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Week 3: Advanced tactics for AI chatbots

US/EMEA cohort: Tuesday, July 22 at 9am PT | 12pm ET | 5pm UK
Pacific cohort: Tuesday, July 22 at 4pm PT | Wednesday, July 23 at 9am AEST

Overview

In this session, we took a deeper dive into AI chatbots, including advanced prompting tactics and the latest advanced features. And Fiona briefed all on the Capstone Project.

Quick Links
📺 Session recording
🌟 Key points
💻 Session slides
💭 Workout
📚 Further resources
👩‍💻 Capstone Project brief

Key points

Top 5 prompting techniques:

  • Prompt chaining: Start with a base prompt, refine through iterative follow-ups (e.g. “make it shorter”, “rewrite less formal”). Also used to repurpose content (e.g. turn a speech into a follow-up email).

  • Quick probing replies: Use fast follow-ups like “argue the other side” or “what risks exist?” to deepen reasoning and expand creativity—your “cognitive trampoline.”

  • Tree of Thoughts (ToT) prompting: Complex decision-making method involving generating multiple options, scoring them, and iterating. Best for big personal or strategic decisions.

  • Prompt chunking: Break large tasks (e.g. planning an offsite) into smaller subtasks for better quality output and easier synthesis.

  • Megaprompting + meta-prompting: Mega = highly detailed, interactive prompts. Meta = ask AI to help write your mega prompt collaboratively. Time-consuming upfront, but saves time for large tasks (e.g. survey analysis, strategy planning).

Advanced AI chatbot features

  • Advanced Reasoning Models: Use for complex tasks like onboarding plans or career development—more nuanced outputs.

  • Advanced Research Models: Ideal for sourcing vendors, writing briefings, or digesting technical content.

  • Advanced Voice: Talk through challenges, draft on-the-go, or rehearse difficult conversations.

  • Pages/Canvas/Artifacts: Split-screen UI for editing documents while prompting.

  • Connected apps: Some experimented with inbox summaries via Copilot or Zapier integrations.

  • Memory: Use custom instructions to preserve tone, voice, and preferences.

Capstone Project Brief — you have three options, debrief due August 15; share progress in WhatsApp.

  1. Beginner: Prompting playbook

  2. Intermediate: Build your own AI assistant

  3. Advanced: Automate your workflow (e.g. via Zapier or Power Automate)

Top ways for EAs to use advanced models:

Advanced Reasoning models

  1. Decision support: Compare options or scenarios using structured frameworks (e.g. SWOT, ToT)

  2. Calendar optimization: Restructure your exec’s week to reduce context switching and protect deep work time.

  3. Meeting summaries & next steps: Turn raw notes into clear, prioritized follow-ups with owner/action/deadline formatting.

  4. Message crafting & tone shaping: Tailor comms (internal or external) with the right voice, structure, and framing for impact.

  5. Critical thinking partner: Pressure-test your assumptions, explore alternative solutions, or work through complex challenges step-by-step.

Advanced Research models

  1. Industry & trend intelligence: Summarize market shifts, AI use cases, or regulatory updates tailored to your exec’s domain.

  2. Meeting & stakeholder briefings: Build insight-rich profiles on new investors, speakers, board members, or partners.

  3. Tool & vendor evaluation: Compare software or service providers side-by-side, based on your team’s needs and constraints.

  4. Event & venue scouting: Research high-end, well-matched locations for offsites, strategy days, or executive dinners.

  5. Synthesize across sources: Combine learnings from multiple reports, articles, or decks into a single digestible briefing with strategic insight

Session slides

Workout

AKA your post-session actions to take

1️⃣ Create a writing style guide to use in future prompts, using the following prompt:

  • Act as an experienced copywriting coach. Take the below samples of my [emails] and analyse them. Create an extremely comprehensive tone of voice and style guide that describes my particular style of [email] writing. Include specifics like commonly used phrases and emojis, structure of [emails], and any other details to describe the [email] writing style with as much specificity as possible. 

2️⃣ Test either a Reasoning or Research model, share reactions in Whatsapp