JO’s Newsletter 📰

Hello, and welcome to the retro newsletter. This week, I’m sharing how I used proud and worried as a frame to gather data about tech and processes.

“Technology is nothing. What’s important is that you have a faith in people, that they’re basically good and smart, and if you give them tools, they’ll do wonderful things with them.” – Steve Jobs

What's in this newsletter

• Proud and Worried

• Decisions workshop

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Proud and Worried

I like using this as an exercise to gather data when my team needs to take a critical look at their tech or their process. Depending on your context you could also use this to focus only on the one at a time or include both. You can also use this to explore other spaces that the team might need to focus on such as collaboration, or technical practices or documentation, or anything you believe the team needs tothink about deeply. Here’s how it works and why it’s a valuable addition to our retros.

1. First, create an artifact.

Create a physical artefact that is divided into four quadrants:

• Proud: Tech

• Proud: Process

• Worried: Tech

• Worried: Process

2. Gather Input Individually or as a Team:

Individually: Team members can independently add thoughts to the matrix throughout the sprint or during the retrospective. This allows for more personal reflections and less groupthink. You can have the matrix available for the sprint and people add to it as they think of something, or you can spend 7 - 10 minutes getting everyone to add stickie notes to each quadrant.

As a Team: During the retrospective, team members can discuss and add items directly to the matrix, encouraging dialogue and shared understanding.

3. Add Examples and Specifics:

Encourage the team to be as specific as possible. For instance, a “Proud: Tech” example might be completing a new API integration ahead of schedule, while a “Worried: Process” entry might highlight delays in approval chains, slowing down delivery momentum.

This specificity helps the team focus on actionable insights and avoids overly general or vague feedback.

4. Generate Insights 😀 

Go through each quadrant at a high level. Allow people to ask questions about things that are confusing, but don’t try to talk about all of the sticky notes because you will run out of time.

The matrix helps us quickly identify areas that need attention or celebration. This clear visual organization aids in prioritizing which “Worried” items are most pressing and which “Proud” items we should continue building on.

Help the team celebrate the wins and generate insights about what they notice. Ask questions about patterns, differences, and exceptions and challenge the team's thinking.

Once they have identified patterns and generated insights about what they are noticing, move the conversation towards looking for actions.

5. Prioritize Actions:

Once you have identified action items based on your generated insights, use a decision technique to help the team decide. I would like to give each team member a virtual $100 for all the options. That way you can see what is more important to people and where the energy lies.

Help the team choose 1 or maybe 2 action items to take action on and remember to make sure that each action has a champion.

Benefits of the Proud vs. Worried Matrix

• Encourages Balanced Reflection: By intentionally setting aside space for both “Proud” and “Worried” reflections, the matrix promotes a balanced mindset. We celebrate our strengths while also being proactive about addressing concerns.

• Clear Focus on Tech and Process: By breaking feedback into these two categories, we can better pinpoint where our wins and challenges lie—whether they’re due to our tech stack and tools or our workflows and processes.

• Boosts Team Morale: Acknowledging achievements reinforces positive behaviours and allows team members to feel appreciated for their hard work.

• Facilitates Constructive Problem Solving: The “Worried” insights are a valuable source of improvement ideas. I also find that using words like worried instead of broken or bad means that people are more able to engage and add their fears.

Close

Find a nice closing for the retro. Maybe something about what people liked or what they would changed or what challenged their thinking.

Decisions workshop

Myself and Marcus Blankenship are running a 2-hour workshop on decision-making.

This workshop will allow you to explore your organisation's decision-making culture and find ways to enable your teams to make decisions effectively without waiting for you. It is next week and being run as a pilot, so you can join for free if you give us feedback. Email me for more.

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Next Issue

I am busy scheduling the interview with Esther. She was travelling, so it will only be in the next few weeks. In the meantime, next week, I will go into some detail about large-group facilitation. Contact me at [email protected] and share what you want me to discuss or ask for help with specific scenarios.