Design x Cassie McDaniel
Senior Design Manager at Webflow
Illustration by Bonnie Kate Wolf
Interview conducted by Allie Wrubel on September 11, 2020
Tell us about the moment you discovered design. How did you know it was the field you wanted to pursue?
There were two things I wanted to be growing up: an artist and a writer. These magically synthesized for me with design. But I didn’t know what design was until I was 20 years old. There wasn’t as much public design literacy then as there is now. I was taking an art class at the University of Florida that exposed us to many different creative disciplines like ceramics, painting, and sculpture. I remember making a drawing that incorporated type, and my professor told me to look at graphic design. The concept of communicating with words and pictures absolutely suited me, and I spent the last two years of my university degree taking design classes.
Then I was fortunate to be exposed to all these other aspects of design, especially interactive design, early in my career. I graduated at a time when the industry was maturing and I was able to learn so much. I’ve been lucky.
How would you describe your transition into design and your relationship to the field?
Design is so many things! I’ve been very intentional about insisting that design and my skills work for the sort of life I want, and not the other way around.
I think the industry tends to name things in a way that boxes them in. For instance, the “Product Designer” title wasn’t a thing a few years ago. It used to just be “Web Designer” or, even better, “Designer.” Now “Product Designer” is all everyone wants to be, all they want to define themselves as. I wouldn’t go so far as to say titles don’t matter—they do matter, but they also change. I’ve seen a lot of that over my career, and there is an opportunity in that. Operating outside of your title or predefined “role” is a powerful thing.
In broad strokes, design is a way of solving problems, which is how I’ve been able to work across industries in a few different settings. The same can be said of management. When I was at the Mozilla Foundation, being a manager was the most effective tool for solving the particular problems I was faced with.
The designers who inspire me tend to have more fluid careers. Even old-school designers would design almost anything.
“The designers who inspire me tend to have more fluid careers. Even old-school designers would design almost anything.”
I love that. I’m inspired by that. That’s how I’ve tried to navigate my own career. I follow problems that interest me, where it seems like design can help, and that has taken me everywhere from agencies to healthcare to tech startups. If you’re starting a business or designing a garden or a digital product, it’s all related. It’s all shades of design.
I think this gives a designer’s career some longevity too. Because it’s a way of thinking and questioning and problem-solving, the skills never really go out of date.
How have your varied interests in writing and art influenced you as a designer?
I am definitely a person who likes to explore. Part of what appealed to me about being a designer in the first place, when I thought of it mostly as client services, was that I got to pop into lots of different industries to learn more about them and meet with different kinds of people. One day I could be talking to a client who works for the UN, and then the next day I could be talking to a small business owner or entrepreneur. I still like that aspect of it.
I would say the common thread for me between writing and art is having a curiosity in people, processes, and creative output, as well as a desire to share. Even as a design manager, my curiosity allows me to connect with a lot of different people, whether they’re my team, clients, students, or other leaders. That exposure has certainly taken me places I would not have been able to dream up on my own.
How was it making the transition from design to design management?
I don’t know if it’s always this way, but for me, and certainly for a lot of people I talk to, it’s a messy transition. It may not appear that way from the outside, but it feels that way. You have no idea what you’re doing. You feel as if you’ve been thrown into the deep end. You feel probably as if you don’t have as much support as you’d like. It’s disorienting. But ultimately, transitioning to a managerial role is an opportunity to invest in your own competence, and to invest in a belief that you can do whatever you set your mind to. To me that has been one of the more powerful things in my career.
The other thing that I had to let go of was my own practicing of the craft. There’s a period of transition between being an individual contributor and becoming a manager, where you are wrestling with your identity as somebody who makes something, and then the new identity of someone who enables others to make things. For me, it was an emotional shift, having to let go of myself as a designer and thinking of myself more as a leader and a person who enables success in others.
One of the big enlightening moments for me happened at the Mozilla Foundation when I realized, while reading feedback in my annual reviews, that my team wasn’t expecting me to make anything anymore. I didn’t need to get my hands dirty. I thought, “That kind of sucks.” But I realized that when I was doing a good job as a manager, I was making the lives of the designers I worked with so much easier.
That meant a lot to me, and that’s what keeps me going. That’s why I like being a manager. I appreciate the immediacy of helping people in perhaps an even more direct way than when I was designing.
How would you describe your managerial style?
I’m still learning a lot about leadership and management, but I try to practice servant leadership, which is responding to the needs of others. And those needs might be known or unknown—that is part of what I like about guidance and mentorship, the sussing out of true need.
Personally, I like to move fast. I’m pretty bad at twiddling my thumbs. I like to be doing something, even if it’s a mistake to be doing something. I’d say that a common thread between my design process and managerial style is wanting to try things and being open to the possibility of them working.
There’s also something about joining a complex organization and working on a complex product that leaves you dealing with more personality types than if you were working just within a design department. I like working with people who think differently than I do, who make decisions differently than I do. It forces me to broaden my idea of what I consider to be true, or what I consider to be important. It’s challenging for me, and that’s what I like about it. By exposing myself to people who are different from me, I am able to grow.
“By exposing myself to people who are different from me, I am able to grow.”
Have you ever felt that there are contradictory demands made of designers to be both specialists and generalists?
I’m not sure I entirely agree with the premise. I mean, who is making the demands? Says who?I think we tend to want to box ourselves in because it feels safe, but the reality is that you can do either. If you want to be a generalist, there’s room for you. If you want to be a specialist, there’s room for that too. It comes down to knowing yourself and being true to your own vision of your life and career, and trying not to please too many people.
Knowing what you want is the hardest part, and then being uncompromising in your vision is something you owe yourself.
What kind of advice would you give to young designers who struggle with building confidence?
This hits close to home. When I had my first baby, I was moving from a lead designer position into management and had also started working remotely for the first time. I was a new mom. I was balancing so much. I went through a period of a couple of years during which I had very little confidence. I had so little time, and even less sleep! But this was ultimately one piece of advice that helped me build my confidence back up: Know what you need to do, and just do it. If you’re doing anything less than that, you are further undermining your confidence.
“Know what you need to do, and just do it. If you’re doing anything less than that, you are further undermining your confidence.”
If you can, try to quiet that voice that sets limits on yourself or prevents you from getting started.
The caveat is that there are situations and times in your life when you’ve got other things going on—you might have a small baby or an illness or be taking care of your parents. When you don’t have time to focus on your career, it’s totally okay to just be bringing in a paycheck! Or sometimes not even that! But the thing that worked for me was simply doing the work. Usually you know what you have to do.
You recently moved back to your hometown in Florida. What’s it like living in Florida again? How has living there impacted your relationship to design?
I came back to Florida in 2018 after 10 years away, living in England and Canada. I’d moved away right after university. It feels like I’m experiencing Florida as an outsider now, with new eyes, not as a teenager whose world was just happening to her.
I’ve always felt this was a place where you could connect with any kind of person. So much of Orlando feels “underground” like there’s something for everyone—you can find the music that you like or the art that you like and there’s so much of it. So much nature, too. And being interested in different cultures, which is something I’ve carried with me as I worked in different countries, was baked into my upbringing here. Those parts are nice.
I don’t think I need to explain to anyone that it is a strange place! But in that strangeness there is a lot of opportunity.
There is a big arts scene here, and a great class of design students coming from the University of Central Florida that are sticking around. I don’t think Orlando has completely established its design identity yet. People forget, maybe because of its large reputation, that it is still a relatively small city. So I’ve been thinking lately about what it means to be a good local community leader who helps bring different pockets of designers and artists together.
Do you feel the urge to contribute to the greater design community in Orlando?
I do! It’s been a challenge, especially this year having to do all of it remotely. And it’s always a challenge to find time when you have young kids. I think people here are hungry for community, but they’re also worn out and there’s only so much you can do when people are exhausted. So, while making incremental connections, it’s been slow. But I’m excited to contribute more.
When I lived in Canada, my husband and I ran a creative meetup series that felt really important to the small town we lived in. It created this environment that let people share ideas, connect with each other, even find jobs, learn new skills. I miss that, and I would love to do something similar here, but it’s not the right time and I do think timing is everything.
Rapid Fire Questions
What’s your morning ritual?
Basically wake up whenever my four-year-old decides to jump on my bed. Grab a coffee. Feed the kids. I may or may not eat some oatmeal. Get dressed, stumble over to the office, start a meeting. I wish it was more ritualistic! For a while I was running before everyone woke up, getting out to see the sunrise. That’s probably my ideal, but it’s not always realistic.
What’s your favorite quarantine activity?
Going for hikes, hands down! We just got back from a trip to the Smoky Mountains in Georgia. My girls who are four and six climbed to the top of Blood Mountain and we swam underneath a waterfall. I definitely did not know that was possible in Georgia. It’s not exactly obvious but Florida has a lot of great trails too, so we try to get out as much as we can for hikes. That’s one thing people don’t know about Central Florida—just how much access to nature there is. It’s a very unique habitat. And now that we’re going into fall and winter, it’s going to be so nice, with no mosquitoes. Just beautiful hiking and biking weather!
What’s your favorite iPhone app?
Can I pick two? My new favorite productivity app is Todoist. I had been looking for a new to-do list app since Wunderlist died, and this lets me organize my personal life and work stuff at the same time. Having a good system here is critical for me because I have a wandering mind. I need to have things in one place.
The other one that I like is Challenges, an exercise app that syncs with your Apple Watch and lets you compete month-by-month with a team. I have a team with my husband, brother, and sister-in-law and it really works. It motivates me to exercise for at least half an hour a day and keeps us all a little more connected. It reminds me to be active when I can. It’s a nice example of an ambient technology that facilitates positive connections to people in your real life.
