The Ultimate AI-Powered Productivity Stack for Entrepreneurs
Implementing Systematic Productivity Stack Design with AI-Enhanced Decision Making
Participant Workbook
Framework #1
First Principles Productivity Audit
Your Current Productivity Stack:
Business type:
Team size:
Annual revenue:
Primary work activities:
Current productivity pain points with specific examples:
Current tools I'm paying for and why I bought each:
AI Prompt Application:
Use the First Principles Productivity Audit prompt with your specific details above.
Key insight from AI about fundamental problems:
Real vs. assumed constraints identified:
Real constraints:
Assumed constraints:
AI's recommendations for what I need:
New tool needed:
Better process with existing tools:
Behavior change needed:
Work to say no to:
Biggest shift from my original thinking:
Framework #2
Tool Stack Opportunity Cost Analysis
Tool Being Evaluated:
Tool name:
Purpose:
Monthly cost:
Why I'm considering it:
Current alternative:
Cost of current solution:
My context:
Current number of tools:
Team size:
Technical skill level:
Time available to learn:
AI Prompt Application:
Use the Tool Stack Opportunity Cost Analysis prompt with your details above.
01
Initial setup time:
02
Learning curve hours:
03
Migration effort:
04
Integration complexity:
05
Mental overhead:
TOTAL REAL COST:
Opportunity cost (what I'm NOT doing):
Total cost of ownership AI calculated:
AI's go/no-go decision:
Reasoning:
Framework #3
System Integration Design
Current Tool Stack:
Task management:
Note-taking/docs:
Communication:
Calendar:
File storage:
AI tools:
Current integration pain points:
AI Prompt Application:
Use the System Integration Design prompt with your stack details above.
AI's information flow map:
Where info enters:
Where stored long-term:
Recommended integrations:
Tools to consolidate or eliminate:
Single source of truth for each info type:
Tasks:
Projects:
Documents:
Communication:
Framework #4
Build vs. Buy vs. AI Decision Matrix
Productivity Functions to Evaluate:
List 5-10 functions and their current approach:
Function: _______________________ Current approach: _______________________
Function: _______________________ Current approach: _______________________
Function: _______________________ Current approach: _______________________
Function: _______________________ Current approach: _______________________
Function: _______________________ Current approach: _______________________
Function: _______________________ Current approach: _______________________
Function: _______________________ Current approach: _______________________
Function: _______________________ Current approach: _______________________
Technical skill: _______________________
Budget available: _______________________
AI tools I have: _______________________
AI Prompt Application:
Use the Build vs. Buy vs. AI Decision Matrix prompt with your functions above.
Functions AI can handle at 80%+ quality:
Function: AI tool: Cost savings:
Function: AI tool: Cost savings:
Function: AI tool: Cost savings:
Functions that need specialized tools:
Function: Tool needed: Why:
Function: Tool needed: Why:
Functions best with AI-enhanced tools:
Function: Tool + AI approach:
Function: Tool + AI approach:
Framework #5
Implementation and Continuous Optimization
My New Productivity System Design:
Tools to keep:
_______________________
_______________________
Tools to eliminate:
_______________________
_______________________
Tools to add:
_______________________
_______________________
Integrations to set up:
_______________________
_______________________
AI workflows to implement:
_______________________
_______________________
AI Prompt Application:
Use the Implementation and Continuous Optimization prompt with your system design above.
Implementation sequencing AI recommended:
Week 1 quick wins:
_______________________
Weeks 2-4 changes:
_______________________
Months 2-3 migrations:
_______________________
What NOT to change yet: _______________________
Usage metrics to track:
Time saved: _______________________
Tool adoption: _______________________
Cost metrics: _______________________
Problem resolution: _______________________
Quarterly optimization framework:
Review date: _______________________
What to check: _______________________
Decision rules: _______________________
My first action this week:
_______________________
Troubleshooting Guide for Workshop Challenges
Challenge: AI gives generic or obvious advice
Response: The prompt needs more specific context about your unique situation
Solution: Add more details about current tools, specific pain points, business context, and constraints
Challenge: Can't identify actual productivity problems
Response: Focus on concrete examples of daily frustrations
Solution: Track your time for one day, note every productivity friction point
Challenge: Too many tools to analyze in workshop time
Response: Focus on highest-cost subscriptions and most-used tools first
Solution: Analyze 3-5 tools during workshop, schedule follow-up sessions for rest
Challenge: Don't trust AI recommendations
Response: AI is analysis tool, not decision replacement
Solution: Use AI insights to challenge assumptions, make final decisions based on your judgment
Challenge: Team has different tool preferences
Response: Focus on solving problems, not defending tool choices
Solution: Use Framework 1 to identify shared productivity problems, then evaluate tools objectively
Ongoing Resources
Team Template for Regular Use
Monthly Productivity Stack Review Using Advanced Prompts
Monthly Productivity Stack Review
Week 1: Problem Identification
Week 2: Cost Analysis
Week 3: Integration Review
Week 4: AI Capability Review
Quarterly Review:
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