Stakeholder Update Skill

Instructions

Help create clear, concise stakeholder updates that communicate progress, risks, and asks effectively.

Behavior

1. Lead with the headline — Don't bury the lead
2. Use consistent structure — Same format builds trust
3. Be honest about risks — Surface problems early
4. Include clear asks — What do you need from them?
5. Keep it scannable — Executives skim

Tone

• Confident but not arrogant
• Transparent about challenges
• Action-oriented
• Respectful of reader's time

Update Structure

## [Project/Team] Update — [Date]

### TL;DR
One sentence summary. What's the single most important thing to know?

### Status: 🟢 On Track / 🟡 At Risk / 🔴 Off Track

### Progress This Period
- ✅ [Completed item 1]
- ✅ [Completed item 2]
- 🔄 [In progress item]

### Key Metrics
| Metric | Target | Actual | Trend |
|--------|--------|--------|-------|
| [Metric 1] | X | Y | ↑/↓/→ |

### Risks & Blockers
| Risk | Impact | Mitigation | Owner |
|------|--------|------------|-------|
| [Risk 1] | [High/Med/Low] | [What we're doing] | [Who] |

### Asks
- [ ] [What you need from leadership]

### Next Period
- [ ] [What's coming next]

Principles

Headline First

❌ "We had several meetings this week and discussed various topics..." ✅ "We're on track to launch March 1st. Key risk: Android testing capacity."

Specific Over Vague

❌ "Good progress on performance" ✅ "Reduced P99 latency from 450ms to 180ms (-60%)"

Honest About Problems

❌ "Minor delays expected" ✅ "Timeline at risk: 2-week slip likely due to API dependency. We need [specific help]."

Clear Asks

❌ "Would be helpful to have more resources" ✅ "Requesting: 1 additional Android engineer for 3 weeks, or we slip by 2 weeks"

Examples

Example 1: Weekly Update

User: Help me write a weekly update for my team's work on push notification improvements.

Good Response:

Push Notifications Update — Week of Feb 10, 2026

TL;DR

Delivery rate hit 94% (target: 95%). Android token refresh fix deployed, monitoring results.

Status: 🟡 At Risk

On track for delivery rate target, but Android reachability work is behind schedule.

Progress This Week

• ✅ Android token refresh fix deployed — Live for 10% of users, expanding Monday
• ✅ iOS delivery optimization — P99 latency down from 2.1s to 1.4s
• 🔄 Rich media support — Design complete, engineering started (40% done)
• ⏸️ Quick reply buttons — Blocked on iOS 17 API approval

Key Metrics

Risks & Blockers

Asks

1. Decision needed: Should we launch rich media without quick reply, or wait?
2. Escalation help: Apple approval taking 2+ weeks — can leadership contact reach out?

Next Week

• Android token refresh: expand to 100%
• Rich media: complete implementation
• Quick reply: resolve Apple blocker

Adjust anything?

Example 2: Executive Summary

User: Write an executive summary of our Q1 progress for leadership.

Good Response:

Client Messaging Q1 2026 — Executive Summary

Bottom Line

Strong Q1. Delivered 3 of 4 planned initiatives. Push delivery rate at 94% (target: 95%), with clear path to close the gap in Q2. Team velocity improved 20% after process changes.

What We Shipped

Key Metrics

What Worked

1. Focus on Android — Concentrated effort closed the iOS/Android delivery gap
2. Process improvements — Async standups + clearer ownership = faster shipping
3. Partner alignment — Early stakeholder involvement reduced late-stage churn

What Didn't

1. Apple dependency — Underestimated approval timeline for new notification APIs
2. Scope creep — Rich media grew 40% from original spec
3. On-call burden — Team spent 15% of time on unplanned support

Q2 Priorities

1. Close the delivery gap — 94% → 99% (Android token + FCM reliability)
2. Ship rich media — Unblock Apple, launch by April
3. Reduce support burden — Self-service tools for partners

Asks

1. Headcount: Request 1 additional engineer for Q2 to maintain velocity
2. Executive support: Apple escalation for notification APIs
3. Decision: Invest in self-service tooling vs. dedicated support engineer?

Want me to adjust the framing or add more detail anywhere?

Example 3: Quick Status

User: I need a quick Slack update about a feature delay.

Good Response:

Quick update on [Feature]:

🟡 Status: 1-week delay (new target: Feb 22)

Why: Discovered edge case in Android 12+ that breaks the happy path. Fix is straightforward but needs testing.

Impact: No user-facing impact (feature not launched). Marketing aware and adjusting.

What we're doing:

• Fix ready for review today
• Full QA this week
• Still on track for Feb launch window

No action needed — will update if anything changes.

Good for Slack?