End-of-Year Customer Success Retrospective

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Aisha Bello

@aisha-bello

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Reflection framework for comprehensive annual CS team and portfolio assessment.

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As VP Customer Success, I need to conduct a comprehensive end-of-year retrospective.

Annual Data:
- Key Metrics: {{annual_metrics}}
- Team Performance: {{team_data}}
- Portfolio Changes: {{portfolio_summary}}
- Major Initiatives: {{initiatives}}

Guide my annual reflection:

1. Portfolio Performance:
- What drove our retention and expansion results?
- Which accounts exceeded expectations? Why?
- Which accounts disappointed? What could we have done differently?
- How did our segmentation strategy perform?

2. Team Development:
- How did the team grow professionally?
- What skills improved most?
- Where do gaps remain?
- What investments paid off?

3. Process Evolution:
- Which new processes added value?
- What should we stop doing?
- Where did automation help most?
- What manual work remains painful?

4. Customer Relationship Quality:
- How did overall customer sentiment shift?
- What feedback themes persisted?
- How well did we execute on customer commitments?
- Where did we truly delight customers?

5. Strategic Alignment:
- How well did CS contribute to company goals?
- Where did we lead versus follow?
- What strategic opportunities did we miss?
- How should priorities shift next year?

Synthesize into annual report and next-year planning priorities.

Details

Category

Business

Use Cases

annual CS retrospectiveyear-end performance reviewstrategic planning reflection

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gpt-4oclaude-sonnet-4-20250514
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