// CEO-level strategic planning framework — OKRs, annual strategy, scenario modeling, decision frameworks, QBR and weekly review templates
[HINT] Download the complete skill directory including SKILL.md and all related files
| name | strategic-planning |
| description | CEO-level strategic planning framework — OKRs, annual strategy, scenario modeling, decision frameworks, QBR and weekly review templates |
| tags | ["skill","strategy","planning","okr","ceo"] |
| triggers | ["strategic planning","use strategic planning","run strategic planning","ceo-level strategic planning framework — okrs"] |
Strategy without execution is fiction. This skill turns CC's ambition into quarterly OKRs, scenario models, and weekly checkpoints that keep the $5,000 MRR north star visible every day.
Trigger: /strategic-review, "set OKRs", "quarterly planning", "run QBR", "what's the strategy"
Related skills: skills/financial-modeling/SKILL.md, ../../CMO-Agent/skills/competitive-intelligence/SKILL.md, skills/ceo-briefing/SKILL.md
## OKRs — Q[X] [YEAR] ([Month] - [Month])
**Set:** [Date] | **Grade due:** [Last day of quarter]
---
### O1: [Objective — inspiring, qualitative, directional]
| # | Key Result | Owner | Start | Target | Current | Confidence |
|---|-----------|-------|-------|--------|---------|------------|
| KR1 | [Measurable outcome] | CC/Bravo | [baseline] | [number/date/%] | — | —% |
| KR2 | [Measurable outcome] | CC/Bravo | [baseline] | [number/date/%] | — | —% |
| KR3 | [Measurable outcome] | CC/Bravo | [baseline] | [number/date/%] | — | —% |
**Why this matters:** [1 sentence connecting to north star]
---
### O2: [Objective]
| # | Key Result | Owner | Start | Target | Current | Confidence |
|---|-----------|-------|-------|--------|---------|------------|
| KR1 | | | | | | |
| KR2 | | | | | | |
| KR3 | | | | | | |
---
### O3: [Objective]
| # | Key Result | Owner | Start | Target | Current | Confidence |
|---|-----------|-------|-------|--------|---------|------------|
| KR1 | | | | | | |
| KR2 | | | | | | |
| KR3 | | | | | | |
Every Monday, update the Confidence column (0-100%):
## OKR Check-In — Week of [Date]
| KR | Last Week's Confidence | This Week's Confidence | Delta | Blocker / Note |
|----|----------------------|----------------------|-------|----------------|
| O1-KR1 | X% | X% | +/- | |
| O1-KR2 | X% | X% | +/- | |
| O2-KR1 | X% | X% | +/- | |
**Action items this week:**
- [ ] [Action to move a lagging KR]
Grade each KR on a 0.0-1.0 scale at quarter end:
| Score | Meaning |
|---|---|
| 0.0-0.3 | Failed — didn't make meaningful progress |
| 0.4-0.6 | Partial — progress made but fell short |
| 0.7-0.9 | Success — hit the target (this is the goal) |
| 1.0 | Exceeded — either a win or the target was too easy |
Average KR scores to get the Objective score. OKR grade = average of all Objective scores.
Vision (10-year: where are we going?)
→ Mission (why does this business exist?)
→ Annual Goals (what must be true by Dec 31?)
→ Quarterly OKRs (what do we ship in 90 days?)
→ Weekly Priorities (what moves the needle this week?)
## SWOT — [Business/Product] — [Date]
### Strengths (internal, we control)
- [Specific advantage — not generic]
- [Specific advantage]
- [Specific advantage]
### Weaknesses (internal, we can fix)
- [Specific gap — not generic]
- [Specific gap]
### Opportunities (external, we can capture)
- [Specific market opportunity with signal]
- [Specific opportunity]
### Threats (external, we must mitigate)
- [Specific risk with probability estimate]
- [Specific risk]
### Strategic Implications
**Double down on:** [Strength × Opportunity]
**Fix urgently:** [Weakness blocking an Opportunity]
**Hedge against:** [Threat we can't ignore]
## Porter's Five Forces — [Market/Product] — [Date]
| Force | Rating (1-5) | Evidence | Strategic Response |
|-------|-------------|----------|-------------------|
| Threat of New Entrants | X/5 | [Why easy/hard to enter] | |
| Bargaining Power of Buyers | X/5 | [Client switching cost] | |
| Bargaining Power of Suppliers | X/5 | [Key dependencies] | |
| Threat of Substitutes | X/5 | [Alternatives available] | |
| Competitive Rivalry | X/5 | [Number and strength of competitors] | |
**Overall attractiveness:** [Favorable / Neutral / Unattractive]
**Recommended positioning:** [Where to compete based on force analysis]
## Blue Ocean Canvas — [Product] vs [Competitors] — [Date]
Rate 1-10 on each factor for each player:
| Compete Factor | [Competitor A] | [Competitor B] | [Our Product] | Target |
|---------------|---------------|---------------|--------------|--------|
| Price | | | | |
| Speed to value | | | | |
| Ease of use | | | | |
| [Factor specific to market] | | | | |
| [Factor specific to market] | | | | |
**Eliminate:** [Factors competitors invest in that buyers don't value]
**Reduce:** [Factors well below industry standard]
**Raise:** [Factors well above industry standard]
**Create:** [Factors the industry has never offered]
**Insight:** [The uncontested market space identified]
For each planning cycle, define three scenarios before committing resources.
## Scenario Model — [Initiative/Quarter] — [Date]
### Assumptions Matrix
| Variable | Bear | Base | Bull |
|----------|------|------|------|
| New clients per month | 0 | 1-2 | 3+ |
| Average deal size | $500 | $1,000 | $1,500 |
| Churn rate | 5%/mo | 2%/mo | 0.5%/mo |
| [Key variable] | [pessimistic] | [realistic] | [optimistic] |
### Financial Impact
| Metric | Bear | Base | Bull |
|--------|------|------|------|
| MRR at end of period | | | |
| Revenue change | | | |
| Cost change | | | |
| Net outcome | | | |
### Timeline
- **Bear:** Hits by [date] if [trigger]
- **Base:** Hits by [date] if [trigger]
- **Bull:** Hits by [date] if [trigger]
### Probability (must sum to 100%)
- Bear: X% | Base: X% | Bull: X%
### Expected Value = (Bear × P) + (Base × P) + (Bull × P)
= $X
### Trigger Events
| If this happens → | Shift to scenario | Action |
|-------------------|-----------------|--------|
| [Event] | Bear | [Specific response] |
| [Event] | Bull | [Specific response] |
Scenario: Bennett churns
Scenario: 3 new clients in Q2
Scenario: PropFlow launches to first 10 paying users
EV = (Probability of Success × Upside) - (Probability of Failure × Downside)
If EV > 0 and you can afford the downside → take the bet
If EV > 0 but downside is catastrophic → hedge or reduce position
If EV < 0 → don't do it, regardless of how exciting it feels
Example: Hiring a VA at $800/mo
HIGH IMPACT + REVERSIBLE → Do it fast, iterate
HIGH IMPACT + IRREVERSIBLE → Decide slowly, execute decisively
LOW IMPACT + REVERSIBLE → Delegate or automate
LOW IMPACT + IRREVERSIBLE → Avoid or delay
Irreversible decisions: dropping a product line, ending a client relationship, committing to a co-founder, signing a long lease.
Time to payback = Hiring cost ÷ Monthly value generated
Monthly value generated = (Tasks offloaded × CC's hourly rate) + (Revenue generated)
Acceptable payback threshold: ≤3 months for contractors, ≤6 months for full-time
Most decisions are two-way doors. Treat them as such. Only slow down for genuine one-way doors.
## QBR — Q[X] [YEAR] — [Date]
### 1. Financial Review
| Metric | Q[X-1] | Q[X] Actual | Q[X] Target | Delta |
|--------|--------|------------|------------|-------|
| MRR (end of quarter) | | | | |
| Total revenue | | | | |
| Total expenses | | | | |
| Gross margin % | | | | |
| Net profit | | | | |
**Key financial insight:** [1 sentence]
---
### 2. Pipeline Review
| Stage | Start of Q | End of Q | Change |
|-------|-----------|---------|--------|
| Leads (new) | | | |
| Qualified | | | |
| Proposals sent | | | |
| Closed won | | | |
| Closed lost | | | |
**Conversion rate:** [Leads → Won] = X%
**Average deal size:** $X
**Average sales cycle:** X days
---
### 3. Client Health Summary
| Client | MRR | Health | Deliverables | Risk |
|--------|-----|--------|-------------|------|
| [Name] | $X | HEALTHY/AT-RISK | [Status] | [None/Risk] |
**Net Revenue Retention this quarter:** X%
---
### 4. OKR Grades
| Objective | KR Scores | Objective Grade | Notes |
|-----------|----------|----------------|-------|
| O1: [Name] | X.X / X.X / X.X | X.X/1.0 | |
| O2: [Name] | X.X / X.X / X.X | X.X/1.0 | |
| O3: [Name] | X.X / X.X / X.X | X.X/1.0 | |
**Overall OKR score:** X.X/1.0
---
### 5. Competitive Positioning
- [Key competitive development this quarter]
- [Any positioning shifts needed]
- [Win/loss insights]
---
### 6. Top 3 Wins
1. [Specific win with impact]
2. [Specific win with impact]
3. [Specific win with impact]
### 7. Top 3 Misses
1. [What didn't happen and why]
2. [What didn't happen and why]
3. [What didn't happen and why]
---
### 8. Next Quarter OKR Draft
[Use OKR template above — based on learnings from this quarter]
---
### 9. Key Risks for Next Quarter
| Risk | Probability | Impact | Mitigation |
|------|------------|--------|------------|
| [Risk] | X% | [High/Med/Low] | [Action] |
---
### 10. Strategic Adjustments
- **Continue:** [What's working]
- **Stop:** [What's not working]
- **Start:** [What to add next quarter]
Run every Monday morning. Target: 15 minutes.
## Weekly CEO Review — Week of [Date]
### Revenue This Week
- MRR: $X,XXX (vs $X,XXX last week)
- Cash collected this week: $X
- Outstanding invoices: $X
### Pipeline Movements
- New leads this week: X
- Leads moved to qualified: X
- Proposals sent: X
- Deals closed: X ($X ARR)
- Deals lost: X (reason: [])
### Top 3 Priorities This Week
1. [Priority — specific deliverable — deadline]
2. [Priority — specific deliverable — deadline]
3. [Priority — specific deliverable — deadline]
### Blocked Items
- [What is stuck and what unblocks it]
### Last Week's Priorities — Did We Hit Them?
1. [Priority] — [YES/NO/PARTIAL]
2. [Priority] — [YES/NO/PARTIAL]
3. [Priority] — [YES/NO/PARTIAL]
### Next Week's Focus
[1 sentence on the single most important thing to accomplish]
python scripts/revenue_engine.py for financial data, python scripts/lead_engine.py pipeline for pipelinepython scripts/competitive_intel.py reportpython scripts/financial_model.py unit-economicsmemory/ACTIVE_TASKS.md for current quarter tracking, brain/STATE.md for north star progress/qbr workflowScore each Key Result on a 0.0–1.0 scale at quarter end. Use this rubric consistently — do not adjust scores retrospectively based on what happened.
| Score | Color | Meaning | What to Do |
|---|---|---|---|
| 0.0–0.3 | Red | Did not make meaningful progress | Root cause analysis required. Was the KR realistic? Was effort applied? |
| 0.4–0.6 | Yellow | Made progress but fell short of target | Partial credit. Carry forward or revise for next quarter. |
| 0.7–0.9 | Green | Hit the target — this is the goal zone | Validate and build on the success. |
| 1.0 | Blue | Exceeded target | Validate the win. Also ask: was the target too easy? |
70% is the success threshold. An average score of 0.7 across all KRs = a successful quarter. If you score 1.0 on everything, your targets were not ambitious enough.
Objective Score = Average of all KR scores for that Objective
OKR Grade = Average of all Objective scores
Example:
O1: KR scores = 0.8, 0.6, 0.9 → Objective score = 0.77 (Green)
O2: KR scores = 0.4, 0.5, 0.3 → Objective score = 0.40 (Yellow)
O3: KR scores = 1.0, 0.9, 0.8 → Objective score = 0.90 (Green)
OKR Grade = (0.77 + 0.40 + 0.90) ÷ 3 = 0.69 (Yellow — just below target)
After grading, answer these before setting next quarter's OKRs:
A structured 90-day cycle. Every quarter has the same shape.
Run during the first 5 days of the quarter.
brain/OKRs.mdEvery Monday:
memory/ACTIVE_TASKS.md and act this weekEvery 30 days:
Final 5 days of the quarter:
brain/STATE.md with new MRR and north star progressBefore each quarter starts, define the time, money, and attention budgets. These are constraints — not wishes.
Estimate based on current commitments:
| Block | Hours/Week | Non-Negotiable? |
|-------|-----------|----------------|
| Sleep (7hrs/night) | 49 | Yes |
| Nicky's Donuts (weekend job) | ~12 | Yes |
| Gym | ~5 | Yes — health is infrastructure |
| Client delivery work | ~15 | Yes — revenue at risk if missed |
| Sales (discovery calls, outreach) | ~8 | Yes — north star depends on this |
| Content creation | ~6 | Yes — #1 inbound source |
| Building / Bravo work | ~10 | Yes |
| Admin, comms, misc | ~5 | Yes |
| **Available for new commitments** | **~58** | Context-dependent |
Rule: Any new initiative must justify its time cost against the available budget. If it doesn't fit, something else comes out — not sleep.
Fixed costs: $184/month
Variable capacity: remaining from MRR — set a monthly cap for new tool spend
Cap: No new tools > $50/month without a written ROI case (saves X hrs or generates $Y)
Max 3 active priorities at a time. Everything else is backlog.
Active priorities this quarter:
1. [Priority — the one that hits the north star fastest]
2. [Priority — the one that protects existing revenue]
3. [Priority — the one that builds future leverage]
Backlog (not this quarter):
- [Everything else — logged in memory/ACTIVE_TASKS.md as backlog]
When to double down vs when to pivot. Use this framework for major directional decisions.
Before considering a pivot, answer these 4 questions:
Have we actually tested it? If the strategy has not been executed for at least 90 days with full effort, it is not a pivot situation — it is an execution problem.
Is the feedback signal clear? Anecdote is not signal. Data is signal. What do the numbers say specifically?
Is this a strategy failure or a tactics failure? Strategy = what we're building and who it's for. Tactics = how we're reaching them. Changing tactics is not a pivot.
What is the opportunity cost of not pivoting vs pivoting?