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

Jenna Josepher is an award winning director, designer, artist, and contributor based in New York. She has led creative and strategy for commercials, campaigns, brand identities, social media, branded content, music videos, and editorial projects. Having spent years at organizations like The New York Times and Function of Beauty, she currently runs an independent practice.

Below is our conversation with Jenna, edited for length and clarity.

How did you become a creative director and what does the role mean for you?

My background by trade is as a graphic designer. Much of my career development leading me into creative directing has been a matter of seeking and taking opportunities that allowed me to learn what I wanted to learn, very intentionally. When I was at The New York Times, for example, I was doing pitch work and concepting. Part of what excited me about that role was the opportunity to learn team management, workflow and process-building, and ultimately administrative work.

As an in-house creative, the more you advance, the more administrative and process-oriented your work really becomes. There are plenty of people who just want to do the actual creative work, and that's great. These are the artists of the world — not everyone wants to or should be managing vacation time and pay and raises and so on. I enjoy creative work, but I also enjoy my work now, which is often about mentoring, facilitation, feedback, or process. 

What’s a piece of advice you were given that’s been foundational to how you operate? Is there a different piece of advice you’d give to younger people starting their careers?

Oftentimes, the most useful piece of advice is just to care a little bit less. You should always care about the people around you, on a human level — what I mean is you should always be prepared to be less precious about your work. If the client or company you’re working for wants you to do something differently, just do it. That’s the job.

When I've managed teams of more green-to-intermediate people, people on those teams will often come to me and say, “Oh, [the client] keeps ruining my work,” but look — there's really no way around that if you want a job. I'm never going to tell those people to stifle their feelings or not to vent, but I do tell them to try to be a little less precious about the work. Do what the client needs and keep it moving, because that’s the only way the process is going to smooth itself out. It doesn't always feel good to give that advice, but it does feel right. 

A piece of advice given to me that I’ve found particularly powerful is: don’t expect anybody else to want you to win. You have to be your own cheerleader. Know that you might very often be walking into a room full of skeptics. Just continue doing your work and doing as best you can. Prove them wrong. Manage up. Make sure you're always learning and contributing to the ecosystem you've stepped into.

What’s your approach to mentoring the creatives you work with?

Mentoring is my favorite part of my job. I’m never as fulfilled as when I’m helping other people shine. That's where I'm at right now, but of course if you’d asked me 10 years ago what this work is all about, I’d say, “I want to win awards.” That’s not the purpose I find in this work anymore.

I want other people to win — not just win awards, but to get the job they want, produce the work they want. I had a couple of humbling experiences early on in my career that showed me how not to be a manager. If I have a team member who is starting to question why they got into this industry, that’s a negative reflection on my managerial skills. It’s my job to keep people inspired, to nurture them creatively, and clear the path in front of them.

Everybody has different goals. If someone I’m managing hasn’t figured out their goals yet, then it's my job to show them their options. Here are the different directions and routes you can take — where do you want to go? I want to help you nurture the skills you need to walk the path you want to walk.

Is there a way to measure how “successful” a creative team is besides just whether or not they’re hitting deadlines?

There are a few different signals of success. How are we as a team all functioning together? Do we have smooth processes? Do we have time to help each other? If one person is staying until 9:00 PM and everybody else is leaving at 6:00 PM, that’s a team-level failure. If a few of us stay in the office to help out, then maybe everybody can leave at 7:00 PM. That level of teamwork, of caring for and helping each other, is really important to me.

When you're at any given company, they tend to have KPIs for how your team should function and they tend to impose these numbers on the creative team. Functionality, from that perspective, has always been a bizarre and abstract concept for me, but I've learned a few methods to make it make sense. 

Nobody likes the sound of “performance reviews,” but performance reviews built around goal setting are so helpful. A good review lets you connect company-level KPIs to the individual. I enjoy finding creative ways to make both sets of goals one and the same. Of course, it's not always possible. Performance review metrics allow the company — the bosses — to see how people are aligning with their goals, of course, but they also show the team that you, as their manager, are invested in their progress individually.

Performance reviews do not have to be and should not be a dictatorial process. I like to approach it by writing these goals together with the people who they’re for. Work quality is always included on the list. Deadlines are always part of it. The most important thing about hitting deadlines is really team happiness. So if an individual isn’t hitting their deadlines, it might be a problem on their end, but it might be that management is pushing unrealistic deadlines in the first place, which drives down morale.

Ultimately, if you've built trust with your team, you can really just ask them how it's going and they'll be honest with you. That’s the simplest way to gauge the success of a team. They don't always want to be honest with you, though, because you’re their boss — and that’s fine.

Over the last decade, what’s the most positive — and the most negative — change you’ve seen in the creative industry?

My answer to both questions is AI.

I love AI. It's the coolest thing. I've been messing around on Midjourney and DALL-E quite a bit recently. As somebody who does creative direction for video and campaigns, I’m tasked with conceptualizing an idea that does not exist yet. That's the point of “having an idea,” of course, even if it's inspired by something, but it’s time-consuming to bring that idea into the world, even in the concepting stage. 

There are clients also who don't have the biggest imagination and there are creatives who can struggle with getting their point across sometimes — but using AI, you can literally create an image of what you're imagining, with just a few words and in just a few moments. Using AI as a tool to create pitches is just incredibly cool to me, not to mention useful and time-saving.

What I don’t love is AI as more than a supplementation tool. Like, you’re telling me these ads were all written by AI in 0.2 seconds? I can tell. Things like that make me a little sad, like we're watching the design of our own obsolescence in real time. AI isn’t a replacement for actual human artists and craftspeople — but it can definitely be helpful during the creative process.

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