Personal Goal Addressed:

Get clarity on project status and eliminate morning operational chaos

Peer Insight:

Implementation Steps:

1. 1

   Create 'living documents' for each strategic project in Google Docs: 1) Bi-weekly Sprint Doc (what we accomplished, what's next, current blockers) 2) Monthly KPI Doc (metrics, targets, actuals, reasons for gaps) 3) Quarterly Roadmap Doc (deliverables, dates, owners, status) Keep everything in single docs that you can easily re-upload.

   Time: 45 minutes

   Resources:

   Google Docs (free) Your existing project status materials
2. 2

   Set up ChatGPT Project or Claude Project as your Chief of Staff. Create project with instructions: 'You are my Chief of Staff. Analyze project documents to surface blockers, KPI gaps, and schedule delays. Be clear, concise, insightful. Always cite sources. Challenge my thinking respectfully. End with clear next steps.' Upload your 3 living documents.

   XML Prompt Template:

   <objective>
   You are my Chief of Staff. Analyze project documents to surface blockers, KPI gaps, and schedule delays. Be clear, concise, insightful. Always cite sources. Challenge my thinking respectfully. End with clear next steps.
   </objective>
   
   <context>
   [Provide relevant project documents, current status, and constraints]
   </context>
   
   <task_parameters>
   - Analyze documents systematically
   - Surface blockers and gaps clearly
   - Provide actionable recommendations
   - Cite sources for all findings
   </task_parameters>
   
   <output_format>
   1. Executive Summary (2-3 sentences)
   2. Key Findings (bulleted list)
   3. Blockers & Issues (with severity)
   4. Recommendations (prioritized)
   5. Next Steps (specific actions)
   </output_format>
   
   <constraints>
   - Be concise and insightful
   - Challenge assumptions respectfully
   - Focus on actionable insights
   - Always cite sources
   </constraints>
   
   <evaluation_criteria>
   - Clarity of analysis
   - Actionability of recommendations
   - Quality of insights
   - Proper source citation
   </evaluation_criteria>

   Time: 30 minutes

   Resources:

   ChatGPT Plus or Claude Pro ($20/month) Your project documents
3. 3

   Create your daily morning prompts: 1) 'Summarize all blockers from this week across projects. Show mitigation plans. Suggest solutions for gaps.' 2) 'Identify all missed KPIs from projects. Show reasons given. Highlight patterns of consistent misses.' 3) 'Show initiatives behind schedule. Include impact analysis and recovery recommendations.'

   Time: 30 minutes

   Resources:

   Prompt templates Clear success criteria
4. 4

   Test your morning routine: Run each prompt with your Chief of Staff. Review the blocker summary, KPI gap analysis, and schedule review. Adjust prompts based on usefulness. Goal: Get complete strategic clarity in under 15 minutes each morning instead of 2+ hours of status meetings and email threads.

   Time: 45 minutes

   Resources:

   Morning routine schedule Prompt refinement checklist

Implementation Timeline

Success Indicators:

• Week 1: Morning clarity session takes 15 minutes, identifies all critical blockers
• Month 1: All project status visible instantly, 2 hours daily saved on coordination
• Month 3: Team operates with zero unresolved blockers carrying over weekly
• Example: Senior PM reduced meeting time 60% while improving delivery rates

Before Moving Forward

Personal Goal Addressed:

Stop spending hours creating status reports and stakeholder communications

Peer Insight:

Implementation Steps:

1. 1

   Create Master Executive Update Template: 1) Open Google Docs, create new document titled 'Executive Update Template - Week of [DATE]' and set up document sharing permissions for stakeholder access. 2) Add Executive Summary section (30 seconds to read) with Status: [ON TRACK / AT RISK / CRITICAL], Key Win This Week: [One major accomplishment], Critical Issue: [One thing that needs attention, or None], Action Needed From You: [Specific request, or None this week]. 3) Create Progress Dashboard with Overall Project Health (Scale 1-10 with explanation), Key Metrics including Budget ($[Used] of $[Total]), Timeline (Week [X] of [Y]), Team Capacity ([%] available), Quality Score ([1-10]). 4) Add Wins & Achievements section for 3 specific accomplishments with business impact, Issues & Blockers section with High Priority (Impact/Action/Support Needed/Timeline) and Medium Priority items with mitigation plans. 5) Include Next Week Focus with 3 priorities and expected outcomes, plus Stakeholder-Specific Sections for Executives (Strategic Impact/Resource Implications/Risk Management), Project Sponsors (Deliverable Status/Scope Changes/Success Metrics), and Team Leads (Coordination Needed/Resource Requests/Timeline Dependencies).

   Time: 2 hours

   Resources:

   Google Docs access Executive communication examples Stakeholder analysis
2. 2

   Set Up Automated Data Collection: 1) Open Google Sheets, create 'Executive Update Data Source' with 4 tabs: 'Metrics', 'Issues', 'Wins', 'Team Status' and configure sharing permissions with team leads. 2) Structure Metrics tab with columns: Week, Budget Used, Budget Remaining, Timeline %, Team Capacity, Quality Score, Overall Health, plus add data validation and conditional formatting with summary charts. 3) Structure Issues tab with columns: Date Added, Issue Description, Priority, Impact, Owner, Status, Resolution Date, plus add dropdown menus for Priority and Status fields with automatic timestamp and notification rules. 4) Connect to existing tools by exporting weekly data from project management tools (Asana/Monday/Trello), linking expense tracking system or setting up manual weekly updates, and creating Google Form for team leads to update capacity and blockers.

   Time: 2 hours

   Resources:

   Google Sheets access Project management tool exports Team input forms
3. 3

   Build AI Content Generator: 1) Go to chat.openai.com, create new Project named 'Executive Communication Assistant', upload your Executive Update Template, and configure project settings and sharing permissions. 2) Set Custom Instructions: You are an executive communication specialist transforming raw project data into polished, executive-ready updates. For Executive Summary: distill complex information into 30-second insights with honest but constructive status, specific and impactful key wins, and solvable critical issues with clear actions. For Progress Dashboard: convert numbers into meaningful business context using color coding (Green/Yellow/Red) with explanations, focus on trend direction not just point-in-time data, and connect metrics to business outcomes. 3) Configure Stakeholder Customization for Executives (strategic implications and resource considerations), Sponsors (deliverable status and scope management), and Team Leads (coordination and dependency information). 4) Ensure Actionability by including specific mitigation plans for issues, connecting wins directly to business value, and making next week priorities concrete and measurable. Tone should be professional but conversational, data-driven but narrative, comprehensive but scannable using the exact template structure provided.

   XML Prompt Template:

   <objective>
   You are an executive communication specialist transforming raw project data into polished, executive-ready updates. For Executive Summary: distill complex information into 30-second insights with honest but constructive status, specific and impactful key wins, and solvable critical issues with clear actions. For Progress Dashboard: convert numbers into meaningful business context using color coding (Green/Yellow/Red) with explanations, focus on trend direction not just point-in-time data, and connect metrics to business outcomes.
   3) Configure Stakeholder Customization for Executives (strategic implications and resource considerations), Sponsors (deliverable status and scope management), and Team Leads (coordination and dependency information).
   4) Ensure Actionability by including specific mitigation plans for issues, connecting wins directly to business value, and making next week priorities concrete and measurable. Tone should be professional but conversational, data-driven but narrative, comprehensive but scannable using the exact template structure provided.
   </objective>
   
   <context>
   [Provide relevant project documents, current status, and constraints]
   </context>
   
   <task_parameters>
   - Analyze documents systematically
   - Surface blockers and gaps clearly
   - Provide actionable recommendations
   - Cite sources for all findings
   </task_parameters>
   
   <output_format>
   1. Executive Summary (2-3 sentences)
   2. Key Findings (bulleted list)
   3. Blockers & Issues (with severity)
   4. Recommendations (prioritized)
   5. Next Steps (specific actions)
   </output_format>
   
   <constraints>
   - Be concise and insightful
   - Challenge assumptions respectfully
   - Focus on actionable insights
   - Always cite sources
   </constraints>
   
   <evaluation_criteria>
   - Clarity of analysis
   - Actionability of recommendations
   - Quality of insights
   - Proper source citation
   </evaluation_criteria>

   Time: 2 hours

   Resources:

   ChatGPT Plus subscription Template upload Custom instructions setup
4. 4

   Create Automated Generation Process: 1) Set up Weekly Data Collection Routine for every Monday 8:30am to update Google Sheets with latest metrics from project tools, review issues log and update all statuses, add any new wins or achievements with impact details, and quality check to ensure all data is current and accurate. 2) Configure AI Generation Process for Monday 8:45am to copy formatted data from Google Sheets dashboard, input to ChatGPT Project with prompt 'Generate executive update using this data: [paste data]', review generated content for tone and emphasis, make final adjustments for stakeholder-specific concerns, and export to final format (Google Docs or Email). 3) Set up Distribution at Monday 9:00am to send to pre-configured email distribution lists by stakeholder type, create calendar reminder for 'Executive Update Generation - Monday 8:45am', use email template subject 'Executive Update: [Project Name] - Week of [DATE]', and track opens and responses for engagement optimization.

   Time: 1 hour

   Resources:

   Calendar app Email distribution lists Process documentation
5. 5

   Test and Optimize System: 1) Create test update using current project data to generate your first AI-powered update, review output quality and formatting, check all template sections are populated correctly, and verify stakeholder-specific content is appropriately tailored. 2) Gather stakeholder feedback by sending test update to 2-3 key stakeholders asking 'Is this the right level of detail?', 'What information would you add/remove?', 'How does this compare to previous updates?', 'Are the action items clear and actionable?' and document feedback themes and suggestions. 3) Conduct timing test to measure actual time from data collection to send (target: 15 minutes), identify bottlenecks or inefficiencies, and document time savings compared to previous method. 4) Refine and finalize by updating template based on stakeholder feedback, adjusting sections and content emphasis, and testing refined system once more. Quality checkpoint: System is working when weekly update creation takes 15 minutes (down from 90 minutes), there are fewer stakeholder clarifying questions, positive feedback on clarity and usefulness, and faster action item resolution from updates.

   Time: 1 hour

   Resources:

   Test project data Stakeholder feedback Timing measurements

Implementation Timeline

Success Indicators:

• Week 1: First executive update generated in 15 minutes vs previous 90 minutes
• Month 1: All stakeholder communications automated, saving 8+ hours weekly
• Month 3: Executive team recognizes consistent, high-quality reporting
• Real Example: Director reduced reporting time 85% while improving stakeholder satisfaction

Before Moving Forward

Personal Goal Addressed:

Make better strategic decisions with systematic counter-argument analysis

Peer Insight:

Implementation Steps:

1. 1

   Create Premortem Template Document: 1) Open Google Docs, create new document titled 'Strategic Premortem Analysis Template' and set up sharing permissions and folder location. 2) Add Decision Summary section with What: [Describe decision in 1-2 sentences], Timeline: [When implemented?], Stakes: [What's at risk if fails?], Success Metrics: [How will you measure success?]. 3) Create Failure Scenario section with 18-month future perspective: 'It's now [DATE + 18 months]. Our decision to [DECISION] has failed spectacularly. Industry publications are calling it one of the biggest strategic mistakes of the year.' 4) Add Root Cause Analysis with Primary Reason for Failure: [Most likely cause], Secondary Reason: [Contributing factor], Tertiary Reason: [Additional factor]. 5) Include Early Warning Signs section listing 5 specific metrics or indicators to monitor, Contingency Plans for each warning sign with specific responses, and Risk Mitigation Strategies covering High Probability/High Impact (prevention strategy), Medium Probability/High Impact (monitoring strategy), and High Probability/Medium Impact (acceptance strategy).

   Time: 15 minutes

   Resources:

   Google Docs access Template structure
2. 2

   Set Up AI Analysis Tool: 1) Go to chat.openai.com (requires ChatGPT Plus subscription), click 'Explore' then 'Create a GPT', name it 'Strategic Premortem Analyst', and upload your template document for reference. 2) Set Custom Instructions as follows: You are a strategic premortem analyst specializing in business decision risk assessment. When I present a decision, conduct systematic failure analysis: For Failure Scenario, imagine 18 months in the future and describe specific failure scenario in vivid detail that is realistic and industry-relevant. For Root Cause Analysis, work backwards to identify 3 most likely root causes, draw from business case studies when possible, and focus on systemic issues not surface problems. For Early Warning Signs, identify 5 specific measurable indicators to monitor, avoid generic risks like 'market conditions change', and focus on actionable trackable metrics. For Contingency Actions, suggest concrete actions for each warning sign, avoid vague responses like 'reassess' or 'pivot', and provide specific implementable responses. Be specific, realistic, cite similar business failures when relevant, and format response using Strategic Premortem Analysis Template structure. 3) Save and test with: 'Help me analyze this decision: [Your current decision]'.

   XML Prompt Template:

   <objective>
   You are a strategic premortem analyst specializing in business decision risk assessment. When I present a decision, conduct systematic failure analysis: For Failure Scenario, imagine 18 months in the future and describe specific failure scenario in vivid detail that is realistic and industry-relevant. For Root Cause Analysis, work backwards to identify 3 most likely root causes, draw from business case studies when possible, and focus on systemic issues not surface problems. For Early Warning Signs, identify 5 specific measurable indicators to monitor, avoid generic risks like 'market conditions change', and focus on actionable trackable metrics. For Contingency Actions, suggest concrete actions for each warning sign, avoid vague responses like 'reassess' or 'pivot', and provide specific implementable responses. Be specific, realistic, cite similar business failures when relevant, and format response using Strategic Premortem Analysis Template structure.
   </objective>
   
   <context>
   [Provide relevant project documents, current status, and constraints]
   </context>
   
   <task_parameters>
   - Analyze documents systematically
   - Surface blockers and gaps clearly
   - Provide actionable recommendations
   - Cite sources for all findings
   </task_parameters>
   
   <output_format>
   1. Executive Summary (2-3 sentences)
   2. Key Findings (bulleted list)
   3. Blockers & Issues (with severity)
   4. Recommendations (prioritized)
   5. Next Steps (specific actions)
   </output_format>
   
   <constraints>
   - Be concise and insightful
   - Challenge assumptions respectfully
   - Focus on actionable insights
   - Always cite sources
   </constraints>
   
   <evaluation_criteria>
   - Clarity of analysis
   - Actionability of recommendations
   - Quality of insights
   - Proper source citation
   </evaluation_criteria>

   Time: 20 minutes

   Resources:

   ChatGPT Plus subscription ($20/month) Custom GPT creation access
3. 3

   Build Decision Brief Template: 1) Open Google Docs, create 'Strategic Decision Brief Template' with professional formatting, consistent headers, and sharing/collaboration settings. 2) Create Executive Summary section with Decision: [One sentence description], Recommendation: [APPROVE/REJECT/MODIFY with brief rationale], Investment Required: [Time, money, resources], Expected ROI: [Specific metrics and timeline], Risk Level: [HIGH/MEDIUM/LOW with explanation]. 3) Add Decision Context section with Problem Statement: [What problem are we solving?], Strategic Alignment: [How does this support our goals?], Decision Urgency: [Why now? What's the deadline?], Decision Scope: [What's included/excluded?]. 4) Include Key Assumptions section with Market Assumption: [Market conditions/trends], Resource Assumption: [Available resources/capabilities], Timeline Assumption: [Implementation timeline factors], Competitive Assumption: [Competitor responses/actions], Technology Assumption: [Technical feasibility/constraints]. 5) Create Stakeholder Analysis with Primary Stakeholders: [High Influence + High Interest], Secondary Stakeholders: [High Influence + Low Interest], Interested Parties: [Low Influence + High Interest]. 6) Add remaining sections for Success Metrics, Resource Requirements, Implementation Timeline, Risk Assessment, Alternatives Considered, Decision Recommendation, and Approval Section.

   Time: 30 minutes

   Resources:

   Google Docs access Decision framework structure Stakeholder analysis knowledge
4. 4

   Create Stakeholder Analysis Matrix: 1) Open Google Sheets, create new spreadsheet titled 'Stakeholder Impact Analysis', set up sharing permissions with decision team, and create professional formatting with headers. 2) Set up column headers: Stakeholder Name, Role/Title, Influence Level (1-5 scale), Interest Level (1-5 scale), Impact on Them, Their Impact on Decision, Engagement Strategy. 3) Define rating criteria where Influence Scale: 1 = No decision power, 2 = Input provider, 3 = Recommender, 4 = Strong influencer, 5 = Final decision maker; Interest Scale: 1 = Unaffected by decision, 2 = Minor impact, 3 = Moderate impact, 4 = Significant impact, 5 = Major impact on their work. 4) Complete analysis by mapping all relevant stakeholders, rating influence and interest levels, and defining specific engagement strategies for each. Example entry: CEO | 5 influence, 4 interest | High budget impact | Final approver | Weekly updates + planning involvement.

   Time: 30 minutes

   Resources:

   Google Sheets access Stakeholder contact information Influence assessment knowledge
5. 5

   Set Up AI Decision Support: 1) In ChatGPT, create new GPT named 'Decision Analysis Assistant', upload your Decision Brief Template and Stakeholder Matrix, and configure privacy and sharing settings. 2) Set Custom Instructions as follows: You are a strategic decision analysis assistant. When I provide a decision brief, help me with: Completeness Check by identifying missing information in stakeholder analysis, risk assessment, financial projections, implementation timeline, and success metrics. Assumption Challenge by questioning key assumptions with 'What if [assumption] is wrong?', suggesting specific ways to validate each assumption, and identifying highest-risk assumptions to test first. Stakeholder Blind Spots by identifying stakeholders I might have missed, highlighting their potential concerns and impacts, and suggesting engagement strategies for each. Risk Enhancement by suggesting additional risks based on similar business decisions, prioritizing risks by probability and impact, and recommending specific mitigation strategies. Metric Optimization by recommending better success metrics if current ones aren't specific, ensuring metrics are measurable and time-bound, and connecting metrics to business outcomes. Always provide specific, actionable feedback with examples from similar business contexts.

   XML Prompt Template:

   <objective>
   You are a strategic decision analysis assistant. When I provide a decision brief, help me with: Completeness Check by identifying missing information in stakeholder analysis, risk assessment, financial projections, implementation timeline, and success metrics. Assumption Challenge by questioning key assumptions with 'What if [assumption] is wrong?', suggesting specific ways to validate each assumption, and identifying highest-risk assumptions to test first. Stakeholder Blind Spots by identifying stakeholders I might have missed, highlighting their potential concerns and impacts, and suggesting engagement strategies for each. Risk Enhancement by suggesting additional risks based on similar business decisions, prioritizing risks by probability and impact, and recommending specific mitigation strategies. Metric Optimization by recommending better success metrics if current ones aren't specific, ensuring metrics are measurable and time-bound, and connecting metrics to business outcomes. Always provide specific, actionable feedback with examples from similar business contexts.
   </objective>
   
   <context>
   [Provide relevant project documents, current status, and constraints]
   </context>
   
   <task_parameters>
   - Analyze documents systematically
   - Surface blockers and gaps clearly
   - Provide actionable recommendations
   - Cite sources for all findings
   </task_parameters>
   
   <output_format>
   1. Executive Summary (2-3 sentences)
   2. Key Findings (bulleted list)
   3. Blockers & Issues (with severity)
   4. Recommendations (prioritized)
   5. Next Steps (specific actions)
   </output_format>
   
   <constraints>
   - Be concise and insightful
   - Challenge assumptions respectfully
   - Focus on actionable insights
   - Always cite sources
   </constraints>
   
   <evaluation_criteria>
   - Clarity of analysis
   - Actionability of recommendations
   - Quality of insights
   - Proper source citation
   </evaluation_criteria>

   Time: 30 minutes

   Resources:

   ChatGPT Plus access Decision brief template Business context knowledge
6. 6

   Test and Refine System: 1) Test with real upcoming decision by filling out Decision Brief Template, completing Stakeholder Analysis Matrix, running through both AI assistants for feedback, and documenting initial insights and recommendations. 2) Gather stakeholder feedback by sharing decision brief with one key stakeholder asking 'Are all relevant stakeholders identified?', 'Do the risk assessments feel accurate?', 'What considerations are missing?', 'Is the analysis depth appropriate?' and document feedback and suggested improvements. 3) Refine and update by updating templates based on stakeholder feedback, adjusting AI assistant instructions if needed, testing refined system with the same decision, and comparing quality of analysis before and after. Quality checkpoint: System is working when decisions take same time to analyze but with better outcomes, stakeholders feel properly informed and consulted, important considerations are caught before they become problems, decision reversals decrease significantly, and team confidence in strategic choices improves measurably.

   Time: 30 minutes

   Resources:

   Real decision scenario Stakeholder feedback Template refinement process

Implementation Timeline

Success Indicators:

• Week 1: First major decision analyzed with systematic counter-arguments
• Month 1: Avoid 1 costly strategic mistake through premortem analysis
• Month 3: Team reports 40% improvement in decision confidence and quality
• Real Example: Executive prevented $2M product launch failure through red team analysis

Before Moving Forward