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Dave Connis is back on Writers of Silicon Valley after a very different eighteen months.

Since his last appearance, Dave has been laid off, thrown himself into experimenting with AI, built new product workflows, and started creating System Design Lab: an education platform focused on systems thinking for product and content designers.

In this episode, we talk about the emotional fallout of layoffs, the strange new roles appearing in content design, what AI actually looks like when you use it every day, and how to actually prove you're a systems thinker - both in an interview, and on the job.

What we talked about:

✅ What getting laid off did to Dave's confidence, identity, and relationship with work ✅ Why trying to constantly "prove your value" can lead straight to burnout ✅ The new roles emerging around AI, including design technologists, system architects, and content architects ✅ Why today's job descriptions increasingly seem to be looking for impossible "unicorn" candidates ✅ What Dave learned from months of actually building with Claude, Figma MCP, and other AI tools ✅ Why AI workflows are much harder to make reliable than LinkedIn posts would have you believe ✅ How systems thinking helps designers define concepts, objects, attributes, and relationships before AI starts building ✅ How to demonstrate systems thinking in an interview ✅ Why Dave is building System Design Lab

Where to find Dave:

• System Design Lab
• LinkedIn

⭐⭐⭐ PODCAST OFFER! Get 50% off workshops and courses at UX Content Collective until Monday, August 24. Just use PODCAST50 at checkout. ⭐⭐⭐

Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.

Jenny Williams is one of the most experienced content designers in the world. And now she's written a novel about a content designer.

Jenny's worked at places like Microsoft and Google, where's worked on AI products. She could already see that the technology was exciting, terrifying, and likely to change far more than the products being built with it - including the role of content designers themselves.

Then she left tech and wrote House of Liars: a novel about writers brought to a remote island to compete for a publishing prize.

At the centre of the story is Anna, a former content designer with a complicated history with AI - and, in Jenny's words, a "warped or twisted" version of herself.

Jenny joins me to talk about turning her experience in content design and AI into fiction, why the best product writing requires the writer to disappear, and what we lose when content designers stop writing words and become overseers of systems that write them.

What we talked about:

✅ How working on Microsoft's AI ethics team inspired House of Liars✅ Why the book began as a memoir and became a novel about a content designer confronting AI ✅ Why content design turned out to be the perfect job for the story's protagonist ✅ How AI has become an ethical litmus test for writers, designers, and technologists ✅ What it felt like to discover that Jenny's first novel had been used to train AI without her permission ✅ Why Jenny left tech as content design shifted from writing words to overseeing systems that write them ✅ Whether UX practitioners can challenge harmful AI decisions without putting their careers at risk

Where to find "House of Liars":

• Website
• Jenny's Newsletter

Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.

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IT'S A "BEST OF" SERIES!

We're digging back into the archives and resurfacing some of the best episodes of the Writers of Silicon Valley podcast i the conversations that have held up, and in some cases gotten more relevant since they first aired.

This one's with Chelsea Larsson. She currently leads content design at Anthropic, but when this conversation happened she was at Expedia.

We got into the future of content design, UX writing, how AI is reshaping the work, and why content designers shouldn't cling to old definitions. And maybe…why content designers should learn Python?

Worth a second listen if you caught it the first time, and a good place to start if you didn't.

Things we discuss during this episode:

• Generative artificial intelligence
• Information Architecture for the Web
• Open AI, ChatGPT, Gemini
• Python

Chelsea and her stuff:

• Chelsea on LinkedIn
• Smallish Book (newsletter)

🎧 Start listening on Apple Podcasts, Spotify, subscribe on YouTube, or wherever you get your podcasts.

Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.

Oleksii Tkachenko has worked across software engineering, UX, and content design, which makes him unusually well-positioned to talk about what's happening in content design right now.

In this episode, we talk about the growing identity crisis inside content design: the pressure to become more technical, the race to automate workflows, and the uncomfortable question sitting underneath all of it...what parts of the craft are actually worth keeping?

We explore why so much AI discourse online feels detached from reality, why many companies still don't know what they want from content designers, and why the profession risks redefining itself around tools instead of outcomes.

Enjoy!

What we talked about:

✅ Why LinkedIn creates a distorted picture of AI adoption ✅ The three different types of companies hiring content designers right now ✅ Why "AI curiosity" means different things at different organizations ✅ The danger of optimizing for output instead of product quality ✅ The tension between craft, speed, and automation ✅ Why content designers are becoming the "context bearers" for AI systems ✅ The risk of redefining content design around tools instead of outcomes ✅ Why some people are quietly mourning the old version of the profession ✅ The similarities between today's AI shift and the rise of UX writing years ago

Where to find Adedayo:

• Website
• LinkedIn

Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.

🎧 Start listening on Apple Podcasts, Spotify, subscribe on YouTube, or wherever you get your podcasts.

Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.

Adedayo Agarau is a poet, a Stanford Wallace Stegner Fellow, and a content designer who has worked on AI search at Google and on Grok at XAI. He came to content design through web writing, a Nigerian fintech startup, a browser company, and an MFA at Iowa - not the path anyone would have predicted, and exactly the kind of path that produces someone worth listening to.

We talk about what it actually means to design for a large language model: how personality gets built, why guide rails are a writing problem, why the distinction between an ideal response and just a response is what separates well-designed AI from the rest...and why content designers are the best ones to do this type of work.

What we talked about:

✅ How Adedayo discovered poetry through a Nigerian social app ✅ What it was like contributing to AI-powered Google Search ✅ Designing voice, tone, and personality for Grok ✅ Why the X algorithm amplifies shock value and what that does to content designers ✅ Why AI hype creates both overclaiming and unhealthy skepticism ✅ What engineers actually want from content designers when building AI systems ✅ The case for treating data as content, not just content as data ✅ Why designing an AI agent is fundamentally the same as writing a character

Where to find Adedayo:

• Website
• LinkedIn
• Github

Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.

Want to learn how to use AI to build with other content designers? Join the Content Design AI Accelerator. Applications open until January 30.

Why wearable tech will change content design

Smart glasses and wearable devices have been "just around the corner" for years. But quietly, that's starting to change.

In this episode, I speak with Carly Gray, a content designer who's spent years working on AR and wearable products, including smart glasses at North and Meta. While much of the industry debates AI and screens, Carly has been designing content for products where there's little or no screen at all.

We talk about what changes when content moves off phones and into the physical world, why wearables raise entirely new design and ethical challenges, and what content designers need to start learning now if they want to stay relevant as new platforms emerge.

What we talked about:

✅ How Carly moved from technical writing into content design for AR and smart glasses ✅ Why smart glasses are different from VR, and why wearability matters more than novelty ✅ Designing content with extreme space constraints (or no screen at all) ✅ Using sound, voice, and companion apps to communicate when text isn't an option ✅ Why "designing for the bystander" is as important as designing for the user ✅ What wearable tech reveals about the future skill set of content designers ✅ Why conversation design and systems thinking matter more in emerging platforms

Where to find Carly:

Website: carlygray.ca LinkedIn: Carly Gray Twitter: @carlygray

THANK YOU FOR 50 EPISODES!

This is the 50th episode of Writers of Silicon Valley. Thank you for listening all this time - through my bad editing skills, a three year break, and me saying "absolutely" a lot.

It means so much that you'd tune in once, let alone 50 times. So thank you :)

As an extra 'thank you' I'm offering 35% off Advanced UX Content for Product at UX Content Collective. Use PODCAST35 at checkout :)

Here's to 50 more.

Content design for AI agents

Christopher Greer has been creating cool content design resources for years, but his latest is a real accomplishment: a Claude Skill that hooks into Figma and critiques UX writing.

It turns out Chris is quite optimistic about the state of the content design market.

We talk about his work at Stripe, what it actually means to design content for AI agents and internal systems - not chatbots for end users, but the infrastructure, context, and governance that sit behind them.

Chris shares how content design skills translate directly into agent design, why context management is now a core capability, and how content designers can scale their influence by working closer to engineering and systems.

What we talked about:

✅ Why content design skills map closely to designing AI agents and systems ✅ Context management, "context rot," and why structure matters more than prompts ✅ How content designers can scale influence through internal tools and governance ✅ Working as a content designer inside an engineering-led company like Stripe ✅ What Chris learned building and open-sourcing a Claude skill for UX writing critique ✅ Why GitHub and version control are becoming practical skills for content designers ✅ The risks AI poses to junior roles, and the strategic work that won't disappear ✅ Why qualitative judgment, taste, and human evaluation still matter

Where to find Chris:

• LinkedIn
• Chris's blog
• Chris's Claude Skill

👉 Get up to 35% off everything at UX Content Collective until December 16!

It's the end of the year, which means it's time for a little reflection.

I've picked 5 clips from the most popular episodes of the year.

Have a wonderful end of the year / holiday season, and I'll see you all in 2026.

Any suggestions, interview ideas? Hit me up at [email protected].

Do you enjoy the podcast? Please leave a review!

👉 Buy Margo's book, "Good Job", at her website

👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.

👉 Sign up to our UX writing newsletters

How to ace your design interview

Interviews are horrible. No one likes them. But does it have to be that way?

Margo Stern's new book, Good Job, takes on design interviews - both for candidates and for the people creating the interview process. She goes into great detail about how to actually ace a design interview, and for hiring managers, how to design an interview process that treats people like human beings.

We delve into all sorts of great discussions about interviews. How to ace them, what they get wrong, and what companies need to do to make the interview process better for designers.

Enjoy!

What we talked about:

✅ Why interviewing is a separate skill from doing the job ✅ How candidates can prepare through self‑reflection, rehearsal, and storytelling ✅ Why the STAR method works (and why most people use it badly) ✅ The real reason case studies fall flat and how to make yours a story, not a status report ✅ How to research a company without crossing the line into oversharing ✅ The advantages extroverts have in interviews and how introverts can level the field ✅ How candidates can show genuine interest without being performative ✅ How to read red flags in interview processes (ghosting, unclear expectations, chaotic loops) ✅ The danger of applying to too many jobs and why "less, but better" works for both sides ✅ The key questions both candidates and interviewers should ask

Where to find Margo:

📖 Margo's website Do you enjoy the podcast? Please leave a review!

👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.

Do you enjoy the podcast? Please leave a review!

👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.

👉 Sign up to our UX writing newsletters

Ditto 2.0 is here, and wants you to rethink product content

Five years ago, Ditto launched as one of the first tools built specifically for managing product copy at scale. Now? It's powering content systems for some of the biggest design teams in tech and it just relaunched with a major update.

In this episode, I catch up with co-founders Jess and Jo about what they've learned since founding Ditto, what it's like to rebuild a product from the ground up, and why strong content systems are more essential than ever especially in the age of AI.

Learn what these founders are hearing from the heads of design teams about content, why systems thinking is more important than ever, and why they're optimistic about the future of content design.

What we talked about:

✅ How Ditto's vision has changed (and stayed the same) ✅ Why rebuilding the product from scratch was the right call ✅ What they've learned from working with dozens of enterprise teams ✅ How to support content systems in companies with messy, legacy infrastructure ✅ What sales has taught them about communicating the value of content ✅ How AI is shaping expectations—and where it actually adds value ✅ Why more content designers should think like founders

Where to find Ditto:

📖 Ditto

Do you enjoy the podcast? Please leave a review!

👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.

Do you enjoy the podcast? Please leave a review!

👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.

Should content designers care about "vibe coding"?

AI prototyping has taken the design world by storm. Replit, Cursor, Lovable, Figma Make...all of them are certainly very cool. But do they actually change the way we design? And if they do, should we even care?

David Hamilton joins me to talk about it.

What we talked about:

✅ Designing content for cars across screens, systems, and contexts ✅ The stakes of language in safety-critical interfaces ✅ Why consistency across app and vehicle language really matters ✅ How content designers can shape AI systems ✅ What "vibe coding" is and why content still plays a key role ✅ Why the last 5% of polish is the new differentiator ✅ The importance of taste, trust, and systems thinking

Where to find David:

📖 LinkedIn

📖 David's Substack

Do you enjoy the podcast? Please leave a review!

👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.