Toolsday

October 20, 2026 · Last updated on September 12, 2026

AI Toolsday: Real AI, Real Agile, Real Workflows

# Continuous Improvement

Practical AI workflows for Agile teams

Use AI to Design a Better Workshop

You’ve got 60 minutes, a room full of people, and an important outcome to achieve.

Now…what should you actually do with them?

Whether you’re preparing for a retrospective, Inspect & Adapt workshop, problem-solving session, PI Planning activity, or team working session, AI can be a surprisingly useful facilitation partner.

This week’s workflow uses AI to help you move from “We need a meeting about this” to a thoughtfully designed session with clear outcomes, purposeful activities, stronger questions, and a backup plan when things inevitably don’t go exactly as expected.

📌 Before You Start

The AI tools featured in this workflow are examples, not requirements. Every organization has different approved tools, security policies, and ways of working.

The goal of AI Toolsday isn’t to recommend one specific product—it’s to share practical AI workflows that you can adapt using the tools available to you.

Focus on the workflow, not the tool.

🛠️ Tools Used

ChatGPT

Use ChatGPT as your workshop design partner to clarify the outcome, brainstorm activities, build the agenda, and generate facilitation questions.

Claude

Use Claude to pressure-test the workshop from the participants’ perspective and identify potential problems before you’re standing in front of the room.

Miro, Mural, or your approved collaboration tool

Once the workshop is designed, build the activities and collaborative space participants will actually use.

⚙️ How It Works

Step 1: Start with the outcome—not the agenda

Before asking AI to build anything, tell it what needs to be different when the workshop is over.

Instead of:

“Create an agenda for a dependency workshop.”

Try:

“By the end of this 60-minute workshop, representatives from five teams need to identify their highest-risk cross-team dependencies, agree on owners, and determine the next action for each.”

Then give AI the context it needs:

Who is attending?

How much time do you have?

Is the session virtual, in-person, or hybrid?

What do participants already know?

What decisions need to be made?

What tensions or challenges might exist?

What absolutely must be accomplished?

Now AI can design toward an outcome rather than filling 60 minutes with activities.

Step 2: Design the experience with ChatGPT

Ask ChatGPT to propose a workshop flow that gets participants from where they are now to your desired outcome.

Have it recommend:

Opening and framing

Individual thinking time

Small-group activities

Full-group discussions

Decision points

Reflection questions

Timing for each section

A clear close and next steps

You can also give it constraints.

For example:

“I don’t want slides.”

“This group tends to have a few people dominate the conversation.”

“Participants are joining from multiple time zones and may have low energy.”

“I need everyone to contribute—not just the leaders.”

Those details can dramatically change the workshop AI designs.

Step 3: Build your facilitation question bank

A great activity can fall flat if the facilitator doesn’t have the right questions ready.

Ask AI to generate questions for different moments in the workshop.

For example:

To open the conversation: “What would make this session worth your time?”

To dig deeper: “What makes us believe that's the root problem?”

To challenge assumptions: “What might we be missing?”

When the room goes quiet: “What feels hardest to answer about this?”

When the group gets stuck: “What is the smallest decision we can make right now that moves us forward?”

You won’t use every question. But having them ready gives you options in the moment.

Step 4: Pressure-test the workshop with Claude

Once you have your agenda, give it to Claude—but don’t ask Claude to improve it immediately.

Instead, ask it to play the role of different participants.

For example:

The skeptical engineer

The overwhelmed Product Owner

The senior leader who wants to jump directly to solutions

The quiet team member who rarely speaks

The participant who doesn’t understand why they’re there

Ask:

“Where would each person disengage, become confused, or struggle to participate?”

Then use those observations to adjust your design.

Step 5: Create your Plan B

Workshops rarely go exactly according to plan.

Ask AI:

What if this activity takes twice as long?

What can I cut without losing the outcome?

What if nobody talks?

What if one person dominates?

What if the group can't reach agreement?

What if we uncover a much bigger problem?

What should I do if we finish 15 minutes early?

Now you've got a facilitation backup plan instead of having to invent one under pressure.

Step 6: Build the workshop

Once you're happy with the design, create the actual experience in Miro, Mural, or your preferred collaboration tool.

Use AI-generated content as a starting point for instructions, prompts, activity descriptions, and facilitator notes.

Then apply your own knowledge of the participants.

You know the people in the room. AI doesn't.

💡 Why Agile Pros Care

Agile professionals facilitate a lot of conversations.

And good facilitation isn't about having the fanciest activity or the most creative virtual whiteboard.

It's about intentionally creating the conditions for people to think, contribute, make decisions, and move forward together.

AI can dramatically reduce the preparation time required to explore activities, generate questions, anticipate challenges, and create contingency plans.

That gives you more time to focus on the part that matters most:

the people in the room.

💬 Prompt to Copy

You are an experienced Agile facilitator helping me design a workshop.
Do not begin by creating an agenda. First, help me clarify the desired outcome and what participants need to accomplish before the session ends.
Then design a workshop that includes:
A clear opening and framing
Activities that directly support the desired outcome
Opportunities for every participant to contribute
Individual thinking and group discussion where appropriate
Decision points
Facilitation questions for each activity
Timing
A clear close and next steps
Then pressure-test the design by identifying:
Where participants may disengage
Where instructions may be unclear
Where one or two voices could dominate
Activities that may take longer than expected
What I can cut if time runs short
Finally, create a Plan B for a quiet group, an overly talkative group, and a group that cannot reach agreement.
Workshop Context: Purpose: Desired outcome: Participants: Time available: Virtual/In-person: Known challenges or constraints:

✅ Try It This Week

Take the next workshop or collaborative meeting you're responsible for and don't ask AI to create the agenda.

Instead, start with:

“Here's what needs to be true when this meeting ends. Help me design an experience that gets us there.”

See how different the result is.

💬 Continue the Conversation

What’s your biggest facilitation challenge: getting people to participate, keeping the conversation focused, managing dominant voices, getting to a decision, or something else?

And what's your favorite facilitation trick when a session isn't going according to plan?

🤝 AI Toolsday Tip

AI can generate dozens of creative workshop activities in seconds, but more creative doesn't necessarily mean more effective. Start with the outcome, then choose the simplest activity that helps the group get there. Your job as a facilitator isn't to impress the room with the workshop design—it’s to help the room accomplish something together.

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