Design Better

This episode kicks off a special series recorded live at our Creative Leadership Retreat in Sonoma, which we co-hosted with our friends at September Works in late September. We gathered 40 leaders from design, business, the arts, and politics for two days around the theme of coalition building. Our first guest is Paul Dichter, who first came on Design Better for Episode 173 this past Spring. Most of us think of a coalition as something you build once. Paul had to keep one alive for a decade. He joined the Stranger Things writers’ room as a writer’s assistant in season one and left as co-executive producer at the finale, writing three of the show’s most memorable episodes along the way. We asked Paul what he learned about moving ideas forward as a junior writer, before he had the authority to push them, and how conflict over creative direction gets sorted out. He tells the story of the final season, months of arguing and pitching under the weight of ten years of work, and a fanbase waiting for the ending. Then the audience took over. Attendees, many of them leading creative teams of their own, asked what you do when a team loses its mojo and how you rally it back. They asked which personality types flourish in a collaborative room, and how you build alignment when there’s no clear user to test against. They also asked how he sells a creative idea to people on the other side of the table, and how he made peace with the show ending after investing so much of himself in it. *** This series is presented in partnership with September Works, a product design studio. They envision, evolve, and reinvent digital products. Learn more at september.works or reach them at [email protected]. Learn more about your ad choices. Visit megaphone.fm/adchoices

Maurice explains how AI is speeding up problems the design industry always had, including the shrinking junior role, and argues that the modern designer has outgrown traditional design organizations.

We talk with Tom about how cultural context shapes letterforms, how to balance heritage with something that feels modern, and Tom’s practical framework for pairing typefaces, which starts with calligraphic roots and vertical metrics rather than vibes.

Kevin Flores has been part of the Design Better community for years — we first met him in 2017, while he was leading design at 23andMe, back when we were researching how design teams are structured for the Design Genome Project. So it’s a real pleasure to finally have him on the show to talk about his new book, Find Your Inner Rebel. Find bonus content and more on our Substack: The book is built around what Kevin calls his punk rock formula for career reinvention: resistance plus resilience equals reinvention. But don’t mistake the attitude for advice to quit your job. Kevin is candid that sometimes the smartest move is to hunker down, keep working toward change from where you are, and be ready when it comes, whether you choose it or it’s chosen for you. Get the book We talk about why strong generalists struggle to get hired (and how to fix it), why your personal brand matters more than ever when you’re competing against hundreds of applicants, and a simple test for your portfolio’s opening statement: swap in someone else’s name and photo and see if it still works. As Kevin puts it, “you are the unique thing in the equation.” We also get into misalignment burnout, why designers should look beyond big tech to places like local government, and servant leadership. Bio Kevin Flores is a design leader, mentor, and author of Find Your Inner Rebel. He has built and led product and design teams in every work environment: agency, freelance, startup, and mid-to-large companies, including Verizon, 23andMe, and LinkedIn. He and his wife Jeanine met as design undergraduates at the University of Illinois and went on to co-found an interactive agency in Silicon Valley in the 1990s, and together they co-wrote the Design Career Handbook. Kevin spent six years as a mentor in First Round Capital’s Fast Track program, and serves as an industry advisor for design and user research for the Mission College Design and Diablo Valley College Digital Media joint advisory board. Learn more at innerrebelbook.com. Learn more about your ad choices. Visit megaphone.fm/adchoices

We chat with Randy about what he calls “whole design,” which means treating a push notification with the same care as the main dashboard. He explains why hotels and restaurants inspire him as much as any software, and traces that back to growing up near Disney’s carefully spaced trash cans in Orlando and to the bowl of fresh fruit that always sat in Glaser’s studio. Bio