Director session

Working in
Claude Cowork.
Five moves.

Beyond prompting tips. The habits that compound.

60 min 2026-04-29
02 / 11
Move 01

Feed it the
real thing.

Paste the actual document. The email thread. The screenshot. Claude reasons FROM material — not from your description of it.

→

Describing your situation is a lossy compression. Just show it.

03 / 11
Move 02

Correct, don't
restart.

"Too formal. Match the tone of this email I sent last week." "Good structure, wrong audience. This is for the board, not eng." "Keep the first half. Rewrite the recommendation."
→

Every correction teaches Claude for the rest of the conversation.

04 / 11
Move 03

Think together,
don't just delegate.

"I'm leaning toward splitting the platform team in two. Here's my reasoning. What am I not seeing? What will people push back on? Then help me draft the message."

→

The highest-value use isn't production. It's decision quality.

05 / 11
Move 04

Build all of them,
then pick.

Don't ask "what's the best narrative for the board?" Ask for three options — growth story, efficiency story, platform story. Draft a one-pager for each. Then pick.

→

Generation is cheap. Judgment is yours. Make Claude do the cheap part.

06 / 11
Move 05

Set up your project.

Add project instructions — who you are, how you work, what matters
Upload key files — strategy docs, org charts, templates
Let memory accumulate — corrections become permanent knowledge
Week 1: you brief Claude like a new hire.
Week 4: Claude briefs you.
→

A single conversation is disposable. A project compounds.

07 / 11 Live demo

Try a move. Right now.

claude cowork — director-session
Welcome to Claude Cowork. Type a message to begin.
❯

Click the terminal and type. Press Enter to send.

08 / 11 Your turn

Pick a door.

Each one leads to a different way to use your next hour with Claude.

Decide
Draft
Explore

Click a door to reveal your challenge.

09 / 11 Recap

The five moves.

01 Feed it the real thing. Paste the doc, the email, the screenshot. Don't describe it.
02 Correct, don't restart. Push back in the conversation. Each correction teaches.
03 Think together. Use it for decisions, not just drafts.
04 Build all of them. Ask for three options. Pick the best one yourself.
05 Set up your project. Instructions + files + memory = compound returns.
10 / 11

Every conversation
grows the network.

What you teach it today, it knows tomorrow.

11 / 11

You haven't gained a tool.
You've gained a coworker.

Tend the relationship. The rest follows.

JC · Director session · 2026-04-29
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