strategic-planning

SKILL.md

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.

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).

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:

Current state: Where they are now (revenue, channels, constraints)

Desired state: Where they want to be (goals from FOUNDER_CONTEXT or questions)

Gap analysis: What's blocking them from getting there

Leverage points: Where small actions create outsized results

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.

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).

---

## 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.

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.

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.