personal-strategic-planning

What this skill does

# Personal Strategic Planning Skill

Annual strategic review and goal-setting system combining interview-driven planning with evidence-based reflection across five personal life/work domains.

> **Note:** For organizational/K-12 district strategic planning, use the `strategic-planning-manager` skill instead.

## When to Activate

This skill activates when the user requests:

**Annual Review (Primary Mode):**
- "Let's do my annual review"
- "Help me plan for [year]"
- "I want to do strategic planning"
- "Set goals for next year"

**Quarterly Check-In (Lighter Mode):**
- "Quarterly check-in"
- "Review my progress"
- "How am I tracking against my goals?"

**Domain Modes:**
Each review covers 5 domains:
1. **CIO Role** (day job - Technology, Communications, Safety/Security)
2. **Consulting/Speaking** (reputation building, CoSN board, conferences)
3. **Product Development** (AI products: voice app, survey tool)
4. **Real Estate Investing** (portfolio management)
5. **Financial Planning** (entrepreneurial income, retirement prep)

## Available Scripts

### `scripts/generate_annual_review.py`
Generates formatted annual review markdown file in Obsidian.

**Usage:**
```bash
uv run scripts/generate_annual_review.py '{json_data}' --year 2026
```

**Input:** JSON with interview data (all domains, goals, indicators)
**Output:** Markdown file at `Personal_Notes/Reviews/Annual/{YEAR}-Annual-Review.md`

### `scripts/generate_quarterly_review.py`
Generates quarterly check-in markdown file in Obsidian.

**Usage:**
```bash
uv run scripts/generate_quarterly_review.py '{json_data}' --year 2026 --quarter Q1
```

**Input:** JSON with progress data per domain
**Output:** Markdown file at `Personal_Notes/Reviews/Quarterly/{YEAR}-Q{N}-Review.md`

### `scripts/sync_to_omnifocus.js`
Creates OmniFocus projects and tasks from Priority Goals.

**Usage:**
```bash
osascript -l JavaScript scripts/sync_to_omnifocus.js '{json_data}'
```

**Input:** JSON with goals, indicators, actions, milestones
**Output:** OmniFocus projects created, returns confirmation JSON

## Annual Review Workflow

The annual review follows a 6-phase interview pattern modeled after the `writer` skill.

### Phase 1: Domain Selection & Context Loading

**Objective:** Set scope and load relevant context for each domain.

**Geoffrey:**
1. Displays 5 domains with mission from `identity-core.json`:
   - CIO Role → TELOS Technology/Communications/Safety sections
   - Consulting/Speaking → TELOS Economics (reputation building)
   - Product Development → Short-term goals (AI products)
   - Real Estate → TELOS Economics (income streams)
   - Financial → Long-term goals (retirement, entrepreneurial income)

2. Asks: "Which domain(s) do you want to review?" (allow multi-select for first run)

3. For first annual review: Offer "Retrospective (2025) + Prospective (2026)" or "Prospective only"

**Output:** List of selected domains with loaded context

---

### Phase 2: Year-in-Review Reflection (Per Domain)

**Objective:** Ground planning in reality by examining what actually happened.

**Interview Questions (one domain at a time):**

**Q1:** "What were your top 3 priorities in [domain] this year?"

**Q2:** "For each priority, what actually happened?"
- **Challenge:** Require evidence/outcomes, not just activities
- **Push for:** Specific metrics, concrete changes, measurable results

**Q3:** "What worked exceptionally well in [domain]?"
- **Challenge:** Require specifics, not generalities
- **Push for:** Root causes of success, replicable patterns

**Q4:** "What underperformed or stalled?"
- **Challenge:** Require root causes, not just symptoms
- **Push for:** Honest assessment, systemic barriers

**Q5:** "What surprised you—positive or negative?"

**After all domains reviewed:**

**Q6:** "Looking across all domains, what patterns do you see?"

**Q7:** "What's one lesson you'd apply everywhere next year?"

**Challenge Mechanisms:**
- **Vague answer** → "Say more? What would that look like specifically?"
- **Activity-focused** → "That's what you did. What was the result?"
- **No evidence** → "What metric or outcome would prove that?"

---

### Phase 3: Strategic Direction (Per Domain)

**Objective:** Define clear vision for next year aligned with core mission.

**Interview Questions (one domain at a time):**

**Q1:** "At the end of [next year], what does success look like in [domain]?"
- **Must be:** Specific, measurable, stakeholder-focused
- **Challenge:** Push beyond vague aspirations to concrete outcomes

**Q2:** "Who are the primary stakeholders for [domain]?"
- **Follow-up:** "For each stakeholder, what specifically changes for them if you succeed?"

**Q3:** "How does [domain] success contribute to your core mission?"
- **Display:** Relevant TELOS section + constitution values
- **Challenge:** If alignment is weak, ask "Is this the right priority?"

**Q4:** "What are 2-3 major initiatives or changes in [domain]?"
- **Challenge if >3:** "Which would you protect if capacity gets constrained?"
- **Challenge if maintenance:** "Is this strategic work or keeping lights on?"

**Q5:** "What will you explicitly NOT do in [domain]?"
- **This is the hardest question** - use scaffolding if stuck:
  1. "What requests have you said no to—or wish you had?"
  2. "What did you consider but decide against?"
  3. "If someone proposed adding [new initiative], what would you tell them?"
  4. "What are you currently doing that you should stop?"
- **Why it matters:** "Every 'yes' is an implicit 'no' to something else. If you can't name what you're not doing, you haven't made strategic choices."

**Q6:** "What's the biggest barrier to success in [domain]?"
- **Follow-up:** "What needs to be true for you to succeed?"

**Q7:** "What resources/support do you need that you don't have?"
- **Challenge if "nothing":** "Most meaningful work requires time, development, or coordination—not just money."

**Challenge Progression:**
1. **Curious:** "Say more?" / "What would that look like?"
2. **Gentle push:** "Help me see this concretely. If I walked into your office in December [next year], what would I notice?"
3. **Direct challenge:** "This is staying abstract. Let's get specific—what's one concrete outcome?"
4. **Support scaffolding:** Offer frameworks, examples, different angles

**After domain completed:**
- Summarize strategic direction back to user
- Get confirmation before moving to next domain

---

### Phase 4: Priority Goals with Success Indicators (Per Domain)

**Objective:** Translate strategic direction into measurable progress.

**Constraints:**
- **Maximum 3 Priority Goals per domain** (hard cap)
- Each goal requires **2-3 Success Indicators** with baselines + targets
- Each goal requires **Key Actions** with owners, dependencies, timeline
- Each goal requires **Quarterly Milestones**

**Interview Process:**

**For each domain:**

1. **Establish Priority Goals:**
   - "Based on our conversation, what are your 2-3 Priority Goals for [domain]?"
   - **Challenge if >3:** "You've listed [N]. Research shows more than 3 priorities means none get focus. Which would you cut?"
   - **Challenge if activity-focused:** Reframe as outcome (e.g., "implement curriculum" → "students demonstrate deeper engagement")

2. **Define Success Indicators (for each goal):**
   - "How will you know you're making progress on [goal]?"
   - **Require:** Current state (baseline) → Target state (end of year)
   - **Accept:** Both quantitative and qualitative
     - Quantitative: "Student re-enrollment: 92% → 95%"
     - Qualitative: "Faculty report feeling supported: 45% agree → 70% agree"
   - **Challenge if no baseline:** "How will you establish one?" or "Is this a learning year?"
   - **Challenge if vague target:** "Too easy or unrealistic?"
   - **Challenge if activity metric:** "That measures what you did, not the result. What outcome changes?"

3. **Identify Actions, Owners, Dependencies:**
   - "What are the key actions that will drive [goal]?"
   - For each ac