Mentor Spotlight: Courtney Leonard, Product Designer at Apple Podcasts

Courtney is a product designer at Apple, currently working on the Podcasts app. Previously, she was a principal brand designer at Vox Media.

Team Designlab
Team Designlab
Mar 12, 2021
Min Read

Based in Austin, Texas, Courtney Leonard has been mentoring Designlab students since 2016. We spoke with Courtney about her dual degree in music and graphic design, what the most enjoyable part of being a mentor is, and her advice for Women’s History Month. Read on to learn more about this Designlab mentor!

Hey, Courtney! Thanks so much for talking with us. To start, we’re curious, how did you get into the field of design?

I went to school to study music, but after seeing some print design work my aunt created, I jumped into some 101 courses for Illustrator and Photoshop. My professor challenged me to go beyond what I thought I was capable of, and that encouraged me to add design as a second major. I worked as an on-campus designer for a few departments, and eventually got some internships and freelance work in DC. Between the AIGA student group and my colleagues in the industry, the network I became a part of is what set me up for success post-graduation. 

Music 🎼 and design 🎨 is a beautiful combination of study. Where did your career take you after graduating with that dual degree? 

I worked at a healthcare company as a marketing designer, a digital agency, and a smaller design/dev company (both in DC), as well as having a short stint at another design agency here in Austin — a lot of this overlapped with my time in grad school. I’m actually in the last week of working at Vox Media right now, and I’ll be moving on to work at Apple on the podcasts team moving forward! 

We’re so excited for you and your new job at Apple! Tell me, how did your design journey bring you to Designlab?

My former coworker and friend Kyle Conrad actually recommended Designlab to me. He knew about my past life of being a music instructor, and that I was interested in mentoring new designers. There’s so much I wish the industry had shared with me when I was getting started, and I’m still really excited to help grow skills and confidence in others while also learning to be a stronger design lead. 

It’s so great of you to give back, the world definitely needs more design mentors and leads! What does an ordinary day look like for you?

My days generally start with some sort of designers sync, either on the product team or brand team, and sometimes both. I’d say my role as a principal designer is 40% project planning and organization and 60% doing the design work itself. 

And what does your role as a principal designer entail?

As a principal designer, I’m “design lead” on a lot of high-priority work. I feel like there’s a lot of autonomy and space to bring new solutions, collaborate with designers on the team, and do a bit of direction and delegation. Our design leadership leans on principals to help bridge the gap between the designers and directors, so it’s a bit of communication work as well. Anticipating team and leadership needs, then suggesting processes and adjustments to help folks do their work better for example. The Vox Media brand team is always churning out incredible work, so another part of the role is just amplifying that and making sure people feel supported in their growth. 

On the other hand, it doesn’t really feel like the team roles necessarily define the impact you can have. I’ve learned so much from designers of all levels and responsibilities across the organization, which eventually led to my doubling onto the product team. 

We agree that the role and level doesn’t necessarily define the impact that a person has — a good thing for fledgling designers to remember! What parts of being a designer do you find most fulfilling?

Connecting with project partners to help them feel confident using design solutions has been really fun. On one hand, some of our work is educating non-designers about why some solutions work better than others but as a designer, you can also learn so much about a business through the lens of, say, a sales lead. It’s not glamorous stuff, but I really believe those are the moments that are going to elevate your skills. Cross-functional collaboration shows how you fit into the industry at large, and at which moments you can leverage design to solve particular challenges.

Cross-functional collaboration is often where it’s at and certainly looks to become even more important in the future! On another note, what do you like to do in your free time?

Thinking about the After Times, reading, staring at my dog! I’ve started and abandoned so many hobbies over the last year 😅 My friend and I have been making candles and experimenting with different scents and molds, and I’ve also been using a lot of time to check in with and have deeper conversations with family and friends. 

Candle-making was my go-to quarantine hobby as well 🕯 What’s a favorite design or designed product of yours?

I’ve been following the team at QuarterLab Design Build for a while now, and I’m always so impressed and inspired by their solutions for living spaces. My dad ran his own carpentry business when I was growing up and my uncle was in landscaping, so I’ve always been interested in how the two come together. Could be a new career path some day!

Ooh we see a living solutions app in your future. What are your favorite projects to work on?

Designing for podcasts is generally my favorite! Creating visuals for storytelling is so fun, and you can really push the boundaries because it’s still a relatively new business. 

Podcasts are a great way to consume quick storytelling. What people in design do you look up to?

So many! Off the top of my head…

Yesenia Perez-Cruz, Greg Bernstein, Bethany Heck, Devon Ko, Ethan Marcotte, Cymone Wilder, the Hood(zpah) crew, Tatiana Mac, Yelitsa Jean-Charles, Lara Hogan, Lindsey Morgan.

Those are great follows. Are there any tragically designed products or services that you think could use a revamp?

The U.S. government. Lol but really, anything that makes assumptions about its audience without testing and iterating based on feedback. There are so many examples out there, but I think the relationships and processes between design, research, and data teams could generally use some work. That might solve issues for a lot of “tragically designed” things! 

LOL 😂 What’s the best piece of advice you’ve ever received?

Several people have shared the advice that “if you’re experiencing something, chances are, others are too.” This applies to a lot of areas while navigating a new career, finding your individual voice, style and professional values. When I was a “new” designer it definitely helped me feel less isolated. Now, as someone in a more senior role, I can identify these moments as an opportunity to support inclusive environments where everyone can thrive. 

We are all for designing with inclusion at the forefront. What is the best piece of advice you have to give someone entering the world of design?

There are a lot of really popular paths and ways of learning design, but my advice would be to build your own curriculum. Learn design history that isn’t taught at universities. Find seasoned type designers that aren’t in big NYC publications. Use social media to discover the “unsigned” illustrators and photographers. Read UX case studies written by junior level employees. 

Write about your findings! Too often, we make assumptions about who can write about design, and how “perfectly edited” it should be. I would 100% subscribe to a newsletter that featured interviews from people with 0-5 years of design industry experience. What’s working? What’s not? What ideas do you have for how we can continue to improve? I really enjoy listening to thoughts from those joining design from other fields too, like architecture and sociology, and what we can learn from them. 

Writing and reflecting is a great way to learn. What predictions do you have for product design in 2021 and beyond? 🔮

There’s been a bit of conversation around this already, but I think contracting is going to become much more common than it already is. Of course there will be teams and roles that remain in one space for years at a time, but I’ve experienced how people in those positions will be somewhat replaced by experts in a given discipline. Companies are getting better at finding and onboarding the right contractors for specific challenges, which can both save and create space for better resourcing. On the flipside, contractors (along with product managers and strategists) are really leading the design industry in how to set process and compensation boundaries. 

That’s not to say new designers should only aim to master a specific skill, because early in your career I think it’s important to understand the detailed mechanics across disciplines, and try things out to see what fits your individual goals.

That’s good advice for graduating students of UX Academy. What attracted you to becoming a mentor in the program?

I spent years teaching private music lessons and assisting band directors around the state of Virginia as a part-time instructor. I didn’t realize how much I loved it until I was about 2 years into my design career, and started seeking out ways to bring the two together. 

Designlab has given me the space to mentor folks with both similar and very different communication styles from my own. In such a fast-paced environment, it’s as compelling as it is challenging to “get to know” someone’s learning style quickly. And while the goal is to guide them to resources and help them complete assignments, I’ve stayed with Designlab because I learn so much from the students about how I can be a more supportive design leader. 

It really is a win-win situation! What do you find most exciting or rewarding in mentoring?

I get several emails a month from former students updating me on their new jobs or telling me about how they helped their friend through an interview process. Building confidence in such a subjective field is something I still struggle with, so helping others find and flex their strengths is really fulfilling.  

We definitely feel fulfilled by it too. What has surprised you most about the students you’ve worked with?

Designlab students have way better work/life balance than I did when I was entering the field. I can’t describe how much second-hand empowerment I feel from a student who makes the best of their situation without compromising their values. 

Work/life balance is so important ⚖️ What has been the ultimate student win throughout your mentor experience?

It’s really great to hear about jobs and interviews, but the ultimate student win is hearing how much more clarity and confidence they see for their futures. The design industry can be really intimidating, and while new designers often flock together for support, I think it’s impactful to have someone in the industry on their side early on. 

We’ve noticed a strong community and support system are game-changers. What do you think makes a good mentor?

A person who listens well and asks thoughtful questions. I don’t think it’s a mentor’s job to say what answers are right or wrong, but instead someone who pushes a student to think outside of their comfort zone and get creative with solutions. 

Similarly, what do you think makes a good student?

Someone who has genuinely dedicated time and headspace to their craft, being mindful and open to different ways of thinking. We’re all students all of the time though, right? We should carry that kind of focus with humility into any space.

So true. Finally, since it’s Women’s History Month, what advice would you give to your women students who are hoping to break into the world of tech?

Similar to how one might have a “medical team” of doctors, you might consider building a “team of mentors” across industries. This can range in formality, and you can decide how to maintain it! My mentors work in product, branding, event and experiential marketing, podcasting, journalism, career coaching and even real estate. Some are more like friends that I talk with weekly, and some are people I chat with once a quarter or when we’re at pivotal career moments. It’s rarely a one-way street, and each relationship requires its own setup.

Watch Courtney’s on-demand webinar with Designlab, “How to Sell Your Design Solutions” and check out her portfolio, LinkedIn and Twitter.

If you’re interested in learning UX/UI design with a mentor like Courtney, we invite you to explore our UX Academy program. If you’re interested in becoming a mentor with Designlab, we encourage you to learn more and apply here.

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Launch a career in ux design with our top-rated program

Top Designers Use Data.

Gain confidence using product data to design better, justify design decisions, and win stakeholders. 6-week course for experienced UX designers.