This is part of our 100 Creative Directors interview series. It has been edited for length and clarity. To return to the series homepage and browse other interviews, click here.

What did it mean to you to be a creative director? And now that you're a director, how has your focus shifted?

As a creative director, the name of the game was translation. 

You have a client, who has a bunch of ideas in their head — what the brand is, how it relates to the world, how the brand is performing — and those ideas present a problem. They’re murky, they’re not yet well-defined. And a lot of times clients aren't very eloquent in conveying those ideas. 

You have your strategists, who are business experts. They’re refining the client’s problem and identifying opportunities. They give you a different version of reality than the client — the client thinks they’re doing really well with young women, maybe, but the strategist knows that some competitor is actually crushing it with that demographic and the client is struggling. 

Then you have your creative team, whose job it is to come up with solutions for these problems. But their solutions will be amorphous: what if Wes Anderson made an underwear commercial, and it was in the 70s? Wouldn’t that be cool? Sure, I guess?

Finally, you, as a creative director, have to connect all these different people and make them understand each other so everyone can agree on a direction and commit potentially millions of dollars towards a solution.

Ultimately, for me, the idea was always that as a creative director your responsibility is to speak the same language as the strategist, the client, and the creative, so everyone can communicate with each other and feel good about spending all that money on a few minutes of video and some pictures. You’re the glue that connects everything. 

Now that I’m a director, it’s essentially the same thing. Only now the translation work is honed down to one very specific aspect. The creatives come to me and say, “Hey, we’ve got an idea. We’ve got a thought on execution, that part is a little murky. Can you help us nail it down?” So it’s my job to make that crystal clear. Let’s do the first shot like this, then we’ll do the second shot with this specific lens.

As you translate everything, you’re trying to make it better without altering the intent. It’s like people who translate poetry from one language to another — I’ve always thought, damn, they’ve gotta be making some of that up. They’ve gotta be leaving stuff out. But that’s what it is: you make executive decisions. It’s not going to be 100%, one-to-one accurate, but it’s going to get the point across.

So a big part of your job is to be decisive and be able to back up those decisions. Tell me what that means to you, how you stake a point of view.

Very early on in my career, when I was just doing basic design stuff — I’m talking banner ads — I had a coworker who told me: every decision you make should be defensible. Maybe nobody will ever ask you to defend it, but you should have a defense ready to go and it should be airtight. If you can learn that thought process, you’ll be able to make very confident decisions, and when you make confident decisions, it allows everyone else to calm down a bit and come along with you on the journey.

I’ll sit there and really try to think through every reason why we’re doing something. Sometimes you honestly just want to do a certain thing because it’s cool. Sure, maybe that’s the motivating factor. But how are we going to defend that? How are we going to translate into something the strategy person, who doesn’t think it’s as cool as you do, will also get behind? What data backs it up? Can you make the client understand? Can you get everyone on board with it to make it serve everyone’s goals? That’s on the creative director.

What do you find to be the hardest challenges between the point when you receive a brief and the point where you’re done and it’s out in the world?

One of the hardest things about working with any brand is that all the people you’re working with on the in-house side are indoctrinated into the way the company sees the world and its place in the world. Every company believes they’re the best in this, that, and the other category. We’re the best basketball team to ever exist, et cetera. And that’s great — it’s aspirational, it’s how a company pushes forward and motivates people.

Oftentimes, that internal confidence clashes with reality. Those clients are coming to agencies because they have problems to solve. The real problem you’re tasked with on the agency side is working through that distorted, overconfident worldview. You’re coming to them with reality, you’re saying, “Hey, you’re not number one, you’re actually number four. To get from number four up to number one, even number two, you’re going to have to change A, B, and C.” And they’re like, “Why would we do that? We’re number one.”

Trying to deprogram those strongly held beliefs without offending the client or destroying their whole confident mindset is a very tricky bit of rhetoric, an exercise in ego massage. It becomes very psychological, a challenge of empathy and worldview. You can’t figure out how to bring someone a solution they’ll be receptive to until you understand how they see the world. 

I’m talking about a layered type of empathy. You need to understand not only how the company understands the world, but how your client understands the world — the actual person you’re talking to. What are they afraid of? That’s the big question I’m always asking. What are you afraid of? You’d be surprised at the answers you can get to that.

People will say, “Oh, we’re afraid of losing market share in China.” Alright, I get that. “I’m afraid that Frank over in apparel will take my job if I don’t hit XYZ market with this campaign.” There we go. If you can get these answers, you’re golden. After that, it’s just about getting enough creative people in the room, making sure you have enough time, and figuring it out. The key is just understanding your client’s idea of reality and not destroying it.

How do you think about building a team, selecting the right people for a project and creating an environment that's conducive to producing really good work?

Ideally, what you want to do is find people who have complementary skills. You want people who are different enough that you can give them the same brief and get different results. But you want them to be similar enough that they’re not going to want to kill each other when they have to be on a shoot for 14 hours, and it’s hot, and it’s dark, and everyone really just wants to go home. It’s really hard to ascertain that from just a portfolio.

From a high level, looking at a person’s credentials, you might see a bunch of awards. Maybe this person has a bunch of great comedy stuff. Great, she can do comedy. But maybe that’s all she’s ever been given the opportunity to do, and in person she’s very dour. Or maybe she can write something anthemic, but nobody has ever put her in that position. You just don’t know any of that until you actually meet someone.

It’s not much different from being a coach putting together a sports team, where you’re looking to mesh a group of people with just the right mix of skills and personalities. And it’s really, really hard. The interview aspect of hiring people is the most challenging, because you’re hoping you’ll be able to invest time in this person, that they’ll be able to do things you need them to do but may have never properly done before, but it’s always a risk.

Giving people the work they really want to do is the best way to retain them. You can hire somebody to do whatever boring job, but if you’re also giving them the mentorship and help to do what they really want to do, they’ll pay you back. “Sure, I’ll give you two years working on this account I’m not passionate about, because you’re clearly going to make me a better writer. And then I’ll be able to go work on what I really, really want to work on.”

People will make that trade, especially earlier on in their careers. Again, so much of being a CD is psychology. That’s probably true of being any sort of leader. It’s balance, it’s living up to your promises. It’s giving people opportunities that’ll open the doors they really want to get through.

What are three things that you couldn’t do your job without?

I could not do my job without YouTube. Especially when you’re in the early concepting phase, you just sit around thinking, well, what if we did this? What about that? Inevitably, someone tells you Nike already did that, so-and-so did this. So you pull it up and take a look. Alright, the concept is the same, but the execution I was thinking about is totally different. And you start to develop the idea. YouTube is one of the greatest inventions of the internet era, especially as someone who makes visual work.

Second is really wild analogies. So many great ideas are best communicated and iterated upon like this: what if this but also this and this, what if we did this times that times that times that. Like: what if Wes Anderson made a Transformers movie?

There’s no right answer to what that would look like, but it’s a ride we can take to an interesting place. I start putting down what I think that would look like, you start doing the same, and by the end of it, we have a third, worse thing. But we’ve found something usable along the way, or something we can build on. That’s how I get to so many great ideas. It’s just a game you play.

The last thing I would say is close friends and partners. Not work partners, but romantic partners. You need people who will give you the benefit of just listening to you talk for 5-10 minutes, but who aren’t actually involved in what you’re talking about. 

Especially if you’re working on a big campaign or film, if you can explain it to someone when you’re just sitting at the bar or on someone’s couch, with no visual aids, and keep their interest? That’s when you have something. Especially if they’re not in the industry, if they’re more of a “normal consumer.”

When you’re working on a big pitch, a rebrand, a shoe campaign, and you have a 60-page deck that’s been manicured to death, every word crafted and re-crafted by 17 people… but a lot of times, CEOs and CMOs are bored. They don’t have a lot of time. You get 5 minutes of actual attention — they’re not going to see that whole deck. You can only really prepare for and test for that kind of thing by first showing it or explaining it to someone who does not work at your agency, who really doesn’t give a fuck. Them not giving a fuck is crucial — you’ll see in their faces when they stop paying attention, and that’s when you know you don’t have it right yet.

You started your career in web design at Rockstar, you became a creative director, now you’re a director, and you’ve done a bunch of other stuff in between. What’s been the throughline in your career?

The throughline is that I've always just been interested in telling stories. Not just that, but trying to make them as unexpected as possible, because unexpected stories keep your attention. Unexpected stories are the things that, when you show your friends who work in the industry, they're like, “Man, I wish I would have done that shit.” 

It goes back to when you're hanging out with your friends, and you’re telling them a story. “Man, I went to the club last night, you won't believe what happened…” And everyone's sitting forward, they’re listening. All of my work has just been trying to recreate that high, just in different ways.

When was the first time you got paid to feel that thrill?

When I was at Rockstar, most of my job was just making 2D art. They’d put it out as downloadable wallpapers, the only real caveat being it needed to have the Rockstar logo on it somewhere.

So I did this photo collage series of animals fighting. It wasn’t even that great, looking back, but it was these giant battle scenes of, like, a giant koala attacking an elephant with an eagle shooting missiles and lasers, nonsense. Just something I made with a free afternoon, I thought it was funny. I figured my boss would never approve it, hopefully he would at least have a reaction — “this is stupid, get the hell out of here,” something like that.

My boss thought it was great. They put it out and I thought it was so cool I got paid to make it, just this dumb thing that made me laugh. It was my own voice. It had their logo on it, but it was as irreverent and nonsensical as my brain could be. Since then, I’ve always just been chasing that feeling.

What is a piece of advice or multiple pieces of advice that you would pass on to people just beginning a creative career?

There's a really famous Ira Glass quote that gets passed around Instagram every once in a while. I’m paraphrasing, but the point is when you start your career, you have great taste but shitty execution. That’s totally true. It takes a while to build up to having consistently good execution, shrinking the gap between what’s in your head and what you can put on paper.

But there’s an addendum: realize that your specific experiences will make your shitty execution better and keep you from becoming a carbon copy of your influences.

I have a therapist, like everyone else does because of advertising and capitalism, and often I’ll tell her I’m working on a thing. “Hey, here’s the broad idea behind it.“ She always asks me this one question, which stumped me for the longest time. Now I see it’s actually the key to making good things: “Where are you in this?”

What I’ve found is, regardless of what the script I’m working on is, no matter what product; however fantastical or specific it is, I can and have to find a way to make it true to me in some way. If you can make that thing real and true to you, that’s when your crazy, shiny-object idea actually becomes impactful. If that nugget is in there that’s real to your experiences, other people will relate to it, because there’s a good chance it’ll be real to their experiences, too.

For example, a lot of people have made movies about aliens. Steven Spielberg has made three. They’re all about divorce. They’re very different, one’s a kids’ movie, one’s an action flick, the other kinda a drama; but they all feature that recurring theme. It’s something true to his life, but also really common in life. It's part of why his movies are so beloved.

I think about Spike Lee. This is a man who is very angry about politics, racism, and injustice. And he makes movies that are so blatantly about that. But he also loves musicals. And that is very apparent in his work. Honestly, those two things should not go together, you’d never think so. What makes Spike Lee, Spike Lee, is that he’s gonna have a dance sequence in the middle of a three-hour-long Malcolm X biopic. Bless him for that.

Define your “but I love musicals.” It takes time, but that’s the key thing. When you find that, the sky’s the limit. We can try to copy Spike Lee movies, but we’ll never really hit it. Get to the point where only you can make your stuff. Once you get there, people are going to start calling you nonstop.