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 kind of creative director are you — how do you approach creative work?

The core of my approach to creative work is to hire people I trust deeply.

I love to be in the weeds, but not so in the weeds where I’m micromanaging the creative work. If you’re a creative leader and you’re micromanaging everything, something is broken.

It’s my job to hire people I trust and make sure they feel comfortable operating with creative freedom. The creative process is a vulnerable one; at the end of the day, we’re going to present such-and-such campaign to our CEO, once it’s gone through me, so I need to feel confident in the work. 

But the people on my team, who are actually thinking through and making the work, I need them to feel confident, free, and most importantly, fearless. So that’s how I look at my role: it’s to foster an environment where my creatives feel fearless.

I’m a player coach. I do love to do creative work myself — participate in brainstorms, work on treatments, all of it — but at the same time, I need to stay high-level enough to give people space to breathe. 

If everything we’re doing is 100% influenced by me, I’m not doing my job correctly.

What is the hardest part of shipping great creative work?

We always want what we put out to be perfect and we’ve built a benchmark for ourselves, a very high standard, which is awesome.

 But we’re constantly trying to outdo ourselves and compete with ourselves to make the next thing even better, to raise the bar even higher. That pressure is necessary but it’s also the biggest challenge — if the last thing was perfect, how do we make the next thing even better?

Regardless of what form the creative takes, the goal is to reach the next level of how people will receive and react to it. I don’t know if that’s how other creative teams look at their work, but I find that’s the best way to approach creative work. We never want to just repeat the same thing, elicit the exact same reaction. We want to take the brand to the next level every chance we get.

So how do you hit that next level every time? 

Regardless of the weight of the project, from social ads to huge campaigns, it’s about putting that same thoughtfulness into it, or at least a percentage, so it feels unified and ladders up to the brand vision. As you make these more micro movements, you start to think about how each one ladders up to the larger picture you’re moving towards, which gets quite complex when you’re working on thousands of different projects. The hardest part of this work is balancing that big-picture push for perfection with the every-project push for perfection.

How do you define ‘success’ in creative work?

Success in creative work is multi-dimensional.

 Does the work accomplish what it set out to accomplish? Has our audience received the message we sought to translate? Did we get that message across in the most effective, creative, and groundbreaking way possible? Is it differentiated, in a positive way, from everything else we’re seeing in the market?

Obviously, sometimes there are specific metrics attached to a project. In SaaS, you want certain creative projects to produce conversion. But there’s other metrics too: 

Did it create a conversation? Are people talking about it? Did it win media or awards? Is it viewed as best-in-class? Can we say we’ve leveled up the brand?

Success is a spectrum from performance to anecdotal.

What are three things you could not do your job without?

1. Good leadership. I need people who trust me to do my job as I think it should be done, with the people I think can do it best. Everybody needs leadership that trusts and enables them to fully realize their own creative potential and ability. If you don’t have people that support you, it’s very hard to do your best work. You’d just be fighting an uphill battle.

2. Great team. This is tough to achieve without that great leadership. You need a team you can rely on and trust to produce best-in-class work with no ego involved. I’ve worked in many teams, and the ClickUp team is just made up of some of the best people I’ve ever worked with. They’re so close, they have great relationships, they love working together, and that makes the creative we put out so much better.

3. Great tools. The less you have to think about the process, the easier the work is, because so many steps are already done for you. When you’re not thinking about how to send something to someone, you have more room to focus on actually making the thing. Most creatives don’t really want to think about project management, or how to get annotated feedback from leadership on a video they’re working on. When tools can take care of that feedback and project management, when they’re integrated into the work, we can focus on the work we want to do and are meant to be doing.

What’s a piece of advice you’d give to people looking to build a career in creative?

I came into each of my roles at BuzzFeed, Cheddar, and ClickUp in situations where I was naive in a certain way — I didn’t know enough to understand the reasons why someone would say that something isn’t possible. I’ve always come into these roles with this belief that anything is possible. When you have this fully optimistic view of work, the world, and everything, you’re able to break through barriers you couldn’t break through if you have a glass-half-empty point of view.

Your perspective and attitude have a huge effect on not just your potential, but the potential of people around you. 

My anything-is-possible viewpoint has always helped me challenge the status quo and get the best out of my teams.

My advice to people is to come into situations really thinking that anything is possible. 

Have a little naïveté.

Pretend you’re starting with a blank slate; get rid of any preconceived notions about what is and isn’t possible. It’ll free your mind in a way that will allow you to achieve more than you ever thought you could.