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Strategic Planning

Purpose

Analyze the founder's business and current situation to deliver 3 specific, actionable next moves that will drive measurable results in marketing or sales.

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Execution Logic

Check $ARGUMENTS first to determine execution mode:

If $ARGUMENTS is empty or not provided:

Respond with: "strategic-planning loaded, proceed with additional details about your current situation or business goals"

Then wait for the user to provide their requirements in the next message.

If $ARGUMENTS contains content:

Proceed immediately to Task Execution (skip the "loaded" message).

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Task Execution

When user requirements are available (either from initial $ARGUMENTS or follow-up message):

1. Read Business Context

Check if FOUNDER_CONTEXT.md exists in the project root.

• If it exists: Read it and extract: company name, industry, target audience, value proposition, products/services, business goals, stage, team size, competitors, current channels.
• If it doesn't exist: Proceed to Step 2 and gather this information through questions.

2. Diagnose Current Situation

Evaluate whether you have enough information to produce high-confidence, actionable strategies:

Required information to proceed without questions:

• What the business does (product/service)
• Who they serve (ICP/target audience)
• Current revenue stage (pre-revenue, $X MRR/ARR, etc.)
• Primary growth goal (more leads, higher conversion, retention, etc.)
• Current biggest bottleneck or struggle
• What they've already tried
• Available resources (team size, budget, technical capability)

If you have enough context: Proceed directly to Step 4.

If critical information is missing: Proceed to Step 3.

3. Ask Diagnostic Questions (When Needed)

Use the AskUserQuestion tool to gather missing information. Ask between 3-10 questions based on what's needed:

Core diagnostic questions:

• What's your biggest struggle in the business right now?
• What have you already tried to solve this?
• What's your current main bottleneck preventing growth?
• How are you currently getting clients/customers?
• What's working? What's not working?
• What resources do you have available (budget, team, time)?
• What's your timeline for seeing results?

Context-specific questions:

• For lead generation issues: "Where does your ICP spend time? What conferences, communities, or platforms?"
• For conversion issues: "At what stage do prospects drop off? What objections do they have?"
• For retention issues: "Why do customers churn? Have you asked them?"
• For scaling issues: "What breaks when you try to grow? What's the constraint?"

IMPORTANT: Only ask questions for information you truly need. Don't ask for information you can infer from FOUNDER_CONTEXT.md or the user's initial message.

4. Analyze and Identify Opportunities

Based on the context gathered, analyze:

1. Current state: Where they are now (revenue, channels, constraints)
2. Desired state: Where they want to be (goals from FOUNDER_CONTEXT or questions)
3. Gap analysis: What's blocking them from getting there
4. Leverage points: Where small actions create outsized results
5. Quick wins vs. long-term moves: Balance immediate impact with sustainable growth

Critical analysis principles:

• Identify the ONE constraint that, if removed, would unlock the most growth
• Look for underutilized assets (audience, content, network, product features)
• Find competitive gaps (what competitors aren't doing that would work)
• Spot channel-market fit mismatches (selling in wrong places)
• Detect execution issues vs. strategy issues

5. Generate 3 Next Moves

Create exactly 3 strategic moves, ranked by impact:

Selection criteria:

• Impact: Will this measurably move the needle? (revenue, leads, conversion, retention)
• Specificity: Is this concrete enough to execute today?
• Feasibility: Can they actually do this with current resources?
• Differentiation: Each move should attack the problem from a different angle
• Confidence: Only recommend if you're confident it will work for THIS business

For each move, write:

Part A — The Strategy (What & Why)

• One-line strategy name
• 2-3 sentences explaining WHAT to do and WHY it will work for this specific business
• Reference the real constraint or opportunity it addresses

Part B — The Exact Playbook (How)

• Step-by-step execution plan with specific actions
• Use their actual company name, product, ICP, and industry
• Include concrete details: which platforms, which conferences, which messaging, which metrics to track
• Specify timeline and expected results

Part C — First Action (Do This Today)

• One specific task they can complete in the next 30-60 minutes
• Concrete enough that there's no ambiguity about what to do

6. Format and Verify

• Structure output according to Output Format section
• Complete Quality Checklist self-verification before presenting output

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Writing Rules

Hard constraints. No interpretation.

Core Rules

• Zero generic advice. Every recommendation must be specific to THIS business.
• Use actual company names, product names, ICP details, and industry specifics.
• Lead with the highest-impact move first.
• Every strategy must include a concrete playbook, not just a concept.
• Specify metrics to track for each move.
• No motivational fluff. Only actionable strategy.
• Active voice only.
• Strategies must be executable within their resource constraints.

Specificity Rules

• BAD: "Run Facebook ads"

• GOOD: "Run Facebook lead ads targeting healthcare CFOs in Texas with this exact hook: [hook]. Budget: $500/month. Track: cost per qualified lead. Goal: 15 leads in 30 days."

• BAD: "Network at events"

• GOOD: "Attend HealthTech Summit in Austin (March 15-17). Book a booth ($2,500). Approach 30 attendees with your value proposition. Collect LinkedIn profiles. Follow up 2 days later with a personalized connection message referencing your conversation."

• BAD: "Improve your website"

• GOOD: "Add a self-serve product demo at try.yourcompany.com. No signup required. Pre-load it with dummy data showing your product solving [specific problem]. Add CTA at end: 'Want this for your team? Start free trial.' Track: demo completion rate, demo-to-trial conversion."

Context-Based Adaptation

• Early-stage / bootstrapped: Prioritize low-cost, high-leverage tactics (content, outbound, partnerships, guerrilla marketing)
• Growth-stage / funded: Include strategies that require budget or team (paid acquisition, events, product-led growth)
• B2B: Focus on outbound, LinkedIn, partnerships, conferences, case studies, product-led growth
• B2C: Focus on virality, social, influencers, retention loops, community
• Product issues: Don't recommend marketing if the product isn't solving a real problem yet. Recommend customer development instead.
• Distribution issues: If product is great but nobody knows about it, recommend distribution-first moves.

Quality Filters

Before finalizing ANY recommendation, ask:

• Would this work if they executed it exactly as written?
• Is this specific enough that they could start in the next hour?
• Does this leverage their unique position, audience, or assets?
• Would I personally bet money that this will produce results for THIS business?
• If the answer to any is "no" → rewrite or replace the recommendation.

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Output Format

## Your 3 Next Moves

Based on [Company Name]'s current situation, here are your 3 highest-impact next moves:

---

### Move 1: [Strategy Name]

**The Strategy:**
[2-3 sentences: What to do, why it works for this business, what constraint/opportunity it addresses]

**The Exact Playbook:**

**Step 1:** [Specific action with details]
**Step 2:** [Specific action with details]
**Step 3:** [Specific action with details]
**Step 4:** [Specific action with details]

**Metrics to Track:**
- [Specific metric 1]
- [Specific metric 2]
- [Specific metric 3]

**Expected Results:**
[Concrete outcome with timeline, e.g., "15-20 qualified leads within 30 days"]

**Do This Today:**
[One 30-60 minute action they can take immediately]

---

### Move 2: [Strategy Name]

**The Strategy:**
[...]

**The Exact Playbook:**
[...]

**Metrics to Track:**
[...]

**Expected Results:**
[...]

**Do This Today:**
[...]

---

### Move 3: [Strategy Name]

**The Strategy:**
[...]

**The Exact Playbook:**
[...]

**Metrics to Track:**
[...]

**Expected Results:**
[...]

**Do This Today:**
[...]

---

## Execution Priority

**Start with:** Move [X] — [One sentence explaining why this is the highest priority right now]

**Why this order:** [2-3 sentences explaining the strategic sequencing — why doing these in this order maximizes impact]

---

## Success Criteria

You'll know these moves are working when:
- [Specific metric/outcome 1 with timeline]
- [Specific metric/outcome 2 with timeline]
- [Specific metric/outcome 3 with timeline]

If you don't see these results, revisit your execution or reach out for a strategy adjustment.

Example:

## Your 3 Next Moves

Based on CalendarAI's current situation (early-stage SaaS, 50 users, struggling to get new signups), here are your 3 highest-impact next moves:

---

### Move 1: Build a Viral Self-Serve Playground

**The Strategy:**
Replace your "Book a Demo" CTA with a zero-friction playground where visitors can try CalendarAI instantly with dummy data. Right now you're losing 80% of interested visitors who don't want to book a call just to see if it works. A playground removes that barrier and lets them experience the Aha moment in 30 seconds.

**The Exact Playbook:**

**Step 1:** Create try.calendarai.com — a sandbox version of your product pre-loaded with a fake calendar showing 15 meetings, 3 conflicts, and typical scheduling chaos.

**Step 2:** Let visitors click "Auto-Schedule" and watch CalendarAI resolve conflicts in real-time. No email required, no signup, just instant value.

**Step 3:** At the end of the demo, show the CTA: "Want this for your real calendar? Connect Google Calendar in 30 seconds."

**Step 4:** Add a tracking pixel to measure: playground visits, completion rate, and playground-to-signup conversion.

**Metrics to Track:**
- Playground visits (goal: 200/week)
- Completion rate (goal: >60%)
- Playground-to-signup conversion (goal: >15%)

**Expected Results:**
3x increase in signups within 30 days. You'll convert 15-20% of playground visitors vs. 2-3% of "Book a Demo" clicks.

**Do This Today:**
Sketch the 3-screen playground flow on paper. Screen 1: Messy calendar. Screen 2: Click "Auto-Schedule". Screen 3: Clean calendar + CTA. Share with your developer.

---

### Move 2: Use CalendarAI FOR Your ICP, Then Send Them the Results

**The Strategy:**
Find 20 busy founders on LinkedIn who are your ideal customers. Use CalendarAI to analyze their public availability (from Calendly links) and create a free "scheduling efficiency report" for each of them. Send it as a personalized gift. This proves your product works before they're even customers, and you've given them value before asking for anything.

**The Exact Playbook:**

**Step 1:** Search LinkedIn for founders posting about being overwhelmed, working 70-hour weeks, or drowning in meetings. Filter by industry: SaaS, tech, startup. Target: 20 people.

**Step 2:** Find their Calendly links (usually in bio, website, or pinned posts).

**Step 3:** Run their availability through CalendarAI and generate a 1-page report showing: hours lost to scheduling conflicts, double-bookings, inefficient gaps between meetings.

**Step 4:** Send a personalized LinkedIn DM within 24 hours of their "overwhelmed" post. Reference their specific struggle, mention the report you created for them, and offer value before asking for anything.

**Metrics to Track:**
- Reports sent: 20
- DM open rate (LinkedIn shows this)
- Responses (goal: >30%)
- Demos booked from responses (goal: 6-8)

**Expected Results:**
6-8 demo calls booked within 2 weeks. 2-3 new paying customers within 30 days. These will be your warmest leads because they've already seen your product work.

**Do This Today:**
Find 5 founders on LinkedIn who posted about being busy in the last 48 hours. Save their profiles. Check if they have public Calendly links.

---

### Move 3: Launch a "Calendar Audit" Productized Service

**The Strategy:**
You're building a product for busy people, but your current positioning is "scheduling automation" (abstract). Reframe it as a service: "We audit your calendar and give you back 10 hours/week." People buy outcomes, not features. Offer a paid "Calendar Efficiency Audit" ($199) where you personally review someone's calendar, identify time-wasters, and set up CalendarAI to fix them. This generates immediate revenue AND gets you intimate customer knowledge.

**The Exact Playbook:**

**Step 1:** Create a landing page: calendarai.com/audit

**Step 2:** Offer: "Calendar Efficiency Audit — $199. We analyze your calendar, identify where you're losing time, and set up CalendarAI to automate it. Guarantee: Save 8+ hours/week or your money back."

**Step 3:** Limit to 5 audits/month to create scarcity and keep it manageable.

**Step 4:** Deliver the audit as: 30-min Zoom call reviewing their calendar + 1-page report + CalendarAI setup + 30-day support.

**Step 5:** Upsell them to annual subscription after 30 days when they see results.

**Metrics to Track:**
- Landing page visitors
- Audit bookings (goal: 5 in first month)
- Audit-to-subscription conversion (goal: 60%)
- Average hours saved per customer (use this as social proof)

**Expected Results:**
$1,000 MRR from audit service in Month 1. 3-4 long-term customers from the 5 audits. Plus you'll learn exactly what problems your ICP faces, which will improve your product roadmap.

**Do This Today:**
Write the landing page copy with a clear outcome-focused headline. Don't build the page yet — validate demand first by posting about it on LinkedIn asking if people would pay for this service. Track responses.

---

## Execution Priority

**Start with:** Move 2 — Use CalendarAI FOR Your ICP

**Why this order:** Move 2 requires zero development work and can start today. It'll give you 6-8 warm leads within 2 weeks. While you're running that outbound motion, build Move 1 (playground) with your developer — it'll take 1-2 weeks to ship. Launch Move 3 (audit service) once you've done 3-4 demos from Move 2, because those conversations will help you refine the audit offering. This sequence gets you immediate traction (Move 2) while building sustainable growth engines (Moves 1 & 3).

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## Success Criteria

You'll know these moves are working when:
- 20 personalized reports sent + 6 demo calls booked within 14 days (Move 2)
- Playground live + 15% playground-to-signup conversion within 30 days (Move 1)
- 5 paid audits sold + 3 audit-to-subscription conversions within 45 days (Move 3)

If you don't see these results, revisit your execution or reach out for a strategy adjustment.

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Quality Checklist (Self-Verification)

Before finalizing output, verify ALL of the following:

Pre-Execution Check

• I read FOUNDER_CONTEXT.md or gathered equivalent context from the user
• I have enough information about: product, ICP, current stage, main bottleneck, resources available
• If information was missing, I used AskUserQuestion to gather it (and didn't guess)

Analysis Check

• I identified the real constraint blocking growth (not just symptoms)
• I analyzed leverage points specific to THIS business
• I considered what they've already tried (don't repeat failed approaches)
• I matched strategies to their resources (team, budget, capabilities)

Strategy Selection Check

• All 3 moves are ranked by impact (highest first)
• Each move attacks the problem from a different angle (no overlap)
• Each move is feasible with their current resources
• I'm personally confident each move will produce measurable results
• No generic advice — every recommendation is specific to this business

Specificity Check

• Every move uses actual company name, product, ICP, and industry details
• Every playbook has step-by-step actions with specific details
• Metrics are specific and measurable
• Expected results include concrete outcomes with timelines
• "Do This Today" actions are completable in 30-60 minutes

Writing Rules Compliance

• Zero generic advice (no "send more cold emails", "improve your website", etc.)
• Active voice throughout
• No motivational fluff or filler
• Every recommendation passes the "would I bet money on this?" test
• Strategies are adapted to business stage and type (B2B/B2C, early/growth, etc.)

Output Check

• Output matches the Output Format exactly
• All 3 moves are complete with all sections filled
• Execution Priority section explains the strategic sequencing
• Success Criteria section has measurable outcomes with timelines

If ANY check fails → revise before presenting.

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Defaults & Assumptions

Use these unless the user overrides or context suggests otherwise:

• Number of moves: 3 (exactly)
• Move focus: Balanced between quick wins and sustainable growth
• Stage: If unclear, assume early-stage/growth (limited resources)
• Business type: If unclear, infer from FOUNDER_CONTEXT industry field
• Budget: Assume limited unless stated otherwise (prioritize low-cost, high-leverage tactics)
• Timeline: Assume user wants to see initial results within 30 days
• Metrics: Track leading indicators (actions taken) and lagging indicators (revenue/growth)
• Tone: Direct, actionable, confident. No fluff.

Document any assumptions made at the top of the output.

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Weekly Installs

101

Repository

ognjengt/founder-skills

GitHub Stars

100

First Seen

Feb 9, 2026

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