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The Curiosity Department

Design Better co-hosts Eli Woolery and Aarron Walter explore the intersection of design, technology, and the creative process through conversations with guests across many creative fields, helping you hone your craft, unlock your creativity, and learn the art of collaboration.
Whether you’re design curious or a design pro, Design Better is guaranteed to inspire and inform. Vanity Fair calls Design Better, “sharp, to the point, and full of incredibly valuable information for anyone looking to better understand how to build a more innovative world.”

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Jessica Hische and Chris Shiflett first crossed paths at Studiomates, a Brooklyn based co-working space where some of New York’s most talented designers built businesses and influential organizations.

Visit our Substack for bonus content and more: https://designbetterpodcast.com/p/jessica-hische-and-chris-shiflett

Jessica, known for her lettering and illustration work with clients like Wes Anderson and The New York Times, and Chris, whose career spans from the early foundations of the web to co-founding Brooklyn Beta, both experienced firsthand what happens when passionate, independent creatives come together.

Today, they’re channeling those lessons into Studioworks, a business platform built specifically for independent studios and creative professionals. They’re tackling the unglamorous but essential parts of running a creative practice—invoicing, project management, client relationships—with the same care and community spirit that defined those Brooklyn days.

In this conversation, we talk about the magic of Studiomates and Brooklyn Beta, what they learned from running their own studios for years, and why they decided to bootstrap a tool for the creative community rather than chase venture capital. It’s a story about building something sustainable, beautiful, and genuinely useful for the people who make things.

Bios

Jessica Hische is one of the most beloved and influential designers of the past two decades. She’s best known for her lettering and illustration, but equally for her generosity in sharing what she knows. Jessica was part of the original Studiomates community in Brooklyn, has worked with clients like Wes Anderson, The New York Times, and Penguin Books, and now brings her creative leadership to Studioworks, where she and Chris are building better tools for independent creatives and small studios.

Chris Shiflett is a longtime friend of the design community whose career spans the deep foundations of the early web and the heart of the creative world. His early books on HTTP and web security became unexpectedly influential at a time when the internet was still taking shape, opening the door to some extraordinary projects — including one that generated nearly half of the internet’s traffic and another responsible for a fourth of the world’s email. After years helping big internet companies solve scalability problems, he realized he was more inspired by the people creating them — the designers, founders, and builders making things people love. That shift led him to the original Studiomates community, to co-founding Brooklyn Beta, and ultimately to the work he and Jessica are doing today with Studioworks.

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books:

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

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Jessica Hische and Chris Shiflett: Designing business tools that support how creatives actually work

It’s that time of year again—our favorite episode to put together. A moment to look back at the objects, experiences, and ideas that sparked creativity for us this year. From books that moved us to tools that surprised us to experiences we can’t stop recommending, we’ve gathered a set of gift ideas for the designers, makers, and curious people in your life (including you).

We’re starting with budget-friendly picks and moving up from there, so whether you’re filling a stocking or going big, you’ll find something here. Let’s get into it.

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Before we get to the list, if you’re looking to give (or get) the gift of education, for the next week only you can get or gift a year of premium for 25% off, our only sale of the year. Buying a year-long subscription will get you to our ever-expanding Design Better Toolkit (with over $2K in discounts on tools and courses), as well as monthly AMAs, ad-free episodes, and our library of books. Doing this also supports anyone who can’t afford a subscription through our scholarship program.

25% off a year, expires in 1 week

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Find the full gift list on our Substack: https://designbetterpodcast.com/p/2025-holiday-gift-guide

2025 Holiday Gift Guide

Changing the culture of a 400,000-person company isn’t just hard—it’s the kind of transformation most leaders wouldn’t even attempt. But when Phil Gilbert joined IBM as General Manager of Design in 2010, that’s exactly what he set out to do. And remarkably, he had a lot of success.

Visit our Substack for bonus content and more: https://designbetterpodcast.com/p/phil-gilbert

Phil led one of the most ambitious design transformations in corporate history, hiring over 1,000 designers, creating IBM’s design thinking framework, and embedding a new way of working across nearly 180 countries. Now, with his new book Irresistible Change, Phil is sharing the blueprint for how he did it—and more importantly, how you can apply these lessons to your own organization.

In this episode, we talk with Phil about treating change like a high-stakes product, why IBM’s transformation was opt-in rather than top-down, and what it takes to win over engineers who’ve spent decades deeply entrenched in a technical worldview. We also explore the design thinking bootcamp that became legendary within IBM, the intentional design of physical studio spaces, and what happened after Phil left the company.

Phil’s insights aren’t just for those leading massive organizations—they’re for anyone trying to spark meaningful change, build enthusiasm without mandates, and create work that actually matters to the people doing it.

Bio

Phil Gilbert is best known for leading IBM’s 21st century transformation as their General Manager of Design. After selling his third startup to IBM in 2010, Phil was asked by IBM in 2012 to use design thinking, coupled with agile, to update how IBM’s teams worked. The transformation became the subject of a Harvard Business School case study, the documentary film The Loop, and feature articles in the New York Times, Fortune Magazine, Forbes, Bloomberg, INC and many others.

Phil’s 45-year career spans startups, large corporations, and board memberships, where he has led organizations ranging from solo ventures to those with 400,000 employees. In 2018 Phil was inducted into the New York Foundation for the Arts’ Hall of Fame. In 2019, the State of Oklahoma (Phil’s native state) named him an Oklahoma Creativity Ambassador for his achievements in the world of creative thinking and innovation.

Phil left full-time operational responsibilities at IBM in 2022 in order to focus on helping the next generation of entrepreneurs, business, and military leaders understand how to impact culture at scale, to improve innovation and team performance. Phil lives in Austin, Texas.

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Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books:

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

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If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

Phil Gilbert: Making a 114-year-old, 400,000 person company care about design

We’ve talked to many design leaders who have burned out after a decade or more of corporate work. But after 17 years at Philips designing health innovations, Cecilia Brenner wasn’t burnt out…she loved it. And she wanted to find a way to scale her sense of purpose, so she joined Design for Good as Managing Director, and found a way to work with hundreds of designers who want meaningful impact without leaving their day jobs.

This is a preview of a premium episode, find the full episode on our Substack: https://designbetterpodcast.com/p/cecilia-brenner

Design for Good mobilizes what Cecilia calls a “radical global action collective”—1,600 designers from companies like Philips, Lloyds Bank, and others—to tackle UN Sustainable Development Goals through focused, two-year cycles. Their first cycle addressed clean water and sanitation. Now they’re working on quality education. And here’s the twist: everything they create is open source.

In our conversation, Cecilia explains how Design for Good measures real impact (not estimated future impact), why they chose to focus on one SDG at a time instead of spreading resources thin, and what it means to design for “all life,” not just human life. If you’ve ever wondered how to find more meaning in your design work—or questioned whether purpose-driven projects actually move the needle—this episode offers a surprisingly practical model.

Bio

Cecilia Brenner is the Managing Director of Design for Good, a global alliance dedicated to creating lasting, measurable impact for the United Nations Sustainable Development Goals (SDGs). Since joining in May 2024, Cecilia has successfully led the charity in mobilising hundreds of creatives to design in close collaboration with NGOs and affected communities worldwide.

With over 25 years of international experience in design and leadership, Cecilia is a catalyst for inclusion, innovation, and impact. She previously served as an Experience Design Director & Business Partner at Philips, where she spent 17 years improving people’s health and well-being through meaningful innovation, building high-performing, engaged global design teams and communities, as well as leading transformational programmes with a unique blend of network leadership, team-building excellence, and strategic insight.

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Premium Episodes on Design Better

This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. Premium subscribers also get access to the documentary Design Disruptors and our growing library of books:

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Cecilia Brenner: Moving beyond design theater to measurable impact

This is a preview of a premium episode. You can find a video version of the full episode on our YouTube channel: ⁠https://www.youtube.com/watch?v=3dvoGPZEY1g⁠

We’ve been on the road this week, recording some in-person episodes in Portland Oregon, with Ryan Coulter—co-founder of The James Brand, and the wonderfully hilarious graphic designer Aaron Draplin.

We’re excited to bring you this episodes soon, and in the meantime we’re rewinding to one of our favorite episodes this year with Prince of Persia creator Jordan Mechner. You may have heard that we’re publishing more video from our episodes, and you can now find a video version of this episode on YouTube. Enjoy!

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As a kid in the 80’s, Eli fell in love with games on computers like the Apple II, Commodore 64, and later the Amiga and Macintosh. One of the very first games he played was called Karateka, which was inspiring for the realistic movements of its digital karate antagonists, even on a black-and-green Apple II monitor.

Our guest today, Jordan Mechner, created Karateka while an undergrad at Yale University in 1984, and it went on to be a commercial success. He followed it up with the game Prince of Persia (you’ll hear a clip from the soundtrack in the introduction, which Jordan’s father composed and which Jordan invented a way to transpose onto the Apple II’s tinny speakers before game soundtracks were widespread on the machine).

Jordan documented the creation of the game in a wonderful published version of his diaries called The Making of Prince of Persia, and we spoke with him about how he taught himself the skills to build successful video games in a pre-internet era, why he journaled about his work process (and what it taught him), and about his new graphic novel Replay, a memoir recounting his own family story of war, exile and new beginnings.

Karateka on the Apple IIPrince of Persia on the Apple II (play the Mac version online here)

Video Rewind: Jordan Mechner: Pioneering game designer on creating Prince of Persia, Karateka, and a new graphic novel memoir

As educators, we’ve grown wary of the term “safe spaces,” especially when what many students really need is a space to engage with “dangerous” ideas. But true dialogue doesn’t begin with risk—it starts with trust. Our guest today, Ben Swire, wrote the book Safe Danger, which offers a thoughtful, practical approach to building the psychological safety that allows curiosity, connection, and even productive disagreement to flourish.

Find bonus content and more on our Substack: https://designbetterpodcast.com/p/ben-swire-former-ideo-design-lead

Ben’s career took him from the buttoned-up world of financial marketing to IDEO—a shift he describes as going “from Kansas into Oz.” At IDEO, he discovered that world-class work could be fueled by something radically different than what he’d experienced everywhere else. That discovery led him to spend years exploring a deceptively simple question: How do you get people to fail but enjoy doing it?

The answer became the foundation of his book and his work—a concept he calls “Safe Danger,” that sweet spot where people feel safe enough to leave safety behind, but challenged enough to grow. In this conversation, we’ll explore why team building desperately needs reclaiming, how an introvert ended up running a team building company, and why the quality of your relationships at work matters way more than you think.

Get the book

Bio

Ben Swire is an award-winning designer and writer, and former Design Lead at IDEO. His work spans design thinking, philosophy, cinema, and psychoanalytic theory, driven by curiosity about the hidden factors that shape our lives.

At IDEO, Ben created Make Believe Time, a bi-weekly creative play date where colleagues learned, created, and meaningfully connected. When interest spread beyond IDEO, Make Believe Works was born—now helping organizations from Fortune 500 companies to startups build the creative and emotional muscle memory that leads to healthy, innovative, collaborative cultures.

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New tools in the Toolkit

We’ve just upgraded the Design Better Toolkit, with new tools and other perks (now worth almost $2K in total).

Here’s what’s new in the Toolkit:

 
TextExpander (a wonderful productivity tool, 6 months free)

 
Kittl (tools and templates to support your creative process, 6 months free)

 
Subatomic: The Complete Guide to Design Tokens (20% off)

 
Design Better Coffee & Tea (fuel your creativity, 15% off).

Some of these perks are very limited and will sell out quickly.

Get the Toolkit

Ben Swire: Author of "Safe Danger" on the hidden reason team building efforts fail

Design is a problem solving discipline. We research user needs, explore solutions, make things, and ship them. But one important stakeholder is often missing from the conversation: the world we live in. What toll do the products we design impose upon the environment? Sustainability is an essential part of the discipline of design, but not understood by designers. If only we had a manual to get us up to speed.

This is a preview of a paid episode. Access the full episode on our Substack: https://designbetterpodcast.com/p/jeremy-faludi

Our guest today, Jeremy Faludi, has spent a lot of time researching, writing, and thinking about environmental impact and design. He’s a researcher and author of Sustainable Design: From Vision to Action. Jeremy has spent decades helping companies move beyond good intentions to evidence-based decisions—from working with Stanley Black & Decker to pioneering biomaterial 3D printing at Delft University of Technology.

How much power do you think large language models use? The answer is surprising. We explore why a hairdryer company wasted nine months of engineering time on plastic reductions, how systems thinking reveals the true environmental impact of our designs, and the materials research going into sustainable 3D printing.

Bio

Jeremy Faludi is an assistant professor of Design for Sustainability at TU Delft’s Faculty of Industrial Design Engineering, where he focuses on sustainable design methods and additive manufacturing. He created the Whole System Mapping method and in 2004 designed the Biomimicry Institute’s first online database, now known as AskNature.org. His work spans from practical design—including a bicycle featured in the Smithsonian Cooper-Hewitt Design Museum’s 2007 “Design for the Other 90%” exhibit—to developing tools for life cycle assessment, product reparability, and health hazard assessment. In green 3D printing, he’s a leading voice, having written the OECD’s policy recommendations and the Additive Manufacturer Green Trade Association’s first white paper, along with publishing the industry’s most comprehensive life cycle assessments.

Originally trained as a physicist (he helped improve LIGO’s vibration damping system to pay for design school), Jeremy worked as a sustainable designer in industry for fifteen years before returning to academia. He’s taught at Stanford, Dartmouth, and Minneapolis College of Art and Design, and has contributed to six books on sustainable design, including Worldchanging: A User’s Guide for the 21st Century. He’s also created multiple online courses for organizations like VentureWell, the Cradle to Cradle Product Innovation Institute, and Autodesk. In 2012, he created StreetNatureScore.com, which used 11 billion satellite imagery datapoints to provide nature scores for any US address.

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Premium Episodes on Design Better

This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. Premium subscribers also get access to the documentary Design Disruptors and our growing library of books:

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Jeremy Faludi: Sustainability professor on why most sustainable design fails before it starts

We’ve worked alongside people for years, only to realize that we know nothing about their personal life. And it probably affected our working relationship. Knowing your colleagues as humans reframes inevitable challenges at work. Had we known our colleagues better, would we have worked through disagreements better or found new ways to collaborate? Yeah, we sure would have.

Alison Rand, who helped establish the discipline of design operations through roles at Hot Studio, Frog, Automattic, and SAP, explores building relationships at work in her new book Sentido—a term that encompasses both making sense of things and feeling them deeply.

In our conversation, Alison challenges the Silicon Valley orthodoxy of radical candor with her concept of radical humanity. She also explains why designops is fundamentally heart-driven work, and draws unexpected parallels between organizational dynamics and the regenerative systems of Puerto Rico’s El Yunque rainforest.

Bio

Alison Rand brings a unique perspective forged in the crucible of real experience. A native NewYorker who lost her mother at sixteen, she learned early that life rarely follows neat narratives. Her career trajectory—from navigating the male-dominated agency world to building design operations practices at scale—taught her that the skills needed to thrive professionally often mirror those learned navigating the New York subway in the 1980s. After being laid off the same week MIT Press accepted her book proposal, she retreated to the woods to write what became part memoir, part radical reimagining of design leadership.

She makes the case that organic intelligence matters as much as academic credentials, and that the future of design leadership lies not in prescriptive frameworks but in building cultures of genuine mutualism.

Whether you’re wrestling with organizational transformation or questioning the artificial boundaries between personal and professional identity, Alison offers hard-won wisdom about leading with both courage and compassion in spaces that often reward neither.

***

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books:

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Alison Rand: Leading with radical humanity instead of radical candor

In this issue of The Brief, we’re reflecting on what we learned about the past and future of design from our conversation with Paola Antonelli (The Museum of Modern Art), Mark Wilson (Fast Company), Kate Aronowitz (GV), Mike Davidson (Microsoft), and Meaghan Choi (Anthropic).

Looking back at 30 years of design

by Eli Woolery

Roughly thirty years ago, I was an undergrad, sitting in our dorm’s computer cluster —this was before the days when most students had laptops. I ran into something I hadn’t seen before. It was called Netscape Navigator, and it was one of the first commercial internet browsers (which our very first guest on Design Better, Irene Au, helped design).

I clicked on one of the buttons (probably, “What’s Cool”), and along with a nifty loading animation, the browser took me down some early internet rabbit hole.

I don’t remember where exactly I ended up, but I do remember being blown away by the experience. As a computer nerd kid in the 80’s, I had spent plenty of time with bulletin board systems (BBS’s) and things like America Online, which we could access through a dial-up modem from home.

But this was very different. It was fast—compared to what I was used to—and it felt like I could almost instantaneously access content from all around the world (even though the content online at the time was a miniscule fraction of what it is today).

I had entered school to study product design, but this was for products in the physical world…digital product design didn’t exist as we know it today. The first use of the phrase “User Experience” in a job title was Don Norman’s role a a User Experience Architect at Apple in the mid-90s.

Browsers like Netscape Navigator, and then the introduction of the iPhone in 2007, opened up a new world of opportunities and challenges for the field of design. In our conversation with Paola and Mark, we talked about four: the democratization paradox, design’s loss of innocence, the fragmentation of the design profession, and the shift from tangible to intangible design.

The Democratization Paradox

“We democratized all the tools and we democratized none of the platforms. And that gap is just in a nutshell, kind of what’s broken about the individual’s ability to communicate.”—Mark Wilson, Fast Company

While design tools and capabilities have been democratized (everyone can now access design software, create content, etc.), the platforms and systems remain highly centralized within a few large companies—Meta, Google, TikTok, etc.

The early, messy days of the internet (Geocities, MySpace) have been largely tamed, which can make for better user experiences, but we also miss the wild creativity that came from having an infinite number of ways to express yourself online. Back then, your personal web page could be a nightmare of animated GIFs, visitor counts, and autoplay music—terrible for usability, but at least it was yours.

Today, we’re all posting in the same formats, and are subjected to the same algorithmic rules for engagement. The tools to create have never been more powerful or accessible, yet we’re increasingly creating within narrower and narrower boundaries defined by a handful of tech giants.

Visit our Substack to read the whole article: ⁠https://designbetterpodcast.com/p/the-brief-how-our-recent-past-should⁠

The Brief: How our recent past should prepare us for the age of AI

This is a preview of a premium Design Better episode. Visit our Substack to hear the whole interview, for bonus content, and more: ⁠https://designbetterpodcast.com/p/fitz-and-the-tantrums

With the 150th official episode of Design Better, we’ve got something special for you.

For many of us, if we haven’t had creative success by our 40’s, we feel like we may have missed the boat. But Michael “Fitz” Fitzpatrick of Fitz and the Tantrums didn’t achieve pop star status until he was well into his 40’s, and now that he’s in his 50’s he feels like he’s just getting started.

Haven’t heard of Fitz and the Tantrums? Yes you have...their hit single "HandClap" has rocked stadiums at sporting events around the world.

In our conversation, Fitz reveals how the band prototypes their live performances and why constraint has been essential to their creative evolution. He talks to us about the parallels of songwriting and product design, the importance of reading the room—whether it’s 50 or 50,000 people—and why the best performances, like the best designs, create space for the audience to become co-creators.

Fitz also opens up about how even after achieving his creative dreams, there was an emptiness that he struggled with, and where he found true happiness.

Bio

Michael “Fitz” Fitzpatrick (born Michael Sean Fitzpatrick on July 21, 1970) is a French-American musician, singer, and songwriter best known as the frontman and creative force behind the indie pop and neo-soul band Fitz and the Tantrums. Born in Montluçon, France and raised in Los Angeles, Fitzpatrick studied vocal music in high school and later attended the California Institute of the Arts, where he explored experimental film. Before forming his own band, he worked behind the scenes as a sound engineer, collaborating with producer Mickey Petralia.

In 2008, Fitzpatrick bought a used church organ for fifty dollars and wrote “Breakin’ the Chains of Love” that same night — the song that would inspire the creation of Fitz and the Tantrums. As lead vocalist and keyboardist, he helped the group rise quickly with their debut album Pickin’ Up the Pieces (2010), which drew praise for its blend of Motown soul, indie pop, and modern energy. Subsequent albums such as More Than Just a Dream and their self-titled 2016 release, featuring the breakout hit “HandClap,” cemented the band’s place in the modern pop landscape.

Fitz and the Tantrums: Finding your creative voice in your 40's and why success feels different than you think

Show notes: https://designbetterpodcast.com/p/che-douglas
Che Douglas led the transformation of the design team at The Wall Street Journal, from a service-based organization to a strategic component of an embedded Engineering, Product and Design (EPD) structure. We chat with Che, who is now VP of Design at Booking.com, about how he got the right people involved to transform their design organization and spread design throughout the company. Che discusses the use of design sprints and how he showed the value of design to the organization through some of the team's key initiatives.
Takeaways:

How the design team can best collaborate with key partners

Showing the value of design with a direct impact on the bottom line

Going beyond defensiveness and being open to critique

Che Douglas: Transforming design at The Wall Street Journal and Booking.com

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