Day 2 - Session 1: Basic Prompting Foundations

How do we populate the context window effectively?

Author

Dr Brian Ballsun-Stanton

Published

September 9, 2025

Good Morning!

Today’s Big Question

How do we populate the context window effectively?

This Morning

  • Share your annotated prompts
  • Learn basic prompting theory
  • Practice iterative questioning
  • Begin systematic annotation

Show Me Your Prompts! (15 min)

Our First Sharing Session

  1. Who tried the homework prompt?
  2. What surprised you about the AI’s questions?
  3. What did you highlight in pink (didn’t work)?
  4. What did you highlight in blue (worked well)?
  5. What other prompts did you experiment with overnight?

Remember: We learn from failures as much as successes


What We’ll Learn This Session

By the end of this morning, you will be able to:

  • Explain: How iterative questioning builds context
  • Identify: Which AI questions advance vs. derail your work
  • Track: When prompts succeed vs. fail through annotation

Basic Theory: Rules of Thumb

The Engineering Method

“Solving problems using rules of thumb that cause the best change in a poorly understood situation using available resources” - Bill Hammack

For Prompting, This Means

  • We don’t know exactly why things work
  • We develop local heuristics through practice
  • What works depends on context
  • Iteration beats perfection

Key Prompting Principles

1. Context is Everything

The AI only knows what’s in the current conversation

2. Specificity Matters

Vague instructions → vague outputs

3. Iteration is Expected

First attempts rarely perfect

4. Structure Helps

Break complex tasks into steps


Exercise: Weakening the Prompt (15 min)

Remember Yesterday’s Prompt?

Take the “ask me one question at a time” prompt from yesterday.

Now Break It

Try: “Help me figure out my goals for the week” without any of the setup.

Compare Results

What changes? Put up green sticky when complete.


What Makes Prompts Effective?

Good prompts

  • One task at a time
  • High scaffolding
    • Is it clear what the intention of the conversation is?
    • Is it clear what the register is?
    • Are the answers easily falsifable?

Bad Prompts

  • Generic
  • Fact based
  • Poorly populated context window
  • Multiple questions

Annotation Practice (20 min)

On the Conceptboard

With your conversation from the weakening exercise:

  1. Your prompts: Mark what instructed useful behavior
  2. AI responses: Note where it followed/ignored instructions
  3. Patterns: What words consistently trigger better responses?

Share with Your Neighbor

Compare annotations - same patterns?


The Context Window

Think of it as a bucket: - Everything must fit inside - New information pushes out old - Quality matters more than quantity - You control what goes in

Your prompts are the recipe for filling this bucket effectively.


Exercise: Playing with GPT-2 (10 minutes)

Go visit mirror.zad-giessen.de/perplexity

We will talk about why the context window matters so much as you play with it.

Other concepts:

  • Tokens
  • Temperature

Thou shalt not allow an error to live.


Looking Ahead

Today: Metaprompting

  • Can AI write its own prompts?
  • The blank page problem
  • Epistemic humility (or lack thereof)

Tomorrow: What Can We Verify?

  • Working with documents
  • Extracting vs. interpreting
  • Model differences matter

Key Takeaways

  1. Prompting is engineering - rules of thumb, not laws
  2. Iteration is required - expect to refine
  3. Context accumulates - each exchange builds on the last. Do not allow errors to remain.
  4. Your judgment develops - through annotation and reflection

Before the Break

  • Save your annotated conversations
  • Add all prompts to our grimoire
    • Let us know which ones worked and which ones didn’t
  • Think about: What patterns are you noticing?

See you at 11:00 for metaprompting!