A working artifact for the cohort — what was taught, what was asked, what to do next. Built from the full audio and chat transcripts of the April 29 session.
AI won't fix what's broken — it scales it. Start at data, not at the application. Move from tasks to systems. Most of us are still at the chatbot stage of the maturity ladder, and that's fine. The unlock for this cohort is to stop typing prompts and start talking to Cowork like an intern — describe the outcome, ask it to build the skills, schedule the workflow. Then iterate the skill, not the prompt.
Five principles Andy and Jonathan kept returning to. If you internalize only these, you'll outperform the cohort.
Bolting AI onto messy data, undefined process, or disconnected systems just makes the mess faster and louder. Sequence matters: data → process → systems → application.
"People start at the application layer. Start at the data layer and work your way up." — Jonathan Moss
"Write me an email" is a task. "Watch my calendar, prep me for next week's calls, and surface signal from CRM activity" is a system. Tasks are great — but the system is what compounds.
Roughly 30¢ of every dollar gets eaten by searching, decision delay, missed signals, and threading people together. The biggest AI wins target coordination — not just individual productivity.
The 5-question maturity assessment showed the cohort clustered at Levels 1–2 (chatbots and simple automation). The class isn't behind. The point of these 8 weeks is to climb.
"Be authentic with where you are. Resist the urge to run if you're really crawling." — Andy Jolls
Both demos started with a voice-style description of the desired outcome — not a hand-crafted prompt. Cowork's skill creator turns that conversation into reusable skills, scheduled tasks, and connectors automatically.
The cohort's tool mix has shifted dramatically in one quarter. In January the class skewed ChatGPT; today it skews Claude. Use the right tool for the job — most attendees run two or more.
| Tool | Where it wins | Where it struggles | Cohort signal |
|---|---|---|---|
| Claude (Chat / Cowork / Code) | Enterprise, deep work, agentic workflows, building skills | Capacity limits hit by noon for heavy users; ARM laptop gaps in Cowork | Dominant — ~80% of class |
| ChatGPT | Consumer reach, breadth of integrations, polished output | Less flexible for skill-based agentic patterns vs Claude | Still strong globally |
| Microsoft Copilot | "Approved at work" — already wired into M365 stack | Less expressive; many here feel "forced" to use it | The default many didn't choose |
| Gemini | Visuals, Google Workspace deep integration, "Gems" | Lagging on agentic UX vs Claude/ChatGPT | Up and coming |
| Perplexity | Quick research, multi-model access in one UI | Less suited for building durable workflows | Personal/research go-to |
| Specialty (Lovable, Replit, Wispr Flow, NotebookLM, Manus, Clay) | Purpose-built lifts: portfolio sites, voice capture, doc synthesis, vibe-coding, prospecting | Stack sprawl & cost adds up | Power users layer them in |
Both demos showed the same loop: describe the outcome conversationally → let Cowork create the skills → schedule the workflow → iterate the skill, not the prompt.
Built so the April 1, May 1, June 1 reports run themselves — instead of Andy doing it manually each quarter.
Built end-to-end in one prompt: research → PowerPoint deck → interactive HTML dashboard, on the 1st of every month.
A common point of confusion. Here's the mental model the instructors landed on.
Always-on rules. Tone, voice, output formats you want everywhere. Set once.
Scoped context for one body of work. Files, references, reusable assets. Folders = local + flexible. Projects = cloud + tighter scope.
Specialized "interns." Domain expertise + an output spec. Invoked when the situation calls for them. Iterate the skill, not the prompt.
The actual ask in the moment. Should mostly say what and why — the skill handles the how.
From the live assessment, ~106 respondents clustered at Level 1. The 30-question version goes deeper — take it during the week.
Pick three. Resist the urge to do all ten.
CLAUDE.md, _reference/, _templates/, then per-project folders with their own CLAUDE.md + HANDOVER.md.These came up in chat or on mic and didn't get a clean answer. Future classes — and the Slack — will keep working them.
Cohort survey: tool mix, deployment patterns, blockers.
10K rows, 30+ columns. Use it if you're between roles or blocked from real data.
Scott Wueschinski (GTMify) is curating a deployable GitHub repo of Cowork + Claude Code skills built for GTM teams. He's taking skill requests from the cohort right now — send yours in before Class 4 to get it in the package.
Drop your skill request