symplr’s Adam Dines on making brave decisions

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 to be a creative director?

At every company where I’ve held the role, I’ve been the creative director as a facilitator, a conductor, and a generalist. The core creative principle that I was taught in my transition from school to the working world is: you should be able to take on any client’s messaging need and craft a narrative and visual solution to answer it. It doesn’t matter what vertical or industry they’re in; it’s your job as a creative to identify a solve for their challenge.

There are certainly limits to what you can solve as an individual creative — maybe you don’t have the technical expertise for a certain deliverable — but you shouldn’t be afraid to take on any kind of challenge. You can always engage experts to get certain technical aspects handled.

That core principle has led me on a wild and unpredictable run over the last 20 years or so. I’ve never turned down a job just because it’s in a particular field, or because it’s B2B versus B2C. I’m just looking for people who are brave enough to make good creative with me.

The real work of a creative director, to me, is facilitation. It’s aligning stakeholders, ensuring the creative aligns with the brand, and managing the creative production. You have a responsibility to three things as a creative director: your stakeholders, your audience, and the actual work. In the middle of those three things, you’re a conductor: pushing and pulling each one towards a goal.

What is the hardest part of actually getting really good ideas through that process and into the world?

Time and trust are the two biggest challenges. 

Trust can solve for time in that you can come into a project’s first presentation, flesh out 3-5 great ideas, and build that trust quickly. Once both of those challenges are solved for, the necessary brave decisions can be made much faster and with a higher degree of bravery, because everyone is locked in. In shorter freelance engagements I’ve done, it takes more time to build shorthand or trust. When you’re in a full-time role or working with collaborators you have history with, that trust and bravery is there from the beginning.

As long as you can bring your stakeholders into the process in a way they feel good about, without blocking the creatives, you’re good. But that can take time.

You speak of bravery — how do you draw that out of people?

When I’m starting with a new client or collaborator, I ask them to share some of their favorite pieces of creative. I try to determine where their bar sits, in terms of taste or appetite for risk. 

I also ask potential employers to look at my portfolio and tell me which work resonates with them. I have Apple on my resume — but I need to know if that name is the only reason someone wants to work with me, or if they’re actually interested in making work I care about making. It’s really hard for people to articulate what they like or don’t like, and why — but you’ve got to do it to see where you stand and build that trust. You want to establish their appetite for risk and potential for bravery before you start a project.

How do you assemble and really effectively manage a strong creative team when you’re first coming into an organization?

Well, there’s not one specific answer. It depends on the organizations I’ve been at. Is it well-resourced and established, or is it more scrappy and still finding its fit? Do you have 1 year? Or 1 month?

If you're granted generous time and resources, you can build up a team of specialists. If you’re not granted much in the way of time and resources, you may want to start with a generalist.

A really high quality generalist is invaluable. Maybe they’re not able to do production-level output, but they can get close enough. They usually leverage strategy and messaging, can usually write well, and can spin up some striking visuals to accompany everything. I have personally tried to work within that realm. A good generalist shines in terms of connecting stakeholder desires to creative solutions. They can move things along and push all the pieces into place.

A good generalist will also set the table for specialized work to continue. They can get different pieces of a project far enough along that it becomes efficient to bring in a really strong specialist to advance it further or resolve it. 

Really talented creatives aren’t all as adept at connecting the high-level dots. Which is fine! Maybe a designer has built an amazing deliverable in Figma. It's beautifully crafted and could launch tomorrow, but is perhaps not empathetic enough to the brand or stakeholders, so it falls flat. That failure falls on the creative director. Which is why I’ve often preferred to start with idea-driven generalists before advancing deeper into more specific creative.

When I’ve been part of bigger, more established orgs — like at Apple or established agencies — I’ve been able to work among a rich team of specialists. But many organizations aren’t like that.

What are three things — could be anything — that are crucial to how you do your job?

Empathy is number one. My empathy for a brand, its audience, and its stakeholders. It wasn’t until my fifth year or so of being a designer, when I moved to New York, that I truly came to appreciate this. Until then, I’d cared so much about just making beautiful work, or creative expression. It felt like unlocking a new level of thought, to see how much more can be accomplished by getting into the heads of a brand I was working on, or their audience, or their stakeholders. I began hitting the mark faster and more effectively, and still with unique ideas.

Energy is number two — my own energy. It’s a resource that has to be protected, cultivated, and renewed, just like the battery in my laptop or ink in my pen. I learned that right away, coming out of school and being expected to show up every morning with energy to create. You don’t always get to pick your team, or cadence, or schedule, but you do always have to come energized.

Protecting and cultivating my energy has required some discipline. For me, sleep is vital. Emotional regulation is important, in terms of choosing not to obsess over things that aren’t going my way. Spending my free time doing things that recharge me, using music to give me energy while working — people find what works for them.

Relevance is number three. As a generalist, it’s tempting to fall back on tricks, techniques, or strategies that worked in one vertical when faced with a challenge in another vertical. That’s fine — if you’re always working in fashion or entertainment, maybe similar approaches can work. But you can’t take that for granted, especially when crossing verticals.

As someone who’s served clients across different industries, working on different types of deliverables, I find that initial phase of discovery and learning to be especially important. You can’t take for granted what you don’t know yet. I’ve been burned in the past by suggesting solutions that, while they may have worked for me in the past, were completely inappropriate for a particular vertical or client. It’s those bruises that taught me to force more time into the discovery phase. 

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

The best piece of advice I’ve been given was the piece about empathy I mentioned above. Former colleagues and mentors had to explicitly impress that on me.

As a creative, most of us generally aren’t being paid to create whatever we want to create. We’re being paid to solve a client’s business need. You’re doing them a disservice if you don’t get in their heads, or in their audience’s heads, and figure out what the situation demands. You’re not going to succeed. You may create something that’s super personal, but which doesn’t address the business challenge at hand. 

The biggest thing I look for when I’m reviewing the first round of work internally — whether it’s my own or my team’s — is if we’ve answered (or asked) the right questions from our stakeholders. Have we really absorbed their perspective? Do we really understand what they’re trying to solve, and why?

In design school, you’re taught to speak about yourself and your work. You’re taught to hone your own creative desires, voice, approach, and expression. But in much of the working creative world, that’s hardly the case. There’s still art and artistry involved, but it’s not about you. You’re here to solve a business need, not to express self-indulgent desires. Ego is important — no good creative comes without some degree of ego playing into it — but it can’t dominate.