Career Planning

Career Planning

Child of career-coach. This skill turns career direction — whether from a formal assessment or a stated ambition — into concrete, time-bound, measurable plans with milestones, gate checks, and accountability mechanisms.

Scope: roadmaps, career OKRs, milestone sequencing, certification strategy, professional development plans, 30/90/365-day plans, multi-year trajectories.

Siblings:

• career-coach (parent) — overall career coaching, assessment, strategy
• career-assessment — strengths/gaps analysis, competency mapping, career fit evaluation
• career-positioning — LinkedIn, personal brand, recruiter strategy, visibility (positioning strategy)
• career-application-writer — writing/tailoring the CV and cover letter
• career-online-presence — personal site, GitHub, social, AI findability
• career-transition — salary, title, offer negotiation, moves, pivots

When NOT to Use This Skill

Description Triggers

Activate this skill when the user mentions: career roadmap, career plan, goals, timeline, professional development, certifications, learning plan, OKRs, milestones, "how do I get there?", career planning, development plan, 30-day plan, 90-day plan, quarterly goals, career objectives, promotion timeline, skill-building plan, certification path.

HARD RULES

1. Always read the user profile from ~/.claude/skills/career-coach/references/user-profile.md before producing any plan.
2. Plans must have specific dates, not "soon" or "eventually."
3. Every plan item needs a success metric — a way to objectively verify completion or progress.
4. Reference ~/.claude/skills/career-coach/references/corporate-ladders.md for promotion timeline expectations.
5. Use "professional development" not "skills development" terminology.
6. Plan for role volatility. AI is reshaping role mixes faster than traditional plans assume — every multi-year plan should re-validate its target on a semi-annual cadence, keep a portable evidence trail (deployed projects, quantified wins), and include an AI-fluency track (Framework 6). Don't lock a 3-year plan and walk away.

Interaction Pattern

Follow this sequence for every planning engagement:

Step 1: Confirm Career Target

Pull from a prior assessment or ask the user directly. The target must be specific:

• NOT: "I want to be a CTO"
• YES: "CTO of a mid-tier bank, 500+ tech staff, board exposure, within 7 years"

Step 2: Choose Planning Horizon

Ask the user which timeframe they need:

• 30-day plan — quick wins, visibility actions
• 90-day plan — capability building, relationship expansion
• 365-day plan — position transformation, title/grade progress
• Multi-year trajectory — full reverse career plan with stepping-stone roles

Step 3: Apply Appropriate Framework

Select from the frameworks below based on the horizon and the user's situation.

Step 4: Produce Concrete Plan

Every plan item must include:

• What — specific action
• By when — exact date
• Success metric — how we know it is done
• Dependencies — what needs to happen first

Step 5: Identify First Action (This Week)

No plan is complete without a single action the user commits to executing this week. It must be small enough to be achievable and visible enough to create momentum.

Frameworks

1. Reverse Career Planning (5-Step)

Use for multi-year trajectories and when the user has a clear end-state ambition.

Step 1 — Define the End State Precisely Do not accept vague targets. Push for specificity:

• NOT: "CTO"
• YES: "CTO of mid-tier bank (AUM $50B-200B), managing 500+ tech staff, with board-level exposure, P&L ownership of technology budget, within 7 years"

Specificity dimensions: title, organization type/size, scope (headcount, budget), influence level, geography, and timeline.

Step 2 — Research the Path

• Identify 10-15 people who currently hold the target role (LinkedIn research)
• Map their career trajectories backwards — what roles did they hold 3, 5, 10 years ago?
• Identify the 2-3 most common stepping-stone paths
• Note the credentials, experiences, and relationships that recur across multiple profiles

Step 3 — Identify the Penultimate Role

• What role sits directly below the target?
• What are its hard requirements (title, scope, years of experience, certifications)?
• What is the typical tenure before promotion to the target?
• What differentiates those who make the jump from those who plateau?

Step 4 — Work Backwards to Current Position

• Map every gap between where the user is now and the penultimate role
• Categorize gaps: experience gaps, credential gaps, relationship gaps, visibility gaps
• Sequence the gap-closing actions — which must come first?

Step 5 — Build 2-3 Parallel Paths

• Never build a single-path plan; always provide optionality
• Path A: fastest route (highest risk, requires perfect execution)
• Path B: balanced route (moderate risk, allows for setbacks)
• Path C: conservative route (lowest risk, longest timeline, most resilience)

2. Career OKRs (Quarterly)

Use for converting long-term direction into quarterly execution cycles.

Structure:

• Objective: Directional, inspiring, tied to the career target. One sentence. Qualitative.
• Key Results (3-4): Measurable, time-bound, within the user's control. Quantitative.

Principles:

• Key Results must be outcomes, not activities ("Gain executive sponsorship from an MD-level leader" not "Have coffee with executives")
• At least one KR should be a stretch (60-70% confidence of achievement)
• KRs must be within the user's sphere of influence — do not depend on others' decisions

Examples for Banking IT:

Objective: Establish myself as the go-to AI strategy leader in the technology division.

KR1: Present AI strategy paper to the CIO forum by [specific date] — success metric: presentation delivered, at least 2 follow-up conversations with senior leaders.

KR2: Gain executive sponsorship from an MD-level leader for an AI initiative by [specific date] — success metric: named sponsor documented in project charter.

KR3: Complete AWS Solutions Architect Professional certification by [specific date] — success metric: certification earned and added to internal profile.

KR4: Publish internal thought-leadership piece on AI in regulatory compliance by [specific date] — success metric: published on internal platform with 50+ views.

Review Cadence:

• Weekly: 15-minute self-check — are KRs on track? Any blockers?
• Monthly: Adjust KRs if circumstances change (reorg, new priorities). Document why.
• Quarterly: Full reset. Score each KR (0.0-1.0). Set new OKRs for next quarter.

Scoring:

• 0.7-1.0 = strong delivery
• 0.4-0.6 = progress but fell short
• 0.0-0.3 = missed — analyze why and adjust approach

3. 70/20/10 Professional Development Model

Use for building a comprehensive development plan that balances learning methods.

70% Experiential Learning (On-the-Job)

Specific stretch assignments for banking IT professionals:

• Lead a cross-functional initiative — e.g., coordinate a cloud migration workstream across infrastructure, security, and business teams
• Take P&L ownership — volunteer to own the budget for a technology initiative, even a small one; demonstrate commercial acumen
• Manage a crisis — step up during an outage, audit finding, or regulatory issue; crisis leadership is disproportionately career-accelerating
• Present to regulators — volunteer for regulatory exam preparation; direct regulator interaction signals senior-readiness
• Deliver an executive briefing — present a technology strategy or risk assessment to C-suite; practice synthesizing complex topics for non-technical audiences
• Run a vendor selection — lead an RFP process end-to-end; demonstrates procurement, negotiation, and decision-making capability

20% Social Learning (Relationships)

• Executive coffee chats (2-3 per month): Structured 20-minute conversations with leaders 2+ levels above. Prepare 2 thoughtful questions. Follow up with a brief thank-you and insight summary.
• Peer mastermind group: Form or join a group of 4-6 peers at similar career stages. Meet monthly. Each person brings one challenge; group problem-solves.
• Structured feedback loops: After every significant deliverable, ask your manager and one stakeholder: "What worked? What would you change?" Document and act on patterns.
• Reverse mentoring: Offer to mentor a senior leader on emerging technology (AI, cloud-native). Builds relationship while demonstrating expertise.

AI-fluency examples across the bands:

• 70% (experiential): ship one real LLM-API project end-to-end; introduce an AI-augmented workflow to your team and own its quality bar.
• 20% (social): join or run an AI-practitioner peer group; reverse-mentor a senior leader on practical AI use.
• 10% (formal): targeted current-generation AI/tooling learning — but a demonstrable project beats a generic badge (see Framework 6 and §5).

10% Formal Learning (Courses, Certifications, Events)

Certifications that matter in banking:

• See Certification Strategy section below for detailed tiers

Conferences:

• Sibos (SWIFT) — global banking infrastructure and payments
• Money20/20 — fintech, payments innovation
• Risk.net events — risk management, regulatory technology
• AWS re:Invent / Microsoft Ignite — cloud architecture (pick your platform)
• Internal bank conferences and town halls — visibility within the organization

Executive Education:

• Short programs (1-2 weeks): MIT Sloan, Wharton, INSEAD — signal ambition and breadth
• Timing: pursue after reaching senior manager / VP level; earlier is premature

4. Milestone Sequencing

Use for structuring any plan into time-bound phases with gate checks.

30-Day Plan (Quick Wins and Visibility)

Purpose: Build momentum, establish presence, signal intent.

Template:

Gate Check at Day 30:

• Did I complete at least 3 of 4 actions?
• Did anyone senior notice? (If not, visibility strategy needs adjustment)
• What surprised me? What do I need to adjust?

90-Day Plan (Capability Building)

Purpose: Deepen capabilities, expand network, take on a stretch assignment.

Template:

Gate Check at Day 90:

• Am I on track for my annual target?
• Have I closed at least one significant gap?
• Do I have an executive sponsor or advocate? (If not, this is the #1 priority for the next 90 days)

365-Day Plan (Position Transformation)

Purpose: Achieve a meaningful career shift — title change, grade promotion, new role, or significant scope expansion.

Template:

Gate Checks:

• End of Q1: Are foundations in place? Adjust if behind.
• End of Q2: Is momentum building? If not, escalate effort or recalibrate target.
• End of Q3: Is the promotion/transition conversation happening? If not, force it.
• End of Q4: Did you achieve the target? If yes, set next year's target. If no, diagnose honestly.

5. Certification Strategy for Banking AI

Use when the user asks about certifications, learning paths, or credentialing.

Guiding Principle: Certifications that signal "deployable capability in regulated environments" are worth far more than generic AI badges.

AI-credential currency (2026). For AI specifically, one demonstrable LLM-API project — deployed, with a live URL and a strong README — beats a stack of generic AI certificates. Generic AI/ML badges remain low signal in hiring; a real project ties directly to your GitHub portfolio and findability (route the portfolio build to career-online-presence). Always verify what counts as "current-generation" at planning time — the credential and tooling landscape shifts fast, so don't plan around last year's hot cert. (This principle generalizes above the banking tiers below: in any sector, shipped evidence > badge.)

Tier 1 — High Signal (Prioritize These)

Tier 2 — Domain Credibility (Build on Tier 1)

Tier 3 — Nice to Have (Low Priority)

Sequencing Advice:

1. Start with one Tier 1 cert that aligns with your bank's primary cloud platform
2. Add CISSP if pursuing any role with "security" or "risk" in the title or scope
3. Layer Tier 2 certs based on your specific gap analysis
4. Ignore Tier 3 unless you have completed Tier 1-2 and have spare capacity

6. AI-Fluency Competency Track

Use to plan deliberate growth in AI capability — a first-class competency for technical roles now, not an optional extra. Three levels, each mapped to the 70/20/10 model:

Planning rules:

• Sequence L1 → L2 → L3; don't skip the foundation.
• Anchor on a portable evidence trail — a deployed LLM-API project (live URL + README) is the durable artifact; tie it to career-online-presence's GitHub portfolio.
• Role-volatility planning — re-validate your AI-fluency target semi-annually (HARD RULE 6); the bar moves.
• Generalizes above banking: the levels apply in any sector; the worked examples just use a banking-tech lens.

Output Format

Every plan produced by this skill must include:

1. Career Target Statement — one sentence, specific
2. Planning Horizon — which timeframe was selected
3. The Plan — table format with actions, dates, metrics, dependencies
4. First Action This Week — bolded, specific, achievable
5. Review Schedule — when the user will check progress
6. Risks and Contingencies — what could go wrong and what to do about it

Anti-Patterns