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The Ultimate AI-Powered Productivity Stack for Entrepreneurs

Implementing Systematic Productivity Stack Design with AI-Enhanced Decision Making

Participant Workbook

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Framework #1

First Principles Productivity Audit

Your Current Productivity Stack:

Business type:

Team size:

Annual revenue:

Primary work activities:

  1. _______________________
  1. _______________________
  1. _______________________
  1. _______________________
  1. _______________________

Current productivity pain points with specific examples:

  1. _______________________
  1. _______________________
  1. _______________________
  1. _______________________
  1. _______________________

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:

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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:

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Framework #3

System Integration Design

Current Tool Stack:

Task management:

Note-taking/docs:

Communication:

Calendar:

File storage:

AI tools:

Current integration pain points:

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AI Prompt Application:

Use the System Integration Design prompt with your stack details above.

AI's information flow map:

Where info enters:

  • Where processed:

Where stored long-term:

Recommended integrations:

Tools to consolidate or eliminate:

Single source of truth for each info type:

Tasks:

Projects:

Documents:

Communication:

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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:

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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:

_______________________

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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

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Ongoing Resources

Team Template for Regular Use

Monthly Productivity Stack Review Using Advanced Prompts

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Monthly Productivity Stack Review

Week 1: Problem Identification

  • Identify new productivity pain points that emerged
  • Use Prompt 1 to analyze if new tools needed or behavior change
  • Document actual vs. assumed constraints

Week 2: Cost Analysis

  • Review any tools being considered for addition
  • Use Prompt 2 to calculate true opportunity costs
  • Make go/no-go decisions based on full cost analysis

Week 3: Integration Review

  • Identify integration friction points from past month
  • Use Prompt 3 to design solutions
  • Implement highest-impact integration or consolidation

Week 4: AI Capability Review

  • Research new AI capabilities that launched this month
  • Use Prompt 4 to evaluate if AI can now replace paid tools
  • Test one AI replacement for 30 days

Quarterly Review:

  • Complete stack audit using all 5 prompts
  • Review usage metrics vs. optimization goals
  • Eliminate tools below usage threshold
  • Update decision rules based on learnings
  • Use Prompt 5 to optimize implementation for next quarter

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