The Brief: What designers can learn from writers and storytellers

Summary

Podcast Summary: Design Better - Episode: "The Brief: What Designers Can Learn from Writers and Storytellers"

Introduction

In the February 28, 2025, episode of Design Better, hosted by The Curiosity Department, LLC’s Eli Woolery and Aarron Walter, the discussion delves into the invaluable lessons designers can glean from the realms of writing and storytelling. Titled "The Brief: What Designers Can Learn from Writers and Storytellers," this episode explores how the creative processes of writers and storytellers can enhance design practices, fostering creativity, empathy, and effective collaboration.

The Power of Writing in Design

The episode opens with an insightful account of Jony Ive, the renowned former head of design at Apple, who emphasizes the significance of writing over sketching in the design process. Woolery recounts Ive’s visit to a design capstone class at Stanford, where he demonstrated the versatility of writing in design.

Jony Ive on Writing as a Design Tool [00:02]

Ive shared an anecdote about collaborating with a landscape designer in the UK. Instead of conveying ideas through drawings, Ive chose to describe the sensory experiences of the environment:

"The designer could have shared drawings, but instead he wrote about the night garden and how the flagstones would radiate heat from the warmth of the day and the fragrance of the flowers along the pathway." – Jony Ive (Transcript [00:02])

Ive argues that writing allows for a more comprehensive expression of a design’s attributes, capturing not just the visual but also the tactile and emotional elements:

"If I were to draw this glass, you would understand only 20% of its nature. You'd have no sense of its weight or material or temperature." – Jony Ive (Transcript [00:02])

Lessons from Writers: Observation and Iteration

Transitioning from design to literature, the podcast highlights how writers’ methodologies can inform and enhance design practices. Madeline Miller, author of Circe and Song of Achilles, exemplifies the iterative and empathetic approaches that designers can adopt.

Madeline Miller on Iterative Writing [02:55]

Miller discusses the importance of perseverance and iterative refinement in the creative process:

"The difference between writers and non-writers is that writers go back again and again. My old classics teacher used to say that the people who succeed in classics were the people with the highest tolerance for failure." – Madeline Miller (Transcript [02:55])

Her approach to reimagining characters, such as transforming Circe from a peripheral figure in Homer's Odyssey to the protagonist, underscores the value of empathy and redefinition in storytelling, which parallel essential design principles.

David Sedaris: Observational Skills and Iterative Refinement [04:18]

David Sedaris, the acclaimed author and humorist, is celebrated for his acute observational skills and iterative writing process. Sedaris shares a poignant story illustrating his disdain for excessive phone use, which hampers genuine observation:

"They never, ever stopped photographing each other, this mother and daughter. And the restaurant was on the 60th floor. So, okay... it was as if one of them was going to be executed at the end of the meal." – David Sedaris (Transcript [04:36])

Sedaris emphasizes the importance of capturing real-life details and refining narratives through continuous iteration:

"The point is just to stack up the pages, you know. The point is just to write new things and learn from it and then move on and write something new." – David Sedaris (Transcript [07:01])

Applying Writers’ Techniques to Design

Eli Woolery connects these literary practices to design, advocating for designers to cultivate observation habits and iterative testing akin to writers:

• Keep a Journal: Document user interactions, pain points, and design ideas.
• Iterative Feedback: Test prototypes with real users, akin to writers reading aloud to refine their narratives.
• Visual Sketching: Use early sketches as foundational elements for more polished designs, reminiscent of Paula Scher's napkin sketch of the Citibank logo.

Effective Pitching Through Collaboration: Insights from Dan Pink

Shifting focus to the business side of design, the episode explores the art of pitching ideas, drawing from Dan Pink’s principles in his book To Sell as Human. Pink challenges the traditional performance-centric approach to pitching, advocating instead for collaborative engagement.

Dan Pink on Collaborative Pitching [09:20]

Pink critiques the theatrical nature of many pitches and emphasizes the importance of inviting collaboration:

"Successful pitches invited the other side in as a collaborator... what you want is, 'huh. That's really cool. It's really interesting. Have you thought about such and such?'" – Dan Pink (Transcript [09:20])

He underscores the necessity of authentic communication, free from jargon, to foster genuine connections and collaborative environments:

"Talk like a human being in all of your materials... just be an authentic human being who talks like a real human being." – Dan Pink (Transcript [10:49])

Practical Strategies for Better Pitching [10:34]

Building on Pink’s insights, Woolery offers actionable strategies for designers to enhance their pitching skills:

1. Craft Purposeful Pitches:

   • Articulate not just the design’s features but also its significance and impact on users’ lives.

2. Invite Collaboration:

   • Engage stakeholders by encouraging questions and feedback, transforming the pitch into a participatory dialogue.

3. Eliminate Jargon:

   • Use clear, human-centric language to communicate ideas effectively without alienating the audience.

Recommended Practices:

• Pitch Practice Workshops: Encourage teams to engage in short, focused pitching sessions with open-ended questions to simulate collaborative discussions.
• Reflect on Authenticity: Emphasize genuine communication to strengthen the pitch’s impact and foster trust with stakeholders.

Conclusion

This episode of Design Better illuminates the profound intersections between design and storytelling. By adopting writing’s observational and iterative techniques, and embracing collaborative pitching strategies, designers can enhance their creative processes, foster deeper user connections, and effectively communicate their visions. The insights from Jony Ive, Madeline Miller, David Sedaris, and Dan Pink collectively offer a multifaceted approach to building more empathetic, innovative, and impactful design practices.

Key Takeaways:

• Embrace Writing in Design: Use writing to explore and articulate multidimensional aspects of design beyond visuals.
• Cultivate Observation and Iteration: Adopt writers’ habits of keen observation and iterative refinement to enhance design quality.
• Foster Collaborative Pitching: Engage stakeholders as collaborators rather than mere audiences to facilitate more effective and meaningful pitches.
• Communicate Authentically: Use clear, jargon-free language to build genuine connections and convey ideas compellingly.

For those looking to deepen their understanding of integrating storytelling into design, this episode provides a wealth of practical advice and inspirational insights.

Transcript

[Eli Woolery]

This is an audio version of the Brief the Design Better newsletter that takes you deeper into the insights we've uncovered through hundreds of interviews with creative thinkers. I'm Eli Woolery. What designers can learn from writers and storytellers Jony I've the famed former head of design at Apple starts all of his projects with writing. I was surprised to learn this when he visited our design capstone class at Stanford a few years ago. I'd always assumed he would grab a pencil and whip up a quick sketch, but Johnny gave our class a powerful example of why writing is a far more versatile tool than sketching. He spoke of working with a landscape designer on his property in the uk. The designer could have shared drawings, but instead he wrote about the night garden and how the flagstones would radiate heat from the warmth of the day and the fragrance of the flowers along the pathway. Here's Johnny in an interview with mackenzie Quarterly. I write because I realized at art school you can only draw a small percentage of the attributes of an object. You know, if I were to draw this glass, you would understand only 20% of its nature. You'd have no sense of its weight or material or temperature. You'd have no sense of the way that it reacted to its environment. Writing helps me frame the problem. A lot of mistakes are made when you frame a problem because you could already be dismissing 60, 70% of the potential ideas. Free from the constraints that even the best drafts person would face, Johnny and his team can conceptualize not only the look of the products, but the touch, weight, and even emotions that they trigger. Perhaps it shouldn't surprise us that good design can start with writing. Good writers are adept at taking an iterative approach to creativity. They create memorable characters through empathy, their characters evolve, and they often reimagine old stories with new, innovative approaches. Here's Madeline Miller, the author of Circe and Song of Achilles. The difference between writers and non writers is that writers go back again and again. My old classics teacher used to say that the people who succeed in classics were the people with the highest tolerance for failure. I think the same is true for writers. Madeline Miller is a great example of an author who uses all of these techniques in her writing. Her book Circe takes the titular character, who is a peripheral, if important, part of Homer's Odyssey, and reimagines her as the protagonist. Her empathetic approach to the enchantress in exile reframes the story in a way that makes us feel a human connection to the not quite human character. Professional writers also aren't afraid to make mistakes as they go. Many have a bias toward action, creating the rough outlines parallel to a prototype of the work before going back to refine it. Here's Madeline Miller again. My husband's a master carpenter. When I asked him if master carpenters make fewer mistakes than regular carpenters, he said no, but they recognize the mistakes more quickly. It's the same for writers as they gain experience. In this article, we'll explore what writers like David Sedaris and Dan Pink could teach us about becoming better designers. David Sedaris, observe and iterate.

[Meredith Black]

Hey there. I'm Meredith Black, co founder of Design Ops assembly and formerly of Pinterest and Figma. I co host a podcast called Reconsidering alongside two of the design world's most respected voices, Bob Baxley, formerly of Apple and Pinterest, and Erin Walter, co host of this very podcast Design Better. Reconsidering is a show about looking at the big questions and challenges that we face in everyday life. With a fresh perspective, we dive into topics like building a fulfilling career, navigating tough conversations, making meaningful friendships as adults, and even handling life's biggest transitions like illness and loss. We bring in authors and experts to provide actionable advice and thoughtful guidance to help us all develop the skills needed to thrive as well rounded and healthy adults. We spoke with New York Times bestselling author and TED speaker Dan Pink on the power of regret and how we can make smarter decisions to deepen our sense of meaning and purpose. And Tina Roff Eisenberg, the founder of Creative Mornings, joined us live to talk about the importance of creating community and friendships. It turns out it has a huge impact on longevity and the quality of your lives. And we spoke with MIT professor of philosophy and bestselling author Kiran Setia about facing life's inevitable hardships and what ancient philosophers can teach us about living the good life. We explore so many topics and we'd love for you to give the Reconsidering podcast a listen. Listen and [e-mail] that's reconsidering.org or find us wherever you get your podcasts.

[Eli Woolery]

Reconsidering.org David Sedaris, the author and humorist, has a painfully sharp sense of observation, a key to his success as an author and humorist. He told us a story about a mother and daughter he encountered who most definitely did not take his advice to us about putting down your phone to become a better observer.

[David Sedaris]

Yes, stay off the phone. I mean, I can't remember the last time I Rode an elevator, and the person or persons with me weren't on the phone. You know, I don't know what they're doing or, you know, people get on an escalator and then they decide that's a good time to pull out their phones. I don't know. I just never. I'm on my phone, so that's part of it right there. Plus my livelihood, right to look for things that are striking for some reason. And if you're staring down at a phone, you're definitely not going to see anything, right, except what's on your phone. And I understand there's a lot online, right? There's a whole world there. But you can go to that world anytime, I suppose, you know. But when you're out in the real world, I don't know, I just like being out at, you know, it's my livelihood. I'm trained at this point to always be searching, to always be aware of what bothers me, what I find irritating or what pleases me or. I mean, there was a woman and her daughter at breakfast this morning, and the daughter was, like, 30. I have never seen anything take so many pictures in my life. They needed an intervention. And the waiter said, well, you know, it's a special restaurant. I said, this is not a today thing. This has been going on for a long time. They literally couldn't even eat. The food came, and then they started photographing their food, and then they started photographing each other eating the food. They never, ever stopped photographing each other, this mother and daughter. And the restaurant was on the 60th floor. So, okay, you know, use and all that stuff. But it was as if one of them was going to be executed at the end of the meal. And this is her last chance to remember the mother or the daughter, either one of them. I couldn't take my eyes off of them.

[Eli Woolery]

David's creative process is rooted in observation and the habit of capturing life's unexpected headline moments. He carries a notebook everywhere, recording details that might otherwise slip by unnoticed. Later, he refines these raw observations into compelling narratives by reading his work aloud, an iterative process that reveals the rhythm and nuance of his stories.

[David Sedaris]

I dropped out of college, like, when I was 19, and then I dropped back in when I was 27. And then I. Maybe when I was 28, I took a creative writing class at the Art Institute, and the teacher asked me to read something out loud. I'd written a short story, and she asked me to read it out loud. And when I read it out loud, people laughed and I thought, I want to write things and read them out loud. I don't want to memorize them. I don't want to be an actor. I just want to read things off a page that I wrote. The point is just to stack up the pages, you know. The point is just to write new things and learn from it and then move on and write something new and write something new and write something new.

[Eli Woolery]

As designers, we can sharpen our toolset by mirroring some of David's practices, just as he notes the details of everyday life. Designers should develop a habit of observing how people interact with products, what behaviors or pain points do people encounter in their daily lives, and reading stories out loud in front of an audience parallels the practice of testing prototypes with real users. Sharing prototypes and gathering feedback is essential in refining the narrative of your product. Here's a new habit Keep a journal where you jot down user observations, design ideas, sketches and unexpected insights. This could take the form of a bug list, an idea my former colleague Bill Burnett advocates, where you simply jot down notes about things that are poorly designed and that bother you. Or it could be more visual, focused on sketching people, places and ideas. Sometimes early sketches can form the foundation for more polished execution, like former guest Paula Scher's napkin sketch of the Citibank logo. Dan Pink Better Pitches through Collaboration unfortunately, it's not always the job of designers to be purely creative. Sometimes more of our time is spent selling pitching ideas, convincing stakeholders to give us resources, or getting buy in from our engineering counterparts. This is the foundation of author Dan Pink's book To Sell as Human, where he reminds us that we're all in the business of selling ideas, whether it's a product, a design concept, or a feature update. If you're pitching a new idea to your team or your boss or other stakeholders, your impulse might be to give an Oscar worthy performance and blow your audience away with your slide designs and your presentation skills. Dan says this probably isn't the right way to approach it.

[Dan Pink]

This is some research done at UC Davis and Stanford, where they looked at Hollywood pitch meetings and found what were the successful pitches and what weren't. And it turned out the most important factor in pitches was that successful pitches invited the other side in as a collaborator. So the main thing is to think of pitching as a collaborative exercise. I've messed this up so many times until I realized this, because I always looked at a pitch as almost like a performance where you do a little song and dance and you do your tap dance and you Take off your top hat and your cane. And that's not what the evidence says. The evidence says that people want to be participants. They want to be collaborators. And so the response you want in a pitch is certainly not, that's stupid. That'll never work. That's usually not a good sign, amazingly enough. But you, what you also don't want is, oh, my God, that's amazing. What you want is, huh. That's really cool. It's really interesting. Have you thought about such and such? What if we did such and such? Then you're off to the races because you fostered that collaboration. And that for me, truly has fundamentally changed the way that I pitch. It's like, I don't say, like, what's the best, most captivating America's Got Talent performance I can deliver, but what's the best way to invite them in as collaborators?

[Eli Woolery]

It also might be our tendency to load our pitch with jargon, roi, core competency, or my personal favorite, synergize. And while it's important to speak at least some of the language of our business and cross functional partners, loading our pitch with jargon can be counterproductive.

[Dan Pink]

Another thing is to talk like a human being in all of your materials, whether it's in person or whether it's in your documents. Like, I see things like describe, like what companies do or what their mission is or what their purpose is, and it's fricking gobbledygook, all right? They are not words that human beings use when they go out for a walk with their spouse. They're not words people use when they're sitting around the table with some friends having a pizza. So just talk like a human being, for God's sake. And I think people can see that. So just like, be an authentic human being who talks like a real human being. Among the things that drive me nuts is it gives you an example of what companies would say and even what leaders would say, but human beings would never say. All right, so let's say that I have an Internet provider here in Washington, D.C. because of their screw up, the Internet connection to my house was disrupted for six hours. Okay, what do they say in those circumstances? They say, and I'll give you the words. All right, we know these words. We can recite it like we're at church. We regret any inconvenience this might have caused you. Now, no one would say that to another human being in a real setting, right? You would say, oh, my God, I'm so sorry. So if you as a leader can just talk the way you talk to another person. I think that goes along, you know, like, like instead of saying, wow, we really optimized our relationship with our stakeholders today. Like, you know, it's like, oh man, that customer is going to be psyched that they have our product. That client over there. We really solved their problem. They're going to be better off. And I'm proud of you guys for doing that. That's what you say.

[Eli Woolery]

Here are a few ways you can improve your pitches using Dan's Principles Craft Purposeful Pitches when when pitching a design concept, articulate not just the what but also the why. Is your design solving a significant problem? Capital P purpose or making a tangible contribution to users daily lives? Small P purpose Invite Collaboration A good pitch invites questions and feedback. Instead of delivering a monologue, engage your audience by asking, how would you approach this problem? Or what are some of the things you've seen in this situation that worked? This creates a participatory environment that will encourage more alignment with your stakeholders. Here's a new habit. Run a pitch practice workshop with your team. Have designers prepare short, focused pitches for their concepts and invite colleagues to ask open ended questions. Emphasize that the goal is not to impress, but to collaborate. Reflect on how authenticity and clear purpose enhance the pitch's impact. To read and share this episode with friends and colleagues, visit designbetterpodcast.com and while you're there, you can become a premium subscriber, which will get you access to the brief newsletter in your inbox every month, plus ad free episodes, extra episodes every month, and so much more. Just visit designbetterpodcast. Com.