So this one was different. Instead of an author interview, Ilia Karelin from Prosper got on and walked me through Claude Cowork live, the simpler cousin of Claude Code that runs without a terminal and works with the actual folders on your computer. We got into the setup most people skip, the global instructions, plus how to make Claude show its sources and its confidence level so you catch hallucinations, the security stuff nobody warns you about, and the part I keep coming back to: skills and scheduled tasks that do real work while you’re not even at the keyboard.
If you’ve ever wondered whether there’s a version of Claude built for people who don’t code, this is the one to watch.
Outline
(00:00) – Welcome and a different kind of session
(01:17) – Ilia, Prosper, and a data background
(04:31) – What Claude Cowork actually is
(05:33) – Global instructions, the setup most people skip
(07:04) – The new-employee-every-day problem
(10:24) – Security: sensitive folders and prompt injection
(14:52) – Skills and the skill creator
(18:21) – Scheduled tasks that run while you sleep
(21:03) – Live artifacts you can actually chat with
(28:32) – Building a project brief skill, live
(37:29) – Dispatch: running Claude from your phone
(45:59) – The four levels of Claude
Main Takeaways
The new-employee-every-day problem. Ilia started where almost nobody looks, the global instructions buried in your Cowork settings. It’s the main thing Claude reads before it answers anything, and most people leave it completely blank.
“I highly recommend using the global instruction and putting something in there, about yourself and about the work you do.” — Ilia
Here’s how I think about it. If you’ve never touched your instructions, it’s almost like you’re bringing in a brand new employee every single day, teaching them everything about your company, then letting them go and starting over with somebody new the next morning. The instructions are what stop you from re-onboarding the same hire every day.
Make the hallucination show itself. One thing I added to my own instructions: anything with a source, cite the source in the answer. Anything without one, give me a confidence level. That’s one of the ways I deal with hallucinations, because a low-confidence answer tells me exactly where to go double-check before I trust it.
“Sometimes Claude was making up numbers, and I’d say, I don’t think this is real. I’d ask it to do a web search, and it’d come back like, yeah, these numbers don’t exist, I’m sorry about that.” — Ilia
I’d rather Claude tell me it’s guessing than hand me a clean number that turns out to be fiction.
Skills you don’t have to build by hand. Skills are the first thing I’d point a new leader toward. The piece Ilia showed that’s worth stealing: Anthropic built a skill whose only job is to build other skills, and it tests its own work as it goes.
“It’s called Skill Creator Skill, and it runs through different tests to improve the skill. Definitely recommend using that one if you’re creating a new skill.” — Ilia
And the thing I like about Cowork specifically is it shows you which skill it’s pulling up under context, so there’s no mystical thing happening in the background, you know exactly what it has access to.
Tasks that run while you’re not there. This is the part I keep going over. Ilia has a brain dump processor that watches his Notion through a scheduled task and surfaces anything worth expanding on. Mine runs every Wednesday at 6am, cleans my whole desktop, files everything into the right business folder, and deletes the screenshots before I’m even awake.
“It connects to Notion through MCP and looks through everything happening over there, then puts out a new page for me to look at and see if anything’s worth expanding on, or just drop it and forget it.” — Ilia
Pair that with Dispatch, which Ilia described as a walkie-talkie with Claude, and you can fire a task off from your phone and walk away while your laptop does the work.
Executive Coaching: If you’re looking at your own role and wondering how any of this applies to the way you actually work, that’s exactly what I help leaders figure out. My calendar is here, book a free call!
About Ilia Karelin
Ilia Karelin writes Prosper, a Substack covering AI and Claude workflows from a data professional’s point of view. He spends most of his day in data work, which is part of why his walkthroughs stay practical and skip the hype. He’s written a few pieces for Leadership in Change worth reading, including AI Research 201: 10 Perplexity Features and Why Apple Just Admitted Google’s AI Won. Subscribe to his newsletter at Prosper.
About me
Joel Salinas is an author and an Executive AI Coach for leaders at small and mid-sized businesses and nonprofits. 1:1 coaching, team workshops, and AI strategy work built around amplifying what your team is already good at. Creator of the AI Leadership Triad. He writes Leadership in Change. If you want help thinking through your own AI strategy or online presence, start here.
Written by a human, for humans.
Thank you Farida Khalaf, Claire Machado, Salt Air Nomad 🌴, India Pryor, and many others for tuning into my live video with Ilia Karelin! Join me for my next live video in the app.
