Barbara: Okay. Hi, Margaret. Thanks for joining today. Glad to have you here, and to talk through our history together. Long ago we got connected through a mutual client, and wondering if you…

Margaret Pickard: Thanks for having me. It wasn’t though.

Barbara: It wasn’t Humanus?

Margaret Pickard: Well, yeah, but were they a mutual client? I thought it was that you were dating Manny, and Manny is the one that connected us.

Barbara: It was, but I was also doing work for Humana at the time too. Yeah, the introduction was definitely Manny. That’s hilarious.

Margaret Pickard: I didn’t know you were doing work for them. They had a designer on…

Barbara: They do. I was actually doing content work for them, like in proposals and that kind of stuff.

Margaret Pickard: Okay.

Barbara: What were your first impressions when we first started working together?

Margaret Pickard: Well, I was amazed. You were truly the first person I had met in my own industry that was also successfully running an agency of any kind, any size, in this world. You were the first woman I had ever met that was doing what I was doing and being successful at it. And I actually, you know, sort of had a little crush on you. I crushed for a few years and just considered you to be a mentor. You were very generous with your time. You sent me some references, materials, things that had helped you grow your business and get more confident in this world of business, and inspired me to finally start charging somewhat closer to what I’m worth. Yeah, that was my initial impression formed over the series of a couple years of crushing on you.

Barbara: That’s awesome. Thank you. I remember being so impressed with your work and really appreciating how we worked together. It was really important for me, even in that early stage of my own business development, to work with people that I really, really like and click with and can communicate easily with, and I feel like we’ve always had that. We did some early project exchanges when we were trying to navigate how we were working together. I can remember doing some badges for you for a website and a sheet for one of your bigger clients and just wondering what you remember about that early period of us figuring out how we fit together.

Margaret Pickard: Well, also you were the first designer I’d ever worked with besides myself. And it was in desperation that I sent you that sheet for that big client of mine. They had this enormously complicated children’s program at their luxury dude ranch, and I couldn’t wrap my brain around how to make a brochure for it. I just couldn’t put the pieces together. For the first time in my life I was stymied, and I just sent the whole mess to you, and you made sense out of it, and they loved it. So that was when it occurred to me that I don’t always have to figure everything out myself, and it was this huge burden off my shoulders. And the more we’ve worked together—unfortunately I haven’t needed help with design since on anything that I can recall—but being able to work on websites with you that you’ve designed has been really fun, because I don’t have to design them. I just get to build them, which is the fun part as far as I’m concerned.

Barbara: Yeah, I think that’s one of the great things about our collaborations is we each get to do the part that’s fun for us, you know? And especially for me now, I know that when my clients are getting a website that you have built, it is chef’s kiss, perfect, technical. You will hunt down any question. It’s going out there with the back end and the front end squeaky clean, and they’re always so fun for me, because I know that my clients are getting something really excellent. So this sort of leads us to talking about how we partner on things. At this point, I don’t put out a website proposal without you in it. I don’t even really think about doing websites on my own anymore. And it’s part of that relief, right? There’s this whole part of things where I’m maybe a power user, but I’m not really a developer, and I would always tell people that. But now it’s so great to know that you’re just part of the package for what I offer to people. And so I’m curious from your side, how you experienced that shift in our relationship, because I feel like we do a lot more work together now even than in prior years.

Margaret Pickard: Well, contemplating my answer to this question… Number one, I hadn’t really realized there was a shift. I guess I just assumed you were bringing me in on the projects where you needed me, and you had other projects where you didn’t, so I didn’t know about them. But I’ve always felt kind of bad that I don’t reciprocate very much. I don’t get the clientele that need branding, or even really much in the way of design. Usually I’m just picking up something and fixing it or upgrading it. I haven’t actually gotten a request to build a new website from anybody that wasn’t you. So that’s just kind of weird, I just realized. And most of them are on a strict budget that are in the small business category, which I like. That’s who I want to work with. But they’re not… You have a lot of finance and industry clients, so they have deeper pockets than my clients, it seems. So I feel bad that I don’t reciprocate by bringing projects to you that we can collaborate on. If I ever get one, I swear I will.

Barbara: You know, it’s interesting. I don’t feel like the relationship is one-sided because I wouldn’t be able to make those proposals to those clients. It’s not like I still don’t make money on them, right? The whole thing is revenue generating for me, but I would not be able to do them without you. So there’s definitely, to me, it feels very balanced. And I think it’s also not surprising because in the course of working with a small business that needs a brand, like a logo and total branding, of course they need a website. They don’t have anything, right? So it makes sense to me that because of the other kind of work that I do, I frequently run into people who are needing website stuff in general. But now you know. I don’t do websites at all anymore without you. Surprise! So, let me think about this. We’ve talked a little bit about how I like to handle the design piece and you like to handle the development execution, and that looks pretty simple on the surface. But I think it really undersells what you actually do, which is much, much more. How would you describe your parts of the project if someone asks what you do?

Margaret Pickard: Well, I first of all admire the gorgeous design that you come up with for this client, so I don’t know where you pull this stuff out of. It is amazing. I was floored by the SUTC design. Just gorgeous. And immediately my brain starts ticking on exactly how am I going to build this element? How am I going to affect these elements? How am I going to put this thing together? And I start putting bricks together in my brain and thinking about how to keep it fast, because websites have to be fast nowadays. And also, especially for some clients, it has to be accessible. It has to pass accessibility guidelines. So looking at how to do that. And eventually, once I have a little bit of a plan in place, I get started and then I scrap a few things and try again. And eventually it starts to actually come together and form a page. I start with usually the building blocks, like the menu, the header, the footer, and then I do the homepage. That all takes up like 75% of the website time, and then the rest of the pages start going faster and faster as I have sections built and how to make the design come to life on the page worked out. It’s fun. I love it. It’s probably my funnest thing to do, is to build a website from scratch.

Barbara: Awesome. I know one of the reasons why I won’t do websites without you is, through other clients, I’ve been in a situation where I’ve been required to work with other developers, and none of them have been able to execute the design that I see the way that you can. You really get my design work and you know, when I look at my mock-ups and what you’ve created, I’m like, “Yeah, that’s the same thing.” And I haven’t had that experience with any other developer that I’ve had to work with over the course of other client projects.

Margaret Pickard: I think that is because I do have design experience. I can look at your design and I can see what you’re going for. You like large type. You like bold fonts. You manage your white space in a whole different way than what I would if I was designing, but I can see what you’re doing. I just do the same thing. I mean, in your XD file, like you’ll have the font size set to something like 66 pixels or something, and I know that’s gonna be a little bit large on mobile screens. So I have to make sure it looks like that on a screen, and it’s probably not 66 pixels or whatever, but…

Barbara: Yeah. And it’s funny that you say that because I know that a lot of times I’m going for the visual feel and the ratios, and I’m not necessarily being very precise about “this is actually the point size that it needs to be on the site.” But I know from experience that you can interpret what it is I’m actually aiming for without me being a precision master, ’cause it’s one thing I’m not, is precise.

Margaret Pickard: And it’s about all I am. Like, if it’s not pixel perfect, it’s not done.

Barbara: Which is great, which is why this works, right? Awesome. Thank you. What do you wish more clients understood about the design to development handoff before a project starts?

Margaret Pickard: I honestly don’t have an answer to that question because we work together so seamlessly. There is nothing they need to understand. I suppose in some world I could say, “Well, I wish they would understand that what you’re showing them is a mock-up. It’s not gonna look like that in the final version,” but really, that’s my job. There’s nothing for them to understand. What I do wish clients understood is that websites have a shelf life. I will make it as modern as possible, and in some cases, when a website has taken a year to build, sometimes the technology changed while we were building it. So I wish they would understand that, yes, this is an investment, but it’s not going to be this awesome in five years because the technology will have moved on and there will need to be things done. It will need to be rebuilt with modern technology. And I wish everybody understood that about websites. Even my own clients seem to think that if I build a WordPress theme for them, that they can keep using it for infinity years. And then you end up in this technological debt that’s really expensive to climb out of when it would’ve been easier to just redo it like every five years.

Barbara: Yeah. Or even, I think in some cases, I’ve worked with clients on websites and they’ve wanted to do even their own maintenance, and then they don’t. They skip something simple like updating plugins and that kind of thing, and then their site breaks in a year and they don’t know why, you know? I wish that was something that they actually really needed to take seriously. In the same way, in theory, you don’t skip oil changes on your car, because that catches up with you. So as we’ve discussed, you have both design and development expertise. And I’m curious how those two parts of your brain talk to each other when you’re deep in a project. Are they separate parts of your brain? Are they kind of the same? Because it sounds like your page building process that you talked about, where you try some things and you scrap them, really sounds an awful lot like my design process too.

Margaret Pickard: I don’t know that the two sides talk to each other. And let’s be clear, I don’t really consider myself a great designer. I do it but I have a lot of respect for people who have an actual talent in it, like yourself. The designer I hired to build my website, Zakira. She is a designer. I don’t have that kind of design chops, but I can, with great difficulty, spend three days and come up with a homepage design that I start to like myself, but it takes me forever. I don’t know how you whip these things out the way you do. So again, that’s why I like our collaboration so much, because I don’t have to go through that process first. I get to use the design knowledge I have and the artistic abilities that I have to take your flat design and turn it into a website. But that’s about as much as I ever want to do anymore. I’m spoiled building websites designed by you.

Barbara: One of the things I really appreciate about our collaborations is how you come up with solutions when we run into a design roadblock. Maybe the color wasn’t quite right for accessibility or something. Like we ran into it with a recent project. But also because you’re in website pages building every day, how you take the flat designs and breathe some life into it. Like, “I’m just going to have this come forward a little bit, or I’m going to have something move.” And I love that you’re in the process and making those design choices real time. And they typically fit really well with the flat design that I’ve made. So I like that you’ve definitely still got some design things happening in your process too.

Margaret Pickard: That’s what… But as for whether my brains talk to each other, I don’t know.

Barbara: Your brains. Is this thing on? Right. We talked about this a little bit, I think, but I’m going to ask it again just in case there’s more you want to add. The web has changed enormously in the time that we’ve worked together, and what do clients consistently underestimate about what a well-built website actually requires?

Margaret Pickard: Yeah, the shelf life is one thing they underestimate. And part of that shelf life is the continuing changes that are happening, like with this AI boom thing that’s going on. We’re retrofitting some sites to be AI friendly, search friendly, you know? Now it’s all about schema and things like that, a word that I didn’t even know three years ago. So I don’t know. It is pretty much like your phone. You buy the latest model and the minute you walk out of the store they drop a newer one. It’s like that with websites too. We can try to make it as flexible and forward-thinking as possible so it will work. My really large client, I built their WordPress theme in 2016. That thing is literally 10 years old and still going. It’s duct taped and patched to pieces, and it’s the good example of the technology debt that I was talking about. It desperately needs to be rebuilt, but I guess as long as I can keep it working and performance optimized, then they’re happy. So I guess I totally lost track of where I was going with that.

Barbara: We were just talking about what clients underestimate…

Margaret Pickard: Namely yes, how long it is going to be modern. It will become dated and behind the scenes outdated technologically in as soon as two or three years. So…

Barbara: Yeah, I feel like compared to 13 years ago, that cycle is shorter. You know, five years is old for a website.

Margaret Pickard: Yes, I do. I think it is shorter just because technology has been exploding. And I don’t know. I’m curious about how all the AI tools that can now build a website for you are going to impact business. I’m using AI to help build websites to get my work done faster, because AI can write a page of code faster than I can type. Well, on the other hand, I find I start losing some skills. Like I can’t remember the syntax for a query that I’ve written many, many times, but because I didn’t write it myself, the AI did, I’m going to misremember things or forget them. So that worries me, too.

Barbara: Yeah, that is a consequence of using those tools to do our thinking for us. I find it some places where I use those kind of tools myself and…

Margaret Pickard: Right. I’m kind of being watchful about that because I want to keep the skills that I’ve got. Unless I have to, I guess, in order to stay current.

Barbara: Yeah. But I think there’s something to be said for when something in a project goes sideways, right? Like something unexpected happens. You having the deep inside knowledge of the guts of a page lets you troubleshoot that in a way that someone who’s only had an AI tool coding wouldn’t know how to fix necessarily. And maybe there’s a way to use that same tool to fix it, but I don’t know how much I would trust that given that it can make mistakes and put them in.

So looking back, we’ve built a lot of websites together for some really interesting organizations doing some cool stuff. Is there any project that really sticks out as one of your favorites that we worked on or something that just went really, really well?

Margaret Pickard: Well, it’s Melissa Boyd. Oh, yeah. The way that we put that together and executed it for her, I thought was probably our best work yet. I was stunned you didn’t win the award for it. Absolutely stunned. I had no idea what they messed up. And it’s still gorgeous.

Barbara: It is. I love that site. I’m really proud of that design work, and I know she loves it too. You know? And one of the things that I appreciate about it is how flexible it is, right? Like, as her content has evolved, as her offerings have evolved, it just all still works really well together. And that to me speaks to a really strong technical setup and a really flexible brand system. So yay us.

Margaret Pickard: Yes, and but beyond that, some clients aren’t really great at expressing their thoughts, so it’s kind of confusing. And that was your ability to understand what she wanted and translate that, because I usually didn’t understand what she was saying, honestly. But your ability to do that and translate it for me is why that project turned out so successfully. And I know one of your other questions about projects going sideways, what happens… The answer to that question is communication. Again, communication has been probably the best part of our collaboration. I have been told many times by people who are a little thin-skinned that I am too blunt.

Barbara: You will say it. I know that about you. Like, you’re just going to say it, and that’s great. I want to hear it.

Margaret Pickard: I do say it. I also am starting to get closer to an age where I don’t really care if you can’t handle it. But always from the get-go, I’ve been direct and honest with you, and you’ve been direct and honest with me back, and that kind of communication to me is priceless.

Barbara: Yeah. I really appreciate that, and I think there’s an awful lot of trust too.  I very much appreciate that sometimes you’re doing other work for clients that we’ve worked on together that’s outside of what I do, but you still always check in about it. You know what I mean? I feel like there’s a great deal of trust and transparency, and taking mutual care for each other’s clients and our relationship, right? Like, that to me feels like that’s worth more to us than any particular dollar amount on any particular project.

Margaret Pickard: Well, that’s part of my own value system that we don’t steal other people’s clients, which is really kind of funny because my big client, I did actually steal from someone.

Barbara: I don’t know. Did you steal them, or did you just do better work and so they chose you?

Margaret Pickard: Well, that is exactly what happened. The guy that they fired… This was back in the day when I was still doing SEO before the whole update. He had brought me on to do some SEO for their site, but it was a mess. It was an absolute mess of a site. I’m like, “Well, we can put in some meta tags and stuff, but the real problem with this site is it’s very badly coded,” which was his code. But doing what I did, I got them onto the first page of Google, and so then they wanted to know if I could just take over doing all of the work. I was like, “Well, yeah, but you need to have your site rebuilt.” That was the start of a very long relationship, and they’re still my client. So yeah. But he accused me of stealing them. And I said, “Well, I mean, it’s a free country.”

Barbara: Yeah, they can choose who they want to do their work and sounds like you did a better job.

Margaret Pickard: Yeah. I did. That was a case of a really, really good designer who kinda wasn’t a great developer.

Barbara: Yeah. And I didn’t want to be that, right? I knew that I was not a great developer. I’m basically a WordPress power user, but to try and pretend like I’m… So it’s like, yeah, I didn’t want to be that.

Margaret Pickard: Right. In his defense, I think that he decided he wasn’t going to do that either. He actually went back to college and got a master’s degree in art, is a fantastic artist now. He has had some of his art featured somewhere in New York, somewhere hoity-toity. I can’t remember the name of it. So I think it worked out for him.

Barbara: Yeah, it sounds like it did. Sounds like it sent him the right direction. So last question. What do you hope the next chapter of our collaboration looks like?

Margaret Pickard: I don’t think too much about the future. I want us to continue working together on pretty much all things. I’d like to start strengthening wherever I see some deficits in my agency that I’m working on strengthening, and one of them is the new project of providing a care plan, a care plan for website owners. That is something that I would like that we’re going to work together on. I don’t know. I mean, in a wild world, maybe we merge our agencies. I know both of us are trying to figure out how life works in retirement. I just figure I’m not going to retire. I’ll be trying to write website code when I’m 90.

Barbara: From the nursing home.

Margaret Pickard: Right? I’ll be like, “Give me my laptop. I can’t stay in this nursing home. The Wi-Fi’s not good enough.” But I think that through it all, through whatever comes at us, we need to stay friends and stay collaborators and seize any opportunity that will make our agencies stronger and more sellable so that we can retire.

Barbara: Mm-hmm. Yeah. I love that. I agree, we’re going to continue to work together. I have, just so you know, a bunch of new things in the pipeline that we’ll be talking about soon.

Margaret Pickard: That is something about you that amazes me. You go out there and get deals. You go out there and get leads, and you get these things. I actually don’t market myself at all.

Barbara: Well, I’m doing enough for us both, hopefully.

Margaret Pickard: Well, that is where I am benefiting hugely from this collaboration, because you are marketing yourself, and it’s definitely benefiting me. And so I’m very impressed and also very grateful.

Barbara: Yeah. And I’m also really actually excited about the maintenance service, and we’re going to talk about that offline. But rolling that out to my clients and getting that to be a more integrated baseline service that I’m offering, and frankly, getting my clients that I do web maintenance for better support and that forward-looking, “Okay, we’re doing the maintenance, but we’re also looking at what you actually need to do under the hood for your website to keep it up to date,” so that they don’t end up in that technology deficit. And I’m really excited about that. And I’m also even thinking about… Sorry, I was at a concert last night, so I’ve got shouting at the band voice still. It was Journey. It was phenomenal.

Margaret Pickard: Favorite.

Barbara: But I also have been rolling around in my head, what does having your team become my helpdesk look like? Like, how do we integrate in that way, and how do we price that together? I want a better level of service for my clients, and I know that you and your folks can do that. And so thinking about how I price that, and what’s the offer, I’m excited about that, and that’s where my head’s at right now. And then also just a bunch of proposals that are coming in and rolling around. Hopefully some more award-winning websites. We’ve got a couple, right?

Margaret Pickard: Yeah. I don’t know. It’s amazing. I don’t think I’m submitting anything myself to the Daveys this year. I’m with you. I’m on the fence about the one that you’re thinking of submitting. The most important thing as far as I’m concerned about that site is that it’s accessible and as performant as it can be, but they didn’t put it on a great server. I noticed an immediate drop in speed on their test server versus on our dev server. And I’ve done everything I can to compensate for that.

Barbara: Yeah. And there’s some parts of it that you ultimately can’t control if that’s how they’re choosing to do it, so we can probably not submit them. Yeah. So okay. We have had a great chat.

Margaret Pickard: Okay. No, it was great. Thanks for inviting me to do this. It was fun, and nice to actually discuss some of these things with you instead of just emailing back and forth.

Barbara: Right. Yes. All right, Thank you!