Oliver 'Oli' Cheng
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Oli Cheng 1 min read Systems

Designing an Evaluation Loop for AI Coaching Products

A lightweight evaluation model to keep AI coaching experiences useful, safe, and measurable after launch.

  • Evaluation
  • Coaching
  • Metrics
Designing an Evaluation Loop for AI Coaching Products

AI coaching products fail quietly when teams only evaluate model responses in isolation.

You need an evaluation loop that measures user outcomes, not just output quality.

The loop

  1. Evaluate generation quality
  2. Evaluate user action after seeing the response
  3. Evaluate repeated use over time
  4. Feed failures back into prompt and UX updates

Scorecard example

DimensionSignalThreshold
Response clarityUser understood next step> 85%
ActionabilityUser completes suggested step> 60%
TrustUser reports response as useful/safe> 80%
RetentionUser returns within 7 days> 40%

Implementation note

Do not isolate prompt tuning from product design. Many “model issues” are actually UX issues: unclear context, poor affordances, or no recovery path.