Executive Positioning:
Strategic Intelligence for Your Next Chapter

Board roles. Advisory positions. Speaking circuits. Thought leadership. Portfolio careers.

6-8

Hours Total

6

AI Platforms

1

Master Doc

Real Talk

You're not looking for a job.

You've been EVP. CMO. Chief Something Officer. You've led teams, built brands, transformed businesses. You have 25+ years of strategic leadership.

And now you're asking: "What's next?"

What You're Actually Building

✓ Current bio/CV (even if outdated—we're extracting patterns)

✓ List of major career accomplishments with business outcomes

✓ Board roles, advisory positions, or speaking you've already done

✓ Industries/sectors where you have deep expertise

✓ Networks you're connected to (associations, alumni, industry groups)

✓ Financial requirements (annual income floor, target, ideal)

✓ Time/energy allocation preferences (how much do you actually want to work?)

PROMPT 1: Executive Value Extraction

First: Set notebook goal to "Be an executive positioning strategist"

Analyze all uploaded documents and create a comprehensive EXECUTIVE VALUE PROPOSITION structured as follows:

SECTION 1: EXECUTIVE THROUGH-LINE
- What connects everything across 25+ years?
- Not job titles—the actual transformation you create
- Your leadership philosophy evidenced through decisions
- The story your career tells (that you might not see yourself)

SECTION 2: BOARD-READY CREDENTIALS
- P&L responsibility and scale ($X revenue, Y employees)
- Governance experience (committees, oversight, fiduciary)
- Transformation leadership (turnarounds, growth, innovation)
- Industry expertise with transferable insights
- Risk management and crisis navigation
- What makes you board-ready NOW vs credentials you'd need

SECTION 3: ADVISORY VALUE PROPOSITION
- What do you know that companies will pay for?
- Problems you solve that others can't
- Industries/functions where your expertise commands premium
- Specific outcomes you've delivered that prove capability

SECTION 4: THOUGHT LEADERSHIP PLATFORM
- What are you actually an authority on?
- Topics where you have contrarian or differentiated POV
- Speaking themes supported by your experience
- Where your voice adds something the market doesn't have

SECTION 5: PORTFOLIO CAREER FOUNDATIONS
- Multiple value streams your experience supports (boards + advisory + speaking)
- Time/energy allocation possibilities
- Revenue potential across streams
- What you'd need to activate each stream

Focus on EVIDENCE from documents. Not aspirational. What your actual track record proves.

✓ Why this works:

You just gave NotebookLM permission to be ruthlessly honest. It's analyzing patterns across your career that you've normalized. The gap between what you SAY you do and what you've ACTUALLY accomplished? It's going to surface that.

What you're building:

The "Executive Value Proposition" section of your Master Document. This becomes the foundation everything else builds on.

PROMPT 2: Deep Research (Market Intelligence)

Use Deep Research to investigate: "Executive positioning landscape for [YOUR INDUSTRY] leaders in 2025"

I need intelligence on:

1. BOARD LANDSCAPE
- What boards are actively seeking diverse executive leadership?
- Compensation ranges for board positions (public vs private vs nonprofit)
- Most in-demand expertise for board seats in 2025
- Board placement firms and how they work

2. ADVISORY/CONSULTING MARKET
- Going rates for C-suite advisory engagements
- How executives structure advisory retainers
- Fractional executive trends and compensation
- What companies are paying for strategic advisory

3. SPEAKING & THOUGHT LEADERSHIP
- Speaking fees for executives at my level
- Conference circuits in [YOUR INDUSTRY]
- Media/podcast opportunities for executive voices
- Book/content platforms for thought leadership

4. PORTFOLIO CAREER MODELS
- How are executives structuring multi-stream careers?
- Time allocation across boards + advisory + speaking
- Revenue potential for portfolio executives
- Case studies of successful portfolio careers

Deliver research report with verified sources I can check myself.

✓ Why this works:

Deep Research browses hundreds of websites and creates source-grounded reports. You're not getting AI opinions—you're getting market reality with receipts. The portfolio career models? That's so you can see what's actually working for executives like you.

💾 Save to your Executive Portfolio Doc:

Copy both outputs. Create sections: "Executive Value Proposition" and "Market Intelligence." You'll reference these in every step that follows.

First: Get clear on your parameters

ChatGPT needs your actual constraints, not aspirational thinking. These determine which opportunities are actually viable:

CHATGPT PORTFOLIO STRATEGY PROMPT:

Based on this Executive Value Proposition [paste] and Market Research [paste], develop my EXECUTIVE PORTFOLIO STRATEGY.

MY PARAMETERS:
[Paste your constraints from above]

FRAMEWORK 1: BOARD POSITIONING STRATEGY

Board Readiness Assessment:
• Score my readiness (1-10) for: Public boards, Private boards, PE-backed boards, Nonprofit boards
• Identify credential gaps and how to fill them
• Recommend board types that match my experience NOW
• Flag boards I should wait on and what I'd need first

Board Target Matrix:
• Industries where I'm most credible
• Company stages (startup, growth, turnaround, mature)
• Committee positions I'm qualified for (Audit, Comp, Governance, Risk)
• Specific board characteristics to pursue vs avoid

Board Compensation Intelligence:
• Expected compensation ranges by board type
• Equity vs cash considerations
• Time commitment expectations
• Red flags in board opportunities

FRAMEWORK 2: ADVISORY & CONSULTING ARCHITECTURE

Advisory Value Proposition:
• What problems do I solve worth $X/hour?
• What outcomes can I promise?
• Who are my ideal advisory clients?

Engagement Structure Options:
• Retainer models (monthly, quarterly, annual)
• Project-based engagements
• Fractional executive arrangements
• Recommended pricing for each

FRAMEWORK 3: SPEAKING & THOUGHT LEADERSHIP STRATEGY

Platform Definition:
• What 3-5 topics am I THE authority on?
• What's my contrarian/differentiated POV?
• Who is my ideal audience?

Speaking Circuit Strategy:
• Conference targets (industry, executive, women's leadership)
• Speaking fee positioning
• Keynote vs panel vs workshop strategy

FRAMEWORK 4: PORTFOLIO REVENUE ARCHITECTURE

Revenue Stream Modeling:
Create projections for Year 1, Year 2, Year 3:

| Stream | Year 1 | Year 2 | Year 3 | Time Investment |
| Boards | $X | $X | $X | X hrs/month |
| Advisory | $X | $X | $X | X hrs/month |
| Speaking | $X | $X | $X | X hrs/month |
| Other | $X | $X | $X | X hrs/month |
| TOTAL | $X | $X | $X | X hrs/month |

FRAMEWORK 5: 90-DAY ACTIVATION PLAN

BOARDS (Days 1-30):
• Specific actions to take
• People to contact
• Materials to prepare

ADVISORY (Days 1-30):
• How to signal availability
• Outreach strategy
• Engagement templates to prepare

SPEAKING (Days 1-30):
• Speaker one-sheet to create
• Conferences to target
• Thought leadership to publish

QUALITY CONTROLS:
❌ DO NOT recommend opportunities below my financial floor
❌ DO NOT suggest time commitments beyond my stated availability
✅ DO show revenue potential with realistic ranges
✅ DO include confidence levels (High/Medium/Low) for projections

✓ Why this works:

You just asked ChatGPT to do what it does best: build structured decision models. These frameworks aren't perfect yet—Claude's going to tear into them in Step 3. But now you have something concrete to challenge.

What you're building:

The "Portfolio Strategy" section of your Master Doc. Five frameworks that turn "what's next?" into "here are my options, scored and architected."

Rabbit Hole Warning

Don't spend more than 90 minutes perfecting these. They're meant to be challenged. If you're on your third iteration, stop. Good enough gets you to Claude.

CLAUDE ADVERSARIAL PROMPT:

💡 Use Extended Thinking for this.

Review this Executive Portfolio Strategy [paste frameworks] and challenge EVERYTHING.

I need you to tell me where I'm playing small. Be direct. Don't soften it.

CHALLENGE 1: POSITIONING ANALYSIS
- Where am I undervaluing my experience?
- What should I be positioning for that I'm not?
- Where does my strategy reflect imposter syndrome vs market reality?
- Am I targeting opportunities BELOW my actual level?

CHALLENGE 2: PRICING REALITY CHECK
- Where are my financial expectations too LOW?
- What would someone with my credentials typically command?
- Where am I leaving money on the table?
- What pricing assumptions need challenging?

CHALLENGE 3: BOARD STRATEGY CRITIQUE
- Am I being too conservative about board readiness?
- What boards should I be targeting that I'm not?
- Where am I underselling my governance capability?
- Are there prestige biases limiting my strategy?

CHALLENGE 4: THOUGHT LEADERSHIP AUDIT
- Is my platform thinking too narrow?
- Where is my voice needed that I'm not claiming?
- What am I an authority on that I'm not owning?
- Where could I be bolder?

CHALLENGE 5: PATTERN RECOGNITION
- What patterns do you see in how I'm positioning myself?
- Where does my strategy reflect old corporate conditioning vs executive agency?
- What would change if I positioned from abundance vs scarcity?
- Where am I seeking permission I don't need?

Tell me the uncomfortable truth. That's why I'm asking.

✓ Why this works:

Claude excels at finding blind spots and challenging assumptions. This prevents spiritual bypassing—you can't manifest away market realities or underpricing habits. You're building executive agency, not just optimism.

This Will Probably Hit Different:

You've spent decades in corporate environments where you learned to not take up too much space. To be grateful for opportunities. To prove yourself.

Claude is going to show you where that conditioning is limiting your positioning NOW. Sit with it.

💾 Save to your Executive Portfolio Doc:

Copy Claude's output to "Reality Check" section. Don't edit it to feel better. The discomfort is the value.

Pack Your Bags — Halfway Point

You've done the hard thinking. Before validation, reflect:

PERPLEXITY MARKET VALIDATION PROMPT:

I'm a former [YOUR LEVEL: EVP/CMO/etc] from [YOUR INDUSTRY] building an executive portfolio career. Validate market rates and opportunities for 2025.

1. BOARD COMPENSATION DATA
- What are public company board seats paying in 2025? (cash + equity)
- Private company board compensation ranges?
- PE-backed company board compensation?
- Nonprofit board expectations?
- Committee chair premiums?
- Include sources with actual data, not estimates

2. ADVISORY/CONSULTING RATES
- What are C-suite advisors charging in 2025?
- Day rates for executive advisory?
- Monthly retainer ranges?
- Fractional executive compensation?
- What factors command premium rates?
- Include actual rate examples with sources

3. SPEAKING FEES
- Keynote speaking fees for executives at my level?
- Conference speaking rates?
- Corporate event fees?
- How do speaking fees scale with profile?
- What factors increase speaking fees?

4. THOUGHT LEADERSHIP MONETIZATION
- Book advances for business/leadership books?
- Corporate training/workshop fees?
- Course/content revenue potential?
- Media/podcast monetization?

5. PORTFOLIO CAREER EXAMPLES
- Case studies of executives with multi-stream careers
- How are they allocating time?
- What revenue are they generating?
- What made their portfolio successful?

Provide CITED SOURCES for all compensation data. I need to verify these numbers.

✓ Why this works:

Perplexity's superpower is real-time research with citations. Every claim has a source. If Claude said you're underpricing yourself, Perplexity's data will show you what executives at your level actually command—with receipts.

What you're building:

The "Market Validation" section of your Master Doc. This is where opinion meets evidence. Note where the data supports pricing HIGHER than your original strategy.

Evidence Quality Markers — Use these as you copy:

Rabbit Hole Warning

Market research can become an infinite loop. Stop when you have 3-5 solid data points for each category. You're looking for directional validation, not a dissertation. If you're on your fourth search variation, you're done. Move on.

GEMINI CREATIVE EXPLORATION PROMPT:

Here's my executive background [paste value proposition] and portfolio strategy [paste frameworks].

Don't give me more of the same. I need you to show me what I'm NOT seeing.

1. ADJACENT OPPORTUNITIES
- What industries OUTSIDE my experience would value my capabilities?
- What non-obvious board opportunities match my skills?
- Where could my expertise create value I haven't considered?

2. CREATIVE PORTFOLIO ARCHITECTURES
- What unconventional combinations of roles could work?
- How might I structure my portfolio differently than traditional models?
- What would a "non-traditional" executive portfolio look like for someone with my background?

3. THOUGHT LEADERSHIP EXPANSION
- What platforms am I not considering?
- Where is my voice needed that I'm not claiming?
- What content formats would amplify my expertise?
- How could I build a platform, not just speak on others'?

4. LEGACY PROJECTS
- What could I BUILD that creates both impact and income?
- What would I create if money weren't the primary driver?
- How could my expertise serve communities I care about?
- What would make me excited to work, not just compensated?

5. WILDCARD SCENARIOS
- What if I combined speaking + advisory + content in new ways?
- What if I targeted completely different audiences?
- What opportunities exist because of WHO I am, not just what I've done?
- What would the boldest version of my next chapter look like?

Push my thinking. Show me what's possible beyond the obvious.

✓ Why this works:

Gemini excels at creative scenarios and unexpected connections. After all the analytical work, this opens up possibility space. Some of these ideas won't be viable—but one might be the breakthrough you needed.

What you're building:

The "Creative Possibilities" section of your Master Doc. Not everything here is actionable—but capture it. Sometimes the "crazy" idea becomes the right move 6 months later.

Rabbit Hole Warning

Don't fall in love with a shiny new direction. Gemini is great at showing possibilities, but some won't survive Perplexity's validation. Capture the ideas, but don't pivot your entire strategy based on creative brainstorming alone.

CHATGPT STRATEGIC REFINEMENT PROMPT:

Integrate Claude's challenges [paste], Perplexity's market data [paste], and Gemini's creative scenarios [paste] into a REVISED Executive Portfolio Strategy.

REFINED FRAMEWORK REQUIREMENTS:

1. REVISED POSITIONING
- Update my positioning based on Claude's "playing small" critique
- Where should I aim HIGHER than original strategy?
- What pricing should I adjust based on market data?

2. UPDATED REVENUE ARCHITECTURE
Revise Year 1/2/3 projections with:
- Market-validated compensation ranges
- Adjusted pricing based on challenges
- Creative opportunities from Gemini exploration

3. REFINED 90-DAY ACTIVATION
Update immediate actions based on:
- Higher positioning targets
- Market opportunities validated by Perplexity
- Creative possibilities worth exploring

4. OPPORTUNITY EVALUATION FRAMEWORK
Create decision criteria for evaluating opportunities:
- Financial minimums (based on market data)
- Strategic value criteria
- Time/energy fit assessment
- Legacy alignment check
- "Say yes if..." / "Say no if..." guidelines

5. THOUGHT LEADERSHIP PLATFORM
Refined strategy including:
- Primary topics to own
- Channels to prioritize
- Content strategy
- Speaking circuit targets
- Timeline to build platform

Make it executive-ready. Show me exactly what to do.

✓ Why this works:

You've orchestrated six different AI perspectives on your executive portfolio. Now ChatGPT synthesizes it into one coherent strategy. This isn't asking ChatGPT what to do—it's giving ChatGPT everything you've learned and asking it to integrate.

What you're building:

The final "Portfolio Architecture" and "Action Plan" sections of your Master Doc. This is the executive summary of all your work.

💾 Final Executive Portfolio Doc:

Your "My Executive Portfolio Strategy" document should now have: Executive Value Proposition, Market Intelligence, Portfolio Strategy, Reality Check, Market Validation, Creative Possibilities, and Final Portfolio Architecture.

Pack Your Bags — Final Reflection

You just completed the Oracle Table. That's significant. Before you close this tab:

Oracle Table Complete

You have executive-level strategic intelligence on your portfolio career.

You know what you're worth. You know what to target. You know how to evaluate opportunities.

Next: WORD Module — Transform this intelligence into communication