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Success plan creator

Skill stephenrogan/csm-skills/skills/success-plan-creator

Builds a mutual success plan with the customer that defines what success looks like, how it will be measured, who is responsible, and what the timeline is. Produces a shared document that both sides reference throughout the engagement. Use when asked to create a success plan, build a customer outcome framework, define success criteria with a customer, structure mutual goals, or when a CSM needs to align with a customer on what they are trying to achieve together. Also triggers for questions about success planning, outcome definition, customer goal alignment, mutual accountability frameworks, or how to ensure both sides know what success looks like.From its SKILL.md

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npx -y skills add stephenrogan/csm-skills --skill success-plan-creator

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Success Plan Creator

Builds a mutual success plan that both sides own. The success plan is the single most important document in the customer relationship because it answers the question that drives every renewal conversation: "Did we achieve what we set out to achieve?"

How to Use

Provide:

  • The customer's goals (what outcomes they expect -- from the sales process, onboarding, or direct conversation)
  • Your goals for the account (retention, expansion, advocacy, strategic alignment)
  • Available metrics (how outcomes can be measured)
  • Key contacts on both sides (who is accountable for what)
  • Timeline (when should these outcomes be achieved)
  • The starting baseline (where things stand today on each metric)

Success Plan Structure

1. Shared Objectives

Define 3-5 objectives that both sides agree on. These must be outcomes, not activities.

ObjectiveMeasureBaselineTargetTimelineOwner
Reduce manual reporting timeHours/week spent on manual reports20 hours/week<5 hours/week90 daysCustomer (adoption) + CSM (enablement)
Increase team adoptionActive users / licensed seats12 of 60 (20%)48 of 60 (80%)120 daysCustomer (change management) + CSM (training)
Prove ROI to leadershipEUR value of time saved vs. investmentNo measurement3x ROI documented180 daysCSM (calculation) + Customer (validation)

Objective rules:

  • Outcomes, not activities: "Reduce manual reporting time" not "Complete training"
  • Measurable: if you cannot define the metric, you cannot define success
  • Time-bound: an objective without a deadline is a wish
  • Mutually owned: both sides have responsibilities. A success plan where only the CSM has actions is a project plan, not a partnership

2. Milestones

Break each objective into milestones that show progress:

MilestoneLinked ObjectiveTarget DateStatusNotes
Onboarding complete -- all 60 users trainedAdoptionApr 15Not startedDepends on customer's training schedule
First automated report run by analytics teamManual reportingApr 30Not startedQuick win opportunity
50% of team using product weeklyAdoptionMay 15Not startedChange management critical here
Q2 value report delivered with customer-confirmed metricsROIJun 30Not startedRequires customer data access

3. Responsibilities

AreaCSM ResponsibilityCustomer Responsibility
TrainingDeliver sessions, provide materials, track completionEnsure attendance, allocate team time, manager endorsement
AdoptionMonitor usage data, identify barriers, provide recommendationsDrive internal adoption, address resistance, enforce accountability
Value measurementBuild the ROI model, present evidence, track metricsValidate methodology, confirm outcomes, provide internal data
CommunicationRegular check-ins, QBR preparation, status updatesTimely responses, escalation of blockers, honest feedback

4. Review Cadence

ReviewFrequencyContent
Milestone checkMonthlyAre milestones on track? Any blockers? Status update on each objective
Success plan reviewQuarterly (aligned with QBR)Full review: objectives progressing? Targets still relevant? Adjustments needed?
Annual resetYearlyNew objectives for the next period based on what was achieved and what the customer's priorities are now

5. Risk and Dependency Register

Risk/DependencyImpactMitigationOwner
Customer IT team overloaded -- integration delayedExtends onboarding timeline by 2-4 weeksGet IT resource commitment in kickoff. Escalate to champion if delayedCustomer champion
Low training attendanceAdoption target at riskManager mandate for attendance. Offer flexible session timesCustomer manager + CSM
No baseline data for ROICannot measure value improvementEstablish baseline in first 30 days before process changesCSM + Customer

Creating the Plan with the Customer

The success plan should be built collaboratively, not presented unilaterally:

The conversation:

  1. "What does success look like for you in 6 months?" (Their goals in their language)
  2. "How would we measure that?" (Co-define the metrics)
  3. "What do you need from us to get there?" (Your responsibilities)
  4. "What do we need from your team?" (Their responsibilities -- sets mutual accountability)
  5. "Let me draft this into a shared plan for us both to reference" (Formalise the agreement)

The customer should see the plan as their document, not yours. If it feels like a vendor template they signed, it will be ignored. If it feels like a shared commitment to their goals, it will be referenced.

When to Create a Success Plan

TriggerWhy Now
Post-onboarding (Day 30-60)The customer has enough product experience to set meaningful goals
Start of a new contract yearReset objectives for the next period
After a QBR where goals are discussedFormalise what was agreed
After a save play (relationship repair)Establish a fresh commitment to value delivery
Before a renewal (if no plan exists)Build the evidence framework for the renewal conversation

Output Format

## Mutual Success Plan: [Account Name]
**Created:** [date] | **Review cadence:** [quarterly]
**CSM:** [name] | **Customer lead:** [name]

### Shared Objectives
[Objective table with measures, baselines, targets, timelines, owners]

### Milestones
[Milestone table with dates and status]

### Responsibilities
[Responsibility matrix]

### Review Schedule
[Next milestone check, next QBR, annual reset date]

### Risks and Dependencies
[Risk register]

Quality Gates

  • Is every objective measurable with a baseline and a target? "Improve adoption" fails. "Move from 20% to 80% active user rate in 120 days" succeeds
  • Does the customer co-own the plan? If all actions are on the CSM's side, it is not a mutual plan. Both sides must have responsibilities
  • Are there milestones between now and the target? A 6-month objective with no intermediate milestones will drift. Monthly checkpoints prevent this
  • Is the plan referenced in every QBR and major touchpoint? A success plan that is created and then ignored is worse than no plan -- it sets expectations that are not tracked

Principles

  • The success plan is the renewal conversation in advance. If the plan's objectives are achieved by renewal time, the renewal conversation is "look at what we achieved together -- shall we set new goals for next year?" If they are not achieved, at least you know why and can address it honestly
  • The customer's goals are the plan's goals, not your goals for them. If they want to reduce manual reporting time and you want to increase adoption breadth, the plan leads with their goal. Your goal (adoption) may be the mechanism, but their goal (time savings) is the objective
  • A success plan that is reviewed every quarter is 10x more valuable than one reviewed once. The plan is a living commitment, not a one-time document. Every review reinforces the partnership and surfaces issues early
  • The best success plans evolve. Goals that were ambitious 6 months ago may be baseline now. New priorities emerge. The plan should grow with the relationship, not become a historical artefact

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