stephenrogan/quarterly-planning-builder

Quarterly Planning Builder

Structures the CSM's quarter with clear priorities, measurable targets, and a plan for how to allocate time across a portfolio. The difference between CSMs who grow and CSMs who plateau is often the presence or absence of this kind of intentional planning.

How to Use

Provide:

• Your portfolio (account count, total ARR, health distribution)
• Renewals this quarter (which accounts, ARR, risk level)
• Expansion opportunities (which accounts, estimated value, stage)
• At-risk accounts (which accounts, ARR, what is happening)
• Strategic priorities from your manager or leadership (if any)
• Your own development goals (if any)
• Capacity constraints (PTO, internal projects, ramp -- anything that reduces your available weeks)

Plan Structure

1. Portfolio Snapshot

| Metric | Value | Trend | |--------|-------|-------| | Accounts | [count] | [+/- from last quarter] | | ARR | [total] | [+/- from last quarter] | | Health distribution | Strong: [n], Healthy: [n], At Risk: [n], Critical: [n] | [changes from last quarter] | | Renewals this quarter | [count], EUR [ARR] | [risk breakdown] | | Expansion pipeline | [count], EUR [estimated value] | [stage breakdown] |

2. Quarterly Objectives (Maximum 4)

For each objective:

| Element | Content | |---------|---------| | Objective | What you will achieve, stated specifically | | Why it matters | How it connects to retention, growth, or your development | | Success metric | How you will know you achieved it (must be measurable at quarter-end) | | Target | The specific number or outcome | | Key actions | The 3-5 things you will do to achieve this |

Example objectives:

• "Retain 95%+ of renewing ARR this quarter (EUR 1.2M renewing, target EUR 1.14M retained)"
• "Close EUR 45k in expansion across 3 accounts"
• "Move 3 accounts from At Risk to Healthy"
• "Establish executive sponsor relationships at top 5 accounts by ARR"

3. Account Priorities

Classify your accounts into four management tiers for the quarter:

| Tier | Accounts | Time Allocation | Management Approach | |------|----------|----------------|-------------------| | Strategic | Top 5-8 by ARR + risk | 40% of time | Full strategic plans (account-strategy-builder). Proactive. Multi-threaded | | Managed | Next 10-15 by ARR | 30% of time | Regular cadence. Reactive + proactive. Standard engagement | | Scaled | Next 10-15 | 20% of time | Lighter cadence. Reactive primarily. Digital touchpoints | | Monitoring | Remaining | 10% of time | Automated checks. Engage only on signals |

4. Key Dates and Milestones

| Date | Event | Account(s) | Preparation Needed | |------|-------|-----------|-------------------| | [date] | [renewal, QBR, executive meeting, etc.] | [account] | [what to prepare before this date] |

5. Risk Register

| Risk | Probability | ARR Impact | Mitigation | Status | |------|-----------|-----------|-----------|--------| | [risk] | [H/M/L] | [EUR] | [what you are doing] | [active/monitoring] |

6. Development Focus

One professional development goal for the quarter. Not "get better at everything" -- one specific skill or capability:

| Goal | Why | How | Measure | |------|-----|-----|---------| | [specific development goal] | [how it improves your effectiveness] | [specific actions -- course, practice, mentoring] | [how you know you improved] |

7. Quarter-End Review Criteria

Define now what success looks like at the end of the quarter:

| Criteria | Target | Measurement | |----------|--------|-------------| | ARR retained | [EUR] of [EUR] renewing (%) | CRM renewal data | | Expansion closed | [EUR] | CRM opportunity data | | Health improvement | [n] accounts moved to higher band | Health score comparison start vs. end | | Engagement compliance | [%] touchpoints completed vs. planned | Activity log | | Objective achievement | [n] of [n] objectives met | Self-assessment + manager review |

Output Format

## Quarterly Plan: [CSM Name] -- [Quarter Year]
**Portfolio:** [n] accounts | EUR [ARR] | [health summary]

### Objectives
[2-4 objectives with metrics and targets]

### Account Tiers
[Tier classification table]

### Key Dates
[Timeline of critical events]

### Risk Register
[Top risks with mitigation]

### Development Goal
[One specific development focus]

### Review Criteria
[Quarter-end success definition]

Quality Gates

• Are the objectives measurable? "Improve retention" fails. "Retain 95%+ of EUR 1.2M renewing ARR" succeeds
• Is the time allocation realistic? If 40% goes to Strategic accounts and you also have 12 QBRs, 5 renewals, and 3 escalations, the math may not work. Check capacity before committing
• Does the risk register include at least one risk? If you see zero risks in your portfolio for the next 90 days, you are not looking hard enough
• Would your manager approve this plan? If the plan does not align with what leadership cares about, it will create friction regardless of execution quality
• Can you review this plan in 5 minutes at the end of the quarter and know whether you succeeded? If the review criteria are vague, the plan is vague

Principles

• A plan you review weekly is 10x more valuable than a plan you write once. Schedule 15 minutes every Friday to check progress against the plan. Adjust as reality evolves
• Four objectives maximum. More than four means none get full attention. Pick the four that matter most and execute them well
• The plan should make you slightly uncomfortable. If every objective is easily achievable with your current approach, the plan is not ambitious enough. Growth happens when you stretch
• Share the plan with your manager. It aligns expectations, creates accountability, and gives them the context to support you. A manager who knows your plan can help you when things go sideways. A manager who does not know your plan can only react