Learn by Doing

Milestone Projects

Real projects. Real outputs. Each one builds on the last. Pick the tier that matches where you are and work your way up — by the time you finish Advanced, AI is a genuine part of how you work.

Beginner

Start Here

No experience needed. These two projects take under 30 minutes each and produce something real you can use at work today.

01 ~20 min

Your First AI-Assisted Email

Write a real work email you've been putting off — using AI to draft it. Not a practice email. An actual one you'll send.

Goal

Send one AI-drafted email (edited and approved by you) to a real recipient.

Steps

  1. 1.Pick an email you need to write — a follow-up, a request, an update.
  2. 2.Open Claude or ChatGPT. Use the Email Drafting Assistant prompt from the library.
  3. 3.Paste in your rough notes and fill in the brackets.
  4. 4.Edit the output so it sounds like you. Send it.

You did it when...

A real email goes out with AI-drafted copy you edited and approved.

Recommended Tool

Claude or ChatGPT

02 ~15 min

Summarize a Document in 5 Minutes

Take a report, article, or document you've been avoiding and get a plain-English summary with the key takeaways in under 5 minutes.

Goal

Produce a 150-word summary of a real document that you can share or act on immediately.

Steps

  1. 1.Pick a document you need to read — a report, a policy, a long email thread.
  2. 2.Open NotebookLM (best for PDFs) or Claude. Paste or upload the document.
  3. 3.Ask: "Summarize this in plain English. What are the 3 most important takeaways?"
  4. 4.Ask one follow-up question about something that wasn't clear.

You did it when...

You can explain the document's key points to someone else without re-reading it.

Recommended Tool

NotebookLM (for PDFs) or Claude

Intermediate

Build the Habit

You've tried AI once or twice. These projects make it a real part of how you work — not a one-off experiment.

03 ~60 min

Build Your Personal Prompt Library

Create 5 custom prompts tailored to your specific job — not generic templates, but prompts written for your exact role, team, and recurring tasks.

Goal

A saved, personal prompt library you'll reuse — stored somewhere you can access it in 10 seconds.

Steps

  1. 1.List the 5 most repetitive writing or thinking tasks in your job.
  2. 2.For each, start with the closest prompt from this library and customize it — swap in your actual role, your team's terminology, your typical audience.
  3. 3.Test each prompt on a real task. Refine until the first output is 80% usable.
  4. 4.Save them in a Notion page, a Google Doc, or a plain text file — somewhere fast.

You did it when...

You have 5 tested, saved prompts and used at least 3 of them on real work this week.

Recommended Tool

Claude or ChatGPT + Notion or Google Docs

04 4 weeks

The One-Month Weekly Report Challenge

Use AI to write your weekly status report every week for a month. Track how long it takes and how the quality changes. By week four, this will feel effortless.

Goal

Four AI-assisted weekly reports sent. A repeatable process you can run in under 10 minutes.

Steps

  1. 1.Week 1: Use the Weekly Report Generator prompt. Note how long it takes and what you had to fix.
  2. 2.Week 2: Refine the prompt based on last week's edits. Make your notes more structured going in.
  3. 3.Week 3: Time yourself. Can you go from notes to sent report in under 15 minutes?
  4. 4.Week 4: Under 10 minutes. Write down what you learned. That's your process now.

You did it when...

Four reports sent. Week 4 takes under 10 minutes start to finish.

Recommended Tool

Claude or ChatGPT

Advanced

Ship Something Real

AI is already saving you time. These projects go further — you're building systems and sharing knowledge. Others will notice.

05 2–3 hrs

Design a Full AI Workflow

Pick one recurring, multi-step work task and rebuild it with AI assistance at every stage. Document the workflow so someone else could run it.

Goal

A documented, repeatable AI workflow for one recurring task — ready to hand off or present.

Steps

  1. 1.Choose a task you do at least monthly: a report, a review, a planning cycle, an ops process.
  2. 2.Map every step currently. Then identify where AI can help — drafting, summarizing, analyzing, formatting.
  3. 3.Build a custom prompt (or set of prompts) for each AI touchpoint. Test them on a real cycle.
  4. 4.Write a one-page "workflow doc": inputs, AI steps, human review points, final output.
  5. 5.Run it twice. Refine. Share with one teammate.

You did it when...

The workflow doc exists, you've run it twice, and one other person has used it or reviewed it.

Recommended Tools

Claude + Notion or Google Docs for the workflow doc

06 3–4 hrs

Build a Team Onboarding Guide with AI

Create a complete onboarding document for someone new to your team or role — the kind of guide you wish existed when you started. Build it with AI as your writing partner.

Goal

A real, shareable onboarding guide your team uses — not a skeleton that sits in a drawer.

Steps

  1. 1.Brain-dump everything a new person needs to know: tools, processes, key people, unwritten rules, common mistakes.
  2. 2.Paste your notes into Claude. Ask it to organize them into a structured onboarding guide with sections and clear headings.
  3. 3.Have AI draft the prose for each section based on your notes. Edit for accuracy and voice.
  4. 4.Add a "30/60/90 day" section: what to learn, do, and own in the first three months.
  5. 5.Share it with one current team member for feedback. Publish it somewhere your team can find it.

You did it when...

The guide is published, reviewed by a teammate, and ready for the next person who joins.

Recommended Tools

Claude + Notion, Confluence, or Google Docs

Ready to start? Pick up the right prompt.

Browse the Prompt Library →