stephenrogan/career-dev-planner

Career Development Planner

Maps the path from where you are to where you want to be in your CS career. Not a generic "develop your skills" plan -- a structured assessment of what the next level requires, where your gaps are, and exactly what to do about them.

How to Use

Provide:

• Your current role and level
• Your target role (next level, skip level, lateral move, or specific position)
• Your tenure and key achievements
• Your self-assessed strengths and gaps
• Feedback you have received (performance reviews, manager input, peer observations)
• Your timeline (6 months, 1 year, 2 years)
• Any constraints (company size limits promotion opportunities, need to change companies, etc.)

The CS Career Ladder

Level Progression and Core Requirements

| Level | Title Range | Core Requirement | Key Differentiator | |-------|-----------|-----------------|-------------------| | L1 | CSM, Associate CSM | Execute the playbook. Follow processes. Build foundational skills | Reliability: you do what you say you will do, consistently | | L2 | Senior CSM, CSM II | Operate independently. Manage complex accounts. Drive commercial outcomes | Judgment: you make good decisions without being told what to do | | L3 | Principal CSM, Lead CSM | Strategic thinking across the portfolio. Influence cross-functionally. Mentor others | Leverage: you multiply the team's impact, not just your own | | L4 | CS Manager, Team Lead | Build and develop a team. Own metrics. Design processes | Leadership: you achieve outcomes through others, not through personal execution | | L5 | Director of CS, Senior Manager | Own a segment or region. Drive strategy. Manage managers | Scale: you build systems that work without you in the room | | L6 | VP of CS, Head of CS | Own the function. P&L responsibility. Board communication. Cross-functional leadership | Vision: you define what CS looks like for the company and build the organisation to deliver it |

Skills Matrix by Level

| Skill Domain | L1-L2 | L3 | L4-L5 | L6 | |-------------|-------|-----|-------|-----| | Account management | Execute playbooks. Manage a book. Maintain cadence | Strategic account planning. Complex account ownership. Proactive, not reactive | Define the playbook. Set the standard. Coach others on execution | Set the strategy. Define what "good" looks like for the function | | Commercial acumen | Understand pricing. Support renewals | Drive expansions. Build commercial cases. Own the renewal conversation | Own the segment's NRR. Forecast retention. Build the commercial motion | Own company-level NRR. Present to the board. Align CS economics with company strategy | | Customer relationships | Build rapport. Manage primary contacts | Multi-thread. Engage executives. Navigate politics | Coach others on relationship building. Set stakeholder coverage standards | Build executive-to-executive relationships at the company's most strategic accounts | | Cross-functional influence | Collaborate with support and product | Influence product roadmap with data. Coordinate with sales on expansion | Partner with product and sales leadership. Align cross-functional priorities | Own the CS seat at the executive table. Drive company-wide customer-centric decisions | | Data and metrics | Track your portfolio health. Use a dashboard | Analyse trends. Build reports. Use data to drive decisions | Define the metrics. Build the dashboards. Own the reporting to leadership | Define what the company measures about customer success. Set targets. Report to the board | | Process and systems | Follow the process. Log accurately | Identify process gaps. Suggest improvements | Design processes. Select and implement tooling. Measure operational efficiency | Build the operating model. Define the CS tech stack strategy. Architect agent-augmented workflows | | People development | N/A (IC) | Mentor peers. Share expertise. Coach informally | Hire, develop, and retain a team. Run 1:1s. Build a culture | Build the CS organisation. Define the career ladder. Develop the leadership bench |

Gap Analysis

For each skill domain, assess:

| Domain | Current Level | Required Level | Gap Size | Priority | |--------|-------------|---------------|----------|----------| | [domain] | [where you are -- specific evidence] | [where you need to be for target role] | [Small/Medium/Large] | [High/Medium/Low based on how critical this gap is for the transition] |

Prioritisation logic:

• Must-have gaps (High): skills the target role cannot function without. These are the gates
• Differentiator gaps (Medium): skills that separate strong performers from adequate ones at the target level
• Nice-to-have gaps (Low): skills that add depth but are not required for the transition

Development Actions by Gap Size

| Gap Size | Timeline | Approach | |----------|----------|---------| | Small (Application -> Proficiency) | 1-3 months | Deliberate practice on current accounts. Seek 2-3 opportunities to apply the skill at the target level | | Medium (Understanding -> Proficiency) | 3-6 months | Structured learning + practice. Course or reading + 5-10 real-world applications with feedback | | Large (Awareness -> Proficiency) | 6-12 months | Full development programme. Training, mentoring, practice, feedback, and progressively higher-stakes application |

Development Plan Template

## Career Development Plan: [Name]
**Current:** [Role, Level, Tenure]
**Target:** [Role, Level]
**Timeline:** [months/years]

### Gap Assessment
| Domain | Current | Required | Gap | Priority |
|--------|---------|----------|-----|----------|
| [domain] | [level with evidence] | [level] | [S/M/L] | [H/M/L] |

### Priority Actions (Next 90 Days)
Focus on 2-3 high-priority gaps:

**Gap 1: [Domain]**
- Learn: [specific action by date]
- Practice: [specific opportunity by date]
- Reflect: [feedback mechanism]
- Milestone: [what "closed" looks like for this 90-day period]

**Gap 2: [Domain]**
[Same structure]

### Longer-Term Development (6-12 Months)
[Medium and low priority gaps with approach]

### Support Needed
- From manager: [specific coaching, opportunities, sponsorship]
- From peers: [mentoring, peer coaching, collaboration]
- External: [courses, certifications, communities, reading]

### Review Schedule
- Monthly self-check: [date]
- Quarterly manager review: [date]
- Readiness assessment: [target date for evaluating promotion readiness]

The Readiness Conversation

When you believe you are ready for the next level, structure the conversation:

1. Evidence: "Here is what I have demonstrated at the next level" (specific examples per skill domain)
2. Gaps acknowledged: "Here is what I am still developing" (shows self-awareness)
3. Ask: "I believe I am ready for [role]. I would like to discuss the path and timeline"

Do not wait to be asked. Promotions go to people who demonstrate readiness and articulate it, not to people who wait to be recognised.

Quality Gates

• Is the gap assessment honest? If every domain shows "small gap," the assessment is optimistic. Every level transition has at least one large gap -- that is what makes it a transition, not a continuation
• Are the development actions specific and time-bound? "Read about leadership" is not a development action. "Complete [specific course] by [date] and apply the delegation framework to my next onboarding project" is
• Is the manager involved? A development plan without manager buy-in lacks the sponsorship and opportunity allocation that makes the plan executable
• Is the timeline realistic? Skipping a level in 6 months is unrealistic for most people. Moving one level in 12-18 months with deliberate effort is achievable

Principles

• Career development is a project, not a wish. It requires planning, execution, feedback, and iteration -- the same disciplines you apply to managing accounts. Apply them to managing your career
• The skills for the next level are different from the skills that made you successful at this level. A great CSM is not automatically a great CS Manager. The skills that got you here (account execution, customer relationships) are necessary but not sufficient for the next level (team development, process design, metric ownership)
• Your manager is your primary career development partner. They control opportunity allocation, provide coaching, and advocate for your promotion in rooms you are not in. Invest in this relationship
• Lateral moves are underrated. A CSM who moves into CS Ops, then back to a Senior CSM role, has a broader skill set than one who stayed on the same ladder. Consider breadth, not just height