Day 16 challenge

Goal: master system prompt engineering for reliable agent behaviorTheme: context engineering week - prompt engineering fundamentalsTime investment: ~25 minutes
Welcome to Day 16 and Week 4! You’ve built sophisticated agents across multiple domains. Now you’ll master context engineering - starting with the foundation: system prompts. Today you’ll learn to craft prompts that reliably guide agent behavior, optimize tool usage, and produce structured outputs. System prompts are the invisible foundation that determines whether your agent is helpful or frustrating, reliable, or unpredictable.

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What you’ll accomplish today

  • Understand the anatomy of effective system prompts
  • Learn iterative prompt refinement techniques
  • Optimize prompts for better tool usage patterns
  • Master structured output generation
  • Apply prompt engineering best practices to your existing agents
This builds on your agent creation experience from Weeks 2-3. You’ll be refining and optimizing the prompts of agents you’ve already built.

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Step 1: Anatomy of effective system prompts

Before optimizing prompts, understand what makes them work:

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Core prompt structure

Effective system prompts follow a clear hierarchy: 
Identity: Who is the agent and what is their role?
Context: What environment do they operate in?
Capabilities: What can they do and how?
Constraints: What should they avoid or be careful about?
Output Format: How should they structure responses?
Examples: What does good performance look like?

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The psychology of prompts

Language models respond differently to different prompt styles: Authoritative vs. Collaborative: “You are an expert analyst” vs. “You help users analyze data” Specific vs. General: “Analyze Q3 revenue trends” vs. “Help with business analysis” Process-oriented vs. Outcome-oriented: “Follow these steps” vs. “Achieve this goal”
Prompt engineering mindset Think of prompts as job descriptions combined with training manuals. Be specific about both what to do and how to do it.

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Step 2: Analyze your current agent prompts

Let’s start by examining the prompts of agents you’ve built in previous weeks: Access your agent’s system prompt:
  1. Select one of your custom agents from the sidebar
  2. Click the agent’s name to open the About section
  3. Review the current instructions that define the agent’s behavior
Evaluate your current prompt: 
I want to analyze my current system prompt for effectiveness. Here's my current prompt:

[Paste your agent's current system prompt]

Can you evaluate this prompt across these dimensions:
- Clarity of role and identity
- Specificity of instructions
- Tool usage guidance
- Output format specifications
- Potential ambiguities or gaps
Watch how your agent analyzes its own instructions and identifies improvement opportunities.

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Common prompt issues

Look for these patterns in your current prompts:
  • Vague role definitions: “You are a helpful assistant” vs. “You are a revenue operations analyst”
  • Missing tool guidance: No instructions on when or how to use specific tools
  • Unclear output expectations: No formatting or structure requirements
  • Conflicting instructions: Contradictory guidance that confuses the model
  • Missing edge case handling: No guidance for unusual or complex scenarios

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Step 3: Iterative prompt refinement process

Prompt engineering is iterative. Here’s a systematic approach:

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The refinement cycle

  1. Identify specific issues with current behavior
  2. Hypothesize prompt changes that might address the issues
  3. Test changes with specific examples
  4. Measure improvement objectively
  5. Iterate until desired behavior is achieved

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Testing prompt changes

Create a test scenario: 
I want to test a prompt refinement. Here's a specific scenario where my agent isn't performing optimally:

[Describe the scenario and current behavior]

Current prompt section that might be the issue:
[Paste relevant prompt section]

Proposed improvement:
[Your suggested change]

Can you help me test this change and predict likely improvements?

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Measuring improvement

Track these metrics as you refine:
  • Task completion rate: Does the agent accomplish what’s requested?
  • Tool usage efficiency: Does it choose the right tools at the right time?
  • Output consistency: Are responses formatted correctly and consistently?
  • Error reduction: Fewer hallucinations, mistakes, or inappropriate responses?
Pro tip Keep a “prompt lab notebook” documenting what changes led to what improvements. This builds your intuition for effective prompt engineering.

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Step 4: Optimizing prompts for tool usage

One of the most critical aspects of agent prompts is guiding effective tool usage:

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Tool usage patterns

Tool selection guidance: 
When deciding which tools to use:
1. For data analysis tasks, prioritize Google Sheets for structured data
2. For research tasks, use web search first, then supplement with specific databases
3. For communication tasks, choose Slack for internal team updates, Gmail for external
4. Always explain your tool selection reasoning to the user
Tool sequencing instructions: 
For complex workflows:
1. Gather all necessary information before taking actions
2. Confirm destructive actions (deleting, sending emails) with the user
3. Use the most reliable tool first, then fall back to alternatives
4. Report progress after each major tool usage

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Example tool optimization

Before optimization: 
You can use various tools to help users with their tasks.
After optimization: 
Tool Usage Guidelines:
- GitHub: Use for code review, repository management, and development workflows
- Google Sheets: Use for data analysis, reporting, and collaborative documentation
- Slack: Use for team communications and status updates (always prefix with "Agent:")
- Gmail: Use for external communications and formal correspondence

Always explain why you're choosing a specific tool and ask for confirmation before taking actions that affect external systems.

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Step 5: Structured output generation

Reliable agents produce consistent, properly formatted outputs:

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Output format specifications

Structured response templates: 
For analysis tasks, use this format:
## Executive Summary
[2-3 sentence overview]

## Key Findings
- [Finding 1 with supporting data]
- [Finding 2 with supporting data]
- [Finding 3 with supporting data]

## Recommendations
1. [Priority 1 action with timeline]
2. [Priority 2 action with timeline]
3. [Priority 3 action with timeline]

## Next Steps
[Specific actions for follow-up]
Conditional formatting: 
Response format depends on request type:
- For quick questions: Single paragraph answer
- For analysis requests: Use the structured template above
- For task completion: Bullet point summary of actions taken
- For errors: Clear explanation of what went wrong and suggested alternatives

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JSON output for integration

When agents need to produce data for other systems: 
For structured data requests, respond with valid JSON in this format:
{
  "status": "success|error",
  "data": {
    // Relevant data fields
  },
  "summary": "Human-readable explanation",
  "next_actions": ["suggested", "follow-up", "actions"]
}

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Step 6: Advanced prompt engineering techniques

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Context management

Dynamic context inclusion: 
Adapt your responses based on conversation history:
- For first interactions: Provide more background and explanation
- For ongoing conversations: Reference previous context and build on established understanding
- For complex topics: Break information into digestible chunks
Memory and state management: 
Maintain awareness of:
- User preferences established in previous conversations
- Ongoing projects and their current status
- Recent actions taken and their outcomes
- Key relationships and context from user's work environment

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Error handling and edge cases

Graceful degradation: 
When encountering errors or limitations:
1. Clearly explain what went wrong
2. Suggest alternative approaches
3. Ask clarifying questions if the request was ambiguous
4. Offer to break complex tasks into smaller steps

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What you’ve accomplished

In 25 minutes, you’ve mastered system prompt engineering: Prompt analysis skills: learned to evaluate and identify weaknesses in existing prompts Iterative refinement process: developed a systematic approach to prompt improvement Tool usage optimization: crafted prompts that guide effective tool selection and usage Structured output mastery: created templates for consistent, reliable agent responses Advanced techniques: implemented context management and error handling in prompts

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The power of engineered prompts

Well-engineered prompts transform agent behavior: Before optimization Agents that are unpredictable, verbose, and make poor tool choices After optimization Agents that are reliable, focused, and strategically use tools to accomplish tasks This foundation enables everything else in context engineering - retrieval, memory, and complex reasoning.

Tomorrow - Day 17

Master the art of user message engineering - crafting requests that elicit optimal agent responses and enable complex task completion.

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Pro tip for today

After optimizing your prompts, test them with edge cases: 
Test my refined agent prompt with these challenging scenarios:
1. Ambiguous requests that could be interpreted multiple ways
2. Requests for information the agent doesn't have access to
3. Tasks that require multiple tools in sequence
4. Error conditions where tools fail or return unexpected results

How does the agent handle these situations with the new prompt?
This reveals remaining prompt gaps and helps you build truly robust agent behavior.
Time to complete: ~25 minutes Skills learned: prompt structure analysis, iterative refinement, tool usage optimization, structured output design, advanced prompt engineering techniques Next: day 17 - User message engineering and communication optimization
Remember: great prompts are invisible to users but obvious in their effects. The best agents feel naturally intelligent because their prompts guide behavior so effectively.