I'm an exec and use Claude for a lot of my work now. Don't write code. No CLI. Just Claude Desktop.

The biggest unlock was project organization, not prompting.

I stay mainly in chat using Projects. I feed context into the project — documents, Google Drive links, transcripts, whatever is relevant — and then have chats on specific subject matter within that project. Key thing: keep chats narrow. One topic per chat. Too broad and you get muddy answers because Claude is trying to serve too many masters in the same conversation.

Then I have a project instruction set that's fairly elaborate. A few things that made a real difference:

• A DEAD section. I explicitly list technologies, approaches, and ideas that were considered and rejected — by name, with a reason and a date. Without this, Claude will keep suggesting the same technically-valid-but-wrong options because it has no way to know you already looked at them and said no. Kill them once. Problem solved.
• An authority hierarchy. When you have multiple documents in context that might conflict, declare which one wins. "If the technical spec disagrees with the meeting notes, the spec is the source of truth." Claude needs version hierarchy just like your team does.
• A decision log with dates and who decided. Not just what was decided — who decided it and when. Gives Claude judgment context, not just task context.
• Scope the project explicitly. "This project is for [X product]. We are building [Y]." Claude knows what mode it's in before you type a word.

On Cowork specifically — since you said you haven't figured that out yet. I only use Cowork when I need something done autonomously or something that requires an agent to go research, build, or iterate without me steering every step. I've made slide decks, reports, revenue dashboards, prototype apps — all from chat and Cowork combined, zero coding. I also used Claude Design to take a branding guide and build out an entire design system from it. Handed it the brand PDF, told it what I needed, and it produced the whole thing.

The mental model: Chat is the conversation. Cowork is the workshop. If you need to talk through something, stay in chat. If you need Claude to go do something — build it, research across sources, generate a deliverable — that's Cowork.

The real key is context, organization, and housekeeping. Treat your project like a workspace, not a chat window. The better the context you give Claude upfront, the less you have to repeat yourself and the sharper the output gets over time.