Day 17 challenge

Goal: master user message engineering for optimal agent collaborationTheme: context engineering week - communication optimizationTime investment: ~20 minutes
Welcome to Day 17! Yesterday you mastered system prompts that guide agent behavior. Today you’ll learn the other half of the conversation: user message engineering. You’ll discover how to craft requests that elicit optimal agent responses and enable complex task completion. Great user messages are the difference between agents that frustrate you and agents that feel like the perfect colleague.

What you’ll accomplish today

  • Understand the anatomy of effective user messages
  • Learn communication patterns that maximize agent capability
  • Master techniques for complex task delegation
  • Develop strategies for iterative problem-solving with agents
  • Build repeatable communication frameworks for consistent results
This builds on Day 16’s prompt engineering foundation. You’ll be practicing with the agents you’ve optimized to see how message quality affects outcomes.

Step 1: The anatomy of effective user messages

Just as system prompts have structure, effective user messages follow predictable patterns:

Core message components

  • Context: What background does the agent need?
  • Goal: What are you trying to accomplish?
  • Constraints: What limitations or requirements exist?
  • Format: How should the output be structured?
  • Success criteria: How will you know if it worked?

Message clarity hierarchy

Level 1 - Basic requests Simple, single-step tasks
"Create a calendar event for tomorrow at 2 PM"
Level 2 - Contextual requests Tasks with background information
"Create a calendar event for tomorrow at 2 PM with the client we discussed yesterday - include the project proposal as agenda item"
Level 3 - Strategic requests Complex, multi-step workflows
"Prepare for tomorrow's client meeting at 2 PM: research their recent announcements,
update the project proposal based on our last conversation, and create a follow-up task list based on likely outcomes"
Communication principle Agents perform better when they understand not just what to do, but why they’re doing it and how it fits into larger goals.

Step 2: Communication patterns that maximize agent capability

Different types of requests require different communication approaches:

The CLEAR framework

  • Context: Provide relevant background
  • Limits: Define scope and constraints
  • Expectations: Specify desired outcomes
  • Actions: Suggest approach if helpful
  • Review: Plan for feedback and iteration

Request type patterns

Information gathering requests:
Good: "Research our top 3 competitors' pricing strategies, focusing on their enterprise tiers.
 I need this for our pricing review meeting next week - include key differentiators and market positioning."

Poor: "Look up competitor pricing"
Action-taking requests:
Good: "Create a Slack message for the #engineering channel announcing our API v2.0 release.
Include the key improvements (performance, new endpoints, breaking changes) and link to the migration guide. Schedule it for 9 AM tomorrow."

Poor: "Post about the API release"
Analysis requests:
Good: "Analyze last quarter's sales pipeline data from HubSpot.
I want to understand our conversion rates by source, identify which stages have the biggest drop-offs, and recommend 3 specific improvements for next quarter."

Poor: "Look at sales data"

Progressive elaboration technique

Start simple, then add complexity:
1. Initial request: "Help me prepare for tomorrow's board meeting"

2. Add context: "Help me prepare for tomorrow's board meeting where we're discussing Q4 performance and 2025 strategy"

3. Add specifics: "Help me prepare for tomorrow's board meeting on Q4 performance and 2025 strategy.
I need: current metrics summary, comparison to goals, key wins/challenges, and our top 3 strategic priorities for next year"

4. Add constraints: "Help me prepare for tomorrow's board meeting on Q4 performance and 2025 strategy.
I need: current metrics summary, comparison to goals, key wins/challenges, and our top 3 strategic priorities for next year.
Keep everything concise - the deck should be 10 slides max, and focus on actionable insights rather than raw data."

Step 3: Complex task delegation strategies

Breaking down complex work into manageable agent tasks:

The decomposition approach

Instead of: “Plan our product launch” Try this sequence:
1. "Research successful product launches in our space over the last year - what tactics, timelines, and channels did they use?"

2. "Based on that research and our product features, create a high-level launch timeline with key milestones"

3. "For each milestone, identify what assets we'll need, who's responsible, and what success looks like"

4. "Create a detailed project plan for the first 4 weeks with specific tasks and deadlines"

Dependency management

Help agents understand task relationships:
"I need to create a customer onboarding email sequence.
First, analyze our current customer feedback to identify the top 3 onboarding pain points.
Then, draft email templates that address each pain point.
Finally, suggest an automation workflow in HubSpot to deliver these emails based on user behavior."

Quality checkpoints

Build verification into complex tasks:
"Create a competitive analysis report.
After you gather the initial research, summarize your findings and ask if I want
 you to dive deeper into any specific areas before proceeding to the full report."
Complex task strategy Think of agents as highly capable interns. Give them meaningful work, clear context, and check in at key decision points.

Step 4: Iterative problem-solving techniques

Agents excel at iterative refinement when guided properly:

The spiral approach

Start broad, then narrow:
1. "What are the main approaches to improving our customer retention?"

2. "Focus on the top 3 approaches - give me specific tactics for each"

3. "For the email engagement approach, create a detailed implementation plan"

4. "Draft the first email in that sequence targeting customers who haven't used our key features"

Feedback integration

Help agents learn from your responses:
"That analysis is helpful, but I need more focus on the financial impact.
Can you redo the recommendations section with specific revenue/cost projections for each suggestion?"

Course correction

Guide agents back on track when they drift:
"I appreciate the comprehensive research, but let's refocus on the original
question about pricing strategy. Can you distill those findings into 3 actionable pricing adjustments we could implement this quarter?"

Step 5: Building repeatable communication frameworks

Develop templates for common interaction patterns:

Framework templates

Research requests:
Research [topic] for [purpose/context].
Focus on [specific aspects].
I need this by [deadline] for [intended use].
Format as [output type] and include [specific elements].
Analysis requests:
Analyze [data source] to answer [specific question].
Consider [key factors] and provide [output format].
Include recommendations prioritized by [criteria].
Creation requests:
Create [deliverable] for [audience/purpose].
Use [style/tone] and include [required elements].
Format should be [specifications] and optimized for [intended use].

Situation-specific patterns

Weekly reviews:
"Run my weekly [department] review: check progress on active projects, identify any blockers, summarize key metrics vs. goals,
and flag anything needing my attention this week."
Meeting preparation:
"Prepare me for [meeting type] with [attendees] about [topic].
 Include: recent context about [relevant area], talking points for [specific agenda items], and potential questions I might face."
Project updates:
"Create a project status update for [project] covering progress since [last update],
current status vs. timeline, upcoming milestones, and any risks or blockers."

Step 6: Advanced communication techniques

Context threading

Reference previous conversations effectively:
"Building on the competitive analysis we discussed yesterday,
now create a positioning strategy that addresses the gaps we identified in our enterprise messaging."

Perspective taking

Help agents understand different viewpoints:
"Draft this announcement from the perspective of our customer success team - they'll need to field questions about the changes,
so include likely concerns and talking points for addressing them."

Constraint optimization

Work within realistic limitations:
"Given that we only have 2 weeks and a $5K budget,
what's the highest-impact marketing campaign we could run for this product launch?
Focus on tactics that leverage our existing assets and team expertise."

What you’ve accomplished

In 20 minutes, you’ve mastered user message engineering: Communication frameworks: learned structured approaches to agent requests Task decomposition: developed strategies for breaking complex work into manageable pieces Iterative refinement: mastered techniques for progressive problem-solving with agents Quality optimization: built methods for getting better outputs through better inputs Repeatable patterns: created templates for common interaction types

The power of engineered communication

Well-crafted user messages unlock agent potential: Before optimization Vague requests leading to generic responses and multiple rounds of clarification After optimization Precise requests that elicit targeted, actionable responses on the first try Combined with yesterday’s prompt engineering, you now control both sides of the human-agent conversation.

Tomorrow - Day 18

Begin building RAG (Retrieval Augmented Generation) systems with PostgreSQL and Supabase for dynamic information access.

Pro tip for today

Practice the spiral approach with one of your agents:
"Let's practice iterative problem-solving.
Start by giving me a high-level overview of [complex topic relevant to your work].
Then we'll drill down into specifics based on what I find most interesting or useful."
This builds your intuition for guiding agents through complex reasoning processes.
Time to complete: ~20 minutes Skills learned: message structure optimization, task decomposition strategies, iterative problem-solving, communication frameworks, advanced delegation techniques Next: day 18 - Retrieval systems with PostgreSQL and Supabase
Remember: agents are mirrors of the communication they receive. Invest in crafting better requests, and you’ll get exponentially better results.