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 does it mean for you to be a creative director?

It's sort of like being a farmer.

Let’s say you’ve got a barn full of cows you need to bring out to your pasture for grazing. The laziest ones stop at the first weeds they see. They’re chewing their cud, they’re in the mud, and it’s been trod on a thousand times, but they’re satisfied. If you push the cows out farther into the field they’ll end up finding better grass, greener pastures.

The more you explore, the further you push, the better the results. You might have some crazy cows who keep wandering and stumble on these patches of lush, rich, untouched pasture. Point is, there’s no shortage of fresh concepts, and ideas out there. You can’t just fall for that first idea. 

Of course, if your cows wander too far, they might get hit by a truck. That’s the thing — you have to take care of your herd and make sure they’re supported. Give your people the freedom to roam and explore, but make sure to check in. Recognize their good ideas when they come and teach them to tell the difference between mediocre, good, and great.

What’s your approach to mentorship when you’re managing a team?

When I was a junior art director there were senior creatives who looked out for me and became my mentors. I’m still grateful. I want to pass that down to the young art directors and writers I work with.

I had a creative director who would ask me to make 20 variations of a layout using the same type and the same image. I hated it at the time, but it forced me to explore and not settle for the first solution I came to. He taught me to be that cow that keeps going. It also taught me to be Teflon — if someone rejects your idea, there’s always another solution. You can always come back and solve the problem at hand in any number of ways.

How do you shepherd a really good idea through the trials and tribulations, the stakeholders and budgets, to get it made and into the world?

That's the challenge, right? This world is filled with ‘no,’ and you, again, have to learn to be Teflon. You need to be resilient and persistent, but you also need to have empathy. You have to understand who you're talking to and what their challenges are, what their stressors are.

Much of this comes down to understanding personality profiles in any given situation. Some people are creative, some people are leaders and drivers, some people are analytical, and some people are amiable. It’s not always so neatly segmented, but all these different profiles need to be spoken to differently if you want to successfully sell your ideas. 

You need to understand who you are meeting with and figure out what moves them, what they need out of a conversation, and how your idea fits into their needs. For example, a creative director who isn’t much of a social person just wants the big idea: ‘tell me what it is and make it happen.’ 

The person you're selling that idea to might be an account executive or a client with an analytical bent: ‘tell me how this accomplishes x, y, and z.’ They just need all the boxes checked. You don’t lead with the big idea; you sell all the little ideas and then package them within the big idea at the end. Lastly, someone with a more amiable profile wants to feel heard and be part of the solution. They’re all about people and connections — they want everybody involved to buy into the idea, that’s their priority.

Knowing those personality profiles can really help you.

Be prepared to sell your ideas in different ways, depending on who your audience is.

How do you set up a creative team to operate at the highest level of their potential?

There's a saying that if you hire people who are better than you, you become a company of giants. And just the same, if you hire people who are not as good as you, you become a company that will fail. 

Hire good people and recognize their strengths. Let them do what they’re best at and give them due credit. Let them present their ideas, involve them, make them feel they're part of the team. Junior creatives need experience presenting their ideas to account people, and they need experience presenting to clients. Push them out of their comfort zone, show them you have faith in them, and they’ll succeed in the end.

To support your team, you also need a great creative strategy. If you start with a strategic idea that everybody agrees on, then you're all on the same team and can more easily move forward. That prevents account folks or clients from changing the strategy as you’re executing on it. Also, having a solid strategy gives you a framework for judging creative ideas. Your creative teams will understand it’s not personal; you’re killing the idea, not the person.

What are three things you can't do your job without?

As a creative maker and creative leader, I try to maintain a level of curiosity. It’s about always trying to find a new way to explore something, to find a new answer and see something in a fresh way. Maybe it’s mixing two things that have never been combined before — obviously chocolate and peanut butter go great together, but what if you switched out the peanut butter? You may find other things don’t pair with the chocolate at all, but then you find one combination that’s just incredible and surprising.

Gumption is another thing — not saying ‘that can't be done,’ when you’re trying to solve a problem. It can be done. You just have to find another way. That’s really why I started Swope Films — to bring that kind of scrappy creative process to filmmaking. Big agencies get bogged down, and gumption often gets squeezed out when there’s too many people involved and too much at stake.

The third thing is, of course, a Mac. I could have said ‘Adobe’ — you can't do anything as a creative person without all the apps, of course, but my MacBook is crucial. If you told me I had to work on a PC for the rest of my career…forget it.

What's the best piece of advice you’ve been given in relation to your career?

I love this question because the answer actually became part of the logo for Swope Films. When I was a junior art director, somebody told me about ‘the circle theory of advertising.’ 

[David holds up a piece of paper with two circles drawn on it, as seen below].

Here’s two objects — which one is more interesting for you to look at? 

Air: It’s the one on the right, with the gap.

David: Right, obviously. So, a lot of advertising is exactly like the circle on the left: all it does is tell you everything there is to know about the thing it’s advertising. It doesn’t involve you in any way, just says: ‘here’s the thing, here’s how much it costs, you should buy it.’

The one on the right makes you think. Is this a circle? There’s something else going on; it’s actively engaging you, it’s making you fill in that little gap. When you involve me as a consumer, I start to feel part of your brand. The classic ‘Got Milk?’ campaign is a great example of this. It didn’t say ‘Get Milk;’ it’s a question. You’re thinking, ‘do I have milk?’ 

So the lesson was really to leave something to the imagination and respect your audience. Let them work at it, allow them to feel clever. They’ll feel a much deeper connection with your brand than if you’d just laid everything out for them.

Interview has been edited for length and clarity.

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