New Hire Checklist

Welcome to Online Optimism

New Optimist? This is your AI onboarding checklist. Work through it in your first two weeks. Your progress saves automatically, so you can pick up where you left off.

👋 Hi! Welcome to the team. This checklist walks you through everything you need to know about how we use AI at OO. Check off items as you complete them. Your progress is saved in your browser, so no one else can see it — it's just for you.

Week 1: The foundations

  • Read Module 1: AI Philosophy and Policies.

    This covers the four-tier usage policy, data privacy rules, and the golden rule of working with AI at OO. Everything else builds on this.

  • Get your Claude account access from your VP.

    You'll need access to the agency Claude Pro account to use client Claude Projects. Ask your VP or manager to set this up.

  • Join #ai-and-automations on Slack.

    This is where AI wins, questions, tool updates, and Claude Project changes get posted. You want to be in here.

  • Complete Module 3: Prompt Engineering Fundamentals.

    This is the most-requested training. Learn the CRISP framework and try the interactive Prompt Lab. This is the skill that makes the biggest difference in how useful AI is for your work.

  • Read the full AI Copywriting Words to Avoid doc.

    You'll need to know this list cold. These words show up constantly in AI output and they're a quality tell. Bookmark it. We also have a searchable version in the sidebar of every module.

Week 1–2: Get hands-on

  • Review your assigned clients' Claude Projects and Communication Codexes.

    Log into Claude, find the Projects for the clients you're working with, and read through the instructions and uploaded files. This is what gives Claude the client's voice. If something looks outdated, flag it to your AE.

  • Read Module 4: Claude Projects.

    Understand how projects work, what makes them good, and how they get updated. If you're going to be working with client content, this module is essential.

  • Set up your own personal Claude Project.

    Follow the guide in Notion. Create a project for your own work, upload your most relevant documents, and test it with a real task.

  • Read your department's playbook in Module 8.

    Module 8 has sections for Content & SEO, Social, Design, Digital Ads, Web Dev, and Account Executives. Go straight to yours and learn the workflows that apply to your role.

  • Read Module 5: Writing with AI.

    Even if your role isn't primarily copy-focused, you'll write AI-assisted content at some point. This module covers the OO five-step workflow and the common tells that make AI copy recognizable.

Before your first month is up

  • Read Module 2: Choosing the Right Tool.

    Know when to use Claude vs. ChatGPT vs. Cursor vs. Ideogram. The tool table is a useful reference to bookmark.

  • Read Module 6: The Communication Codex System.

    Understand what a Codex is, what's in it, and how it feeds Claude. You don't need to build one right away, but you need to understand the system.

  • Read Module 7: Automation and Advanced AI Workflows.

    Learn how the AI AE Assistant works, what Zapier is for, and what Claude Code has built at OO. You'll be a better contributor to #ai-and-automations with this context.

  • Use AI for a real work task and share what you made.

    Pick something from your actual work. Use the CRISP framework. Apply the banned words check. Share the result (with context on your process) in #ai-and-automations. You don't have to be perfect. You just have to start.

  • Ask a question in #ai-and-automations.

    No question is too basic. If you're confused about something AI-related, post it. Someone else probably has the same question, and this is how we build a shared knowledge base.

When you're ready to go deeper

  • Complete the full 10-module course.

    Modules 1, 3, and your department's section from Module 8 are priority. The rest are worth doing in full, especially if you're interested in automation or advanced workflows.

  • Take one external AI course.

    The HubSpot AI for Marketers course is free and about 2 hours. Andrew Ng's AI for Everyone is also excellent for building a solid conceptual foundation. Both are listed in the Resource Directory.

  • Complete the Module 10 final project.

    Pick one of the four options (build a Claude Project, write a piece of AI-assisted content, propose an automation, or create a prompt library). Share it in #ai-and-automations when you're done.

A few things worth knowing as you get started

  • AI at OO is still a work in progress. We're figuring this out as an industry and as an agency. Your observations and ideas are genuinely useful.
  • The best way to get good at AI is to use it on real work, not to read about it. The course is a foundation, but experience is what builds skill.
  • Skepticism is welcome. Some Optimists are deeply skeptical of AI on ethical grounds, and that perspective matters. You don't have to be enthusiastic. You do have to use the tools we've adopted, and you do have to follow the policies.
  • When something doesn't work or doesn't make sense, ask in #ai-and-automations. We're building this together.