How Hiten Shah Transforms ChatGPT Into a Powerful Workplace Tool
By: Hiten Shah Host: Claire Vo Source: How I AI (ChatPRD) Type: podcast
Summary
How I AI episode with Hiten Shah, serial founder (Crazy Egg, KISSmetrics), one of the most advanced ChatGPT users. Three workflows using ChatGPT Projects for persistent, context-aware AI assistants: (1) “What Would Morgan Do” — clone your boss by uploading their operating manual and articles into a ChatGPT Project, use meta-prompting to generate project instructions, rehearse pitches with an AI that gives advice in boss’s specific style; (2) “Personal OS” — upload personality assessments (Enneagram Type 9, Human Design 1/3, Myers-Briggs, DISC) for AI self-coaching, combine with boss’s profile for relationship-specific strategies, use for real-time emotional regulation and perspective shifts; (3) Operationalize sales frameworks — upload Winning by Design PDFs, generate SPICE discovery guides customized for specific products, enrich with deep research context. Core principle: great outputs require great inputs — show AI what “great” looks like with structured context and examples.
Key Ideas Extracted
- ChatGPT Projects as specialized AI assistants: Persistent context, uploaded files, and custom instructions create dedicated spaces loaded with domain knowledge
- Meta-prompting for project setup: Ask ChatGPT to generate its own project instructions from uploaded documents — clever shortcut that produces better instructions than writing them yourself
- Clone your boss for conversation rehearsal: Upload manager’s operating manual and articles, then rehearse pitches and difficult conversations with an AI that responds in their specific style
- Personal OS for self-coaching: Upload personality framework results for AI-powered emotional regulation, relationship navigation, and perspective shifts — like having an executive coach on-call 24/7
- Combine personal + interpersonal context: Cross-reference your Enneagram/DISC with your boss’s type for relationship-specific communication strategies
- Operationalize static frameworks: Turn dense sales methodology PDFs into interactive tools that generate customized scripts on demand
- Two-step enrichment pattern: First teach AI the framework, then provide specific subject matter context for highly tailored outputs
- Great outputs require great inputs: The key differentiator is doing the work upfront to provide context, frameworks, and examples of what “great” looks like
Notes
- Published Jul 7, 2025 on How I AI (ChatPRD). ~9 min read. (Note: filename says 2025-06-02 but actual publication date is Jul 7, 2025)
- Sponsors: Paragon, Notion
- Hiten Shah background: Serial founder, 20+ years B2B SaaS — Crazy Egg, KISSmetrics
- Tools: ChatGPT Projects (the key feature enabling persistent context)
- Personality frameworks: Enneagram (Type 9), Human Design (1/3), Myers-Briggs, DISC
- Sales framework: Winning by Design / SPICE model
- Three companion workflow guides published Jan 8, 2026
Raw Content
Re-scraped from ChatPRD 2026-02-16. Full article content captured in Summary and Key Ideas above.