Executive Update Generator
Triggers: "Create exec update", "Generate executive update", "Weekly status update", "Write stakeholder update"
What This Skill Does
Generates a professional executive-level status update summarizing progress, wins, risks, and next steps for your projects. Formatted for busy executives who want the bottom line upfront.
Output: communications/exec-updates/YYYY-MM-DD.md
How to Use
Simply say:
- •"Create exec update for this week"
- •"Generate executive update"
- •"Help me write a stakeholder update"
- •"Weekly status update"
Skill Instructions
When this skill is invoked, follow these steps:
1. Gather Context
Read these files:
- •
projects/prds/*.md- Check project status, progress, blockers - •
databases/tasks/*.md- Review completed and in-progress tasks - •
.workos/context/current-projects.md- Understand active initiatives - •
.workos/context/stakeholders.md- Know your audience and their priorities - •
communications/exec-updates/- Review last update to track progress since then
Look for:
- •Project milestones completed
- •Key metrics or business impact
- •Risks, blockers, or timeline changes
- •Major decisions made
- •Upcoming deadlines or launches
2. Generate Update Structure
Use this executive-friendly template:
# Executive Update - [Week of Date] **Status:** [🟢 On Track / 🟡 At Risk / 🔴 Off Track] --- ## Summary (TL;DR) [2-3 sentence executive summary of the week - what they absolutely need to know] --- ## Progress This Week ### [Project Name 1] **Status:** [Green/Yellow/Red] - [Key achievement 1] - [Key achievement 2] - [Metric impact if applicable] ### [Project Name 2] **Status:** [Green/Yellow/Red] - [Key achievement 1] - [Key achievement 2] --- ## Wins & Impact - [Win 1 with business impact] - [Win 2 with business impact] - [Metric: X% improvement in Y] --- ## Risks & Blockers ### High Priority - [Risk/blocker 1] - **Impact:** [what's at stake] - **Mitigation:** [what you're doing about it] ### Medium Priority - [Risk/blocker 2] - **Mitigation:** [plan] ### Resolved This Week - [Previously flagged risk that's now resolved] --- ## Next Week Priorities 1. [Top priority 1] - [why it matters] 2. [Top priority 2] - [why it matters] 3. [Top priority 3] - [why it matters] --- ## Action Needed (if any) - [Specific ask with deadline] - **Owner:** [who you need] - OR: *No action needed - FYI only* --- ## Additional Context [Optional: Anything else execs should know]
3. Populate Content with Executive Mindset
Summary Section:
- •Lead with impact, not activity
- •Answer: "What changed this week that execs care about?"
- •Example: ❌ "We had 3 meetings" vs. ✅ "Dashboard launch on track for Nov 1, 15% DAU increase projected"
Progress Section:
- •Group by project, not task
- •Use traffic light status (Green/Yellow/Red) for scanability
- •Include metrics when available ("reduced latency 40%" not "improved performance")
- •Be specific but concise
Wins & Impact:
- •Connect wins to business outcomes
- •Quantify when possible (%, $, time saved, users impacted)
- •This is where you highlight value delivered
- •Example: "Shipped mobile app beta → 4.6⭐ rating from 100 early users → validates Q1 launch"
Risks & Blockers:
- •Always include mitigation - Don't just report problems, show you're handling them
- •Tier by urgency (High/Medium/Resolved)
- •Be honest but not alarmist
- •Include what you need from execs (approval, resources, unblocking)
Next Week Priorities:
- •Max 3 priorities - focus matters
- •Connect to business goals when possible
- •Include why each priority matters (not just what)
Action Needed:
- •Be specific: who, what, by when
- •Make it easy for execs to help you
- •If no action needed, explicitly say "FYI only"
4. Apply Executive Communication Standards
Consult Copy Editor for:
- •Polishing tone for specific stakeholders (check
.workos/context/stakeholders.md) - •Softening bad news while staying honest
- •Strengthening impact statements
- •Ensuring BLUF (Bottom Line Up Front)
Writing Guidelines:
- •Concise: Execs are busy - respect their time
- •Scannable: Use bullets, headers, bold for key info
- •Specific: Dates, numbers, names - not vague language
- •Honest: Transparency builds trust
- •Professional: Corporate-appropriate tone
5. Tailor to Audience
Check .workos/context/stakeholders.md for:
- •Communication preferences (detail level, frequency)
- •What each stakeholder cares about (business metrics vs. technical progress)
- •Sensitive topics or hot buttons
Adjust accordingly:
- •Technical stakeholders → More technical detail
- •Business stakeholders → More business impact
- •CEO/Execs → Maximum brevity, maximum impact
6. Save Output
Save to: communications/exec-updates/YYYY-MM-DD.md
Create directory if needed: communications/exec-updates/
Use date format: YYYY-MM-DD (e.g., 2025-10-21.md)
7. Present to User
Show the generated update and offer:
- •"Here's your executive update for [week of date]. Would you like me to adjust tone, add detail, or tailor for specific stakeholders?"
- •"Ready to send? I can polish specific sections if needed."
- •Offer to create subject line for email: "[Project Name] - [Status] Update - Week of [Date]"
Example Output
# Executive Update - Week of October 21, 2025 **Status:** 🟢 On Track --- ## Summary (TL;DR) Dashboard feature launched on schedule (Oct 20), early metrics show 15% DAU increase. Mobile app progressing toward Nov launch, but API dependency flagged as medium risk requiring early testing. --- ## Progress This Week ### User Dashboard (Launched 🚀) **Status:** 🟢 Complete - Launched Oct 20 to 100% of users - Early metrics: +15% DAU (10K → 11.5K daily active) - User engagement: 2.3x more interactions with data - Zero critical bugs reported ### Mobile App (Beta) **Status:** 🟢 On Track - UI complete, in QA review (95% test coverage) - Backend API integration 70% complete - Beta cohort identified: 100 power users ### API Performance Optimization **Status:** 🟢 Complete - Reduced latency 40% (800ms → 480ms) - Improved page load speed 25% - Deployed to production Oct 19 --- ## Wins & Impact - **Dashboard adoption exceeding projections:** 15% DAU increase vs. 10% projected - **Performance improvement shipped:** API latency down 40%, directly improving UX - **Mobile beta on schedule:** Nov 1 public launch achievable --- ## Risks & Blockers ### Medium Priority - **Mobile API dependency** - Third-party API integration more complex than estimated (auth requires custom OAuth not documented) - **Impact:** Could delay mobile launch 1-2 weeks if issues found late - **Mitigation:** Moved integration testing up 2 weeks, adding senior engineer for early validation ### Resolved This Week - ✅ Dashboard deployment blocker (DevOps environment issue) - resolved Oct 18 --- ## Next Week Priorities 1. **Complete mobile API integration** (target: Oct 27) - Critical path for Nov 1 launch 2. **Mobile beta rollout** (100 users) - Validates stability before public launch 3. **Dashboard metrics analysis** - Confirm 15% DAU increase is sustained after week 1 --- ## Action Needed *No action needed - FYI only* (Mobile launch timeline remains Nov 1 pending API integration completion) --- ## Additional Context - Dashboard post-launch monitoring continues through Oct 27 - Planning Q4 roadmap review for next week - will share draft priorities
Customization
Adjust for different audiences:
For CEO/C-Suite:
- •Ultra-brief (1 page max)
- •Business impact only
- •Strategic implications
- •Clear asks
For Director/VP:
- •Moderate detail
- •Balance business + technical
- •Cross-team dependencies
- •Resource needs
For Team/Peers:
- •More technical depth
- •Implementation details
- •Team velocity
- •Blockers to collaborate on
Ask user: "Who's the primary audience for this update? I can adjust the detail level and focus."
Integration with Agents
This skill should consult:
- •Copy Editor - Polish tone and structure (ALWAYS - exec comms are high stakes)
- •Senior PM - Validate business impact claims and priorities
- •Senior Project Manager - Confirm timeline and risk assessments
- •Business Analyst - Verify metrics and data accuracy
Notes for Implementation
- •If no projects found in
projects/prds/, prompt user for manual input - •Check last exec update date - flag if it's been >7 days
- •Scan for "yellow" or "red" project statuses - flag risks prominently
- •Offer to create email subject line + intro paragraph
- •Consider adding "Wins" section by default - positivity builds credibility
Executive Update Generator - Bottom-line-up-front, impact-focused, executive-ready communication