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160over90’s Ramon Ariel on taking the Phil Jackson approach to creative direction

January 31, 2023 · 7 min read

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

Ramon Ariel De Los Santos is an award-winning artist and Creative Director. Beginning his practice as a copywriter, he’s spent time at agencies like VMLY&R, as well as in-house at brands like Converse and REI. He is currently a Creative Director at 160over90, as well as a Creative Director and Partner at The Clever Agency.

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

Tell me about your approach to mentoring your team, as a creative director.

It’s like being a coach, a Phil Jackson type. I'm there to acknowledge the things you do really well, and make sure you keep doing those things really well. I’m also there to help you see your blind spots. I can identify what you’re not doing so well, and — to continue the basketball metaphor — say, “Sure, you’re not great on defense over here, but maybe if we switch to this side of the court, you’ll be able to lean into your strengths.” A creative director puts their team members where they need to be to succeed.

The other side of mentorship is having what some people call difficult conversations, or what I like to call courageous conversations. As a coach, I want to give you all the information I can to ensure that nothing takes you by surprise. As in, if you’re not great at defense, I don’t want you to find that out during your end of year review. I want you to find that out the minute I see that you're struggling with defense. I want to call that out and have a conversation with you: “Hey, I saw you did this and that, let me help you. Here's a book, Here's an article. Let's talk about it.” I want to help you win.

How do you teach people to take feedback well?

It's all in the conversation and genuinely caring about the person’s success. It's empathy, a spoken acknowledgment: “Hey, I know this is hard feedback, but here's the proof and here's what we can do better.” The tough part is that everyone has a different reaction. My goal is just to make sure I'm available and whoever I’m trying to help knows I am here to provide solutions and tools — that they know I’m here for them.

In my career, there’s certainly been moments where I've been given feedback that I wasn't performing to the level I should have been, even growing as a manager and creative director. I’ll admit it, of course I’ve been mad if I don't see the proof or examples of the behavior from whoever is giving me that constructive feedback to reference. Oftentimes, though, I will know exactly what I did — I should have written notes for that meeting, or I should have done this or that. Everyone approaches it differently. 

I like feedback, I embrace it. What I tell my team is you want to know where your blind spots are. Constructive feedback isn’t a personal attack, it’s the opposite. It’s about wanting to help you become the best you can be.

You come from a copywriting background. What’s it like to become a creative director with that perspective, as opposed to starting in graphic design or photography, for example?

I actually trained as an art director, but at my first internship, my partner and I both came in as art directors, so one of us had to be the copywriter. I figured — well, I write poetry on the train all the time, I'm always journaling — why not? So I took on the copywriter role and just fell in love with that process and work. 

Quite honestly, even though I thought I was going to be an art director, I didn't want to spend 80 hours per week in Photoshop. As a designer or art director, it's such a long iterative process, and you need to be in front of your computer the majority of the time. With writing, I can just go somewhere with a notebook and escape the screen while still getting my work done, even producing better work than I would stuck at my desk.

In terms of growing from copywriting to creative directing, I always wanted to be a creative director. That was my vision since college, to run an agency or a department somewhere. My view of the role is, to be a creative director you have to be able to have an opinion, not only on the words, but also on on the design and the visuals and the feeling of it all. Design might not be your area of expertise — or copy, if you come from a design background — but you should have workable knowledge in those fields. A truly good art director can write a really great headline and a truly good copywriter can come up with a really great visual. No matter how you come into creative directing, you have to be able to flex once you get here.

Ramon talked us through how the process he undergoes before production.
Ramon talked us through how the process he undergoes before production.

What advice were you given earlier in your career that’s guided how you operate over the years — and what’s a piece of advice you’d pass on to younger creatives?

Just go lock yourself in a room for an hour — at least ten minutes — every day and work on your craft. Edit in the morning and look at what you’ve done, but my advice is just to go and do the work. It’s simple, it’s obvious, but that’s the key: just put in the work. Every single day.You'll only get as far as the amount of effort time you put into your craft. 

The opportunity multiplier you can leverage on top tier work is how flexible and open you are. Flexibility has always been the key for me. I left New York for a while to live and work in Kansas City and Boston. People were confused as to why I wanted to do that. Well, I'm a marketer, right? I'm a storyteller. I need to know how people live in places outside of New York. That’s the whole reason we travel, to take in other cultures, and it’s really important in this type of work. In the creative industry, we’re all storytellers, and you need to learn all the stories you can.

My other piece of advice for people who want to be a creative director is to think outside of your day-to-day creative work. Find the thing that grounds you outside of your job, whether it's a mindfulness practice or whatever else it is that gives you confidence and purpose. We are in a business of rejection. Not every idea you come up with will make it and that can make you start to doubt yourself and your worth. You need something outside of your job to keep you grounded and confident.

What’s the most positive change in the creative industry you’ve seen during your career — and the most negative change?

It's slow going,  but I'm starting to see more people with a diversity of voices come into this field. Diversity of thought, diversity of background. lt was always the white dudes who were running the agency world and broader creative industry. Now we're seeing more women get into it, more LGBT folks, all these different backgrounds and cultures coming to the forefront. It’s changing the industry layout too, like here's a general market agency, and there's the Hispanic market agency and this is the Black agency. 

More clients are understanding the value and importance of these expertises. They’re also understanding the overlap, that there’s no reason this Hispanic agency can't tackle a general market brief and come up with really interesting ideas. Now people realize, oh, you might actually want to try that angle so you get a different point of view, you might get an incredible creative product you’d never have been able to produce before.

Another change, I don't know if it's negative, per se, but a misinterpretation of data. Rather, an overreliance on data as a tool. You can have all the data in the world, but that doesn’t mean you approach it without bias, or even that the data itself is without bias. I’ve seen people look at data as they build a brief, and the data suggests they should create such and such type of campaign, so they do, but it still flops. My point is, you cannot count out intuition. Data is a great tool, but we’re in the business of hitting moving targets. 

Data is a great tool, but it’s rarely more than the sum of its parts. Good creatives have a vision. Good creatives know when to take risks.

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

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