The How This Works show

Skipper Chong Warson
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The How This Works show

Join us for a variety of conversations around expertise and craft. Our second season focuses in on product strategy, design, facilitation, leadership coaching, and adjacent areas, exploring how a variety of practitioners have developed mastery in these fields. Through discussions with over 30 guests so far, we've uncovered thought-provoking narratives and actionable strategies. Subscribe, follow us, and leave a review wherever you get your podcasts — spread the word!

  1. Drew Burdick

    JAN 29

    Drew Burdick

    Drew Burdick, founder and managing partner of StealthX, shares his unconventional journey into design and entrepreneurship. After growing up in the Philippines (age 4-18) and studying political science and communications in college, a chance internship introduced him to graphic design — beginning with a bootleg copy of Illustrator/Photoshop CS2. During the 2009 recession, Drew scrapped his way forward, balancing freelance design work with jobs like valet parking at the Ritz Carlton and window washing. His path included founding a successful clothing brand for the electronic music scene (complete with 163 street team members) before transitioning into corporate roles and eventually launching StealthX, a consultancy focused on customer strategy, product design, and software engineering. You can listen here or wherever you get your podcasts: https://www.howthisworks.show/033-drew-burdick Or watch on Youtube: https://youtu.be/mxyRWsKJEDg?si=5EmG0VKhiA99US5m Key points from the conversation: What's next for customer experience: Drew emphasizes moving beyond "fast, easy, and cheap" to create memorable moments that build brand loyalty. He applies this philosophy both to client work and to StealthX itself, crafting thoughtful touchpoints throughout the client journey. The future of design teams: Drawing from his experience leading both large and small teams, Drew predicts a shift away from traditional large design organizations toward nimble, high-velocity small teams augmented by AI capabilities. Industry specialization: Drew advocates for designers to develop deep industry expertise rather than remaining discipline-generalists, suggesting that understanding specific sectors like manufacturing or insurance will become increasingly valuable. Community and connection: Despite the rise of remote work, Drew emphasizes the growing importance of local, in-person relationships and community building, particularly in regional tech hubs like Charlotte, North Carolina. AI Inflection Point: Drew likens the current state of AI to the "256MB era" of computing, predicting rapid acceleration in capabilities and encouraging designers to embrace these tools as augmentation rather than threat. Personal philosophy: "Do the next right thing" – tattooed on Drew's arm, this mantra emerged during COVID as a reminder to focus on immediate, actionable steps rather than getting overwhelmed by uncertainty. Drew also predicts that within a year, solopreneurs will increasingly build and launch products independently using AI tools, potentially challenging traditional team structures in larger organizations. He encourages experimenting with these tools, seeing them as opportunities to augment human creativity rather than as threats. You can find Drew on social media as @drewhburdick and at drewburdick.com Learn more about StealthX at stealthx.co Listen to the second part of our conversation over at Drew's podcast, "Building Great Experiences" — • On Apple Podcasts: https://podcasts.apple.com/za/podcast/future-of-cx-beyond-product-into-ecosystems/id1776618976?i=1000686740180 • On Spotify: https://open.spotify.com/episode/329mlkTWefrP7nQr8KMRV5?si=doVa-TrxS52MyNIjGHDDCA • Or watch it on YouTube: https://youtu.be/RShAkpaXRwU?si=KX9sgbXRQDABmL_Z Special Guest: Drew Burdick. Links: StealthXProduct Camp - CharlotteLenny & Friends Summit — A one-day summit on 24 Oct 2024 in San Francisco for senior product leaders hosted by Lenny Rachitsky"Product is dead" - Claire Vo, CPO of LaunchDarkly — Claire Vo, Chief Product Officer at LaunchDarkly and creator of ChatPRD, deliver a groundbreaking talk at the Lenny & Friends Summit on how AI is revolutionizing product managementAndy Polaine on the How This Works showWho Moved My Cheese by Spencer Johnson, Kenneth BlanchardThe Culture Code by Daniel CoyleThe Culture Playbook by Daniel CoyleBuilding Great Experiences w/ Drew Burdick from StealthX

    45 min
  2. Bumhan Yu

    JAN 23

    Bumhan Yu

    Skipper chats with Bumhan Yu, a designer and coder, about his perspective shaped by his linguistics and psychology background. After moving from Korea to New York City, he transitioned from academia to design, where his non-design background enriches his approach to understanding user needs and communication. His career evolved from graphic design to design operations and team dynamics, emphasizing problem understanding before solution creation. Beyond design, Bumhan maintains interests in theoretical physics and the Zettelkasten note-taking method among other topics. You can listen here or wherever you get your podcasts: https://www.howthisworks.show/032-bumhan-yu Or on Youtube: https://youtu.be/O_qGqCS9i0A During the show, we talk through a number of topics, including: German-speaking Bumhan comes from an academic family, with professor parents. Initially studying linguistics and psychology in academia, he left his psychology graduate program, worked various jobs including translation and military service in Korea, then discovered design (read: graphic design) through a trade school for executive assistants in Manhattan. His spatial-visual thinking style, using schematics and diagrams, led him to realize he could build a career making things. He views design as problem-solving beyond aesthetics, distinguishing between specialized "capital D" design and general "lowercase d" design. Bumhan's LinkedIn tagline "business of design, design of business" reflects his dual focus on design operations and organizational dynamics. At DoubleVerify, he maintains design systems, defines visual tokens, and collaborates closely with front-end engineers while focusing on systematic problem-solving approaches. He critiques design thinking's commodification while valuing its core principle of understanding problems before solutions, drawing inspiration from Bruce Lee's philosophy of adaptation and evolution. His coding skills enhance collaboration with engineers through better understanding of backend structures, while his linguistics and psychology background provides unique insights into human behavior and communication. Beyond design, Bumhan's also passionate about theoretical physics, particularly Carlo Rovelli's work. Here's a photo of Bumhan's t-shirt from the episode: Special Guest: Bumhan Yu. Links: International Trauma Studies ProgramEames design process diagramThe Process of Design Squiggle by Damien NewmanAudiobook for "The Order of Time" by Carlo Rovelli"How to Take Smart Notes" by Sönke Ahrens

    1h 2m
  3. Aaron Young

    JAN 3

    Aaron Young

    Skipper chats with Aaron Young, founder of Switch Insights, breaking down the concept of "switch interviews" — a lesser known methodology that reveals the contextual moments leading customers to change products or services, emphasizing the importance of understanding the "why" behind customer behavior rather than just the "what." He explains that while companies often think they know why customers switch, a directed interview can reveal the complex, messy reality of customer decision-making, encompassing factors like grievances, magnetism, and effort underneath and surrounding the change. You can listen here or wherever you get your podcasts: https://www.howthisworks.show/031-aaron-young Or on Youtube: https://youtu.be/vNEZi_RaSN4 During the show, we talk through: The evolution of switch interviews, from Aaron's early discovery of the methodology (while observing Jobs to Be Done expert Bob Mesta) to his specialization in this approach after seeing its unique ability to reveal customer insights that traditional research misses Two case studies of "switches" — Aaron's personal journey moving from Washington D.C. to Atlanta, which unfolded over several years with multiple decision points, and a wedding dress business that used switch interviews to understand why brides choose at-home try-on experiences The critical difference between how companies typically view customer decisions (as single moments) versus the reality revealed through switch interviews: a complex journey involving factors like grievances with current solutions, attraction to new options, and the effort required to change Why traditional demographic-based personas often fall short, and how switch interviews help create more meaningful customer segments based on the progress people are trying to make in their lives The challenge of "hubris" in understanding customer behavior — how companies often think they know why customers make changes, but miss the crucial contextual details that switch interviews can uncover As businesses increasingly turn to technological solutions, Aaron expresses concern about over-reliance on AI for understanding customer behavior, noting that artificial intelligence might miss the nuanced contextual details that human-conducted switch interviews are uniquely positioned to capture His belief in the importance of verbs over nouns in career satisfaction Stay tuned until the end where Skipper tells Aaron about Stephen Colbert's oatmeal rum-soaked bing cherry cookie recipe, which Colbert (yes, him) says is so irresistible you'd "step on a baby's finger for one." Special Guest: Aaron Young. Links: "Competing Against Luck" by Clayton M. Christensen"Demand-Side Sales 101" by Bob MoestaThe Jobs-to-be-Done Mattress InterviewThe Mattress Interview – Q&AThe "commuter" car JTBD interview on the Critical Path show, episode 146 — Bob Moesta talks with Horace Dediu in 2015 on the job to be done for a Porsche Cayman (from archive.org)"Deep Work" by Cal NewportStephen Colbert's favorite cookie to make, an oatmeal rum-soaked bing cherry cookie

    1 hr
  4. Andy Polaine

    11/14/2024

    Andy Polaine

    In this episode, Andy Polaine, Dr. Polaine to some, talks about his career journey, starting with his background in film and interactive media, his transition into service design, and his current focus as a design leadership coach. Andy discusses his coaching approach, which is rooted in his experience as a designer, facilitator, and teacher. He also talks about some of what he's hearing from design leaders right now, emphasizing the importance of reading the room, even in a digital context, and how his work addresses common challenges faced by design leaders, such as imposter syndrome and the "leadership dip" — a period of uncertainty and self-doubt that can arise when transitioning into a leadership role. The interview also touches on the evolving role of design leadership in organizations and how designers can more effectively communicate the value of their work to stakeholders. You can listen here or wherever you get your podcasts: https://www.howthisworks.show/030-andy-polaine Or on Youtube: https://youtu.be/fdC1f-QcUMA Some topics discussed: Andy’s career began in the early '90s as an interaction designer, before "UX" or "user experience" were common terms He studied film, video, and photography, transitioning into interactive media, which later led him to meeting Ben Reason at LiveWork and getting into service design Andy was global Group Design Director of Client Evolution at Fjord and co-leads a Master’s program in service design in Switzerland Fluent in German and having lived in Australia, Germany, and the U.K., Andy developed a deep appreciation for cross-cultural communication and how we use language Andy describes his transition from filmmaking to design, drawn by the way multimedia integrates sound, video, and interactive elements — modes of storytelling persists today Andy’s coaching focuses on supporting design leaders through a number of phases, including "design leadership dip," a period uncertainty common at mid- and advanced-career stages, which he helps leaders navigate Andy shares his personal experience with imposter syndrome/phenomenon, emphasizing that it can affect anyone, regardless of background Andy highlights the skill of “reading the room," focusing on empathy, active listening, and participant engagement He discusses the nuances of digital coaching, using techniques like teleprompters and collaboration tools for increased effectiveness in virtual communication Andy reflects on the future of design, noting that designers must focus on discernment and answering the question, So what?! He concludes by emphasizing relationships, empathy, and plans for a book on the inner journey of design leadership, including "design leadership dip" He talks about the "assembly line" approach to design, likens it to AI — where the subject matter is being treated as a mere tool for rapid prototyping rather than a process for addressing user needs, almost like the discipline is being treated like a GPT itself, which reduces designers to carry out prompts Stay tuned until the end where we hear a behind the scenes (bts) snippet, a peek into our lives today, where we wait for Andy's wife to open/close some doors as she's seeing a patient at home while we're recording. Special Guest: Andy Polaine. Links: Ben ReasonJulian Simpson on Powers of TenMacroMind DirectorZX SpectrumFjord Fika (last updated in 2018)Carl JungImpostor syndrome, also known as impostor phenomenon"The Impostor Phenomenon in High Achieving Women: Dynamics and Therapeutic Intervention" by Pauline R. Clance and Suzanne A. Imes — Published in 1978The Leadership DipAndy's talking about the dip on his YouTube channelElgato PrompterDaniel Stillman - Good TalkMalcolm Gladwell's What the Dog SawPeter MerholzDave Gray's "Gamestorming"Dave Gray's "Selling to the VP of No" — (Amazon affiliate link)You're Inching Me Out — From the first season of Esther Perel's How's Work? They were mates in university before co-founding a successful communications company. They still work together from different coasts, but they barely speak. One wants to move on; the other is grasping for his former friend. Neither can find the words to talk about it.Mitchell & Webb — Nazis sketchhttps://www.polaine.com/https://www.polaine.com/power-of-ten/https://www.polaine.com/coaching/https://www.youtube.com/@apolainehttps://newsletter.polaine.com/

    1h 6m
  5. Joanne Weaver

    10/18/2024

    Joanne Weaver

    Joanne Weaver, who co-runs a design recruiting agency in New York City, discussed her dual career in recruitment and music. She highlighted the importance of networking and tailoring job applications to specific roles. Joanne emphasized the need for efficiency in communication and the value of understanding both job seekers and clients. She shared her journey from starting her agency during a financial crisis to having built a successful business. Joanne also discussed the significance of connection and authenticity, both in her professional and personal life, recommended the show "Alone" for its exploration of human resilience, and talked about her semimonthly show on LinkedIn live with two other design recruiters, Jared Tredly and Erica Fortgang for Design:Unfiltered @DesignedXTalent Keep listening until after the outro music for a bit of tape from our first attempt at recording (Internet connection problems) where Joanne talks about how being a singer and being a performer helps to understand the clients and job seekers she works with. A few specific points from the episode: Joanne's work as a singer, including albums, performances, and cover songs Her musical style blends jazz and trip-hop, with inspiration from sci-fi and the Voyager probes Her indie band, Broanne, and their EP "We're Totally Blowing Up" Her view of the job of a recruiter: matching clients with candidates and guiding them through the hiring process Her journey started at a nanny agency in London, eventually leading her to start her own recruitment agency in New York City Initial struggles in starting her agency and stresses the importance of networking and building personal connections Meeting her business partner, Rebecca Levy, through a mutual connection — advice, "take the lunch" The need for taking breaks and disconnecting to recharge The 2008 financial crisis impacted her business but also led to new opportunities Tailoring resumes and portfolios to specific job opportunities A tip on standing out in the job market: be efficient and professional in communications Common fears like not being good enough and encourages leaning into those fears Strategies for overcoming anxiety: focus on service and giving to others Stresses authenticity and connecting with others in both personal and professional contexts The value of small moments of connection, which can lead to larger opportunities. The importance of connection and talking to people Recommendation for Tunde Oyeneyin's audiobook, "Speak" and the show "Alone" for its exploration of human connection and survival She plans to begin work on a cabaret show about an unnamed 80s/90s pop sensation, inspired by recently reading their biography Special Guest: Joanne Weaver. Links: Rebecca LeviSteve Jobs' commencement speech to Stanford’s 2005 graduating class — “Of course it was impossible to connect the dots looking forward when I was in college. But it was very, very clear looking backward ten years later,” Jobs said. “So you have to trust that the dots will somehow connect in your future. You have to trust in something-your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”Twisted SpritzerRyan Adams - "Wonderwall" (Oasis cover)Simon Sinek on Design Matters in 2015 — With Debbie Millman"Speak" by Tunde Oyeneyin Tara Mohr's "Playing Big" Ted Lasso clip — When Rebecca "makes herself big" to build up courage Tony RobbinsAlone (TV series)Voyager Golden RecordJoanne Weaver GroupDesign:Unfiltered on LinkedInDesign:Unfiltered replays on YouTubeJoanne Weaver's music on SpotifyTwisted SpritzerBroanne

    1h 16m
  6. Carl Cleanthes

    10/08/2024

    Carl Cleanthes

    On this episode of the How This Works show, Skipper Chong Warson talks to Carl Cleanthes, founder of Epic Made, a creative content agency based in Hampton Roads, Virginia. Carl shares his entrepreneurial journey from selling timeshares to establishing an agency that now collaborates with top brands like SyFy, Nickelodeon, USA, TNT, and WWE. He discusses his passion for art and creativity, focusing on his exploration of NFTs as a way to immortalize his late father’s artwork. Throughout the conversation, Carl emphasizes the importance of living authentically, expressing emotions freely, and using his creativity to honor his father’s legacy. Listen above or wherever you get your podcasts: https://www.howthisworks.show/028-carl-cleanthes. You can also listen on Youtube: https://youtu.be/yn74GSse5f0. Key details from the episode: Carl describes himself as a "lifelong, ADHD, extroverted, creative kind of like counter culture, delightful weirdo," heavily influenced by his father’s art Early entrepreneurial ventures included earning money through in-game economics in Everquest After struggling with depression and dissatisfaction in traditional employment, Carl quit his IT job in 2007 and started his agency by hiring art school students, expanding into animation, illustration, and graphic design He embraces an unconventional lifestyle, incorporating barefoot walks, toe shoes, upcycling, and growing his own food The pandemic significantly impacted his business, pushing him to explore NFTs as a new creative outlet and revenue stream Carl launched an NFT project using his late father’s artwork, which he sees as both a healing journey and a new business direction He continues to honor his father’s creative legacy through live streaming sessions where he creates new art incorporating his father’s work Special Guest: Carl Cleanthes. Links: Epic Made — Carl Cleanthes' creative studioEverquest — A MMORPG released in 1999 that immerses players in the fantasy world of Norrath, where they can create characters, complete quests, and engage with others in a shared, persistent online environment. Old Dominion UniversityEpic Made's work includes Nickelodeon, SyFy, USA, network, TNT, and WWEChris Metzen — An American game designer, writer, and voice actor, best known for his influential work at Blizzard where he played a key role in the development of Warcraft, StarCraft, and Diablo. NFTs — Non-fungible tokenWeb3 — Web3 is a decentralized version of the internet that uses blockchain technology to give users control over their data, digital assets, and interactions, enabling peer-to-peer transactions and decentralized governance without relying on intermediaries.On the Origin of Species by Charles Darwin — *On the Origin of Species* is Charles Darwin's seminal 1859 work that introduced the theory of natural selection, explaining how species evolve over time through the survival and reproduction of individuals best adapted to their environment. This groundbreaking book laid the foundation for modern evolutionary biology, challenging traditional views on the creation and diversity of life.About Time (2013) — A (romantic) comedy about a young man who discovers he can time travel, using his gift to improve his life, love, and relationships with Domhnall Gleeson, Rachel McAdams, Bill Nighy, Tom Hollander, and Margot Robbie among othersLive Streaming Art 8 PM ET EVERY Wed — Carl's weekly live-stream art showPixel Retentive podcast with Carl and Ross CiuppaColorful Carl — Colorful Carl, one of Carl's nicknames, is an artist, agency founder, and podcast host who combines his passions for digital art, animation, and storytelling.

    1h 31m
  7. Jen Dary

    12/11/2023

    Jen Dary

    Back in August, Skipper had a conversation with Jen Dary about her personal experiences and insights on leadership coaching, the importance of self-awareness and belief in one's abilities, Plucky's So Now You're a Manager (SNYaM), navigating the publishing industry, and prioritizing self-care in the coaching profession. Other topics include: Jen shares her experience as the oldest of three kids and how it influences her leadership style and ability to empathize with others (it might play it yours as well, dear listener) She highlights the importance of identifying a specific niche in coaching and how coaching is different from consulting Jen emphasizes the importance of setting a finite amount of time for coaching and encourages clients to come as long as they need and go when they're ready She primarily works with clients in technology, including engineers, designers, product managers, professors, academics, and doctors, with a majority of them being women Jen reflects on the importance of understanding one's purpose of work and encourages listeners to measure their current job against that purpose She talks more about So Now You're a Manager (SNYaM), a manager training program that she's developed at Plucky currently modeled after a part-time MBA plus, the importance of community and connection in learning, and the challenges of remote training Jen has observed a trend of people in the tech industry expressing a desire to retire earlier and wanting to "do their own thing" She talks about recently watching "The Andy Warhol Diaries," a six episode Netflix series, and having a greater understanding of the '70s and '80s Stay tuned until the end for an outtake around speaking French to a stranger on the train in front of her sons Special Guest: Jen Dary. Links: PluckyPlucky's So Now You're a ManagerThe Andy Warhol Diaries — In 2022, a Netflix series (titled after Warhol's 1989 book) puts on center stage the life and emotions of the artist after he was shot in 1968. The six episodes utilize Resemble AI and original recordings as Warhol narrates his own diary entries, accompanied by a cast of characters, including his friend Pat Hackett.Plucky's InstagramJen's InstagramDay Of Big Dreaming — Avail from today to end of January 2024, recommendedSNYaM 2024 — There are currently two (2) virtual So Now You're A Manager cohorts planned in 2024, dates are TBA, interested folks should pre-registerPlucky's podcast — This season, released earlier this year, featured eight (8) different mentors on a variety of topics, like negotiation, allyship, performance reviews, first impressions and more

    1h 3m
  8. Karen Faith

    11/03/2023

    Karen Faith

    Karen's personal and professional journey exploring different forms of art, including classical music and site-specific contemporary performance art Empathy and storytelling in design, perspective taking, and understanding the difference between empathy and caring The struggle with showing empathy towards oneself and the importance of non-judgment The concept of being an "a*****e" in social situations and intentional adjustment The unintended consequences of Karen's work on compassion and caring The virtue of patience and its role in creating oneness Practicing love and accepting all things without hierarchy or morality The idea of helpfulness versus rightness and an example of a deer The tagline for Others Unlimited and its focus on empathy, research, collaboration, and citizenship Exploring the relationship between mercy and justice The metaphor of polishing a rough gem and the importance of perspective-taking The importance of empathy, active listening, and being present Accepting others as they are and embracing the truth for personal growth The second season of FX's "The Bear" and the idea of watching television as a kind of babysitter A surprising answer from Karen to the question, "Imagine you unexpectedly had a day off, money was no object, you could bend the laws of space and time, what would you do?" Stay tuned for a bit of tape at the end where Karen and Skipper talk about one's "need to be right." Note from TED: Karen's talk linked below contains a discussion of suicidal ideation. If you are struggling with suicidal thoughts, please consult a mental health professional and/or support organization, as this talk is not a substitute for mental health advice. If you are struggling with self-destructive or suicidal thoughts, call or text 988 to connect with someone who can help. Special Guest: Karen Faith. Links: Others UnlimitedKaren's TEDx talk, "How to talk to the worst parts of yourself" around the subject of Unconditional WelcomeKaren's recorded workshop session on Empathy for A**holes at CreativeMorningsDesign Matters with Debbie Millman: Alex Bogusky and John BielenbergKaren talks to Joe Reichert on More Wiser about ethnography and everything else

    1h 8m
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4.9
out of 5
8 Ratings

About

Join us for a variety of conversations around expertise and craft. Our second season focuses in on product strategy, design, facilitation, leadership coaching, and adjacent areas, exploring how a variety of practitioners have developed mastery in these fields. Through discussions with over 30 guests so far, we've uncovered thought-provoking narratives and actionable strategies. Subscribe, follow us, and leave a review wherever you get your podcasts — spread the word!

Information

  • Creator
    Skipper Chong Warson
  • Years Active
    2020 - 2025
  • Episodes
    34
  • Rating
    Explicit
  • Copyright
    © 2025 How This Works, Inc.
  • Show Website
    The How This Works show

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