Personal Strategic Planning

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:

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:

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 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

4. 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:

5. 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:

1. Display Complete Annual Review

   • Use templates/annual-review-template.md format
   • Show full markdown output for review

2. Get User Approval

   • "Does this capture your strategic plan for [year]?"
   • "What would you adjust?"
   • Iterate until confirmed

3. Save to Obsidian

   • Run scripts/generate_annual_review.py
   • Save to Personal_Notes/Reviews/Annual/{YEAR}-Annual-Review.md

4. Ask about OmniFocus

   • "Create OmniFocus projects from your Priority Goals now or later?"
   • If now: Run scripts/sync_to_omnifocus.js

5. 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

6. 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:

1. Run scripts/generate_quarterly_review.py
2. Save to Personal_Notes/Reviews/Quarterly/{YEAR}-Q{N}-Review.md
3. Update annual review frontmatter with link to quarterly review
4. 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