Technical Writing Uncensored

New interview is up with Anne Cantera, who advises enterprise CEOs on AI strategy and also helps small business owners who have never opened a chatbot in their lives.

She said something that reframed the whole conversation for me. A good conversation designer lives in the failure modes. Not the happy path. The happy path is easy. The skill is what happens when someone's last name breaks the model and the system just keeps asking them to repeat themselves.

That is our work. We have been designing for the moment things go wrong for years.

Also, Anne does not collect email addresses on her free resource site, which means she has no idea who she is helping. Tell her to start a newsletter in the comments and I will pass it along.

https://youtu.be/HPza9xSCAwY

What is the worst failure state you have ever had to write your way out of?

3 days ago | [YT] | 1

Technical Writing Uncensored

New interview is live.

Derek Ciula builds agentic systems for a living. He also thinks technical writers are better set up for this than most of the engineers he works with, which is not what I expected to hear from someone whose day job is architecture.


His argument, roughly: anyone can make an agent write documentation. Making it write documentation consistently takes someone who knows why the docs exist, who reads them, and where the whole thing goes sideways. That's not a developer side quest. That's a job.


Meanwhile the job market is out here demanding a Kubernetes expert who happens to write.


So which is it? Is this the golden era of the generalist, or are the job postings telling us what's actually true? Tell me in the comments.


https://youtu.be/l_zfg7m85kE

2 weeks ago | [YT] | 1

Technical Writing Uncensored

New interview is live. This one's with Brittany Robrahn, a technical writer who's spent most of her career as a team of one.

We talk about the "be twice as productive with LLMs" mandate that never explained how it would be measured, why humor belongs in docs, and what job hunting looks like when half the "remote" postings aren't actually remote.

If your company told you to get twice as productive with LLMs, did anyone ever say how they'd measure it? Tell me below.

https://youtu.be/Eak1vx-GVR0

3 weeks ago | [YT] | 0

Technical Writing Uncensored

New interview just dropped! 🎙️

Brittney Ball went from software engineer to founder of TechniDox (recently acquired!) to the writer behind the Documentation Engineer Substack. We talked AI transparency, why the user you think is using your tool usually isn't, and what companies lose when they hand docs to the wrong source.

She also makes the case that a blank slate is a superpower. You only get to be the new user once.

Watch here: https://youtu.be/rPZuobbMJX8

Have you ever caught something in the docs that the experts missed because you were the fresh set of eyes? Tell me about it. 👇

1 month ago | [YT] | 0

Technical Writing Uncensored

Most technical writers I talk to aren't behind on AI because they're not smart enough to keep up. They're behind because no one's handed them a clear, short list of what actually matters.

I put together a free cheatsheet for exactly that: the AI tools showing up in documentation workflows right now (Claude, ChatGPT, Gemini, Copilot), the concepts worth being able to talk about (agents, skills, routines, hooks), and the people worth following so you can stay current without drowning in noise.

It's free. Enter your email and I'll send it straight to your inbox: links.dianapayton.com/ai-cheatsheet

1 month ago | [YT] | 1

Technical Writing Uncensored

So, 2026. AI is hitting like a hammer. There might be an AI bubble that pops. Looking forward to riding this ride with you!

7 months ago | [YT] | 2

Technical Writing Uncensored

Sorry for the delay in posting, folx. Life has been complicated. I hope to post a new video next week!

9 months ago | [YT] | 0

Technical Writing Uncensored

Hey all! I've had a rough couple of weeks. This week's post might be delayed until next week.

1 year ago | [YT] | 0