Welcome to another Retro Newsletter. If this is your first time here, I highly recommend reading this newsletter first. It will give you the basics.

We live in a world that is increasingly offering to think for us. AI tools, smart recommendations, automated decisions, opinionated frameworks, all of this is designed to make our lives easier. And much of the time, it does. But here's a question: when did you last make a decision - really make it - rather than defer, delegate, or default to something else?

This month's retro is an invitation to get curious about exactly that.

Once a week, before you reach for a tool, a framework, or an AI prompt to solve a problem, spend just 5 minutes thinking about it yourself first. Write down your own instincts and ideas before you look anything up. Notice what you already know.

This retro is about awareness. It's not about whether using AI or leaning on experts is right or wrong; it isn't. Both can be enormously valuable. This is about something subtler: knowing when you are choosing to outsource your thinking, and when it's just happening by default.

Because there's a difference between a conscious delegation and an unconscious one.

The goal of this retro is to help your team surface where critical thinking is happening, where it isn't, and what you want to do intentionally going forward.

Time: 60–90 minutes

Works for: Any team - engineering, product, leadership, or cross-functional

Open by creating safety. This topic can feel a little vulnerable and no one wants to feel like they're being accused of not thinking. So be explicit about the intent.

"Today, we're not here to judge how we work or whether we use the right tools. We're here to get curious about our thinking, where we're confident in our decisions, and where we might want to reclaim a little more ownership."

You might also introduce the idea of first-order and second-order thinking:

Gently plant the idea that both are valuable, but the second is harder and easier to skip.

Use a check-in question that aligns with the theme.
Ask everyone to take a moment and reflect on this question before sharing with the group:

"Where do you do your best thinking?"

Give people 2 minutes to write their answers on sticky notes before sharing. This is a lovely, low-stakes way to get into the topic and remind people that good thinking is something they already do.

Now it's time to map the landscape. Ask the team to think about all the places where they make decisions that require critical thinking. Prompt them with some categories to get started:

Give each person sticky notes and ask them to generate as many examples as they can — one decision per sticky. Don't evaluate yet. Just get everything on the wall.

Take a moment to cluster similar themes and get a shared picture of the full landscape of decisions your team makes.

This is where it gets interesting. Now look at the decisions on the wall together and explore two questions:

Question 1: Which of these decisions are we outsourcing — to AI, to tools, to convention, to someone else — and are we doing that consciously?

This isn't about saying outsourcing is bad. AI can accelerate, tools can improve consistency, and experts can add genuine value. The question is: do we know we're doing it, and have we chosen to?

Some things to listen for as a facilitator:

Question 2: Which decisions do we want to own more fully ourselves?

Invite the team to look across the clusters and ask: where do we feel like we've lost our voice? Where are we producing outputs without really understanding them? Where might that matter, for our code, our architecture, our ways of working?

Some prompts to deepen the conversation:

Where is our critical thinking making us better — and where has it gone quiet?

Question 3: Which of these decisions can only one person on the team make?

Look back at the wall and ask: where does the knowledge, context, or authority live with just one person? Put a dot on any sticky where only 1 person makes the decision.

These are your key person dependencies. And they're worth naming, honestly. If that person is on leave, moves on, or is simply unavailable, what happens to the decision?

Some things to listen for:

This is about awareness. Key person dependencies often develop naturally, and sometimes they're appropriate. But some of them are silent risks that the team has simply stopped noticing.

Ask the team: which of these do we want to change, and how might we start spreading that knowledge or ownership?

🔀 5. Decide What to Do

This retro is about intentionality. Come out of it with one or two concrete commitments:

Use dot voting or a simple show of hands to identify where the team's energy is, and agree on no more than two action items to take forward.

🚪 6. Close

End with a reflection round. Ask each person:

"What's one thing this conversation made you want to think about more?"

Go around the room or the virtual space and let everyone close with one word or one sentence. No discussion, just listening.

Then close with an appreciation. What did the team do well in this conversation? Name it before you leave.

Additional Ideas:

You don't have to use this retro as written. If your team is struggling with bottlenecks, Question 3 alone could anchor a really powerful session. Or try running it in reverse — gather all the decisions your team faces, then sort them: what can AI handle, what needs the team, and what needs leadership? Think of it as the Decisions Retro with an added AI dimension.

🔥 Quick Facilitator's Tip

Watch out for the retro tipping into either defensiveness ("we DO think critically") or despair ("we've been doing it all wrong"). Your job is to keep it curious and forward-looking. If the energy spikes, try: "That's a really important observation — what do you think is behind that?" Curiosity is always your best de-escalation tool.

🌱 More from Jo

Many of you found me through Agile coaching or a CSM course we did together. What you may not know is that what made that work meaningful, for me and, hopefully, for you, was never really about the frameworks.

It was always about people. About change. About what it actually takes to show up differently, not just do things differently.

That's where my work is heading now. Leadership and personal development. Helping people be different, not just better skilled. If that sparks something in you, I'd love for you to explore:

And if you have a brilliant retro idea, a technique that worked, or an insight your team had — send it to me at [email protected]. I'm building a community resource, and your idea could be in it. 🙌

🔥 Stuff I Think You'll Like

🤖 TeamRetro — An AI-powered retro tool that auto-groups feedback themes, generates meeting summaries, and even suggests icebreaker questions. Worth a look if you want to see what AI facilitation actually feels like in practice. 👉 www.teamretro.com

🎨 EasyRetro's AI Template Generator — Type in a theme and it generates a custom retro template instantly. Great for when you're stuck or want to try something fresh. 👉 easyretro.io/tools/ai-retrospective-generator

🧱 LEGO Serious Play — Not new, but having a real moment right now. A facilitation method that uses LEGO to unlock thinking that whiteboards never could. Levels the playing field between loud and quiet voices beautifully. Worth exploring if you haven't already. 👉 Search: LEGO Serious Play facilitation

🃏 SessionLab — An oldie but a goodie - A treasure trove of facilitation activities, icebreakers, and workshop tools. If you ever need a quick energiser or a new check-in idea, this is your library. 👉 www.sessionlab.com

Did You Know? 🤔

WiFi was invented by accident 📡 Australian astronomer John O'Sullivan was trying to detect exploding mini black holes in 1977. The experiment failed, but the signal-processing technology he developed became the foundation for WiFi. He had help from others and five scientists were credited on the patent — O'Sullivan, Graham Daniels, Terence Percival, Diethelm Ostry and John Deane.

Till next time

Jo