The $21K Sprint Planning Hack Every Project Manager Is Missing

This AI prompt saved me over 5 hours per sprint, and I'm sharing the exact template.

Photo by Gary Lee on Unsplash

Happy New Year AI-Powered PM champions!

After reviewing a few Substack newsletters, I’ve made some changes and am taking the newsletter in a new direction.

As project managers, we need to use AI tools and tactics to save time and money for our stakeholders.

We need cheat codes.

I’ve looked for project management prompts online, and they are pretty weak. Or they come from online magazines not focused on project management (like Forbes), and their offerings are for namby-pambys.

The newsletter will focus on providing you with the tools and prompts to help you use AI to your advantage and become a rockstar.

In the online world, you need to give until it hurts, so I’m sharing this with free and paid subscribers. I appreciate my paid subscribers, and I tip my hat to them!

Also, I am adding a feature for paid subscribers.

The amount of AI news that comes out daily is overwhelming. I get over 10 newsletters about AI and agents, so I will distill what I think is the one top story you need to know and send it to your inbox daily. Then, I will send a roundup of the week’s top stories on Sunday and probably an additional story that caught my eye.

• Daily AI Hotness: One top story on AI sent daily with a roundup on Sunday.

I know people who pay for tutors to come to their house once a week and do the exact same thing, but you don’t have to clean up the house for visitors.

One final request: Please share this newsletter so that more project managers like you can use AI to enhance their workflows.

Now that the news is out of the way—onward to the revamped newsletter.

Let's cut through the BS—your sprint planning process is probably taking way too long. Those endless meetings where you're juggling backlog items, trying to guess story points, and praying you've caught all the dependencies? Yeah, we can fix that.

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This Week's PM Time-Saver: The Sprint Planning Accelerator

Here's your new secret weapon—a prompt that turns chaotic backlog items into a structured sprint plan in minutes. Not hours. Minutes.

Act as an expert agile project manager. I'm preparing for sprint planning and need to organize these backlog items into a coherent sprint plan. Consider team velocity, story points, and dependencies. 

Here are my backlog items: [Paste your backlog items here] 

Please:
1. Group similar items
2. Identify dependencies
3. Suggest story point estimates
4. Recommend a sprint sequence
5. Flag potential risks or blockers

Simple, right? But don't let the simplicity fool you. This prompt can be a lifesaver.

A more advanced prompt is in the Premium Prompts that will light your world on fire.

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Prompt Success Story: Show Me The Money

Let's talk turkey (or ham… the holidays are over, but I have tons of leftovers). I implemented this sprint planning prompt last month, and the results are frankly ludicrous:

Traditional Sprint Planning:

• 4 hours prep + documentation

• 2 hours risk assessment

• 1-hour dependency mapping

Total: 7 hours of your life you'll never get back

With AI:

• 1 hour total planning time

• 15-minute risk assessment

• 15 minutes dependency mapping Total: 1.5 hours of focused work

That's 5.5 hours saved per sprint.

At an average PM salary of $120K/year ($60/hour), you're looking at:

• Monthly savings: $1,752

• Annual savings: $21,024

• ROI on this newsletter: 105x

And that's just sprint planning. We haven't even touched daily standups or status reports yet.

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Tool Spotlight: Supercharging Monday.com

Look, Monday.com is great, but it's 2025. Let's add some pizazz to it.

Monday.com + Our Sprint Planning Accelerator Prompt = Magic

Here's what you can automate:

1. Status updates

2. Story point distribution

3. Sprint capacity calculations

4. Dependencies

No more manual data entry. No more guessing at story points. Just clean, consistent sprint planning that practically runs itself.

Check out the full workflow and prompt (the biggest I’ve created) in the Premium Prompts section.

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Prompt Tune-Up

I’ve added a couple of bolt-on prompts to the Sprint Planning Accelerator Prompt and you can find these in the Premium Prompts section.

The Risk Assessment Master:

When: High-stakes sprint planning
Impact: 90% faster risk identification
Key feature: Includes confidence scoring and mitigation strategies

The Team Capacity Calculator:

When: Managing multiple teams
Impact: 80% more accurate sprint loading
Key feature: Accounts for skill distribution and team velocity

Each prompt is designed to solve specific PM sprint planning headaches.

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Final Thoughts

Here's the truth—AI isn't replacing project managers. It's replacing the mind-numbing parts of project management that keep you from doing what you're actually good at: leading teams and delivering results.

You can keep doing things the old way. Spend those hours in sprint planning. Manual entry of those values in Monday.com. Calculate story points by gut feeling.

Or you can join the revolution.

Your choice.

Next week: We're tackling stakeholder communications. Your status reports will never be the same.

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AI-Driven Tools for PMs

Sheet Copilot - Uses AI to complete tasks in Google Sheets.

Retellio - Takes all your company's customer calls and turns the must-hear clips into one awesome weekly podcast

Pointer AI - Integrates AI into Google Docs to automate edits while preserving formatting.

BrieflyAI - Transcribes meetings in real-time and generates AI-powered summaries, action items, and follow-up emails.

Prodhiiv - AI tool for visual notes, task management, and collaboration.

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AI News PMs Can Use

Riding the AI Whirlwind: Gartner's Top Strategic Predictions for 2025

Leading AI-driven Business Transformation: Are You In?

Microsoft’s AI Strategy Roadmap

Building smart workflows with Asana’s AI Studio

Monday.com's Quick Start AI Guide

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Premium Prompts

These are custom-built prompts—you’ll only find these in the AI-powered Project Manager.

Cut and paste these into ChatGPT or Claude—double rules show the end of each prompt.

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Premium Sprint Planning Assistant

✂️—CUT BELOW—

Role

You are an elite Agile Project Manager and Sprint Planning Specialist with 15+ years of experience optimizing agile ceremonies across Fortune 500 companies. You excel at analyzing team dynamics, estimating complexity, identifying dependencies, and creating highly efficient sprint plans that maximize team velocity while minimizing risks. You've helped hundreds of teams increase their sprint completion rates by over 40% through strategic planning and workload optimization.

Task

Transform these raw backlog items into a strategically organized sprint plan that maximizes team efficiency and delivery confidence. Using advanced agile planning techniques, analyze the provided items for a comprehensive sprint structuring that ensures optimal flow and risk mitigation.

Please follow this step-by-step process:

1. First analyze all items for common themes and technical relationships

2. Group items based on both functional areas and technical dependencies

3. Evaluate each item's complexity considering historical velocity data

4. Create a dependency map highlighting critical path items

5. Assign story point estimates using Fibonacci sequence

6. Design an optimal sprint sequence accounting for team capacity

7. Identify potential blockers and suggest mitigation strategies

8. Provide a final sprint plan with confidence scoring

Backlog items: [Insert backlog items here]

Specifics

1. Story point estimates should account for:

   • Technical complexity

   • Integration requirements

   • Testing scope

   • Team familiarity with the domain

   • Historical velocity patterns

2. Dependency analysis must consider:

   • Technical prerequisites

   • External team dependencies

   • System integration points

   • Data dependencies

   • API contracts

3. Risk assessment should evaluate:

   • Technical debt impact

   • Resource availability

   • External dependencies

   • Knowledge gaps

   • Environment constraints

4. Sprint sequence recommendations should:

   • Balance workload across sprint days

   • Account for team ceremonies

   • Include buffer for unknowns

   • Consider team member availability

   • Align with sprint goals

This task is vital to maintaining our team's velocity and delivery confidence. Your thorough analysis will directly impact our sprint success and team morale.

Context

Our agile team operates in a fast-paced environment where accurate sprint planning is crucial for maintaining delivery predictability and team satisfaction. The sprint plan you create will be used in our upcoming sprint planning session to facilitate focused discussions and quick decision-making. Your analysis helps prevent mid-sprint bottlenecks and ensures the team commits to an achievable workload.

The resulting plan will be reviewed by both the development team and key stakeholders to align expectations and resource allocation. A well-structured sprint plan historically leads to a 30% reduction in mid-sprint scope changes and a 40% increase in sprint goal achievement.

Examples

Input:

• Feature A: User authentication update

• Feature B: Database optimization

• Feature C: API endpoint creation

• Feature D: UI components update

Output Example:

Group 1: Authentication & API (Technical Relationship) 
- Feature A: User authentication update (8 points) 
  Dependencies: None 
  Risk: Medium - New auth framework 
- Feature C: API endpoint creation (5 points) 
  Dependencies: Feature A 
  Risk: Low 

Group 2: Performance & UI 
- Feature B: Database optimization (13 points) 
  Dependencies: None 
  Risk: High - Production data impact 
- Feature D: UI components update (3 points) 
  Dependencies: None 
  Risk: Low 

Recommended Sequence: 
1. Feature A (Blocker for Feature C) 
2. Feature B (Can run parallel) 
3. Feature C (After A complete) 
4. Feature D (Can be pulled in anytime) 
Risk Mitigation: [Details here]

Notes

• All story point estimates should use Fibonacci sequence (1,2,3,5,8,13,21)

• Include confidence scores (High/Medium/Low) for each estimate

• Highlight any items requiring tech lead review

• Flag items needing product owner clarification

• Suggest parallel work streams where possible

• Include capacity buffer for unexpected issues

• Format output in clear sections with headers

• Use bullet points for actionable items

• Include a summary of total story points vs team capacity

✂️—END—

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Risk Assessment Prompt

✂️—CUT BELOW—

You are a Risk Management Expert in Agile projects. Analyze our upcoming sprint plan for potential risks:

Sprint goals: [List goals]

Planned stories: [List stories]

Team context: [Team information]

Please provide:

1. Risk identification per story/goal

2. Probability and impact assessment

3. Early warning indicators to monitor

4. Specific mitigation strategies

5. Contingency suggestions

6. Risk-adjusted sprint recommendations

Format as a risk management matrix with actionable monitoring and mitigation steps.

✂️—END—

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Team Capacity Analysis Prompt

✂️—CUT BELOW—

You are an experienced Agile Project Manager with expertise in team capacity planning. I need to analyze my team's capacity for the upcoming sprint.

Team composition: [List team members and their roles]

Upcoming team events/PTO: [List any planned absences]

Previous sprint velocity: [Insert number]

Please provide:

1. A detailed capacity calculation per team member

2. Recommended story point target accounting for holidays/PTO

3. Risk-adjusted velocity prediction

4. Suggestions for workload distribution considering specializations

5. Early warning flags for potential capacity issues

Format the response as an actionable capacity planning document with clear recommendations.

✂️—END—

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Monday.com-Optimized Sprint Planning Prompt

***Disclaimer***

The prompt below should run fine in ChatGPT or Claude.

I have not created boards or implemented the formulas in Monday.com, so you may need to tweak the framework and the Javascript to make it work properly with your project.

***End Disclaimer***

✂️—CUT BELOW—

ROLE
You are an elite Agile Project Manager and Monday.com Automation Specialist with extensive experience optimizing agile workflows in Monday.com. You excel at structuring boards, creating automated workflows, and utilizing Monday.com's unique features like subitems, dependencies, and time tracking to create highly efficient sprint management systems. You've helped teams increase their sprint completion rates by 45% through strategic Monday.com automation and board organization.

TASK
Transform these backlog items into a strategically organized Monday.com sprint plan that leverages the platform's native capabilities for maximum automation and visibility. Create a structure that enables automated status updates, dependency tracking, and capacity management.

Follow this process:
1. Analyze items for logical grouping in Monday.com board structure
2. Define column structure for sprint tracking
3. Establish automation rules for status updates
4. Create dependency visualization system
5. Set up time tracking and capacity monitoring
6. Design cross-board connections if needed
7. Structure formulas for automated calculations

Backlog items:
[Insert backlog items here]

SPECIFICS
1. Board Structure Requirements:
   - Main sprint board
   - Dependency tracking board
   - Capacity management board
   - Sprint metrics dashboard

2. Column Types Needed:
   - Status (Working on it, Stuck, Done)
   - Story Points (Numbers)
   - Priority (Labels)
   - Dependencies (Connect to other items)
   - Time Tracking
   - Owner
   - Groups for feature areas

3. Automation Rules Should:
   - Update parent item status based on subitems
   - Track sprint capacity in real-time
   - Alert on dependency conflicts
   - Monitor team workload distribution

CONTEXT
Our agile team uses Monday.com as our primary project management tool. The sprint plan you create will be implemented using Monday.com's boards, automations, and formulas. Your structure will be used by both the development team and stakeholders to track sprint progress and manage resources effectively.

EXAMPLES
Input:
[List of backlog items]

Output Example:

Board Structure: 
Sprint Board Columns:
Item Name
Status (Status Column)
Story Points (Numbers)
Priority (Labels)
Dependencies (Connect to other items)
Time Tracking
Owner (People)
Risk Level (Labels)

Groups:
Authentication Features
Login update (8 points)
Password reset (5 points)

Performance Optimization [Items listed with points]

Automations:
Status Updates When: Subitem status changes Then: Update main item status
✂️—END—

Now, let's create the step-by-step implementation guide:

# Monday.com Sprint Planning Implementation Guide

## Phase 1: Board Setup

### 1. Create Board Structure
```markdown
1. Main Sprint Board
   Columns:
   - Item Name (Text)
   - Status (Status)
   - Story Points (Numbers)
   - Priority (Labels)
   - Time Tracking (Time Tracking)
   - Owner (People)
   - Dependencies (Connect to Other Items)
   - Risk Level (Labels)
   - Confidence Score (Numbers)
   - Sprint (Dropdown)

2. Sprint Metrics Board
   Columns:
   - Sprint Name (Text)
   - Total Points (Formula)
   - Completed Points (Formula)
   - Team Capacity (Numbers)
   - Buffer Remaining (Formula)
   - Risk Score (Formula)

2. Create Essential Formulas

//javascript

// Sprint Points Calculator
sum(
  filter(
    {story points},
    {sprint} = "Current Sprint"
  )
)

// Capacity Utilization
{total points} / {team capacity} * 100

// Risk Assessment
sum(
  if({risk level} = "High", 3,
  if({risk level} = "Medium", 2, 1))
) / count({risk level})

Phase 2: Automation Setup

1. Status Update Automation

// javascript

// When subitem status changes
when 
  status_changed_to(done) in subitem
do
  if all_subitems_done then
    change_parent_status(done)
  else if any_subitems_stuck then
    change_parent_status(stuck)
  end

2. Capacity Monitoring

// javascript

// Daily capacity check
when 
  schedule.daily()
do
  if sprint_points > team_capacity * 0.8 then
    notify(
      group: "Sprint Team",
      message: "Sprint approaching capacity"
    )
  end

Phase 3: Integration Workflow

1. Sprint Planning Process

1. Create new sprint group
2. Import items from backlog
3. Run sprint planning prompt
4. Create items with structure:
   - Main stories as parent items
   - Subtasks as subitems
   - Connect dependencies
   - Assign story points

2. Dependency Management

//javascript

// Setup dependency visualization
1. Create "Dependencies" view
2. Enable Timeline view
3. Configure dependency columns
4. Set up dependency-based automations

Phase 4: Dashboard Creation

1. Sprint Overview Dashboard

Widgets to create:
1. Sprint Burndown Chart
   - X-axis: Sprint days
   - Y-axis: Remaining points

2. Team Capacity Widget
   - Current utilization
   - Remaining capacity
   - Warning indicators

3. Risk Distribution
   - High/Medium/Low breakdown
   - Trending chart

2. Team Performance Metrics

Create charts for:
1. Velocity tracking
2. Completion rate
3. Risk distribution
4. Dependency impact

Phase 5: Maintenance Process

1. Sprint Transition Checklist

1. Archive completed items
2. Update capacity numbers
3. Reset tracking metrics
4. Verify automation rules
5. Clear old dependencies

2. Regular Maintenance

Weekly tasks:
1. Check automation logs
2. Verify formula calculations
3. Update team capacity
4. Clean up unused connections
5. Archive completed items