Write executive reports, handle difficult conversations, and communicate with confidence
By the end of this module, you will be able to:
It's Friday afternoon. You have 3 executive updates due Monday. Each stakeholder needs different information, different detail levels, different tones. Here's what you're facing:
Wants: High-level summary, business impact, ROI
Time to write: 45 minutes
Wants: Feature progress, sprint velocity, roadmap updates
Time to write: 60 minutes
Wants: Technical details, blockers, resource needs
Time to write: 30 minutes
Wants: Budget vs. actual, burn rate, forecasts
Time to write: 45 minutes
Total: 3 hours just writing updates—and you haven't even started the actual PM work.
With ChatGPT, you can create ALL four tailored updates in 15-20 minutes total. Let me show you how.
Executive stakeholders don't need every detail. They need: Status, Risks, Decisions Required. ChatGPT can transform your raw project data into executive-ready summaries.
Create an executive status report for my [PROJECT TYPE] project.
PROJECT OVERVIEW:
- Name: [Project Name]
- Goal: [What you're building and why]
- Timeline: [Start date] to [End date]
- Budget: [Total budget] | Spent: [Amount spent] | Remaining: [Amount left]
- Team Size: [Number of people]
CURRENT STATUS:
- Sprint/Phase: [Current sprint number or phase name]
- % Complete: [Overall project completion percentage]
- On Track / At Risk / Off Track: [Choose one]
KEY ACCOMPLISHMENTS (This Week/Sprint):
- [List 3-5 major deliverables or milestones completed]
UPCOMING MILESTONES (Next 2 Weeks):
- [List 2-3 critical upcoming deliverables]
RISKS & ISSUES:
- [Risk 1: Description + Impact]
- [Risk 2: Description + Impact]
- [Issue 1: Current blocker + Impact]
DECISIONS NEEDED:
- [Decision 1: What needs approval + By when]
- [Decision 2: What needs approval + By when]
AUDIENCE: [CEO / VP / Board / Client]
TONE: Professional, concise, data-driven
LENGTH: 1 page max (bullet points preferred)
OUTPUT FORMAT:
- Executive Summary (2-3 sentences)
- Status Dashboard (Green/Yellow/Red for Schedule, Budget, Scope, Quality)
- Key Highlights (bullet points)
- Risks & Mitigation
- Decisions Required (with deadlines)
- Next StepsCreate an executive status report for my e-commerce website redesign project.
PROJECT OVERVIEW:
- Name: E-Commerce Platform Modernization
- Goal: Redesign checkout flow to reduce 40% cart abandonment and increase conversion by 30%
- Timeline: Aug 1 - Nov 15 (16 weeks)
- Budget: $250K | Spent: $180K | Remaining: $70K
- Team Size: 8 people (2 designers, 3 devs, 1 QA, 1 PM, 1 content writer)
CURRENT STATUS:
- Sprint: Week 10 of 16
- % Complete: 65%
- Status: At Risk (backend performance issues discovered)
KEY ACCOMPLISHMENTS (Last 2 Weeks):
- Guest checkout feature completed and tested (0 bugs)
- Mobile UI redesign shipped to production
- Real-time shipping calculator integrated with FedEx/UPS APIs
- A/B test shows 15% reduction in abandonment so far
UPCOMING MILESTONES (Next 2 Weeks):
- Complete payment gateway security audit (Oct 28)
- Launch Apple Pay / Google Pay integration (Nov 1)
- Begin load testing for Black Friday traffic (Nov 5)
RISKS & ISSUES:
- RISK: Backend API performance under load (page load times 3+ seconds with 500 concurrent users). Impact: Could crash during Black Friday. Mitigation: Bringing in DevOps contractor next week.
- ISSUE: Design team waiting for final brand guidelines from Marketing (delayed 1 week). Impact: Order confirmation page design blocked.
- RISK: QA engineer out sick for 2 weeks. Impact: Testing backlog growing, may delay launch by 1 week.
DECISIONS NEEDED:
- DECISION 1: Approve $15K for DevOps contractor (2 weeks) to fix performance issues - Need approval by Oct 26
- DECISION 2: Should we delay launch from Nov 15 to Nov 22 to ensure Black Friday stability? - Need decision by Nov 1
AUDIENCE: CEO
TONE: Professional, concise, data-driven
LENGTH: 1 page maxReport Date: October 25, 2025 | Project Manager: [Your Name]
E-commerce checkout redesign is 65% complete (Week 10 of 16) and already showing 15% reduction in cart abandonment in A/B tests. Project is AT RISK due to backend performance issues that could impact Black Friday launch. Decision needed on contractor budget and potential 1-week launch delay.
Schedule
At Risk
Budget
72% spent
Scope
On Track
Quality
0 bugs
🚨 Backend Performance Issue (HIGH PRIORITY): System degrades at 500 concurrent users (3+ second load times). Black Friday expects 2,000+ concurrent users. Mitigation: DevOps contractor identified, can start Oct 28 if approved.
⏸️ Design Blocker (MEDIUM): Waiting on Marketing brand guidelines (delayed 1 week). Order confirmation page on hold. Impact: May slip 2-3 days if not resolved by Oct 27.
👤 Resource Risk (MEDIUM): QA engineer out sick 2 weeks. Testing backlog growing. Mitigation: Developers doing peer testing, but may need contract QA if absence extends.
1. Approve DevOps Contractor Budget ($15K, 2 weeks)
Needed by: Oct 26 | Reason: Fix performance issue before Black Friday | Risk if declined: Potential site crash during peak traffic
2. Launch Date: Keep Nov 15 or Delay to Nov 22?
Needed by: Nov 1 | Trade-off: Nov 15 = ready for Black Friday but higher risk. Nov 22 = more stable but miss peak shopping | Recommendation: Approve contractor, keep Nov 15 target, have Nov 22 backup plan
Technical teams speak in APIs, microservices, and technical debt. Executives speak in ROI, risk, and timelines. ChatGPT bridges this gap.
Translate this technical explanation into non-technical language for a [STAKEHOLDER TYPE] audience.
TECHNICAL EXPLANATION:
[Paste the technical text from your dev team]
AUDIENCE: [CEO / Board Member / Non-technical Client / Finance Stakeholder]
TRANSLATION REQUIREMENTS:
- Remove all jargon (API, microservices, database normalization, etc.)
- Explain in business terms: impact on timeline, cost, user experience, or risk
- Use analogies if helpful
- Keep it to 2-3 sentences maximum
- Focus on "what this means for the project" not "how it works""We're experiencing N+1 query issues in the ORM layer, causing database connection pool exhaustion. We need to refactor to use eager loading and implement Redis caching for the API responses. This will require 3 days of backend work and might introduce regressions in the user service."
The Issue: Our system is running slowly because it's making too many database requests (like opening a filing cabinet 100 times instead of once). This causes page load times to spike during peak traffic.
The Fix: 3 days of optimization work to improve speed by 70%. Small risk: this change might affect user login temporarily, so we'll do it over the weekend.
Business Impact: Faster site = better user experience = higher conversion rate. Worth the 3-day investment.
"We need to deprecate the REST API v1 endpoints and migrate all clients to GraphQL. This will require updating our authentication middleware to support JWT tokens instead of session cookies. Estimated effort: 40 story points across 2 sprints."
What We're Doing: Upgrading our system's "communication language" to a more modern, efficient version.
Timeline: 4 weeks of work, no downtime for users.
Why It Matters: This will let us build new features 50% faster going forward, reducing time-to-market for upcoming releases. It's like renovating your kitchen—short-term disruption for long-term efficiency.
Use ChatGPT to create a cheat sheet of technical terms translated for your specific stakeholders. Examples:
Delivering bad news (delays, budget overruns, scope cuts) is the hardest part of PM work. AI can help you prepare what to say, anticipate questions, and stay calm under pressure.
Help me prepare for a difficult conversation with a stakeholder.
SITUATION:
- What happened: [Describe the problem: delay, budget overrun, scope cut, quality issue]
- Why it happened: [Root cause: technical complexity, vendor delay, scope creep, etc.]
- Impact: [Timeline slip, cost increase, feature removal, etc.]
STAKEHOLDER CONTEXT:
- Who: [Title and personality: CEO (data-driven), Client (emotional), Board Member (risk-averse)]
- Their priorities: [What matters most to them: timeline, budget, quality, reputation]
- Likely reaction: [Angry, disappointed, understanding, nervous]
MY GOAL:
- Primary: [Get buy-in for new timeline / Get budget approval / Manage expectations]
- Secondary: [Maintain trust, show accountability, present solutions]
HELP ME WITH:
1. Opening statement (how to deliver the news clearly but tactfully)
2. Explanation of root cause (without sounding like excuses)
3. Solutions and mitigation plan (what I'm doing to fix it)
4. Anticipated objections and how to respond
5. Closing statement (next steps and reassurance)Help me prepare for a difficult conversation with a stakeholder.
SITUATION:
- What happened: E-commerce redesign launch must be delayed from Nov 15 to Nov 22 (1 week slip)
- Why it happened: Backend performance issues discovered during load testing. System crashes at 500 concurrent users. Black Friday expects 2,000+ users. We need 1 week for DevOps contractor to fix and re-test.
- Impact: Launch happens AFTER Black Friday starts (Nov 24). We miss the first week of holiday shopping season (estimated $200K in lost revenue opportunity).
STAKEHOLDER CONTEXT:
- Who: CEO (data-driven, hates surprises, values transparency)
- Their priorities: Revenue impact, brand reputation (site can't crash on Black Friday), long-term stability
- Likely reaction: Frustrated (this was promised for pre-Black Friday), but will be rational if I have a solid plan
MY GOAL:
- Primary: Get approval for 1-week delay and $15K contractor budget
- Secondary: Maintain trust, show I caught this early, present clear mitigation plan
HELP ME WITH:
1. Opening statement
2. Explanation of root cause
3. Solutions and mitigation plan
4. Anticipated objections
5. Closing statementSay this: "I need to discuss a launch date change. We discovered a critical performance issue during load testing that requires us to delay launch from November 15 to November 22—one week later. I want to walk you through what we found, why this decision protects the business, and our plan to move forward."
Why this works: Direct but not defensive. States the problem upfront. Signals you have a plan (builds confidence).
Say this: "During our Black Friday load testing—which we started early specifically to catch issues like this—we found that the system crashes when we hit 500 concurrent users. Black Friday traffic will be 2,000+ users. If we launched on Nov 15, we'd likely experience downtime during our most critical sales weekend. The root cause is a backend database architecture issue that our team didn't anticipate at the complexity we're now handling."
Why this works: You caught this proactively (hero, not villain). Data-driven (500 vs 2,000 users). Frames delay as risk mitigation, not failure.
Say this: "Here's our plan to fix this and minimize business impact:"
Why this works: Specific timeline. Shows you're already solving it. Includes revenue recovery plan (addresses CEO's concern).
❓ "Why didn't we catch this earlier?"
Response: "We did load testing at 200 users earlier (which passed), but we only reached full Black Friday load levels (500+) in the past week. This is exactly why we scheduled testing 3 weeks before launch—to have time to fix what we find. The alternative would've been launching on Nov 15 and crashing on Black Friday."
❓ "Can we fix it faster and keep Nov 15?"
Response: "We considered that. The fix itself is 3-4 days, but we need 2-3 days of re-testing to be confident. Rushing this would give us maybe 1 day of margin before launch—too risky for a Black Friday deployment. Nov 22 gives us a proper safety buffer."
❓ "What if this happens again with a different issue?"
Response: "That's a fair question. We're also running security audits and full regression testing in parallel. The performance issue was the only high-severity item found. We'll have a 'go/no-go' meeting on Nov 20 to make the final launch decision based on test results."
Say this: "I know this isn't the news you wanted to hear, and I take full accountability for not catching this sooner in testing. The good news is we found it in time to fix it properly. The team is already executing the mitigation plan, and I'll send you daily updates this week. By Nov 22, we'll have a stable, battle-tested system ready for the biggest shopping weekend of the year. Do you have any concerns I haven't addressed?"
Why this works: Takes accountability (builds trust). Ends with confidence and action. Invites questions (shows openness).
Scenario: You're managing a mobile app redesign. You need to communicate with 3 different stakeholders about the same project status.
Project Status:
Your Task: Create 3 different status updates for:
Create 3 different status updates for the same project, tailored to different stakeholders.
PROJECT: Mobile app redesign
SITUATION:
- Status: 2 weeks behind schedule
- Cause: iOS App Store rejected initial submission (technical compliance issue with in-app purchase flow)
- Current state: Issue fixed, resubmitted Oct 20, waiting for Apple re-approval (typically 5-7 days)
- New launch date: Nov 1 (was Oct 15)
- Budget: $50K spent of $75K budget (on track)
- Quality: 4.8 star rating in beta testing with 200 users
CREATE 3 UPDATES FOR:
1. CEO - [Name]
- Cares about: Revenue impact, brand reputation, launch date certainty
- Communication style: Bullet points, data-driven, 5 sentences max
- Focus on: Business impact, not technical details
2. Marketing Director - [Name]
- Cares about: Campaign timeline, messaging, App Store readiness
- Communication style: Conversational but professional
- Focus on: What this means for launch campaign planning
3. Engineering Manager - [Name]
- Cares about: Technical root cause, prevention for future releases
- Communication style: Technical depth okay
- Focus on: What happened and what we learnedOpen ChatGPT, use this prompt, and see how AI tailors the same information for 3 different audiences. Notice how the tone, detail level, and focus changes for each stakeholder.
Status, risks, decisions needed—one page, ready to send
APIs become "system connections," technical debt becomes "efficiency shortcuts"
Anticipate objections, frame delays as risk management, stay calm under pressure
CEO gets business impact, tech lead gets technical details, marketing gets campaign implications
Executives appreciate directness—state the news upfront, then explain
You now know how to communicate with any stakeholder at any level. Next, we'll dive into Email & Professional Writing—mastering PM emails for every scenario, from kickoffs to escalations.
Test your understanding of AI for stakeholder communication!