Mastering ChatGPT: Advanced techniques for workplace communication and productivity | Hiten Shah

Hiten Shah is a serial founder who has started several analytics and security companies, including Crazy Egg and KISSmetrics. The latest one, Nira, was acquired by Dropbox in 2024. In this episode, he shares how he turns ChatGPT from a simple chatbot into a personal workplace coach, sales strategist, and productivity multiplier. *What you’ll learn:* 1. How to create AI versions of your boss by loading operating manuals and personality tests into ChatGPT projects 2. A simple approach for turning sales frameworks into customized discovery call scripts for any product 3. Why context is everything—and how to load ChatGPT with the right information before asking for outputs 4. The “show it what great looks like” technique that dramatically improves AI responses 5. How to build a personal AI coach using your own personality assessments and communication style 6. Why you should use temporary sessions for random queries to keep your main ChatGPT memory clean *Brought to you by:* Paragon—Ship every SaaS integration your customers want: https://useparagon.com/HowIAI Notion—The best AI tools for work: https://www.notion.com/howiai *Where to find Hiten Shah:* Blog: https://hitenism.com/ X: https://twitter.com/hnshah LinkedIn: https://www.linkedin.com/in/hnshah/ *Where to find Claire Vo:* ChatPRD: https://www.chatprd.ai/ Website: https://clairevo.com/ LinkedIn: https://www.linkedin.com/in/clairevo/ X: https://x.com/clairevo *In this episode, we cover:* (00:00) Introduction to Hiten (02:55) Why Hiten primarily uses ChatGPT (04:12) The importance of context and memory management (07:58) Demo: Creating “What Would Morgan Do” project (13:30) Using personality types to improve AI coaching (16:20) Building a personal operating system in ChatGPT (20:55) Mixing structured frameworks and personal context (23:20) Demo: Winning by Design sales framework implementation (30:00) Creating discovery call scripts (31:44) Using ChatGPT’s deep research feature to understand Claire’s leadership style (36:30) Lightning round and final thoughts *Tools referenced:* • ChatGPT: https://chat.openai.com/ • Claude: https://claude.ai/ *Other references:* • Hiten's Google Doc: https://docs.google.com/document/d/1j15hoR3qZLQMJuW-mtfYFyhXM0CpYHQkZJuUgqHBsZs/edit?tab=t.0 • Winning by Design: https://winningbydesign.com/ • Enneagram: https://www.enneagraminstitute.com/ • Human Design: https://humandesign.tools/ • Myers-Briggs: https://www.myersbriggs.org/ • DISC: https://www.discprofile.com/ • Lex: https://lex.page/ • The Lean Startup: https://theleanstartup.com/ • Sean Ellis score: https://pmfsurvey.com/ _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email jordan@penname.co._

Claire VohostHiten Shahguest

Jul 7, 202542mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Hiten Shah’s ChatGPT Projects for context-rich workplace communication workflows today

Hiten Shah explains why high-quality results from ChatGPT come from better inputs—especially persistent context via Projects, curated files, and deliberate memory management.
He demonstrates building “replicas” of key people (your boss, yourself, teammates) by uploading artifacts like operating manuals, writing samples, and personality frameworks, then prompting ChatGPT to generate tailored advice and conversation prep.
He also shows a repeatable pattern for turning great outputs into reusable instructions (“codify the output”), including having a “project for projects” to generate future project setups and prompt templates.
A second major workflow applies an external sales framework (Winning by Design) by loading PDFs into a Project, generating discovery scripts (e.g., SPICED questions), and iterating manually before attempting automation.

IDEAS WORTH REMEMBERING

5 ideas

Treat context as the primary lever for quality.

Shah repeatedly emphasizes front-loading context (files, examples, explicit goals) or building it over time in a Project rather than expecting one-shot prompts to work reliably.

Use temporary chats for anything you don’t want remembered.

He separates “random” or disposable work into temporary sessions to avoid polluting long-term memory, and uses pruning when ChatGPT indicates it stored something.

Exemplars beat abstract instructions—“show it what great looks like.”

Instead of describing desired output, he feeds strong examples (e.g., a manager’s operating manual, past great writing) so the model can emulate style, priorities, and decision patterns faster.

Build a ‘boss simulator’ to prep high-stakes conversations.

By uploading a manager’s operating manual plus related articles and adding simulation instructions, he gets tailored advice on how to pitch ideas, frame updates, and anticipate objections in that manager’s voice.

Add relationship frameworks to personalize communication guidance.

Layering Enneagram/Human Design/DISC/Myers-Briggs context helps the model suggest interaction tactics (e.g., how a Type 9 should work with a Type 5) and propose actionable formats like weekly check-ins.

WORDS WORTH SAVING

5 quotes

Context is everything.

— Hiten Shah

Just show it what great looks like. It’s like a human.

— Hiten Shah

This is a tip for all the ICs out there: Go and replicate your boss, and prep for conversations with them.

— Claire Vo

I think people are racing to automation, and that’s a mistake.

— Hiten Shah

If you’re gonna treat it like a human, think about incentives.

— Hiten Shah

ChatGPT memory hygiene: temporary chats, archiving, pruningProjects as persistent context containers“Show it what great looks like” via exemplarsCodifying outputs into reusable instructionsReplicating your boss for manage-up and pitch prepPersonal OS: personality tests + voice/tone artifactsFramework-driven sales enablement using PDF knowledge bases

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