Retro with AI
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Run retrospectives your team actually looks forward to

Learn how to pair AI assistants with proven Scrum facilitation craft — so every retro surfaces real root causes, generates honest conversation, and produces action items that stick beyond the next sprint.

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Retro with AI

"I built this course because good teams deserve retrospectives that actually move the needle — and AI, used well, is the most practical lever I've found to make that happen."

TrainingHQ

What you'll learn

What you'll be able to do

  • Design AI-augmented retrospective formats tailored to your team's maturity and sprint context
  • Use AI prompting techniques to generate targeted questions that uncover root causes, not just symptoms
  • Analyze sprint data and team sentiment with AI tools to spot patterns across multiple retrospectives
  • Facilitate psychologically safe retro sessions where AI handles note-taking and theme clustering in real time
  • Build a living action-item tracker powered by AI that keeps improvement commitments visible between sprints
  • Measure retrospective effectiveness over time using AI-generated metrics and continuous feedback loops

How it works

A school that adapts to you

This isn't a set of static videos. Every lesson is generated live and tuned to where you actually are.

We learn your level

A quick placement check tailors your starting point so you're never bored or lost.

Lessons adapt as you go

Each lesson is written for your pace and your goal, adjusting as your skills grow.

Your AI coach keeps you moving

Checkpoints, feedback, and gentle nudges turn progress into a real result.

The curriculum

What's inside your school

0 modules · 0 lessons

1

Foundations of AI-Augmented Retrospectives

Establishes why and how AI fits into the Scrum retrospective cycle before touching any tool.

  • 1.1The Modern Retro ProblemIncluded
  • 1.2AI Assistant Landscape for Agile TeamsIncluded
  • 1.3Team Maturity and Sprint Context AssessmentIncluded
  • 1.4Ethical and Psychological Safety GuardrailsIncluded
2

Designing AI-Augmented Retro Formats

Teaches participants to select and customize retrospective structures with AI as a design partner.

  • 2.1Classic Formats Reimagined with AIIncluded
  • 2.2Prompting AI to Co-Design a Retro AgendaIncluded
  • 2.3Choosing the Right Format for the Sprint ContextIncluded
  • 2.4Building Your Own AI-Assisted Format LibraryIncluded
3

AI Prompting Techniques for Deeper Insights

Develops precision prompting skills so AI surfaces root causes and drives richer team conversations.

  • 3.1Prompting Fundamentals for Retro FacilitationIncluded
  • 3.2Generating Targeted Retrospective QuestionsIncluded
  • 3.3Using the Five Whys with AI AssistanceIncluded
  • 3.4Sparking Conversation: AI-Generated Icebreakers and EnergizersIncluded
4

Analyzing Sprint Data and Team Sentiment

Equips participants to feed sprint metrics and qualitative feedback into AI tools that reveal cross-sprint patterns.

  • 4.1Identifying and Collecting the Right Sprint DataIncluded
  • 4.2Sentiment Analysis on Team FeedbackIncluded
  • 4.3Spotting Patterns Across Multiple RetrospectivesIncluded
  • 4.4Visualizing Insights for the TeamIncluded
5

Facilitating Live Retros with AI Support

Covers real-time AI use during the retro session itself — note-taking, clustering, and keeping safety intact.

  • 5.1Setting Up Your AI-Assisted Retro EnvironmentIncluded
  • 5.2Real-Time AI Note-Taking and TranscriptionIncluded
  • 5.3AI-Powered Theme Clustering in the MomentIncluded
  • 5.4Maintaining Psychological Safety When AI Is in the RoomIncluded
  • 5.5Closing the Session: AI-Summarized TakeawaysIncluded
6

Action Tracking, Measurement, and Continuous Improvement

Closes the loop by building AI-powered systems that keep commitments visible and measure retro effectiveness over time.

  • 6.1Building a Living AI-Powered Action-Item TrackerIncluded
  • 6.2Connecting Retro Actions to Sprint PlanningIncluded
  • 6.3Measuring Retrospective Effectiveness with AI MetricsIncluded
  • 6.4Running Continuous Feedback Loops Between SprintsIncluded
  • 6.5Evolving Your AI Retro Practice Over TimeIncluded

Who it's for

Is this you?

Experienced Scrum Masters

You've been running retros for years and want to break out of the same tired formats with AI-powered techniques that surface deeper insights.

Agile Coaches

You coach multiple teams and need scalable, data-driven retro practices — including cross-sprint pattern analysis and effectiveness metrics — to show real improvement.

Product Team Leads

You own team health as much as delivery, and you want retros that produce action items your team will actually follow through on between sprints.

Newly Certified Scrum Masters

You have the theory down but want a concrete, modern facilitation toolkit — including AI prompting and live session support — before your first real retro.

Remote-First Facilitators

Your team is distributed across time zones, and you need AI note-taking, theme clustering, and async feedback loops to make remote retros feel just as real as in-person ones.

Engineering Managers

You sit at the intersection of delivery and people, and you want structured, AI-assisted retrospectives that connect team sentiment to sprint planning in a measurable way.

Questions

Frequently asked

Jaco van Dam

A note from your teacher

TrainingHQ

TrainingHQ

Hey — I'm glad you're here, and I want to start by saying something that might sound a little uncomfortable: most retrospectives aren't working. Not because the teams running them don't care, and not because the formats are wrong. It's because we're trying to surface complex, human, systemic problems with a 45-minute sticky-note exercise and goodwill. That's not a facilitation failure. That's a tooling gap.

I've spent a long time in the Scrum Master and Agile coaching world, running retros with teams at all different stages — newly formed, battle-tested, enthusiastic, burned out, skeptical, and everything in between. And the single most consistent pain I've seen is the action-item graveyard: the commitments that feel real in the moment and then vanish by the next sprint review. I built this course because I got tired of watching good teams spin on that wheel — and because I started seeing real, practical ways that AI could break the cycle.

This isn't a course about AI being magic. It's a course about using AI as a skilled co-facilitator — one that can take notes so you don't have to, cluster themes faster than any affinity map exercise, generate questions that actually go somewhere, and hold your team's improvement commitments accountable between sprints. The human part — the trust, the conversation, the judgment call on when to push deeper and when to let something breathe — that's still entirely yours. AI just handles the parts it's genuinely better at.

What I've tried to do in every section of this course is give you something you can use in your next retro. Not theory to sit with, not a framework to admire — a concrete technique, a prompt to try, a tracker to build. I've drawn on real sprint scenarios throughout, so the examples feel like actual team situations, not textbook cases. And I've been deliberate about the psychological safety content, because I know that's where a lot of practitioners get nervous about bringing AI into the room. We work through it directly.

If you run retrospectives regularly and you're ready to stop guessing whether they're working and start knowing — this is the course for you. Let's get into it.

TrainingHQ

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  • 6 modules, 26 lessons
  • AI-adaptive lessons tuned to your level
  • Quizzes & checkpoints to lock in progress
  • Your own AI learning coach
  • Learn on any device, at your pace
  • Full access for as long as you're subscribed