Context Window

First things first: This newsletter has a new name! Welcome to Context Window, where I'll be sharing everything I'm learning about AI search. (Your girl is over here cooking on a website rebrand, and this is part of it.) Today, we're going to talk about the fact that your content might rank on page one and still be invisible. As you know, Google AI Overviews now answer queries directly at the top of the results page, pulling from multiple sources to construct answers, often without anyone...

Last week, we talked about why the subject matter expert (SME) interview is an important step in the AI-optimized content production process. This week, I want to go deeper into that and tie it into the larger idea/strategy of reputation engineering (as it relates to AI search visibility). This newsletter is brought to you by the lovely folks at AirOps. Your buyers are getting answers from ChatGPT. Are you in them? AirOps analyzed 15M+ AI queries and turned the findings into a 4-play...

There's a step in the AI-optimized content production process that doesn't get talked about enough, and it's the one where most projects quietly fall apart. It’s the subject matter expert interview. An important piece of creating content that LLMs cite in AI summaries includes getting fresh, original insights from experts (both internal and external to your organization). This is part of "owning your topic" efforts we talked about last week. AI can’t (yet) conduct those interviews, so it’s...

How people search for and find answers to questions online has changed in a very big way. For brands working to win traffic via organic search results, it used to be a game of keyword targeting. Rank in spots 1-3 for the right keyword, and you’d win the click (and hopefully, the sale.) But…that’s not how AI search results work. When someone asks ChatGPT, Claude, or Google's AI Overviews a question, that single question triggers dozens of related searches behind the scenes, and the LLM maps an...

Attention spans are short…and no one knows that better than the media industry. This is why journalists learned to front-load the most important information at the top of every story. If the reader fell off after the first paragraph, at least they got the essential facts. Things like the who, the what, the why. That structure became known as the inverted pyramid, and it's been the backbone of journalism training for over 150 years. Here's why I'm telling you this: AI models retrieve content...

If you’ve been hands-on with AI writing tools, you've probably hit that moment where the output feels…off. It’s fine, but maybe it's too generic, too formal, or just doesn't sound like you. There’s a reason for that. AI tools don't magically absorb your brand's voice and personality the way a human writer would. They need LOTS OF CONTEXT. Not just a quick prompting instruction like, “write in a tone that’s irreverent,” or “don’t use jargon.” It needs so much more than that if you want quality...

(First of all, bless you if you got that DCFC song reference in the subject line 🙏) But...so, uh: it's 2026 now, huh? I used to do year-in-review recaps as a reflective exercise here where I'd recap all the wins and good things that happened over the last 12 months, but as I get older (and more averse to the highlight reel that is all things internet these days), I decided maybe it would be all illuminating for *all of us* if I pulled back the curtain a bit this time around. Because you know...

Story time. I've been self-employed for 12 years now, and all along the way, I've sort of fumbled through the business side of things. For the first few years, I worked with a local CPA in my small town. I initially filed as a sole proprietorship, and that was fine for the time being. My business didn't generate a ton of revenue, and I handled my own bookkeeping, so I knew exactly how much to set aside for the tax bill in April. But as time went on, my business became a bit more complex. I...