Catt's Corner: design leadership conversations with senior, staff, and principal designers

Season 1 of Catt's Corner is a wrap! In this bonus episode, host Catt Small reflects on how the podcast came together, shares five lessons that surfaced across all eight conversations this season, and gets transparent about what it would take to make Season 2 happen.The five lessons: understanding the business context, taking ownership of what will benefit you, leading with intention, letting your energy be your compass, and learning to let go. Each one pulled directly from the guests (Meghan, Jess, Theresa, Edwin, Jen, Sara, Tom, and Yoko), who gave their time and their honesty to this show.If you want Season 2, Catt wants to hear from you! Reach out at cattsmall.com/contact.

The first person featured in The Staff Designer woke up one day and completely left design. Yoko Sakao Ohama, former Staff Product Designer at Etsy, has now started a completely different career in accounting and financial services. Catt sits down with Yoko to talk about what burnout actually feels like from the inside, what it means to walk away from an identity you've held for decades, and why quitting can be an invitation rather than a failure. This one's for anyone who has quietly wondered if it might be time to go.─── ୨୧ ─── •ℹ️ In this episodeHow Yoko knew it was time to quit working in design What it feels like to grieve a professional identity you've held for over a decade How Yoko transitioned, and what her work looks like now The skills that Yoko took into her new industry Advice for others who are contemplating leaving design─── ୨୧ ─── •📖 Resources mentioned"Abscission" by Mandy Brown (the essay that inspired Yoko to take the leap): https://everythingchanges.us/blog/abscissionThe Staff Designer book (Rosenfeld Media): https://rosenfeldmedia.com/books/the-staff-designerThe Staff Designer course on Maven: https://maven.com/catt-small/staff-designer─── ୨୧ ─── •🌐 Find Yoko on the internetWebsite: https://yoko.cool

Tom Takigayama has been at Justworks for over ten years. In that time he went from senior designer to staff to head of design to IC again and eventually to principal, a path that almost nobody takes because almost nobody sticks around long enough to see it happen. Catt sits down with Tom to talk about what it actually takes to grow into a role that doesn't exist yet, and why waiting to be promoted might be the wrong question entirely. This one's for anyone who's been at staff for a while and is starting to wonder what comes next.─── ୨୧ ─── •ℹ️ In this episodeWhat Tom learned from managing a team of designers What design work looks like at the principal level Why there has to be a business case for your role before a title exists for you to grow into How to communicate with executives who have 15 minutes and a very full brainHow Tom asked for permission, not forgiveness, in helpful ways─── ୨୧ ─── •📖 Resources mentionedThe Staff Designer book (Rosenfeld Media): https://rosenfeldmedia.com/books/the-staff-designerThe Staff Designer course on Maven: https://maven.com/catt-small/staff-designerTeam of Teams by Stanley McChrystal: https://www.penguinrandomhouse.com/books/317066/team-of-teams-by-general-stanley-mcchrystal-tantum-collins-david-silverman-and-chris-fussell/─── ୨୧ ─── •🌐 Find Tom on the internetLinkedIn: https://www.linkedin.com/in/tomtaki

Ever wondered why doing great work still isn't getting you that promo? This episode's for you! Catt sits down with Sara Kremer, a leadership coach and former design leader who hired Catt into her first staff designer role at Asana back in 2020. Sara left in-house design after a lengthy career in tech and now runs Gradient, her leadership coaching practice, working with senior ICs and creative leaders on influence, communication, and what it actually means to lead (with or without a people management title). ─── ୨୧ ─── • ℹ️ In this episode The difference between helping your leaders manage you vs. doing their job for them The real reason designers struggle to connect with leadership, and what to do about it What tooting your own horn is actually about (hint: its not about you) When it's worth it to hire a career coach Sara's take on where designers are landing with AI ─── ୨୧ ─── • 📖 Resources mentioned The Staff Designer book (Rosenfeld Media): https://rosenfeldmedia.com/books/the-staff-designer The Staff Designer course on Maven: https://maven.com/catt-small/staff-designer ─── ୨୧ ─── • 🌐 Find Sara on the internet Gradient (Sara's leadership coaching practice): https://hellogradient.com LinkedIn: https://www.linkedin.com/in/sarakremer

This one's for anyone who's ever pitched something five times before it landed, or wondered which things are actually worth catching when you can't catch everything. Catt sits down with Jen Pearce, a staff designer at Mercury who Catt met when she joined Dropbox — and immediately knew was someone worth talking to. Jen has spent the last two and a half years riding Mercury's rocket ship growth from 600 to over 1,000 people, switching teams twice, and figuring out what staff design actually looks like at a company where design has been built in from the very beginning. ─── ୨୧ ─── • ℹ️ In this episode What it's like to grow with a company from 600 to 1,000 people as a staff designer Why vision work is a tool, not a trophy — and how to design it for the audience you're presenting to Why Jen pitched the same idea five or six times before it finally took hold The crystal ball versus rubber ball framework for deciding what to delegate and what to drop What good delegation actually looks like when you're sometimes the only designer on something Why Jen thinks this might be her last job with the title "product designer" ─── ୨୧ ─── • 📖 Resources mentioned The Staff Designer book (Rosenfeld Media): https://rosenfeldmedia.com/books/the-staff-designer The Staff Designer course on Maven: https://maven.com/catt-small/staff-designer ─── ୨୧ ─── • 🌐 Find Jen on the internet LinkedIn: https://www.linkedin.com/in/jenpearce

This one's for anyone who's ever wondered what it actually takes to get a self-initiated idea across the finish line. Catt catches up with Edwin Morris — a designer she met on a New York City design community panel back in 2023 — to hear what happened since they last talked. Edwin spent his final year at Datadog shipping a cross-team project he had pitched himself, nurtured through months of internal resistance, and finally launched on the main stage at Dash. Now he's a year into a completely new chapter at Jane Street, building internal tools in a totally different sector. • ─── ୨୧ ─── • ℹ️ In this episode How Edwin pitched a cross-team project with no metrics to back it up and got it built anyway Why the harshest feedback he got ended up saving the project What "leading without authority" actually looks like week to week Why less than 20% of his contribution to shipping the feature was designing the feature How AI has changed the way Edwin prototypes and communicates ideas • ─── ୨୧ ─── • 📖 Resources mentioned Edwin's blog post on the Jane Street blog: https://blog.janestreet.com/i-design-with-claude-code-more-than-figma-now-index Part 1 of Edwin's project at Datadog: https://www.datadoghq.com/blog/incidents-ai-workbench-status-page Part 2 of Edwin's project at Datadog: https://www.datadoghq.com/blog/engineering/steganography-at-scale/ The Staff Designer book (Rosenfeld Media): https://rosenfeldmedia.com/books/the-staff-designer The Staff Designer course on Maven: https://maven.com/catt-small/staff-designer • ─── ୨୧ ─── • 🌐 Find Edwin on the internet Website: https://ehmorris.com LinkedIn: https://www.linkedin.com/in/ehmorris

Catt reconnects with Theresa Slate, a fellow Staff Designer. Theresa has spent the last two years fighting her way out of playing double duty as both staff designer and de facto design manager. She's finally built an operating model that actually protects her time, and has gotten to a place she describes as one of the proudest moments in her career. This episode is for designers who join every single team meeting and wonder why they can't find time for the strategic work they were hired to do. ─── ୨୧ ─── • ℹ️ In this episodeHow Theresa cut 40% of her meetingsWhy "quick wins in a trench coat" is not a design strategyHow to be a good collaborator without being a doormatWhat it took to get public cross-functional praise for the design team ─── ୨୧ ─── • 📖 Resources mentionedThe Staff Designer book (Rosenfeld Media): https://rosenfeldmedia.com/books/the-staff-designer The Staff Designer course on Maven: https://maven.com/catt-small/staff-designer ─── ୨୧ ─── • 🌐 Find Theresa on the internet LinkedIn: https://www.linkedin.com/in/theresaslate

Catt reunites with her former Etsy colleague and longtime mentor Jessica Harlee - the designer who helped inspire the book in the first place. Jess gets into what it actually looked like to switch teams internally at Shopify after realizing growth design wasn't the right fit, how she's leaned into her architect archetype at a company that lives and breathes systems thinking, and why building genuine relationships (not just networking) is the skill that keeps unlocking things for her career.• ─── ୨୧ ─── •ℹ️ In this episode* What an internal team transfer process looks like* How to figure out your staff designer archetype* Why being put on a project outside your strength zone isn't a setback* Building relationships as an introvert: how to maintain genuine connections without it feeling transactional* What to do when leadership doesn't know who you are* How Al is shifting Jess's role• ─── ୨୧ ─── •📖 Resources mentioned* The Staff Designer book (Rosenfeld Media): https://rosenfeldmedia.com/books/the-staff-designer* The Staff Designer course on Maven: https://maven.com/catt-small/staff-designer• ─── ୨୧ ─── •🌐 Find Jessica on the internet* Website: https://jessicaharllee.com#staffdesigner #productdesign #uxdesign #designleadership #designcareer #designcareers #seniordesigner #uxcareer #uxcareers #designthinking #productdesigner #designcommunity #designmentor #design #designer #designpodcast #icdesign #designstrategy #techindustry #womenindesign #careeradvice #careergrowth #designadvice #careerdevelopment #designprofessional #podcastfordesigners #staffic

Catt sits down with Meghan Logan — whose viral product design interview playbook started their whole friendship — to catch up on what's changed since the book came out. Meghan gets real about untangling her self-worth from her design work, what it actually looks like when a staff designer is adding value versus performing the appearance of it, how she adapts her process in a new role at Stripe, and why she thinks creativity is going to matter more than ever in an AI-saturated industry.• ─── ୨୧ ─── •ℹ️ In this episodeWhat genuine staff-level contribution looks like versus performing the role How to adapt your process when you're new somewhere and still earning trust Why treating stakeholders like user research participants still holds up Meghan's honest take on AI for design• ─── ୨୧ ─── •📖 Resources mentionedThe Staff Designer book (Rosenfeld Media): https://rosenfeldmedia.com/books/the-staff-designer The Staff Designer course on Maven: https://maven.com/catt-small/staff-designer Caps Lock by Ruben Pater (Valiz): https://www.artbook.com/9789492095817.html UXpilot: https://uxpilot.ai• ─── ୨୧ ─── •🌐 Find Meghan on the internet Website: https://www.meghanlogan.com LinkedIn: https://www.linkedin.com/in/meghanelogan

Catt's Corner is a podcast that builds on my Rosenfeld Media book, “The Staff Designer”.When I wrote the book, I interviewed a ton of incredible staff and principal designers. I also got feedback from many design thinkers. Some of the conversations and feedback made it into the manuscript. A lot didn't. So I wanted to expand on the topic!I chose a few people to start with, went back to them, and asked: where are you now? What's changed? How are you actually adapting to a design landscape that feels like it's shifting under all of us in real time?Over the next two months I'm releasing eight episodes. The episodes connect to each major arc of the book. We're talking about what it means to be a staff designer right now, finding your archetype, protecting your energy at scale, shipping big ideas without losing momentum, building influence without a title, making the business case for design, what comes after staff... and a special closing episode about what it looks like to leave design.A quick moment of vulnerability: this is my first full podcast. I’ve done shorts here and there, but this is different! I'm learning a lot as I go. The conversations are the whole point, though, and I believe you'll love (and learn from) what you hear.I'm speaking at Config this week, and every guest answered one extra question for me: how they're adapting to AI right now. I'll be quoting a few of them in my talk on Thursday, so be sure to come through for that! A new episode will drop every Wednesday until August 19. Subscribe so you don’t miss it!—Grab your copy of The Staff Designer - https://rosenfeldmedia.com/books/the-staff-designer/Join the next cohort of the Staff Designer course on Maven - https://maven.com/catt-small/staff-designer