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:

CIO Role (day job - Technology, Communications, Safety/Security)
Consulting/Speaking (reputation building, CoSN board, conferences)
Product Development (AI products: voice app, survey tool)
Real Estate Investing (portfolio management)
Financial Planning (entrepreneurial income, retirement prep)

Available Scripts

`scripts/generate_annual_review.py`

Generates formatted annual review markdown file in Obsidian.

Usage:

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:

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:

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:

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

Curious: "Say more?" / "What would that look like?"
Gentle push: "Help me see this concretely. If I walked into your office in December [next year], what would I notice?"
Direct challenge: "This is staying abstract. Let's get specific—what's one concrete outcome?"
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:

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")
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?"
Identify Actions, Owners, Dependencies:
- "What are the key actions that will drive [goal]?"
- For each action:
  - Action/Project: What will be done
  - Owner: Who is accountable (a person, not committee)
  - Dependencies: Other people/teams/resources required
  - Timeline: Q1/Q2/Q3/Q4 milestones
Map Quarterly Milestones:
- "What should be true by end of Q1 (Mar 31), Q2 (Jun 30), Q3 (Sep 30), Q4 (Dec 31)?"

Challenge Mechanisms:

Activity → Outcome reframing: "If you do X successfully, what changes? That's the priority."
No baseline: "Can you establish one now? If not, note this as 'learning year' for baseline."
Vague targets: "If you hit this target, would you be satisfied? What would failure look like?"

After all domains completed:

Confirm Alignment:
- "Looking at all your goals together—do they clearly ladder up to your strategic direction AND to your core mission?"
- If weak alignment: Work to adjust or note misalignment for discussion

Phase 5: Cross-Domain Integration

Objective: Portfolio view, trade-offs, advisor review, identity alignment.

Portfolio Questions:

Q1: "Looking at all 5 domains—what's the overall story of [next year]?"

Q2: "Where are you over-committed? What trade-offs do you need to make?"

Q3: "Which domain gets your BEST energy? Which gets leftovers?"

Q4: "If one domain had to be 'maintenance mode' in [next year], which and why?"

Personal Board of Directors (optional but recommended):

Q5: "Who are your 4-7 advisors across domains?"

For each: Name, Domain expertise, What they help with, Last consulted
Roles to consider: Connector, Accountability Partner, Futurist, Subject Matter Expert

Q6: "Who's missing from your board?"

Prompt: "Do you have a Connector (network access), Futurist (trends), Accountability Partner?"

Alignment with Identity:

Q7: "Do these goals align with your Type 3w4 achievement pattern?"

Context: Meaningful, competent, expert-level impact (from identity-core.json)

Q8: "Which goals leverage your Input/Analytical/Learner strengths?"

Display: How each goal creates opportunities for information gathering, evidence-based thinking, mastery

Q9: "Any goals that require relationship building (your 0% Blue gap)?"

Follow-up: "How will you handle that? Who can help?"

Q10: "Looking at your workload—where's the Type 3 stress risk?"

Context: Type 3 pattern = push harder when stressed
Prompt: "If things get overwhelming in Q2, what's your PAUSE trigger before pushing harder?"

Phase 6: Review & Finalize

Objective: Generate output, get approval, save to systems.

Geoffrey:

Display Complete Annual Review
- Use templates/annual-review-template.md format
- Show full markdown output for review
Get User Approval
- "Does this capture your strategic plan for [year]?"
- "What would you adjust?"
- Iterate until confirmed
Save to Obsidian
- Run scripts/generate_annual_review.py
- Save to Personal_Notes/Reviews/Annual/{YEAR}-Annual-Review.md
Ask about OmniFocus
- "Create OmniFocus projects from your Priority Goals now or later?"
- If now: Run scripts/sync_to_omnifocus.js
Review Personal User Guide for Updates
- Read current User Guide: ~/Library/Mobile Documents/iCloud~md~obsidian/Documents/Personal_Notes/Geoffrey/Kris-Hagel-User-Guide.md
- Compare to this year's review conversation:
  - Role changes (meeting cadences, team structure, responsibilities)
  - New growth areas identified
  - Communication pattern shifts
  - Changed priorities, frustrations, or energizers
  - "What drains me" / "What energizes me" updates
- Propose specific, evidence-based updates:
  - "In this review you mentioned X, but your User Guide says Y. Should I update?"
  - "You identified [growth area] but it's not documented. Should we add it?"
- If updates approved: Edit the User Guide and confirm changes
- If significant changes: Suggest notifying team/peers
Schedule Quarterly Reviews
- Confirm quarterly timing: Mar 31, Jun 30, Sep 30, Dec 31
- Add to OmniFocus as recurring tasks

Final Output:

Annual review markdown file (Obsidian)
OmniFocus projects (if requested)
Confirmation message with file path

Quarterly Check-In Workflow

The quarterly check-in is a lighter interview (15-20 min) focused on progress and adjustment.

Check-In Questions

For each domain with Priority Goals:

Q1: "Progress status on [Goal]?"

✅ On track (will hit target)
⚠️ At risk (may miss target without intervention)
❌ Off track (unlikely to hit target)

Q2: "What evidence supports your assessment?"

Current state vs. Q{N} milestone
What happened this quarter?

Q3: "What's working? What's stalled?"

Q4: "Do Success Indicators still make sense?"

Adjust targets? (yes/no + rationale)
Add/remove indicators?

Q5: "What needs to change for Q{N+1}?"

Actions to add/drop
Resources needed
Trade-offs with other domains

After all domains:

Q6: "Overall portfolio health?"

Energy distribution across domains
Over-committed anywhere?
Mid-course corrections needed?

Q7: "User Guide check against this quarter's insights"

Read current User Guide: ~/Library/Mobile Documents/iCloud~md~obsidian/Documents/Personal_Notes/Geoffrey/Kris-Hagel-User-Guide.md
Compare to quarterly progress discussion:
- Any communication preferences that changed?
- New frustrations or energizers to document?
- Growth areas with visible progress?
Propose specific updates based on evidence from this check-in
If updates approved: Edit and save

Check-In Output

Geoffrey:

Run scripts/generate_quarterly_review.py
Save to Personal_Notes/Reviews/Quarterly/{YEAR}-Q{N}-Review.md
Update annual review frontmatter with link to quarterly review
Confirm adjustments to OmniFocus if targets/actions changed

Output Format

Annual Review

See templates/annual-review-template.md for complete format.

Key sections:

Year-in-Review Summary (cross-domain patterns, lessons)
Per Domain: Review + Strategic Direction + Priority Goals
Cross-Domain Integration (portfolio, trade-offs, advisors, alignment)
Next Steps (quarterly reviews, OmniFocus sync, advisor shares)

Quarterly Review

See templates/quarterly-review-template.md for complete format.

Key sections:

Progress status per Priority Goal
Evidence of progress vs. milestones
What's working / what's stalled
Adjustments for next quarter
Portfolio health check

Integration with Existing Systems

Obsidian

Storage locations:

Personal_Notes/
└── Reviews/
    ├── Annual/
    │   └── YYYY-Annual-Review.md
    └── Quarterly/
        └── YYYY-QN-Review.md

Frontmatter:

---
created: {date}
year: {YEAR}
domains: [CIO, Consulting, Product, RealEstate, Financial]
status: Draft | Final
quarterly_reviews:
  - Q1: [[YYYY-Q1-Review]]
  - Q2: null
  - Q3: null
  - Q4: null
---

OmniFocus

Project structure:

[Domain] - [Goal Name] (e.g., "CIO Role - Improve AI Adoption")
Tasks for each action (owner/dependencies in notes)
Milestones as tasks with Q1/Q2/Q3/Q4 due dates
Tags: domain name + "2026 Goals"

Personal User Guide

Location:

Personal_Notes/Geoffrey/Kris-Hagel-User-Guide.md

Review triggers:

Annual review (Phase 6) - comprehensive review
Quarterly check-ins - light evidence-based updates

Update approach:

Evidence-based: Compare User Guide to review conversation
Specific proposals: Point out discrepancies with examples
User approval required before editing

Identity-Core Integration

Loads from:

~/Library/Mobile Documents/com~apple~CloudDocs/Geoffrey/knowledge/identity-core.json

References:

TELOS mission per domain
Constitution values (equity, excellence, empathy, learning, innovation, integrity)
Strengths (Input, Significance, Analytical, Achiever, Learner)
Personality (Type 3w4, Green-Orange, 0% Blue relationship gap)
Decision framework, stress patterns, growth edges

Uses for:

Alignment checks in Part 3 (Strategic Direction)
Challenge questions in Part 5 (Cross-Domain Integration)
Framing success in terms of Mastery + Legacy + Freedom

Framework Integration

James Clear Systems Focus

Applied in:

Success Indicators: Include leading (process) + lagging (outcome) metrics
During goal-setting: Ask "What system/habit supports this goal?"
Reframe outcome goals → process goals where appropriate

Example:

Outcome: "Launch AI voice app"
System: "Ship feature every 2 weeks" + "User feedback session biweekly"

Personal Board of Directors

Included in: Part 5 (Cross-Domain Integration)

Tracks:

4-7 advisors across domains
Roles: Connector, Accountability Partner, Futurist, Subject Matter Expert
Last consulted date (accountability)

Life Map (Alex Lieberman)

Maps to 5 domains:

Career → CIO Role + Consulting/Speaking
Finances → Real Estate + Financial Planning
Meaning → Product Development (AI products = legacy)
Relationships → Cross-domain question (0% Blue gap)
Health → Not covered (note for future expansion)
Fun → Not covered (note for future expansion)

Ideal Lifestyle Costing (Tim Ferriss)

Optional exercise in: Financial Planning domain

Question: "What does your ideal [year] look like? Cost it out." Use for: Retirement planning milestone

Error Handling

Common Scenarios

1. User can't answer "what you will NOT do" (Q5 in Strategic Direction):

Response: Use scaffolding questions (see Phase 3)
If still stuck: "Let's flag this and come back after Priority Goals are defined."
Note in output: "Strategic exclusions to be determined"

2. User has no baseline for Success Indicator:

Response: "Can you establish a baseline now? If not, we'll note this as a 'learning year' for baseline setting."
Record: Current = "Baseline TBD" → Target = [value]

3. User proposes >3 Priority Goals:

Response: "You've listed [N] priorities. Research shows more than 3 means none get focus. Which would you cut?"
Enforce: Hard cap at 3 per domain

4. User's goals don't align with strategic direction:

Response: "You said your strategic direction was [X], but this goal seems focused on [Y]. Help me see the connection."
If misalignment remains: Note in "Potential Misalignments" section for discussion

5. User wants to skip domains:

Response: Allow skipping for quarterly check-ins
For annual: Recommend covering all 5, but allow "maintenance mode" designation

6. User wants to adjust targets mid-year (quarterly check-in):

Response: "What changed? What's the rationale for adjusting?"
Record: Original target + Revised target with date/reason
Update: OmniFocus milestones if needed

Future Enhancements

Add Health and Fun domains to Life Map coverage
Integrate with calendar for automatic quarterly review reminders
Add mid-year strategic adjustment session (July)
Create visualization dashboard for progress tracking
Add retrospective analysis comparing year-over-year patterns
Integration with knowledge-manager for automatic preference updates based on goals
Add voice AI option for conducting interview (user speaks, Geoffrey transcribes and challenges)

Version History

v1.1.0 (2026-01-26)

Renamed from strategic-planning-manager to personal-strategic-planning
Updated triggers to avoid conflict with organizational planning skill
For organizational/K-12 strategic planning, use strategic-planning-manager

v1.0.0 (2026-01-02)

Initial release
Annual review interview (6 phases)
Quarterly check-in interview
Obsidian integration (Reviews folder)
OmniFocus integration (auto-create projects)
Identity-core alignment checks
Progressive challenge mechanisms
5-domain structure