Executive communication is an art. The higher you go in an organization, the less time people have to read your updates. Yet the decisions made at that level have the biggest impact. Your job is to deliver maximum insight in minimum words.
The best stakeholder updates do not just report what happened. They tell a story: where you are, where you are going, and what stands in the way. This guide gives you AI prompting frameworks to write updates that executives actually read and act on.
Insight
The Inverted Pyramid: Lead with Conclusions
Journalists have used the inverted pyramid for over a century. Put the most important information first, with supporting details following in order of decreasing importance. This works because busy readers can stop at any point and still have the essential message.
Most Important First
Supporting Context
Background Details
Write an update about our Q3 product launch project.
Write a stakeholder update for our Q3 product launch using the inverted pyramid structure. BOTTOM LINE: - We are on track for October 15 launch - One risk: payment integration delayed 5 days KEY CONTEXT: - Beta testing complete with 92% satisfaction - Marketing campaign ready to go live - Engineering has resolved 34 of 36 launch blockers FORMAT: - Lead with the conclusion (on track / at risk / blocked) - Keep to 3-4 paragraphs maximum - Use bullet points for quick scanning - End with specific asks if any
The BRIEF Framework
BRIEF is a structured approach to stakeholder updates that ensures you cover everything executives need without burying them in details. Use it as a checklist for every update you write.
Bottom Line
Risks / Blockers
Impact / Metrics
Efforts Completed
Forward Look
Pro Tip
Prompt Templates
These templates cover the most common stakeholder communication scenarios. Adapt the context sections to your specific situation for best results.
Weekly Status Updates
Weekly updates keep stakeholders informed without overwhelming them. Keep these concise and focused on what changed since last week.
Write a weekly status update email for [PROJECT NAME] using the BRIEF framework. BOTTOM LINE (one sentence): [Are we on track / at risk / blocked? What is the headline?] RISKS / BLOCKERS: - [RISK 1]: [Impact and mitigation] - [RISK 2]: [Impact and mitigation] - [Note if no current blockers] IMPACT / METRICS THIS WEEK: - [METRIC 1]: [This week] vs [Last week] ([change %]) - [METRIC 2]: [This week] vs [Last week] ([change %]) - Key milestone: [What was achieved] EFFORTS COMPLETED: - [Accomplishment 1] - [Accomplishment 2] - [Accomplishment 3] FORWARD LOOK (next 7 days): - [Priority 1] - [Priority 2] - Key date: [Upcoming milestone and date] AUDIENCE: - [Leadership team / Cross-functional partners / Board] - Familiarity with project: [High / Medium / Low] FORMAT REQUIREMENTS: - Subject line should indicate project status (Green/Yellow/Red) - Keep to under 300 words - Use bullet points for scanability - Bold the most important items
Monthly Executive Summaries
Monthly summaries zoom out to show trends and strategic progress. Focus on outcomes and business impact rather than activities.
Write a monthly executive summary for [TEAM/INITIATIVE NAME]. EXECUTIVE SUMMARY (2-3 sentences): [Overall status and the single most important thing leadership should know] MONTH IN REVIEW: Period: [Month, Year] Overall Status: [On Track / Needs Attention / At Risk] KEY OUTCOMES: 1. [OUTCOME 1]: [Description with business impact] 2. [OUTCOME 2]: [Description with business impact] 3. [OUTCOME 3]: [Description with business impact] METRICS DASHBOARD: | Metric | Target | Actual | Trend | |--------|--------|--------|-------| | [Metric 1] | [X] | [Y] | [Up/Down/Flat] | | [Metric 2] | [X] | [Y] | [Up/Down/Flat] | | [Metric 3] | [X] | [Y] | [Up/Down/Flat] | RISKS AND MITIGATION: - [RISK 1]: [Status] - [Mitigation approach] - [RISK 2]: [Status] - [Mitigation approach] DECISIONS NEEDED: - [DECISION 1]: [Context and recommendation] - [DECISION 2]: [Context and recommendation] NEXT MONTH PRIORITIES: 1. [Priority with expected outcome] 2. [Priority with expected outcome] 3. [Priority with expected outcome] FORMAT: - One page maximum (leadership will not read more) - Lead with insights, not activities - Use tables for metrics - Highlight decisions needed prominently
Warning
Board Meeting Prep
Board updates require a different lens: strategic progress, financial health, and governance matters. These are typically quarterly and more formal.
Write a board update for [COMPANY NAME] for [QUARTER, YEAR]. COMPANY CONTEXT: - Stage: [SEED / SERIES A / GROWTH / etc.] - Industry: [YOUR INDUSTRY] - Board composition: [VCs, Independents, Founders] EXECUTIVE SUMMARY: [2-3 sentences on company trajectory and quarter highlights] FINANCIAL HIGHLIGHTS: - Revenue: $[X] ([+/-]% vs plan, [+/-]% YoY) - Burn rate: $[X]/month ([X] months runway) - Key financial metrics: [ARR, MRR, Gross Margin, etc.] STRATEGIC PROGRESS: 1. [STRATEGIC PRIORITY 1]: - Goal: [What we said we would do] - Status: [What we achieved] - Next quarter: [What comes next] 2. [STRATEGIC PRIORITY 2]: - Goal: [What we said we would do] - Status: [What we achieved] - Next quarter: [What comes next] KEY WINS: - [WIN 1 with business impact] - [WIN 2 with business impact] CHALLENGES AND RISKS: - [CHALLENGE 1]: [Impact and response] - [CHALLENGE 2]: [Impact and response] ASKS OF THE BOARD: - [ASK 1]: [What you need and why] - [ASK 2]: [What you need and why] UPCOMING MILESTONES: - [Milestone 1]: [Date] - [Milestone 2]: [Date] FORMAT: - Structured for pre-read (board members will skim before meeting) - Focus on strategic narrative, not operational details - Include appendix for detailed metrics (separate section) - Anticipate likely questions and address preemptively
Investor Updates
Investor updates maintain relationships and build trust for future fundraising. Be honest about challenges while demonstrating progress and learning.
Write a monthly investor update email for [COMPANY NAME]. COMPANY CONTEXT: - Last funding: [ROUND, AMOUNT, DATE] - Key investors: [NAMES OF LEAD INVESTORS] - Business model: [B2B SaaS / Marketplace / etc.] HEADLINE: [One line capturing the month - be honest about both wins and challenges] KEY METRICS: | Metric | This Month | Last Month | MoM Change | |--------|------------|------------|------------| | [ARR/MRR] | $X | $Y | +/-Z% | | [Customers] | X | Y | +/-Z% | | [Key metric 3] | X | Y | +/-Z% | HIGHLIGHTS: - [WIN 1]: [Brief description and why it matters] - [WIN 2]: [Brief description and why it matters] - [WIN 3]: [Brief description and why it matters] LOWLIGHTS (be honest): - [CHALLENGE 1]: [What happened and what we learned] - [CHALLENGE 2]: [What happened and how we are addressing it] PRODUCT UPDATE: [2-3 sentences on what shipped or is coming] TEAM UPDATE: [Notable hires, departures, or team news] ASK: [Specific ways investors can help - intros, advice, etc.] LOOKING AHEAD: [Key milestones for next 30-60 days] FORMAT: - Keep to 500 words or less - Friendly but professional tone - Include one personal note or reflection - Make the ask specific and easy to action
Success
Crisis Communications
When things go wrong, stakeholders need to know quickly. Crisis updates prioritize clarity and action over comprehensive detail.
Write a crisis communication update for stakeholders. INCIDENT: - What happened: [Brief factual description] - When discovered: [Date/Time] - Current status: [Ongoing / Contained / Resolved] IMPACT: - Customers affected: [Number or percentage] - Business impact: [Revenue, reputation, operations] - Duration: [How long the incident lasted/is lasting] IMMEDIATE ACTIONS TAKEN: 1. [Action 1]: [Status] 2. [Action 2]: [Status] 3. [Action 3]: [Status] ROOT CAUSE: [Known / Under investigation] [If known, brief explanation without excessive technical detail] REMEDIATION PLAN: - Short-term: [Actions in next 24-48 hours] - Medium-term: [Actions in next 1-2 weeks] - Long-term: [Preventive measures] COMMUNICATION STATUS: - Customers notified: [Yes/No, how] - External communication: [Press, social media plans] - Regulatory notification: [If applicable] NEXT UPDATE: [When stakeholders can expect the next communication] OWNER: [Who is leading the response and how to reach them] FORMAT: - Lead with current status - Be factual, not defensive - Acknowledge impact honestly - Focus on actions, not excuses - Keep to one page maximum
Warning
Tailoring Updates by Audience
Different stakeholders need different information. Tailor your updates based on what each audience cares about most.
Executives care about strategic alignment, risk, and decisions needed.
- Lead with business impact, not technical details
- Highlight risks that could affect company goals
- Be explicit about decisions needed and by when
- Connect your update to company OKRs or strategic priorities
- Keep it under 200 words for weekly updates
Board members think in terms of governance, fiduciary duty, and long-term value.
- Focus on financial health and runway
- Highlight strategic milestones and pivots
- Include competitive landscape updates
- Be transparent about challenges and course corrections
- Prepare for questions by anticipating concerns
Partners from other teams need to understand dependencies and timing.
- Be specific about what you need from them
- Highlight upcoming milestones that affect their work
- Share blockers that they might help resolve
- Celebrate shared wins to build relationships
- Include more tactical detail than executive updates
Investors want to see progress, learning, and efficient use of capital.
- Always include key financial metrics (ARR, burn, runway)
- Show month-over-month and year-over-year trends
- Be honest about misses and what you learned
- Include specific asks for help (intros, advice)
- Maintain consistent format so they can scan quickly
Frequency and Timing
When you send updates matters as much as what you send. Match your cadence to stakeholder expectations and project phase.
| Update Type | Cadence | Best Day/Time |
|---|---|---|
| Weekly Status | Weekly | Friday afternoon or Monday morning |
| Executive Summary | Monthly | First week of month (covers prior month) |
| Board Update | Quarterly | 1 week before board meeting (pre-read) |
| Investor Update | Monthly | Mid-month (avoids quarter-end noise) |
| Crisis Update | As needed | Immediately, then every 4-8 hours until resolved |
Pro Tip
Visual Formatting Tips
How your update looks affects whether it gets read. Use formatting strategically to guide the reader's eye.
- Use status indicators: Green/Yellow/Red or traffic light emojis in subject lines let readers triage at a glance
- Bold key information: Make the most important numbers and decisions stand out
- Use bullet points: Walls of text do not get read; bullets get scanned
- Include tables for metrics: Numbers are easier to compare in table format
- Keep paragraphs short: 2-3 sentences maximum per paragraph
- Use headings: Clear section headers let readers jump to what they care about
- Put asks at the end: End with a clear call to action if you need something
Format this stakeholder update for maximum readability. CONTENT TO FORMAT: [Paste your draft update here] FORMATTING REQUIREMENTS: - Add a status indicator to the subject line (Green/Yellow/Red) - Bold the 3 most important facts - Convert long paragraphs to bullet points - Create a metrics table if numbers are scattered - Add section headers for scanability - Ensure the ask/next steps are clearly visible at the end - Keep total length under [X] words AUDIENCE: [Who will read this and how much time do they have?]
Next Steps
You now have frameworks and templates for every major stakeholder communication scenario. The key is adapting these to your specific audience and situation. Remember: the goal is not to prove you are busy, but to give stakeholders the information they need to support your success.
Create your stakeholder update with guidance
Instead of filling in templates manually, answer a few questions about your project and audience. AskSmarter builds a tailored prompt that captures your specific context.
Start building freeHow long should a weekly status update be?
Aim for 200-300 words maximum. If you need more detail, link to a document rather than putting it in the email. Respect your reader's time.
Should I send updates when there is no news?
Yes. Consistent communication builds trust. A brief “no major changes this week, on track for X” is better than silence, which stakeholders may interpret negatively.
How do I handle bad news in stakeholder updates?
Lead with it. Put bad news in the first paragraph, not buried at the end. Include what you learned and what you are doing about it. Stakeholders respect honesty and proactive communication.
What if stakeholders ask for more frequent updates?
Negotiate. More frequent updates take time away from the work itself. Offer a compromise like a brief daily standup note or a shared dashboard they can check asynchronously.