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

---

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.

how to use strategic-planning
CursorClaude CodeClineCodexWindsurfGooseGitHub CopilotVS CodeGemini CLIKiloOpencodeKimi CLIRoo ClineAiderContinueZedBolt.newLovablev0Replit AgentSweepSmol DeveloperDevinCavemanAmpAntigravity
How to use strategic-planning on Cursor
AI-first code editor with Composer
1
Prerequisites
Before installing skills in Cursor, ensure your development environment meets these requirements:
›Cursor installed and configured on your development machine
›Node.js version 16.0+ with npm package manager (verify with node --version)
›Active project directory or workspace where you want to add strategic-planning
2
Execute installation command
Execute the skills CLI command in your project's root directory to begin installation:
$npx skills add https://github.com/ognjengt/founder-skills --skill strategic-planningcopy
The skills CLI fetches strategic-planning from GitHub repository ognjengt/founder-skills and configures it for Cursor.
3
Select Cursor when prompted
The CLI will show a list of available agents. Use arrow keys to navigate and space to select Cursor:
◆ Which agents do you want to install to?
│
│ ── Universal (.agents/skills) ── always included ────
│   • Amp
│   • Antigravity
│   • Cline
│   • Codex
│ ●Cursor(selected)
│   • Cursor
│   • Windsurf
4
Verify installation
Confirm successful installation by checking the skill directory location:
.cursor/skills/strategic-planning
Reload or restart Cursor to activate strategic-planning. Access the skill through slash commands (e.g., /strategic-planning) or your agent's skill management interface.
⚠
Security & Verification Notice
We perform automated surface-level scans (Gen AI Scanner, Socket, Snyk) during installation. These checks detect common vulnerabilities but do not guarantee complete security. Always review skill source code and verify the publisher's reputation before production use.
Skills execute code in your development environment. Always verify the publisher's identity, review recent commits, and test in isolated environments before production deployment.
Additional Resources
›View source code on GitHub›Skills CLI documentation›Learn more about Cursor›What are agent skills?