This is part of our 100 Creative Directors interview series. To return to the series homepage and browse other interviews, click here.

David Oswald is a German-born Creative Director, brand marketer, and copywriter living and working in Los Angeles. With a globe-trotting background working on accounts like Volkswagen and Apple in the agency world, and a in-house stint at the health-tech startup GoodRx, he currently works as a Freelance Creative Director.

The title “creative director” is often misused. What kind of creative director are you? What has your experience been?

It's certainly a term that you can just use without any clear qualification. I'm from Germany and we’re used to strict professional rules. If you call yourself a tailor or a butcher, there's a large organization that gives you a little certificate to put in your shop and verify yourself as a vetted professional. Anybody can call themselves a creative director, there’s no such organization. 

When I was 24, I had my own little agency and sort-of as a joke called myself Creative Director, but it took me over 15 years to actually become one. It's fun to give yourself the title, but the main difference between being a creative and a creative director is that you are less so doing “the work,” and more so focusing on “direction.” You shape the work. You're guiding the people around you to do the best work they can. 

I've found recently that the main job of a creative director is handling the internal work with other stakeholders who are not in the creative field. It’s strategy. It's going back and forth with the marketers. In terms of how a creative director engages in the creative process, they just need to have taste and enforce that taste, simply put. 

You need to make calls, often the faster the better, and you have to get rid of that fear of needing to be spot-on 100% of the time — you cannot let yourself get paralyzed by a fear of the less-than-perfect. It’s a balance. You can and should make a faster decision that’s 97% perfect rather than spending twice as long to make the 100% perfect decision. Your taste and experience is what allows you to make strategic decisions quickly and with confidence.

You're from Germany and you've worked there, the UK, Australia, and America. How do people approach creative work differently, based on your experience working in each country?

There's a ton of differences, because in the end, advertising is based on culture. If the culture, the sentiments, and the humans you're trying to talk or advertise to are different, then the work must be different as well. 

One of my main areas of expertise is localization. I once worked on a campaign to launch the iPhone 6, for example, and I had to figure out, how does that work in Germany? It's not only about translating two words. US “funny” won’t necessarily translate to a German audience. What does funny mean in Germany? Funny in what way? Insert stereotypical jokes here, like Germans aren’t known to be the most fun — but that’s because they have a different sense of funny.

Localization is about achieving the same result by adjusting your method to different cultures. Germans are usually very inward. They're known to be very rational, which you see clearly in a lot of their advertising. But still, whenever there is a funny ad, people will talk about it. In the end, humans have more in common than we think. It comes back to the basic human needs: you want to laugh, you want to be loved, and you want to be surrounded by friends. 

I also worked in Norway where everything is very Scandinavian, they're very even-keeled. In Australia the culture was bawdy and all about being together with others, having a beer, having a barbecue. 

Now I’ve been in America for a while. Americans are just so good at storytelling, because, for example, when you are seven years old, you have to sell your baking powder volcano in school. At least, that's my impression coming from Germany, that selling is something ingrained in the American mind from a young age. It goes back to the trope of the snake oil salesman, which still carries through today in things you see around you: investment scams and multi-level marketing schemes. It’s such a part of the culture — for the good and bad — whereas I find a lot of the other cultures are more quiet and less salesman-y. 

So yes, marketing and advertising is inevitably a little different in each locality, but just the same, there’s an underlying shared truth of how people want to be talked to.

Where do the mistakes, or breakdowns, tend to happen in creative work? What tends most to get in the way of shipping quality creative?

A chain is only as strong as its weakest element. It starts with the product — is the product actually good? Bill Bernbach once said, “there's nothing that will make a product fail faster than great advertising.” The best marketing in the world can make an audience flock to a product, but all that attention quickly exposes a poor product.

Long before a creative director gets a brief, there are so many opportunities for flaw or failure in the chain. 

You can never go over 100% perfection at any stage in the process, from the moment a product is created to the moment a campaign is shipped. But any loss you incur along the way will multiply, like an avalanche. If the brief is terrible, maybe great creative or production can save it, but the hurdle is higher.

In the 25 years I’ve loved advertising, it’s rare to see a campaign or ad spot where you sense that no severe mistakes were made throughout that whole journey. An example is the Sony Bravia ad in 2005. This TV has all the colors, so let's throw 500 million rubber balls down a San Francisco street and film it in slow-mo. It’s clear they had the best people doing their best work, that they really thought through every step. Everything makes so much sense.

As a creative director, do you find any software tools crucial to your work?

If there’s one thing, it’s that I'm very pedantic and OCD about my email. I always want to be sure I'm not missing anything. My brain works better with email than Slack or Teams. Maybe it's my German brain. 

I really have a hard time working, focusing, for an hour if I know that there's an ongoing conversation in Slack concerning what I’m working on. I can’t shake the possibility that half an hour into me writing a script about a jogging shoe, for example, somebody says in Slack, “oh, this jogging shoe doesn't exist anymore.” It’s this nagging feeling, which is one of the bad things about remote work. 

Overall I like remote work. The downside is you're not in a room and there's not that energy; the upside is you can move faster, partially because of Slack. Still, Slack is just an anxiety machine. It's super useful but I’m not always sure if the toll it takes in terms of anxiety and focus is worth it.

As long as I have a tool where I can filter and present my thoughts, sometimes visually, sometimes in writing, I’m well-equipped. Slides, Keynotes, whatever, but I'm always trying to not be too dependent on some specific kind of tool. Especially as a freelancer, I don't even know what my next meeting is or what video software the client is able to use. If you become really good at using some app that integrates with Zoom while you're Zooming and then you go to a client who doesn't have Zoom, you come up short.

My aim is to be more software-agnostic, to be flexible. To be clear, that doesn’t take away the value of software built for a certain thing, that makes doing such and such a task much easier. I’m a techy person and I'm always testing things, but I never want to become too dependent on one thing.

Is there a piece of advice someone once gave you that stuck with you, or that you would share with somebody starting off as creative director?

One thing I’ve learned more and more as I climb higher up the chain of command is to always understand why you’re working on what you’re working on. When you start as a design intern or any junior role, your world is very small. Your boss is telling you to make that new car look shiny or whatever highly specific task, but as you get further in life and in the creative field, make an effort to think beyond that. What is your boss’ job? What is your boss's boss thinking? And so on — look at the real motivations all the way up the ladder. 

Think: what are we trying to achieve and can I find a smarter way than just what my boss told me to do? The morning after I’m told to do this task, can I come in with three proposals of how to do it better, faster, more efficiently?

At an agency, the why of what you’re doing is generally very clear. An account manager goes somewhere and comes back with exactly what you, the creative, need to do. It’s a crystal-clear chain of command. This changes when you move in-house; you understand that there's three stakeholders, they all want different things, and trying to make them all happy is like cooking dinner with somebody who doesn't eat gluten, one who really loves tomatoes, and one who hates vegetables. 

When you're assembling people and resources for a project, how do you know that the way you've set up your team is correct, other than that you’re hitting deadlines?

The short answer is you know everything is working well when you don't question if everything is working well. It's like the engine light in a car — as long as it’s not blinking, everything is probably fine.

To be more specific, it's not only the output that signals you’re running an effective team, because there's many ways of creating “good-ish” work. When everybody's feeling miserable, and dreading the next week of work, that's not a sustainable way of working. That’s the engine light telling you something is wrong

As much as whether or not you’ve approached a project successfully is about what you put out into this world, I always want to create an environment where people cherish each other and really value each other's opinion. They don't have to agree all the time, but it's just a vibe that you feel when you’re in an office, or you're in a meeting, and there’s a healthy five-minute chit chat. 

You’ve done a good job when people have some interest in each other — you don't have to love each other, just respect and like each other. This is so important because it sets a background where you can then have challenging conversations that don't feel personal. 

You’ve been in your career for nearly two decades — what are the biggest changes you’ve seen in creative work over that time?

It's the complexity of campaigns. That is probably the most challenging thing for me. It’s less challenging for young people, because they've only known this reality — I see junior people whose portfolios show they're already speaking all these languages like TikTok, BeReal and some other platform that I am too old to even know. 

When I started as a print designer way back, because of the size of the clients, a usual campaign would consist only of print ads. Then I graduated to larger agencies where you’d have only one TV spot and three print ads. It was so formulaic. You knew a year in advance exactly what the deliverables were going to be. It might be a Mercedes Benz campaign — we'll have a 60-second launch spot, and so on. 

Now, if you look at a company like Apple, it’s so complex. When you go to launch, you have three TV spots. You have one asset that plays in the keynote, you have one asset that needs to go to press, you have a 60-second asset after the keynote, there are five edits on Twitter that are each three seconds long. And the list keeps going, that just scratches the surface.

Today, there are so many ways to tell a story. Part of the creative director’s job now is deciding how to tell a story — what deliverables to produce, what channels to utilize — whereas 15 years ago, it was already set for you. 

Another crucial difference is 15 years ago you knew where to go to talk to each target audience. Very clearly, if I want to talk to young people, I went to MTV. Now it’s so fragmented. I might be in a room, and we're discussing a campaign, and I say we should work with this podcaster who to me is huge, so inspiring. But nobody else in the room has even heard of them. Then they share their perfect YouTuber, and I’ve never heard of them. 

The Super Bowl is one of the last examples where, hey, at least you know most of America is watching and you’ll be able to speak to them.

This is part of our 100 Creative Directors interview series. To return to the series homepage and browse other interviews, click here.