Operators Using AI
Your Plan

30-Day Roadmap

You already use AI for basic stuff. This is about going deeper, not starting from scratch. Each week builds on the last.

Week 1Make It Your Default
  • The "Claude Everything" challenge: for one week, go to Claude before Google for everything. Random curiosity, work questions, "help me think through this." You're training a reflex. (A good gut check: next time you're about to ask someone a question, pause and think "could I have asked Claude this first?" Not instead of talking to people — you should still do that — but before. You'll be surprised how often the answer is yes.)
  • Set up your user profile in Claude (Settings → Profile). Tell it who you are, what you do, how you communicate. This makes every future conversation better.
  • Download the Claude desktop app if you haven't. Get Pro ($20/mo) or get your company to expense it.
  • Pick one real work task you'd normally spend 30+ minutes on and do it with Claude instead. A report, a project plan, a vendor comparison, whatever.
Week 2Work With Files
  • Upload something messy to Claude: a spreadsheet that needs cleaning, a PDF to extract data from, a doc to restructure. Get comfortable giving it source material.
  • Try a multi-step task in one conversation: "read this doc, summarize the key points, then draft an email to my team about it." Let it chain things together.
  • Before your next project, ask Claude to get you up to speed: "I'm about to [do X]. Give me a refresher on the key principles of [topic], common mistakes, and questions I should be asking." Works even for stuff you already know.
  • Connect Claude to one tool you use daily: Slack, Google Drive, or Notion. See what changes when it can pull your actual data.
Week 3Build Things
  • Try Cowork mode: point Claude at a folder of files and ask it to do something real with them. Create a report, build a tracker, organize a mess.
  • Try one vibecoding project: describe a simple tool you wish existed ("a dashboard that tracks X" or "a calculator for Y") and see what comes out.
  • Explore a plugin or skill relevant to your role. Install one and use it on an actual task.
  • Quick audit: what have you used Claude for in the past two weeks? What worked? What felt forced? Adjust.
Week 4Make It Yours
  • Look at your week and pick 2-3 recurring tasks that Claude could handle or speed up. Set them up so they're easy to repeat.
  • Look into API keys for tools you use (Notion, Slack, etc.) so Claude can connect to them directly. Ask your IT person or check the tool's settings page under "integrations" or "developer."
  • Show someone else one thing you've been doing with AI. Doesn't have to be a big demo. Just "look at this."
  • Write down your before/after: what used to take you hours that takes minutes now? This is useful for your own clarity, and it's useful if you ever need to make the case internally.
The real goal

By day 30, using AI should feel normal. Not a separate activity, just how you work.