/pair-capability-assess-observability — Observability Assessment

Evaluate and decide on the observability strategy: monitoring platform, logging approach, tracing, alerting, and dashboards. Follows the resolution cascade.

Arguments

Argument	Required	Description
$choice	No	Override: skip assessment, use this observability platform directly (e.g. grafana, datadog)

Composed Skills

Skill	Type	Required
/pair-capability-record-decision	Capability	Yes — records observability decision as ADR or ADL

Proposal Target

The rendered adoption content is destined for this section — the caller writes it via /pair-capability-record-decision:

• Target: adoption/tech/infrastructure.md — observability section only
• Ownership: Observability section (shared file — /pair-capability-assess-infrastructure owns core sections)

Adoption File

• Target: adoption/tech/infrastructure.md — observability section only
• Ownership: Observability section (shared file — /pair-capability-assess-infrastructure owns core sections)

Algorithm

Step 1: Resolution Cascade

Path A — Argument Override

1. Check: Is $choice provided?
2. Skip: If not provided, go to Path B.
3. Act: Confirm the choice. Check for conflicts with existing adoption.
4. Verify: Developer confirms. Proceed to Step 3.

Path B — Adoption Exists

1. Check: Does adoption/tech/infrastructure.md exist and contain a populated observability section?
2. Skip: If no observability section or empty, go to Path C.
3. Act: Read current observability adoption. Confirm it's valid.
4. Check: Does a corresponding decision record exist?
5. Act: If decision record missing, compose /pair-capability-record-decision to backfill.
6. Verify: Done — exit skill.

Path C — Full Assessment

1. Act: Proceed to Step 2.

Step 2: Read Guidelines

1. Act: Read observability guidelines:
   • Observability README — tool comparison, decision matrix, decision tree
   • Observability Principles — three pillars, proactive monitoring
   • Observability Tools — platform options
   • Structured Logging — logging standards
   • Metrics — metrics strategy
   • Alerting — alerting strategy
2. Act: Read project context:
   • adoption/product/PRD.md — scale, budget
   • adoption/tech/infrastructure.md — existing infrastructure choices (observability must integrate)
3. Verify: Guidelines and context loaded.

Step 3: Evaluate Options

1. Act: Use the Observability Platform Options table and Decision Tree from guidelines:

   • Evaluate: DataDog, New Relic, Grafana Stack, ELK Stack, Prometheus/Grafana
   • Consider: budget, scale, AI features needed, self-hosted vs managed

2. Act: Also evaluate:

   • Logging approach: structured JSON, log levels, sensitive data handling
   • Tracing: distributed tracing needs based on architecture
   • Alerting: notification channels, escalation

3. Act: Present recommendation:

   Observability Recommendation:

   • Platform: [name] — [rationale]
   • Logging: [approach] — [rationale]
   • Tracing: [approach or "not needed"] — [rationale]
   • Alerting: [strategy] — [rationale]

4. Verify: Developer approves.

Step 4: Write Adoption File

1. Act: Write or update only the observability section of infrastructure.md:
   • Platform, logging, tracing, alerting decisions
   • Preserve all other sections (owned by /pair-capability-assess-infrastructure)
2. Act: If infrastructure.md doesn't exist, create it with observability section. Warn: "Created infrastructure.md — core sections should be populated by /pair-capability-assess-infrastructure."
3. Verify: Observability section written. Other sections preserved.

Step 5: Record Decision

1. Act: Compose /pair-capability-record-decision:
   • $type: non-architectural (observability tooling is typically a tool choice)
   • $topic: observability-strategy
   • $summary: "[Platform] adopted for observability with [logging approach]"
2. Verify: ADL created. Adoption consistent.

Output Format

ASSESSMENT COMPLETE:
├── Domain:    Observability
├── Path:      [Argument Override | Adoption Exists | Full Assessment]
├── Decision:  [platform + logging + tracing + alerting]
├── Adoption:  [infrastructure.md observability section — written | confirmed | updated]
├── Record:    [ADL path — created | exists | backfilled]
└── Status:    [Complete | Confirmed existing]

Composition Interface

When composed by /pair-process-bootstrap:

• Input: /pair-process-bootstrap invokes during Phase 2, after /pair-capability-assess-infrastructure.
• Output: Returns decision summary and adoption file path.

When invoked independently:

• Full interactive flow. Developer commits changes.

Edge Cases

• Project doesn't need observability (e.g. CLI tool, library): Write minimal section noting "observability not applicable — [reason]".
• infrastructure.md exists but no observability section: Add section, preserve all other content.
• Multiple valid platforms score equally: Present top 2 with trade-off analysis.

Graceful Degradation

• If observability guidelines not found, use minimal assessment: ask developer for platform preference.
• If /pair-capability-record-decision not installed, warn and skip recording.
• If infrastructure.md doesn't exist, create it with observability section only.

Notes

• Observability decisions are typically non-architectural → produce ADL. Exception: if the observability choice requires infrastructure changes (e.g. service mesh for tracing), use ADR.
• Section ownership: this skill writes ONLY the observability section of infrastructure.md.
• Educational content (observability principles, three pillars, WHY) stays in guidelines.