As part of our new series, we’re asking leading designers across the industry to share their work life advice, design do’s and don’ts, and secrets to effective collaboration. Consider it our design take on the Proustian questionnaire, with the aim to give you insight on how top designers work and think about design in a time unlike any other. (And they might just spill a few work-life secrets along the way.)

Gail Anderson is currently the chair of the BFA Design & BFA Advertising programs at the School of Visual Arts in New York City—but that certainly doesn't sum up her design bonafides. In addition to years of teaching at SVA, Anderson launched her own studio with business partner Joe Newton, called Anderson Newton Design. She served as Rolling Stone magazine's senior art director until 2002, and is the co-author of eight books on design with acclaimed designer and writer Steven Heller. In 2013, Anderson designed a now-iconic U.S. Postal Service stamp, which commemorated the 150th anniversary of the Emancipation Proclamation. (It's since sold over 50 million copies.) In 2008 she received the AIGA Medal, which honors lifetime achievement in graphic design.

Here, Anderson shares her advice for leading a design team, the one quality she always looks for in a designer, her dream client (Barack and Michelle Obama, are you listening?), and more.

What's the key to effective collaboration? Trust. You have to feel free to throw stuff against the wall together to see what sticks, good or bad. What's the most surprising difference between in-office collaboration and remote? Ultimately, the biggest surprise is that there’s not much of a difference. That said, the remote version allows you to curl up in a comfortable spot—in comfortable clothes. There’s a lot to be said for that. When is collaboration most important? When you’re stuck with what seems like an insurmountable problem, it’s great to know that someone’s got your back. What is your advice for leading a design team? Empower and then trust people to make decisions so the sun doesn’t rise and set on you. Encourage experimentation without repercussions. And what's your advice for making a design team more collaborative? If everyone’s working in a communal space, put some music on (and gently discourage headphones). I’ve always felt sad when everyone’s sealed off in their own little worlds, isolated. But I think I’m alone in that old-school thinking at this point. What is one quality you always look for in a designer? I’m interested in working with people who are self-starters, people who can take initiative. What’s your proudest moment? Having my family in attendance at the AIGA Gala when I won the Lifetime Achievement Award years back was so great. I was too nervous to enjoy the dinner or ceremony, but the evening was perfect because there was a table of Andersons in the back, complaining about how expensive it was to park in the city and looking fabulous.

The US Postal Service comissioned Anderson to design this 2013 stamp in commemoration of the 150th anniversary of the Emancipation Proclamation. Anderson worked with USPS art director Antonio Alcala and Jim Sherraden of Nashville’s famed Hatch Show Print to produce the final version of the stamp, which was also made into 5000 letterpress posters. Image courtesy Gail Anderson.

What was your biggest learning moment? The first time I took a “real” vacation—two uninterrupted weeks in Italy a decade or so ago—I realized how important it is to step away from work, and from your problems. Your biggest realization from the past year and a half of working amid a pandemic? I was really, really productive working from home even though the TV was right there, begging to be watched. What’s your work mantra? Figure out how to squeeze in one more commitment, project, or hour—sadly, that’s the way I operate, and I’m not proud of it. I’m trying to move towards “pencils down” as I get older. What's the best advice you’ve received? (And from whom?) “The real issue is not talent as an independent element, but talent in relation to will, desire, and persistence. Talent without these things vanishes and even modest talent with those characteristics grows.” — Milton Glaser.

Who is your dream client? Barack and Michelle Obama, call me. What's one design you wish you thought of yourself? The Camus book jackets that Helen Yentus designed are absolutely brilliant. Wow. What's a design faux pas you’re secretly a fan of? Using too many typefaces typically invites a “less is more” response. But not always. What's a design skill that’s overrated? It’s really great if you can draw, but you’ll be okay if you can’t. What's a design skill that’s underrated? The ability to choose great, appropriate, sometimes surprising colors for a project is a real gift that I do not possess. Difference between a good designer and a great one? A great designer transcends the obvious career accolades and achievements. A great designer is that well-rounded hero who’s found a way to give back, teach, or use their gifts to support others. What is your favorite question to ask during job interviews? Can you tell me a little about yourself—what else do you like to do? What's your favorite typeface? In the end, you can’t go wrong with Trade Gothic. How do you avoid team burnout? Encourage people to sneak in a day off here and there, and always provide good snacks. Which song do you listen to when you’re the most productive? That’s the Trouble, by Grace Jones, seems to put me in my happy place these days.

Which project from the past year that most excites you? I started researching a book that I think will ultimately become a good teaching and reference tool. I’m working with a friend who is much smarter than me, and if all goes well, we’ll see the fruits of our labors in 2024. What keeps you up at night? I worry if I’ll have enough money to live on in my old age. That’s pretty standard stuff for my contemporaries, I suppose, but it does unnerve me when I’m staring into the darkness. What gets you up in the morning? I’m still excited about what I do, so I look forward to the new day. (And I have to pee, so that literally gets me up at 4 am, like clockwork.) What’s a piece of advice you’d give your younger self? Use your vacation time and personal days. You’re not indispensable. Design is? Design is storytelling; it’s visual communication. Design isn't? Design isn’t as pretentious as it sometimes seems. What’s a question you wish we asked? (And what’s the answer?) What TV show can you watch on a loop? The Mary Tyler Moore Show, though right now, I keep rewatching Grace and Frankie, my pandemic friends.