Writers of Silicon Valley

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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].