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Strategic Foundation Interview Guide

Created: 2025-10-14 Purpose: Extract founder insights to complete the Executive Summary and achieve 10/10 Strategic Foundation score

Current Score: 4/10 Target Score: 10/10 Gap: Missing founder narrative, market timing, competitive analysis, GTM strategy, and near-term milestones

Validation: ✅ Reviewed with Sequential Thinking + Codex AI (Planner role)

Success Rubric for 10/10 Executive Summary

A complete executive summary must include:

  1. Narrative Core: Founder's catalyst story tied to specific board-level compliance failure
  2. Market Timing: Links regulatory shifts/incidents to why GetCimple must exist now
  3. Differentiation: Why GetCimple wins vs. consultants, Excel, and SaaS competitors
  4. Customer & Problem Fit: Bullseye customer profile and their urgent jobs-to-be-done
  5. Business & Revenue Model: Pricing logic and expansion mechanics with unit economics
  6. Go-To-Market Engine: Acquisition channels, sales motion, and conversion path
  7. Traction & Validation: Current proof points and untested assumptions
  8. Execution Plan & Metrics: 3-6 month milestones with North Star metric
  9. Ask & Decision Gate: Immediate decision criteria for yes/no
  10. Risk & Mitigation: Top strategic risks and de-risking approach

Interview Framework (10 Questions, ~50 Minutes)

Section 1: Insight & Timing (~10 min)

Q1: "Walk me through the moment you knew directors needed GetCimple—what board event or compliance failure made it undeniable for both directors and management?"

Q2: "Why is 2025 the tipping point? Point to the regulatory shifts, headline incidents, or liability changes that prove the urgency."

Section 2: Customer & Advantage (~15 min)

Q3: "Who is the bullseye customer (board role, company profile, compliance maturity), and what painful job are they failing to complete today?"

Q4: "What do you understand about directors and management that others miss? Share specific situations that unlocked this insight."

Q5: "Who do you compete with—from consultants to spreadsheets to other platforms—and where have you already seen customers choose GetCimple? What convinced them?"

Section 3: Business Thesis & Traction (~15 min)

Q6: "Map the ideal acquisition journey: where do directors first encounter GetCimple, who owns the decision, and what signals tell you the deal is progressing?"

Q7: "Give a real or hypothesized example of a NED spreading GetCimple across multiple boards—what has to be true for that flywheel to spin, and what proof do you have so far?"

Q8: "What traction, pilots, or validation do you have today, and which assumptions are still untested? How will you de-risk the biggest unknowns?"

Section 4: Execution & Ask (~10 min)

Q9: "What must happen in the next 3–6 months—milestones, resourcing, partnerships—to stay on track, and what are the decision gates for each?"

Q10: "If you could only track one North Star metric in that window, what is it, why does it matter, and which leading indicators show you're on pace?"

Changes from Original Framework

Original: 8 questions in 4 sections Refined: 10 questions in 4 sections

Key Improvements (from Codex validation):

  1. Added Q3 to explicitly capture bullseye customer profile
  2. Refined Q4 to request concrete examples of unique insight
  3. Added Q8 to capture current traction and risk mitigation
  4. Enhanced Q5 to request proof of customer choice
  5. Improved Q7 to ask for prerequisites of network effect
  6. Strengthened Q10 to include leading indicators

Gaps Addressed:

  • Traction/validation (now Q8)
  • Core customer profile (now Q3)
  • Risk mitigation (now Q8)
  • Proof points for competitive advantage (enhanced Q5)

Execution Instructions

For Interviewer (Celeste AI):

  1. Present questions one section at a time
  2. Timebox each section (~5 min per question)
  3. Capture responses verbatim
  4. Ask follow-up questions to clarify vague answers
  5. After interview: synthesize with existing docs to draft executive summary

For Interviewee (Victor):

  1. Answer conversationally - no need for polished prose
  2. Be specific with examples, numbers, and names where possible
  3. It's okay to say "I don't know yet" or "This is untested"
  4. Total time commitment: ~50 minutes for interview + ~15 minutes to review draft

Next Steps After Interview

  1. Capture: Save raw interview responses in this document or separate notes file
  2. Synthesize: Combine with existing strategic docs:
  3. business-overview.md
  4. business-model.md
  5. vision-to-mvp-map.md
  6. expanding-value-model.md
  7. Draft: Create complete executive-summary.md addressing all 10 rubric components
  8. Review: Victor reviews and refines draft
  9. Re-assess: Update Strategic Foundation score (target 8-10/10)

Interview Responses (To Be Filled)

Section 1: Insight & Timing

Q1 Response: [Victor's answer here]

Q2 Response: [Victor's answer here]

Section 2: Customer & Advantage

Q3 Response: [Victor's answer here]

Q4 Response: [Victor's answer here]

Q5 Response: [Victor's answer here]

Section 3: Business Thesis & Traction

Q6 Response: [Victor's answer here]

Q7 Response: [Victor's answer here]

Q8 Response: [Victor's answer here]

Section 4: Execution & Ask

Q9 Response: [Victor's answer here]

Q10 Response: [Victor's answer here]

Status: Ready for interview session when Victor is available

To resume this session later: Reference this file and the continuation_id from zen clink collaboration if needed: 4f3c22a0-9da4-416c-ba30-5effb73a3da6