Advanced Techniques

Once you've mastered the basics, level up your AI game

These techniques take you beyond basic prompting. Use them when you need deeper analysis, multiple perspectives, or structured workflows that integrate with other tools.

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Chain of Thought Prompting

For complex problems, ask AI to show its reasoning step by step. This dramatically improves accuracy on difficult tasks and helps you understand the logic behind the answer.

When to use:

Strategy decisions, technical architecture, debugging complex issues, financial analysis, anything where you need to understand the "why" behind the answer.

How to use it:

Add phrases like "Think through this step by step," "Walk me through your reasoning," or "Break this down into steps" to your prompts.

Example Prompt:

I need to decide whether to build this feature in-house or buy a third-party solution. Walk me through your reasoning step by step. Consider: cost, timeline, maintenance, customization needs, and team capacity. Show your work.

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Role Playing

Ask AI to take on a specific role or perspective. This changes how it approaches problems and gives you feedback from angles you might not have considered.

When to use:

Getting feedback from different angles, stress-testing ideas, preparing for difficult conversations, understanding stakeholder perspectives, interview prep.

Effective roles:

  • "Act as a skeptical investor" - tough questions about viability
  • "Respond as an experienced product designer" - UX/design feedback
  • "You're a customer who tried this product" - user perspective
  • "Be my debate opponent" - find holes in arguments
  • "Act as a technical architect" - infrastructure decisions

Example Prompt:

Act as a skeptical board member. I'm presenting this strategy: [paste your plan]. Ask me the hard questions an experienced executive would ask. Push back on weak spots. Make me defend every assumption.

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Multi-Perspective Analysis

Get AI to analyze the same problem from multiple viewpoints in one response. This surfaces blind spots and helps you make more balanced decisions.

When to use:

Major decisions, contentious issues, cross-functional projects, product strategy, anything where different stakeholders have different priorities.

How to structure it:

Ask for analysis from 3-5 specific perspectives. Be explicit about what each perspective should prioritize.

Example Prompt:

Analyze this product decision from three perspectives:
1. Engineering: technical complexity, maintainability, tech debt
2. Business: revenue impact, market position, competitive advantage
3. User: UX, friction points, value delivered
For each perspective, tell me the biggest concerns and biggest opportunities. Then recommend a path forward that balances all three.

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Structured Outputs

Request specific formats (JSON, tables, bullet lists) so outputs can be easily used in other tools or workflows. Essential for automation and integration.

When to use:

Building tools, data analysis, API integrations, spreadsheet work, creating databases, any time you need to move AI output into another system.

Common formats:

  • JSON: For APIs and programming
  • Tables: For spreadsheets and reports
  • Markdown: For documentation
  • CSV: For data processing

Example Prompt:

Extract key information from this sales call transcript and return as JSON with this structure:
{
  "customer_name": "",
  "pain_points": [],
  "budget": "",
  "timeline": "",
  "next_steps": []
}

Combining Techniques

These techniques are even more powerful when used together. Here's how to layer them:

Chain of Thought + Role Play

"Act as a CFO. Walk through your reasoning on this budget allocation step by step."

Multi-Perspective + Structured Output

"Analyze from 3 perspectives and return as a comparison table with pros/cons for each."

All Four Together

"Act as three stakeholders. Each should think through this step by step and provide feedback as structured bullet points."

When NOT to Use These

Advanced techniques add complexity and use more tokens. Use them strategically:

  • Simple tasks: Don't overcomplicate. "Write a professional email" doesn't need chain of thought.
  • Creative work: Too much structure can kill creativity. Let AI flow naturally for brainstorming.
  • Quick answers: If you just need a fast fact, keep it simple.
  • When you're experimenting: Start simple, then add techniques if basic prompts aren't working.
Rule of thumb:

If the task is important, complex, or involves tradeoffs between multiple priorities, use advanced techniques. For everything else, keep it simple.

Ready to put these into practice?

Check out the prompt library for ready-to-use templates, or download the context template to supercharge your AI sessions.

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