What It's Like To Be...

A Creative Director

May 21, 2024 Dan Heath Season 1 Episode 19
A Creative Director
What It's Like To Be...
More Info
What It's Like To Be...
A Creative Director
May 21, 2024 Season 1 Episode 19
Dan Heath

Churning out creative possibilities on tight timelines, crafting bespoke stock images with help from AI, and pitching unique ideas to risk-averse clients with Jo Skillman, a creative director in Texas. Why do a lot of creative directors grind their teeth at night? And what is a "swoop and poop"?

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Want to be on the show? Leave a message on our voice mailbox at (919) 213-0456. We’ll ask you to answer two questions:

  1. What do people think your job is like and what is it actually like?
  2. What’s a word or phrase that only someone from your profession would be likely to know and what does it mean?
Show Notes Transcript

Churning out creative possibilities on tight timelines, crafting bespoke stock images with help from AI, and pitching unique ideas to risk-averse clients with Jo Skillman, a creative director in Texas. Why do a lot of creative directors grind their teeth at night? And what is a "swoop and poop"?

Follow us on Instagram!

Got a comment or suggestion for us? You can reach us via email at jobs@whatitslike.com

Want to be on the show? Leave a message on our voice mailbox at (919) 213-0456. We’ll ask you to answer two questions:

  1. What do people think your job is like and what is it actually like?
  2. What’s a word or phrase that only someone from your profession would be likely to know and what does it mean?

Dan Heath: Jo Skillman is a creative director.

Jo Skillman: Creative is kind of like getting up and choosing your clothes every day. So you might be able to look at it and go, ah, do we really care about what people are wearing? That's such a shallow or surface level thing. But the reality is that the clothes that you choose to put on your body convey lots and lots of things to other people, about your identity and what you care about and the way you want to be seen. And brands are the same way. Creative is taking this thing that is like a core belief of your brand and making it visible to other people so that they understand more about you and who you care about.

Dan Heath: And she says that people think about brands too narrowly.

Jo Skillman: There's kind of a misconception that brands are logos, that those are interchangeable terms and they're the same, and they are not at all. Your brand can have hobbies. Your brand can have belief systems, your brand can have a voice. I don't know, if your employees sing opera and all wear weird socks, like, all of these things are brand things.

Dan Heath: I am Dan Heath, and this is "What It's Like To Be..." In every episode we walk in the shoes of someone from a different profession. A standup comedian, a welder, a nurse, we wanna know what they do all day at work. Today, we ask Jo Skillman what it's like to be a creative director. We'll talk about how panic is a good motivator for creativity. Why brilliant ad ideas rarely turn out exactly as planned, and what clients really mean when they ask for a creative idea. Stay with us. So the creative director, your job isn't to, you know, shoot the video or write the copy on the poster or whatever, your main job is to make sure everybody's kind of aligned around the vision?

Jo Skillman: Yes, very much so. And I am actually a working creative director so I do write copy and I do design, but I try to position myself with my team as just kind of a fail safe. Like, yes, I have done this for a lot of years, I can come up with the ideas. I can even build the ideas most of the time, unless they're depending heavily on like illustration or a skillset that I don't really have. But I don't wanna do that because people become creatives because they want to be creative. I would prefer to not build my own ideas, I would prefer to build their ideas. And I'm just kind of a backboard going, "Ooh, I don't know that this is the right audience for humor," or, "well, that's great for this reason, but it doesn't actually consider the business goal that X." And so I make sure that once we jump into actually building something, I can see where it's going and that it will be successful. And then if we are just struggling hard because creative work is difficult, then I try to, you know, kind of be there as a last-minute clutch person. If we just cannot come up with something or we're really struggling with it, then I can jump in and actually help produce.

Dan Heath: What is the most stuck you've ever been? Like, was there a time when you kind of despaired whether it was possible to crack the case?

Jo Skillman: I'm sure there has been, but I will tell you, when you work at an agency you don't really have the time to do that. So you have to get very unstuck very quickly.

Dan Heath: And how do you do that? Like, how do you dig yourself out of a hole?

Jo Skillman: I mean, I think it's a lot of the same things that people talk about when they talk about inspiration. Talk to someone different, look at something different. I'm a very, very big proponent of like, leaning into your random hobbies. I'm a very big proponent of books. And you know, if nothing else, I'm a very big proponent of last-minute panic as a very good motivator. I don't know that I've ever been stuck for very long because I just kind of was like, you know, when I feel stuck, it's because I've stayed up until 3:00 AM and I'm still very optimistically, trying to produce something when my brain is just not working at all.

Dan Heath: I asked Jo, what typically brings new clients to her and she said it's some kind of turning point. Maybe the company is going in a new direction or they figure out the existing brand isn't working for customers. But it's not always a customer issue, sometimes it relates to employees.

Jo Skillman: So for instance, I worked on a project where the Federal Reserve Bank of San Francisco actually approached the agency I worked for and they were like, "Hey, we are having a really difficult time competing with some of these Silicon Valley giants like Facebook and Google, for people. Would you be able to come and talk to our people and get a handle on what motivates them and why they're there and why, you know, working here is different, and help us convey that?"

Dan Heath: So the Federal Reserve Bank asked Jo, and her team to create an employee handbook that could both reinforce to staff the value of their work and also be used as a promotional tool for new recruits. To figure out what messages might resonate, she went to the source.

Jo Skillman: In this case in particular, I, along with some of my teammates, actually flew to San Francisco and sat down with several employees over a span of a couple of days, and we kind of coached our contact there. We said, "Hey, we wanna talk to people who are in charge of things, but we also wanna talk to people who are new and who have different perspectives and who haven't been there that long." We wanna talk to people who have been there long enough maybe, they're not so excited anymore. And we wanna talk to, you know, folks who are very passionate about their jobs. And so basically, we got there and we just sat down with folks, we had some questions in mind, but we let the conversations steer us. And we just kind of started jumping into, you know, what drew you to the Federal Reserve? What do you think is important about this work? Do you think this work is important? If you were going to leave, where would you go? And just kind of pulled at any of the threads that started to unravel.

Dan Heath: And so what were some of the surprises that emerged from those interviews?

Jo Skillman: Oh gosh, I don't know that this was surprising, but I personally, might not have expected it. There was a lot of frustration in those interviews, in particular with regard to public misconceptions of the Fed. So a lot of people think they're the government, a lot of people think they're the Mint, and they felt like they weren't getting the credit that they deserved for doing their level best to keep the economy upright and functional for everyone. So at the core was that they felt misunderstood, which is the struggle of lots and lots of brands.

Dan Heath: And just so it's clear, the Fed is the US' Central Bank, it keeps the economy stable by controlling the supply of money. But how do you get at the heart of what that means? Jo said there was one interview in particular that really unlocked the direction they took with the handbook. She was interviewing a senior executive.

Jo Skillman: And she was telling us that the longer she's worked there and the more that she has had to explain her work to other people, the work of the Fed, that she has landed on this phrase, which is, "the dollar in your pocket has value because of the work done by the Fed."

Dan Heath: Ooh.

Jo Skillman: And we used it verbatim, because the second it came out of her mouth, I thought, that's so wonderful, that makes it so tangible and so immediately relevant to just every single person in America. We all have had to care about the value of a dollar.

Dan Heath: That's so good.

Jo Skillman: And so I know. And we got to do this other very fun thing where on the inside of, I think as the very first page after the front cover, we actually constructed little three dimensional pockets. They looked like a back pocket on your jeans so they had the point at the bottom. And we constructed these little paper pockets with that statement on them, and we you know, glued them to the front page and we actually got a brand new $1 bill, folded it in half and stuck it inside the pocket. So when you, as an employee, are receiving this handbook, which we called, "You Are Here," so kind of not just you're here at the Fed as an employee, but you're here in the pockets of everyday Americans from, you know, rural Wyoming to urban San Francisco, in every produce market, in every small business, in every startup fund, you know, you are here. But also what that boils down to is you are the reason a dollar in the pocket of a single average American has value, and that really drove home this sense of civic responsibility and this sense of impact. And it was all kind of there in this one little sentence, and this one little dollar.

Dan Heath: Jo said that one of the tensions of the job is that you're often relying on the client to put in place the ideas you've conjured. And sometimes, by the time it filters through many layers of an organization, it can come out looking different and somehow, lesser.

Jo Skillman: So you're not around for the implementation, you're not driving it. And of course, occasionally they'll make changes and you see them later and you're like, "Ugh." There's a logo on the side of a parking garage that I drive past periodically, in Houston, and they changed the color of it. And every time I see it, I'm just like, "Ugh, that was not the color, that was not the color-"

Dan Heath: Oh, it was something that you had designed?

Jo Skillman: Yes, yeah.

Dan Heath: Oh, wow. It seems like disappointment might be a frequent emotion in your trade? I mean, I'm just guessing, but you know, it's like you come up with these ideas that are sort of pristine or pure upon pitch and then they slowly get degraded as they contact real budgets and real implementation.

Jo Skillman: Yes, that's very intuitive of you because that is absolutely true. I mean, if it was like that all the time, you might not have anyone in the creative director trade over the age of 30 'cause we've all gotten it beaten out of us and left to go do something else. But I think, one of the kind of saving graces, with regard to that, is that we're a very portfolio-driven job, so creatives, you can't just show up and go, "Hey, I'm capable of doing this thing." You actually build a portfolio of your work over a span of years, and you're kind of constantly updating and curating and making sure that the things you're proudest of are, you know, reflected there. And that's how we get work and it's how we get clients and so you kind of just tell yourself like, okay, the first one is for me and it's the way that I built it and the way that I foresaw it working and the way that I presented it. And then, you know, if it doesn't quite make it into the world in that way, that's okay because I have, you know, this one kind of unadulterated version that I can hang on to. And then if you know, a future employer or anyone else asks me questions about it, then I have this version to speak to.

Dan Heath: Hey folks, casting call here, we are now scouting for future shows. We are looking for these professions, morticians, nightclub bouncers, school bus drivers or city bus drivers, home health aides, mail carriers, electrical line workers, real estate agents, and more. We're looking for two things in our guests. First, this is their career, not a temporary job but their main thing. And of course, they've got to be good talkers. It's no easy thing to talk into a mic while a stranger asks you questions over the internet. But if you have someone to recommend, please send us an email to jobs@whatitslike.com. You can find that email in the show notes, back to the show. So there's a story I remember about Lexicon, the firm that came up with the name, BlackBerry, and many others, BlackBerry being the famous predecessor to the iPhone, such a brilliant name. But anyway, even though the name seems brilliant, in hindsight, what I remember is that the client had been pushing for a safer name, like Easy Mail, and Lexicon sort of had to drag the client, kicking and screaming, into the name, BlackBerry.

So I was curious, how often do you find yourself in that position of feeling like you have to talk the client into the right answer?

Jo Skillman: Fairly often, I would say, you know, one of the things that I hear a lot in client conversations, and the second I hear it, I know that they don't mean it and this is going to suck, is "we wanna do something super creative." Like, literally, the correlation between that and the client not actually wanting to do anything super creative is like 100%.

Dan Heath: Oh, that's interesting, now, why is that?

Jo Skillman: I think it's something that people feel like they should say when they're working with a creative team, like you should say that you want things that are creative. But the reality is that many, many, many clients, especially if they're in fields that are maybe a little stodgier, so for instance, sometimes academia, sometimes medical, sometimes finance, those are not necessarily fields where people feel comfortable coming out with something new or unexpected or different in regards to branding. But they feel like they should say it because they're working with the creative team and they should ask for creative work. Very often they don't mean that.

Dan Heath: So you're often trying to kind of psych them up and maybe get a little bit out of their comfort zone, is that like a recurring issue?

Jo Skillman: Yeah, for sure. Well, because, you know, we want their brand to work. And a brand at its best gets people to notice it and it draws people into it with some kind of story. It generates curiosity, you know, it gives your audiences something to kind of glom onto and notice or ask about. And so if your goal, because you feel comfortable there, is to look like everyone else because then, you know, your CEO can't say anything about how weird it is. And you know, your clients might not be turned off or rebel against you. Like, if you wanna make sure that you're doing something that is like, definitely unremarkable, you wanna look like everyone else, you wanna look like every other bank or you know, educational institution, you wanna kind of stay in your lane as it were. But often that is not where you need to be for people to notice you and to draw in new audiences. And so very often, you know, we'll take that tack, which is just, hey, like, we're not gonna give you something that won't work. We've done the research, we've all talked about it, this is where we've landed, you know, have a little faith, do something a little bit different. You're gonna have to try something that you haven't, that's not the same thing you've been doing.

Dan Heath: What's the most frustrating part of your job?

Jo Skillman: I think the most frustrating thing is that there is so much speed and so much pressure, and very often that is at odds with this idea of like, waiting to be inspired or waiting for the best idea. And very often you have to jump in with your whole team, even though you don't have an idea that you love and you didn't get to do, you know, all of the looking at books and mood boarding and you know, talking with the client, that maybe you wanted to, and you still have to build something that is phenomenal, and that's just difficult to do. I remember one time, standing around a table with a bunch of my coworkers, and I don't remember how we got on a subject, but suddenly all of us realized that we all sleep in mouth guards to prevent us from like, clenching and grinding our teeth at night because we were all-

Dan Heath: Oh, wow.

Jo Skillman: So stressed.

Dan Heath: Yikes.

Jo Skillman: Yeah, it can be a very stressful thing. So for instance, one of the examples of that that I always kind of go back to is I somehow ended up with 24 hours to put an interactive billboard in Times Square-

Dan Heath: What?

Jo Skillman: For a campaign we were building for Michelle Obama, yes.

Dan Heath: 24 hours?

Jo Skillman: Yes.

Dan Heath: What is an interactive billboard? What does that mean?

Jo Skillman: So it's, I mean, I guess it could mean a number of things. In this particular case, it actually meant that people could tweet at it and tag it with Instagram photos. So it actually incorporated user-generated content into the design of the billboard.

Dan Heath: That sounds dangerous.

Jo Skillman: Oh, yes. And so I'm working with a guy whose job it is to help me, you know, get my designs onto the building and help me, you know, figure out how to get these interactive pieces onto the building. And I'm trying to coordinate several other partners. Because when you do work with the White House, lots of people are partnered with you and sometimes it's pro bono and sometimes it isn't. But basically, they'll go, "Oh, well, we have a company that donated this user-generated content platform so that you can, you know, check yes or no on things that, you know, people are, like, photos that people are trying put in Times Square."

Dan Heath: Hmm.

Jo Skillman: And of course, I'm in Texas, they had some cameras in Times Square at the time, they now have more of them, but the very first time I did it, they didn't have any cameras pointed at the building so I couldn't see what anything looked like. And not only am I working with this guy to get him the right files and the right sizes, and that's weirdly complex because it's all these facets of you know, lighted billboards on a building. But there are also things like, I'm over here with the folks building the platform for all of the incoming user-generated content. Like, oh, what kind of words do we wanna make sure are automatically filtered out? Let's get all the cuss words in there. Do we need to think of cuss words in other languages? What about the dirty words that aren't actually cuss words? And we're trying to like, put all of these tags in that's like, every naughty thing that any of us can think of so that our person, who is manually pushing things through, was less likely to do something bad by accident. And you know, we're doing all of this in less than a day, before everything we've built is live in Times Square, and visible to just thousands and thousands of people.

Dan Heath: So Jo, we always end our episodes with a quick lightning round of questions. Let me fire away here. What is a word or phrase that only someone from your profession would be likely to know, and what does it mean?

Jo Skillman: Hmm, ah, I've got a good one for you, the swoop and poop.

Dan Heath: Ooh, the swoop and poop, okay.

Jo Skillman: Mm hm.

Dan Heath: And what does it mean?

Jo Skillman: So the swoop and poop is an agency term for when you've made it like, gosh, 90% of the way through all of your work, you've been in very close contact with you know, your client, often the VP of marketing, the CMO, the marketing team, and you get like 90% of the way done. And like, a CEO or someone like walks by the room, sees the work, jumps in and is like, "I hate everything." They swoop in and they poop on it.

Dan Heath: Oh, I'm with you, okay. All right, I've got another one for you. What's a tool, specific to your profession, that you really like using?

Jo Skillman: Oh man, I am gonna be that guy and go with AI on this one.

Dan Heath: Okay.

Jo Skillman: There are, yeah, there are several like visual and video and animation AIs popping up right now, and they have changed my life so-

Dan Heath: How so?

Jo Skillman: I don't know how well known this is outside the agency world, but if you are a graphic designer, you have spent hundreds, possibly thousands of hours of your life looking for stock photos that are like, authentic and properly diverse and are like, oriented in the right direction, like vertical as opposed to horizontal. You know, whatever you need for your layout. Hours, hours of my life, it is the worst. And now, I can just hop into a program and be like, yes, give me, you know, a doctor who looks like this, talking to a patient who looks like this, and 30 seconds later I have like 18 options and they're all pretty darn close to what I actually need.

Dan Heath: Wow. What phrase or sentence strikes fear in the heart of a creative director?

Jo Skillman: I showed this work to my wife, slash boyfriend, slash daughter's class, slash group of teens standing at a bus stop, and they didn't like it.

Dan Heath: Oh, yeah.

Jo Skillman: It happens so regularly. Like, we're building things very intentionally for your audience, and to achieve very specific business goals that you have given us. If you're just walking up to a random person going, "do you like this?" They might not be your demographic. Furthermore, whether or not they like it is actually a completely different question than, you know, will it work? And I actually have a wonderful example of this where we had done some advertising for a medical entity, here in Houston, targeted at a young, basically like, young adult women, around a certain aspect of their health. And once the client had actually made it all the way through their process with us, they had picked their campaign, they had paid us for it, they had like, gone out into the world with it. Before anything ran, one of them took the work up to a group of, now, I will say to their credit, like, this was actually the correct demographic, but they walked up to a bunch of women at a bus stop and were like, "do you like this?" And every single person there was like, "no, I would never click on that. I would never look at that." And fortunately, we were able to convince them to, you know, go forward with the campaign anyway and it turned out to have been wildly successful. We have some of the best data for that campaign. It reached a ton of people and not even just in the kinda what we call, vanity metrics, which are like, hmm, this many people use the hashtag. It was like people were actually going to their doctors and asking the right questions and submitting questions to a website for information. And we knew that it had worked, but it almost all got derailed right at the very beginning by someone being like, "I shared this to so-and-so and they didn't like it."

Dan Heath: Jo Skillman is a creative director, based in Houston, Texas. To me, there are a bunch of interesting things about the creative director role. It's a profession that creates a bridge between business goals and creative expression. You've gotta be bilingual to be a creative director. You've gotta speak the artistic language and the hard numbers language. It's sort of like in software, you've got product managers and other roles that understand both, development and marketing. The other thing I keep thinking about, which is related, is that the work hinges on being creative within constraints. Lots of constraints. Like we need a campaign for the Federal Reserve Bank and it needs to speak to employees, but also prospective employees. And it needs to take the form of a handbook and it can't cost more than X dollars per copy. And we need it in six weeks and it's gotta be super creative, so go. It seems like you need a special bundle of talents to be able to operate within those confines. You've gotta be able to manage sensitive creative people and internalize the goals of your client organizations and pitch ideas for potential campaigns and churn out creative possibilities on tight timelines. And try not to grind your teeth too much. Folks, that's what it's like to be a creative director. This episode was produced by Matt Purdy. I'm Dan Heath. Thanks for listening.