You if I remember correctly right you went to RISD right the Roudan school design That's not a casual relaxed environment to do design is it no no, it's it's hard work. So What did you take away from your experience there that kind of propelled you or helped you see your career going forward a lot of things like It was hard for me to go to RISD like financial reasons I'm feeling like you know my family was investing in it So when I was there, I was on like 200% all the time I worked And I like aimed for the aid we didn't have a pluses I don't know why I am for the a and every every class that I could I paid as close attention as I could to Learn and grow and I felt a little bit still inside the ecosystem like an an outsider because I cared about Like social good stuff before a lot of my peers did so they're like make a stamp and we're designing stamps And I'm like, this is for the post apartheid Environment encourage people about empowerment. They're like sign a stamp Ashley But you know, I think I learned to give like my all to everything that we Every challenge that came my way and a seek everything as an opportunity We had these great professors to who like didn't just Go I think a lot of design schools do this. You like Focus on the foundations which are usually considered the type Hierarchy visuals things like that. They didn't just let us Rest there and get those foundations, right? We had to do a case study on every project that we finished and produce a book To document our process and talk about our learnings And so we'd have these solid materials for each one and we didn't even get to keep them when we're done We had a hand over so you kind of learn to put everything into it to be really thoughtful and then to to kind of hand it over to a broader community that I think I mean you can kind of Drill into that any way that you want but like all of that kind of crosses over and influenced how I work One of the things I appreciate about it is that notion of introspection, right the After you finish the work to go back and look at the work and then the lessons learn what you do And we have something like that in software development. It just isn't always widely practiced It's more widely talked about than practiced, right, but a post mortem a notion of let's go back and learn And yet it doesn't happen as often right and you guys do it religiously there, right? Like every project you're gonna go back and look over, you know, what you did and what you learned How does that introspection help you with insights, right? How does it develop kind of that notion of developing kind of a reflection a practice of reflection or insights to help you kind of Prove help forward like you can't grow if you don't really learn and really internalize the lessons from the last process and and projects so it's I don't know so for a forcing mechanism to Do you like ingest and repeat and like really hold those lessons dear so that you don't repeat the mistakes that you made in the Past that you can grow from them and move forward I don't know if that exactly answers your question if you were if you were encouraging, right this audience To develop that habit or that practice what tips might you give them so they could start doing more reflection? Um, like document along the way is pretty huge even if it's small like scrappy things like I'm doing what I think about why you're making decisions along the along the course of a project I'm doing this because I think it will have this effect. I I'm doing this because I heard this thing and so I'm I'm taking it the next step further and then as you Find out some of those assumptions Some of that data was slightly off or on you'll you'll be able to say you'll be able to kind of track the the momentum across it But I think that the documentation is key and it'll get probably at first if you're not in the habit of doing it feel Really silly and like you're collecting a bunch of nonsense that nobody else cares about But for me that's been a just a really important part of it is kind of being relentless and documenting Like the thinking behind pieces and making notes about those decision points I find that one of the other pieces I try and have my teams do is write down what they're not going to do and why they're not going to do it right because you get two months later or six months later and Suddenly something comes up with this new brilliant idea, right? Why don't you do it like this? And you're thinking oh, maybe we should look into that instead of going back and going no no We decided not to do that and here's why would oh right right okay, right? But it just helps you from getting distracted it helps you know kind of this is the path we're on Yeah, what the focus what the goal is all those all those things if you saw the worksheet that I put up earlier for the Road mapping through the moment like at the top of that was like a reminder on like the purpose of this event The goal of it the audience keeping those really foundational things like across the project is It's key and then you can always grow the audience or kind of split and have more in the future But that focus is really important those are good points. How many of you are designers in the room? Okay, good amount So you also did a lot with a IG a IG a I almost said a IG I And you were the president in the DC group right and now you're on the national level right? So you've spoken at a bunch of conferences you've interacted with a whole bunch of designers I Find that every time I talk to a designer or freelancer developer right? I find that they're all still struggling through many of the same challenges over and over right clear communication Managing expectations and the big one charging what they're worth Do you have any tips for how to help someone know? What they should be charging or how to get the courage up to ask for it? Honestly like community and conversation is huge just one of the biggest benefits of AI GA is that you're in community with other designers This kind of gets into another like administration Obama thing, but one of our big things and like combating Gender pay discrimination during the second term of the administration was just getting Businesses to commit to allowing people to have conversations about pay and not having that be like a fireable offense Because you don't know you might not know that somebody's getting paid Significantly more than you and that like you're being undervalued and that there's an imbalance there I think similarly in the design community if you want to know like What the going rate is for your work and be paid? To your worth being in community with with folks and having really open dialogues about it AGA also has a solid number of resources online for if you're starting out freelancing the types of contracts Like starting rates and some of that stuff just to kickstart it, but that's that's only one Like that's only one kind of framework to reference because we all know it changes Depending on where you are and the environment ecosystem that you're in so really finding that community and being in dialogue I think is the biggest piece biggest benefit for me at least with AI GA and then also the biggest piece about Really getting paid what you're what you're worth is knowing what the going rates are and also just track Business, I think designers keep some there tend to keep some distance from business speak and like business terms but read about business pick up like Harvard business review every once in a while like be in the know because that's like the broader industry that you're in when you're freelancing or kind of bidding on Contracts and projects. So you've kind of got to know the lingo and be a little bit more involved That'll allow you to be kind of sharper and have an edge It's awesome We have just a few minutes left with Ashley I want to open it up in case any of you have questions for her So raise your hand I'll call on you and we'll get the question in front of her I don't bite If you're introverted you can text Sean and then he'll bring it up Yeah, Constance No, it was not actually It's kind of You know friendly banter type of thing I will say it's very likely that somebody in our team let them know The day that it was gonna come out, but it wasn't a planned thing at all And the president was very excited to finally get on Twitter. We were talking about it for a long time I helped him pick out his profile image Because the last thing you want the president to do is look through images For one that he feels like is good Here if you can speak one I'm pretty sure that I was worried for a little while that that's what he thought my job was because I Come up with these weird things like I swear I do a lot more than the service That's the picture girl, no, that's not my job, right? That's right any other questions Yeah People saw There's so many things that one of the ones that I was coming to mind for questions like that is that Well, we felt so lucky to be included in this environment and to be able to influence so much with our time there We're incredibly hard with that But some of the bus times were able to extend that feeling and that kind of gets into inclusion again But extend that inclusion to others One thing that we did is we created the a White House Student Film Festival our office just kind of invented it the first Version we made about the importance of STEM education and we asked K through 12 folks to submit across the country videos and then we watched all of them and Picked out winners and we had a red carpet event for them that we live streamed for the winners Had the president speak to them and they got to sit in the White House like they did red carpet interviews with Bill Niles science guy and Neil deGrasse Tyson and Sit in the White House and watch their videos be screened and like for us putting that on and kind of making that torque type of like acceptance and Like empowerment Expansive to like future generations. We're like crying on the side. We're like She came back to the second student film festival just like really proud of the kids themselves and that like impact that we're able to Show them that their government cares about them and cares about their creative voice in some Some way my voice is given a platform. Yeah, and that's huge So, yeah, I could cry just You being genius about this If you could give advice What's an idea that just comes into your mind, how would you promote it? How would you or how would you do some things? As marchers as folks going Would say like kind of democratize it like people mark for different reasons Sometimes folks don't know what to put on their sign like the smallest thing can keep somebody from coming out because they're like They're all these beautiful signs. I don't have any witty comments Like like Templatizing it having to fill in the blank like I march for blank and letting them fill it in Having those available having giant sharpies and letting people just come out and write in their thing so that people can bring their own their own reason to it and Feel like they're part of the movement and the movements welcoming them anything that you can do to Kind of lower again the barrier to entry to coming out. It is really useful those Beautiful signs. They are printed in thousands for the march on Washington as much as we can kind of get those things out where people can just pick it up and and march I think is really empowering and Making like kid-friendly versions and stuff, of course, I love seeing you know cross generational Those themes are valuable Not just there which is awesome, but also in the wordpress community, right? How do you engage youth and cross generational and create give them voice give them platform invite them help them feel important in it And also how do you just keep lowering the barrier, right? The more you can lower the barrier the easier it is less friction than people can feel like yeah I want to come in well, let's give it up for Ashley. Thank you very much We're gonna take just a couple minute break and then we'll start again You