Impactiv8

Claude Cowork gave me a perfectly sensible recommendation this week. I said no.

We're mid-launch, and the plan had quietly spread itself across three places: a planning doc, a spreadsheet, and our conversations. Classic. So I asked a simple question: where should all of this live, so both of us can work on it?

Before answering, Claude Cowork did something I want you to notice. It stopped and checked what it could actually do in my tools first. Its exact words: "Let me check whether I have edit access, so I give you accurate advice rather than promising something I can't deliver."

It came back and admitted it could read my spreadsheet but couldn't write to it. No bluffing, no pretending. Then it suggested moving the day-to-day plan into my Asana, project management tool, which it can edit.

Sensible. Logical. And wrong for me.

Because I don't need another tool in the content creation part of my launch workflow. I need fewer. So I pushed back... One place for all the content and its status, or it's not happening (said politely, of course). We landed on a single shared Notion database instead. My AI writes the drafts straight into it, I edit them and flip the status when they're published. One home. Both of us working in it.

The takeaway from this? Claude Cowork knew its own capabilities. I knew my workflow and what I'd actually stick to during this launch. Neither of us could've designed the system alone.

That's what human-led, AI-powered looks like in practice. Not handing over the decisions. Not ignoring the advice, either. A proper working relationship where it's allowed to recommend, and I'm allowed to say "nope, try again".

The best system isn't the cleverest one. It's the one you'll still be using when things get busy.

P.S. If your AI has never told you what it can't do, that's a conversation worth having.

So many people keep asking me what a markdown file is, and what the benefits are when you're working with AI, that I decided to write a blog post on the exact topic. Mostly so I didn't have to keep repeating myself, and could send them the link instead.

So here it is, in case you've ever wanted the answer to that question.

It's a tech-jargon free guide to what markdown files are, why AI tools prefer them, and the other benefits (and drawbacks) of using them.

Whether you're building Custom GPTs, setting up Claude Projects, or simply trying to get better results from AI, this one's worth a read. Link in comments.