Welcome to the good stuff.
The Optimist's Guide to Working with AI
This AI training course teaches Optimists how to successfully use AI in our day-to-day processes. Ten modules covering everything from basic philosophy to best practices to advanced automation, built specifically for how we actually work at Online Optimism.
Start with Module 1 →Course Modules
Work through these in order, or jump to what you need most. Your progress saves automatically.
AI at Online Optimism: Our Philosophy and Policies
What we believe about AI, the four-tier usage policy, data privacy rules, and what to do when Claude is having a bad day.
Choosing the Right Tool for the Job
Claude vs. ChatGPT vs. Gemini vs. Cursor vs. Ideogram. When to use what, and why "just use Claude" is usually right.
Prompt Engineering Fundamentals
The CRISP framework, before-and-after examples, and an interactive Prompt Lab to practice with. This is the most-requested module.
Claude Projects: Setup, Maintenance, and Best Practices
How to build a great Claude Project, what to upload, how to maintain it, and a real case study from Buddy Punch.
Writing with AI (Without Sounding Like AI)
Why AI copy gets flagged, the OO five-step writing workflow, and special rules for Reddit content.
The Communication Codex System
What a Codex is, how it feeds Claude, what's in it, and how to keep it updated when clients give feedback.
Automation and Advanced AI Workflows
Zapier basics, a deep dive into the AI AE Assistant, and what Claude Code can actually build.
Department-Specific AI Playbooks
Tailored guidance for Content & SEO, Social, Design, Ads, Web Dev, and Account Executives.
Advanced Claude Tools
Claude Code on desktop and the web, what you can build with it, and why you might want to.
Final Project
Put everything together in a capstone project and share it in #ai-and-automations. You earned it. 🎉
Resource Directory
Every Notion page, Google Doc, Slack channel, and external course link in one searchable place.
New Hire Onboarding
Just joined Online Optimism? Start here. A step-by-step checklist to get you up to speed on AI at OO.
The golden rule of AI at OO
Never hand off to AI something you don't understand well enough to check.
AI is an assistant. You're the one who knows the client, the brief, and what "good" looks like. That judgment is yours, not Claude's.
Why this course exists
In late March 2026, we ran an internal survey about how Optimists are using AI. Sixteen of nineteen people responded. The results were honest, a little humbling, and genuinely useful.
Most of us feel decent about using AI, but undertrained. Several people said there's been no formal training at all. One person is deeply skeptical. A few people are getting genuinely good results. This course tries to meet everyone where they are.
The top things you asked for
- Clear guidelines on when to use AI and when not to
- Prompt engineering training (the #1 request)
- A centralized place to find all the AI stuff
- Better understanding of how Claude Projects work
- Guidance on privacy, data, and what's safe to put into LLMs
- Help making AI output sound less like AI
All of that is in this course.