Shiloh Gray, Winc’s VP Of Brand, Has Made His Creative Passion Mentoring Other Creatives
Interview by Trey Alston / Working Not Working Member
The first of several, thorough recommendations on Shiloh Gray’s LinkedIn account reads that his “curious mind and keen eye make him the kind of creative every client wants on their brand.” After coming into the world of advertising in 2006 as an intern at Second Thought, Gray progressed rapidly through his work as a graphic design artist and in multiple creative director roles. The now senior-level creative, currently the VP of Brand at wine company Winc, has spent the duration of his career learning, not letting his work define him, and figuring out the metaphysical side of what makes a creative, well, creative.
Now, in addition to his role at Winc, Gray has spent years applying what he’s learned in the industry, and what he’s discovered seeing creatives operate on all levels, through mentoring Black and Brown rising creatives—a subset of people that make for a frustratingly small percentage of existing people within the ad industry. He subscribes to a particular creative philosophy that drives his self-defining pursuits and gives the people that he helps the means to push forward.
Here’s Gray on his creative philosophy, mentoring, and what all creatives should know, below.
What's been the creative philosophy that you use that has been driving your career?
I think the big one for me has been just being able to do the work. When I think about all of the moments in my career where I felt like maybe I didn't have a great idea, wasn't getting the feedback I wanted, or I wasn't progressing the way that I wanted to, I had to return to the zen of focusing on the work and not anything else. So whether that was being a better designer or being better conceptually, I had to recenter my focus.
I gave a speech in 2009 at the college I graduated from called "Don't be an asshole.” It was about the importance of working hard, pressing boundaries, and really trying to be someone that people want to work with. And I think that extends to personal life where, no matter where I work or where I live, the first people I make friends with are security guards, cleaning staff—all the people that are invisible because they're the ones who do the work. They're the ones that can help you in your time of need. And so it's been about putting my head down, doing the work, and at the same time trying to be a decent person.
There's also a growth mindset. In the last five years of my career, there's been this “if you're not growing, you're dying” approach that I've been taking to my work and to who I am. When I feel comfortable, I see if I can find more challenges at the place I'm at. And if I feel like I can't, then I leave. It’s about consistently making myself uncomfortable and only being comfortable in chaos and in the uncomfortable. If you think you know the answer, then you're probably doing something wrong.
“I had to return to the zen of focusing on the work and not anything else. So whether that was being a better designer or being better conceptually, I had to recenter my focus.”
How did you get into mentoring?
When you start working, you get hired to do a specific job. And you're looking for someone to tell you whether or not you're doing that job well. And a lot of times you're connecting your performance to your personal worth. I think a lot of junior creatives and designers judge themselves on that. What you realize you need is someone who technically can help you be better at what you do. Someone who can look at your skillset and say, "Here's where I think you can go and what you can be." And a lot of times that's related to what you're already doing.
And then I think you also need somebody who can look at your skillset, but also your personality, your drive, and the soft stuff that you're made of, and try to help you figure out what you could be that maybe you didn't realize you could be. And so when you look at mentors, I think those are the two types that you think of. Sometimes you can find both in one person and sometimes you can't.
I had a lot of people who would help me be a better designer or a better ideator, a better manager in terms of getting work done and setting processes. But for a lot of years, I felt like I was struggling to find somebody who was really looking at what I was doing in my skillset and who I was, and helping me piece together something that was non-standard.
“You also need somebody who can look at your skillset, but also your personality, your drive, and the soft stuff that you’re made of, and try to help you figure out what you could be that maybe you didn’t realize you could be.”
Aside from that, growing up I was really quiet for a while. For lots of years, I was bullied pretty hardcore. A lot of that was racial issues, where I was either too Black or too white, depending on where I was living, whether it was Upstate New York or Atlanta. And I became very, very quiet. What I was able to do when I became very quiet—I just watched. There were other people that were louder and wanted to say things and be seen. And I really quickly learned people's posture, the things people do when they're hiding something, and what they really mean when they're saying something. When you're not part of it, you start to learn the language a little faster.
I have a very highly-attuned skill where I can speak to someone in person or over the phone, hear what they're not saying, or build a model of what their problem is. And I can quickly identify it and start to work on that problem with them. I think if you take the mentors that I had that were good and bad, you take my need for family and connection, you take me being a nerd and getting bullied and spending a lot of time on the fringes, it built this skillset where I'm highly capable technically, but I'm also highly empathetic and able to help someone do their job technically. But at the same time, work on what I call the whole human. Because that whole human is what comes to work every day.
That's what really got me into mentoring and helped me feel successful. Regardless of awards or what I reach in my life, the effect that I can have on singular individuals is really my legacy. That's what I do at work. When all the racial unrest was happening in June, and I was thinking about what I could do in terms of donating money or marching, I realized that my skillset is super rare nad I could give it away for free to people who really needed it—Black and Brown people.
“Regardless of awards or what I reach in my life, the effect that I can have on singular individuals is really my legacy. That’s what I do at work.”
What are some common problems or issues that you run into with creatives and how are you able to help coach them past those?
One of the big ones is creating versus leading. Trying to identify who is what we would call in the business an individual contributor, who is just a kick-ass writer or art director, somebody who is technically capable and all they want to do is create work. And then identifying people who can become leaders, creative directors, whether it's group or ECD, they might become VPs, and might own brands. Who can lead a team and who can connect with a client or a partner and create success in collaboration? One of the struggles is sometimes identifying who is right for which of those roles. In a lot of businesses, you just get promoted, and with promotion you get more responsibility. And that responsibility usually involves humans. With creatives who are more individual contributors, I think we have to be really careful about determining if management is part of their path versus where you could maybe consider mentorship.
So I might work next to an art director who is more senior, who helps me out with layouts, who helps me out with ideas. But maybe I should never report to them because they're not good at problem-solving, they're not good with people skills, but they're an amazing technician. So I think that's the one problem that I consistently see popping up.
“You just get promoted, and with promotion you get more responsibility. And that responsibility usually involves humans. With creatives who are more individual contributors, I think we have to be really careful about determining if management is part of their path versus where you could maybe consider mentorship.”
I think another is finding that creative mindset that drives them. Depending on the creative’s training, you sometimes have to work through what is the work and what is them. I think a lot of people think they're their work. Sometimes when you're in service of a client or a brand, you're not going to get to make the thing you want, or you're going to really struggle to get the thing that you believe is great to be sold in. How do you help that creative feel successful and feel like they're having growth in those moments?
I think of the Peter principle, which basically is that people in business get promoted to the level of inadequacy. You almost always get promoted to the level where you become not good at your job anymore. That will happen with creatives if you're not really careful about realizing what they're good at, what they need, and what they offer your business. And so it's about making those paths and allowing that opportunity, which I think agencies do really well. There are dope designers that make 200 grand a year who don't manage a single soul because that's not what they're made for.
What have you learned as a mentor that you've applied in your own career or life?
Everyone is a little scared. Everyone's not sure what to do next. Everyone has dreams that they don't know if they're going to reach or how to reach them. And basically, everybody's a human, just a small, complicated little human. When I lived in New York, you sit on the subway and you look around and you can just hate people. That's what you're supposed to do in New York.
But at that moment, I'd be like, "Well, wait, that person, that's a mother. Or maybe that's a sister. Or maybe that person, I don't know, runs a company or donates their time on the weekends." Starting to apply fake stories to these people that were faceless and nameless, is something that helped me maintain my humanity in living in the city. It's the same when I hire someone, when I'm challenging someone at work, or I'm being challenged at work, or people are confused or they're angry.
Especially during the pandemic, we're all a little fucked up. No one really knows what the fuck is going on. No one really knows how they're going to get through the day or to the next stage in their career. And so we're all operating on that. Everybody has crappy ideas. If we can all just be people, both at work and outside of work, then we can have empathy, we can have understanding, we can take time to disagree, but we can approach it in a way that creates more connection, more love, and better success if you're talking about a business.
“If we can all just be people, both at work and outside of work, then we can have empathy, we can have understanding, we can take time to disagree, but we can approach it in a way that creates more connection, more love, and better success if you’re talking about a business.”
Most conflict comes from a lack of a shared understanding. I was speaking a different language. I'm referencing details that you don't find valuable. I'm looking at the problem differently, and if I can share your language, if I can apply empathy to the way you feel about something, if I can look at the project from the way you're looking at it, we can find a common ground. Maybe not consensus. I don't believe in consensus. I believe in a thing called consent-based decision-making. I don't need you to agree with me. I need you to agree that it's my problem. Or I need you to agree that we're going to try my idea, but I don't need you to be fully on board. That human aspect has allowed me to connect with people, whether they're partners, celebrities, other brands, photographers, whoever it is.
Trey Alston is a copywriter and music journalist who writes for Complex, MTV News, BET, and more. He just discovered that he loves egg salad.