Toolsday

October 6, 2026 · Last updated on September 12, 2026

AI Toolsday: Real AI, Real Agile, Real Workflows

# Continuous Improvement

Practical AI workflows for Agile teams

Prepare for a Difficult Agile Conversation with AI

Maybe a stakeholder keeps changing priorities. A team member isn't following through on commitments. A Product Owner and team aren't seeing eye to eye. Or you need to give someone feedback you're not quite sure how to deliver.

Difficult conversations are part of working with people—but going into them unprepared can make an already challenging situation harder.

This week's workflow uses AI as a coaching partner to help you examine a situation from multiple perspectives, challenge your assumptions, and prepare for a more productive conversation.

📌 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.

And for this particular workflow, be especially thoughtful about what you share. Don't enter confidential, sensitive, or personally identifiable information into an AI tool unless your organization's policies explicitly allow it. You can usually describe the situation without names or identifying details.

🛠️ Tools Used

Claude

Use Claude as a coaching partner to unpack the situation, challenge your interpretation, and explore perspectives you may not have considered.

ChatGPT

Once you've thought through the situation, use ChatGPT to prepare conversation starters, questions, and even role-play the discussion before you have it.

⚙️ How It Works

Step 1: Describe the situation objectively

Start by telling Claude what's happening—but try to separate facts from your interpretation of those facts.

Instead of:

"Our Product Owner doesn't respect the team's capacity."

Try:

"Our Product Owner added three high-priority stories after Sprint Planning during each of the last two Sprints. The team completed the new work but didn't finish several items originally planned."

Then provide context such as:

Your role

The other person's role

What you've observed

What you've already tried

What outcome you're hoping for

This gives AI enough context to coach you without starting from your conclusion.

Step 2: Ask AI to challenge your perspective

This is where AI becomes more interesting than simply asking, "What should I say?"

Ask Claude questions like:

What assumptions might I be making?

How might the other person view this situation?

What information could I be missing?

What might their underlying concern or need be?

Where could my own behavior be contributing to the problem?

What questions should I ask before proposing a solution?

You may not agree with everything it suggests—and that's okay.

The point is to widen your perspective before entering the conversation.

Step 3: Decide what a good outcome looks like

Before scripting anything, get clear about what you're actually trying to accomplish.

Ask AI to help distinguish between:

The position: "I need them to stop changing priorities."

and

The desired outcome: "We need a way to respond to urgent work without repeatedly disrupting our ability to meet Sprint Goals."

That shift can completely change how you approach the conversation.

Step 4: Prepare the conversation with ChatGPT

Now bring your conclusions into ChatGPT and ask it to help you structure the discussion.

Have it generate:

A neutral way to open the conversation

Observations you can share without assigning blame

Open-ended questions

Areas where you should listen rather than solve

Possible points of tension

Ways to redirect the conversation if it becomes defensive

A few potential agreements or next steps

You don't need to memorize a script.

You're preparing yourself to enter the conversation with greater clarity and curiosity.

Step 5: Role-play it

Here's the fun part.

Tell ChatGPT:

"Play the other person. Don't make this easy for me."

Then practice.

Ask it to respond realistically based on the context you've provided. Try your opening. Respond to objections. Practice asking questions instead of immediately defending your position.

Afterward, ask:

"Where did I become defensive, make assumptions, or miss an opportunity to ask a better question?"

You might be surprised by what you notice.

Step 6: Have the real conversation

Then put the AI away.

The actual conversation requires something AI can't provide: human judgment, empathy, curiosity, and trust.

Go into it prepared—but stay open to discovering something you hadn't anticipated.

💡 Why Agile Pros Care

Agile ways of working depend on collaboration, transparency, feedback, and the ability to navigate disagreement constructively.

And yet, many of the hardest problems Scrum Masters, RTEs, Product Owners, and Agile Coaches face aren't process problems.

They're people problems.

AI can give you a private space to examine your assumptions, consider another person's perspective, and practice what you want to say before the stakes are real.

It doesn't make the difficult conversation disappear. It can help you show up better for it.

💬 Prompt to Copy

You are an experienced Agile coach helping me prepare for a difficult workplace conversation.
I don't want you to simply agree with my interpretation of the situation. Help me think more critically about it.
First:
Separate the facts I've provided from my assumptions or interpretations.
Identify assumptions I may be making.
Suggest reasonable ways the other person might view the situation.
Identify information I may be missing.
Help me clarify the outcome I actually want from the conversation.
Then help me prepare by:
Suggesting a neutral opening.
Generating five curious, open-ended questions I could ask.
Identifying language that could unintentionally sound accusatory.
Suggesting areas where I should listen rather than immediately respond.
Finally, role-play the other person so I can practice the conversation. Respond realistically and challenge me when appropriate.
Situation: Describe the situation without including sensitive or identifying information.

✅ Try It This Week

Think of one conversation you've been putting off.

Before deciding what you're going to say, describe the situation to your approved AI tool and ask:

"What assumptions might I be making about this situation?"

Then ask:

"What might this situation look like from the other person's perspective?"

You don't have to agree with the answers. See whether they change any of the questions you want to ask.

💬 Continue the Conversation

When you're preparing for a difficult conversation, what helps you most: writing down what you want to say, talking it through with someone, practicing beforehand, or something else?

Have you ever used AI to help you prepare?

🤝 AI Toolsday Tip

AI can help you rehearse a conversation, but it can't know another person's intentions, motivations, or feelings. Treat its interpretations as possibilities—not facts. Use AI to enter the conversation with more curiosity, not more certainty.

Comment (1)

Popular