retrospectives Archives - Scrum Master Toolbox Podcast

BONUS: How Scrum Masters Can Use AI Without Becoming the Human API, With Fred Deichler

AI is already changing the practical, everyday work of Scrum Masters and Agile Coaches. In this BONUS episode, Vasco talks with Fred Deichler about moving from curiosity to real AI-supported workflows: finding team signals faster, preparing better conversations, keeping documentation in sync, and staying focused on outcomes instead of just producing more output.

From Automation to an AI Sparring Partner

“I have this partner I can work with to help me ideate things.”

Fred’s journey into AI started before the current AI wave, with automation in Jira and the practical need to surface bottlenecks without manually watching every board. The turning point came when ChatGPT stopped feeling like a search box and started acting like a thinking partner.

Faced with a team being pushed toward multiple sprint goals, Fred dumped the context into AI and asked for three to five options instead of one “right answer.” That shift helped him move from a deterministic mindset into a problem-solving mindset, using AI to explore options, challenge his own assumptions, and prepare a better conversation with the team.

The Monday Morning AI Context Builder

“It instantly sets that context for me. It sets that tone for the whole week.”

Fred describes his weekly workflow as a very practical use of AI: on Monday morning, he opens Cursor and works with his own AI harness, Atlas. Atlas is built from markdown files containing persona, skills, history, meeting transcripts, notes, and Jira data. When Fred says “good morning,” the system pulls the most relevant signals forward: aging work items, backlog health, sprint goals, and where the next team conversation should focus. Instead of starting the week by hunting for data, Fred starts with questions he can bring into the first stand-up: what is stuck, what needs refinement, and what risk is already visible?

Making Flow Metrics Visible Inside Jira

“If you’re on a page, what do you hope you could learn without asking?”

Beyond using AI as a thinking partner, Fred used AI to build a Chrome extension that surfaces useful Jira insights directly where the team already works. On the active sprint board, it shows work in progress, aging items, sprint goals, and sprint changes. In the backlog, it exposes backlog health and epic health. On the sprint report page, it adds cycle time per item so the retrospective can move from generic discussion to concrete learning. The point is not to shame the team with metrics. The point is to make the right conversation easier to start: what caused this item to take seven days, what blocked it, and what do we want to learn from that?

AI as Extra Eyes and Ears for Team Conversations

“It helps make sure that we don’t lose sight of these things I can bring back to the team.”

Fred also uses AI agents to review meeting transcripts and look for patterns that are easy to miss in the flow of daily work. The system can notice hesitation, unresolved topics, or a requirement problem that was mentioned once and never followed up. For retrospectives, Fred’s Atlas setup can review sprint transcripts around day nine of the sprint and suggest themes for the next retro. It can even generate prompts for a visual retrospective board in Copilot or a Miro board from a prompt. This helps Fred avoid relying only on recency bias and creates a better starting point for the conversation the team actually needs.

Keep the Human in the Loop, Especially for Outcomes

“It’s not about building a faster hammer. It’s about identifying the outcome you’re going for.”

A major warning in the episode is that AI can make Scrum Masters faster at producing more of the same: more notes, more summaries, more documents, more reports. Fred argues that the useful question is not “can we automate this exact process?” but “what outcome are we trying to achieve?” In a Jira-to-Azure DevOps migration, for example, the goal was not to reproduce the current time-tracking process perfectly. The goal was to provide the information accounting needed. That outcome focus keeps the human accountable for direction, judgment, and value, while AI helps explore better ways to get there.

The SPOT Framework for Finding AI Opportunities

“If it meets three or four of those, this is a great opportunity for an automation to free me up to do that more human-centric work.”

Fred uses a simple filter, the SPOT framework, to decide what AI should help with and what should remain human-led. A task is a good candidate when it is simple, predictable, observable, and tedious. Simple means it requires low human judgment and could be explained on an index card. Predictable means it happens repeatedly, either on a schedule or triggered by an event. Observable means the needed data is available to the agent and not locked away in someone’s head or behind policy. Tedious means it consumes energy without adding much human value. When a task matches most of those criteria, Fred looks for ways AI can handle the toil while he stays focused on facilitation, coaching, and decision-making.

A Small Experiment Scrum Masters Can Try Tomorrow

“If a Scrum Master finds himself operating as, like, I’m moving data from point A to point B, that is a great opportunity to say, how might we do this?”

Fred’s concrete advice is to start by noticing where you have become the “human API”: moving data between tools, updating spreadsheets, copying information into reports, or keeping documents manually aligned with reality. Write down one tedious workflow and ask your approved work AI, “How might we automatically populate this, while keeping me in the loop?” Vasco adds a useful ideation tip: if the first five ideas are not good enough, ask for five more without repetition, then five more again. The goal is not to hand over accountability. The goal is to discover what might be possible and choose one safe, small experiment.

Resources for Scrum Masters Exploring AI

“It’s all about building up your own idea of what’s possible to start those how-might-we conversations.”

For listeners who want to keep learning, Fred recommends The AI Daily Brief as a way to stay current with what is happening in AI, and Jack Roberts’ YouTube channel for practical ideas around personal AI and agent-based workflows.

About Fred Deichler

For over two decades, Fred has been a technology leader, who has been intuitively following the Scrum values and Agile principles even before discovering them. He has successfully led multiple teams on their Agile journeys, emphasizing the importance of a harmonious balance between people, processes, and tools, and continuously striving for improvement. For Fred, personal growth is as crucial as professional development.

You can link with Fred Deichler on LinkedIn and connect with Fred Deichler at Triforce Agility.

Joshua McDonald: Using Cycle Time As A Storyteller, Not A Scorecard In Agile Retrospectives

“Metrics is not about telling people do better. It’s about telling that story.” – Joshua McDonald

Joshua brings cycle time as his biggest current coaching challenge. The problem is familiar: when a Scrum Master points to a story with high cycle time, developers can feel blamed, even when the intent is learning. Joshua reframes the metric as a storyteller.

Instead of asking why someone took too long, he asks what journey the story went through, where it changed hands, where it waited, and what the team now knows that it did not know at the start. He also describes practical tactics: warn people in advance before discussing specific stories, keep the language gentle, avoid forcing people to explain themselves publicly, and sometimes skip the metric conversation entirely when the team needs encouragement more than analysis.

Metrics matter because they move coaching away from gut feeling and toward observable patterns. Used well, cycle time becomes a barometer for stress, bottlenecks, missing product owner review, and places where the team needs support.

Self-reflection Question: How do you introduce metrics so the team becomes curious about the system instead of defensive about individual performance?

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About Joshua McDonald

Joshua is endlessly curious about better ways of working. He helps teams grow by blending experimentation, creativity, and AI with practical coaching. When a meeting feels routine, he’s already testing a new approach to make it more valuable. Energetic and inventive, he turns everyday collaboration into opportunities for team growth.

You can link with Joshua McDonald on LinkedIn.

Wasim Osman: When a Scrum Team’s Silence Becomes a Self-Fulfilling Prophecy

“No team is interested in deliberately destroying their outcome or their team. Nobody does that on purpose.” – Wasim Osman

Wasim’s team was building a SaaS product with real potential. They followed Scrum, shipped features fast—and quietly let the bugs pile up. When customers finally pushed back (“you built five features, four of them have bugs”), the team made a confident bet: one quarter for new features, then one month to fix everything. It didn’t work.

The bug-bashing month revealed deeper, structural problems that demanded refactoring, and the roadmap was already packed. Then the fixes got handed to a single team, who felt demoted from the “prestigious” work of building features. Resentment grew between the teams.

At the height of that tension, the company was acquired by a waterfall-driven parent company. The head of engineering left, the chief architect and two senior engineers followed, and it became chaos. Wasim’s hardest lesson wasn’t about the acquisition—it was about voice.

The engineers assumed waterfall was being forced on them and stopped pushing back; leadership assumed the engineers were fine with it. Nobody said what they actually thought, and the fear became reality. As Wasim puts it, there was “no captain on the ship.”

In this segment, we talk about how even conversations need to be iterative, and how a Scrum Master has to balance speaking up (so the team isn’t rudderless) without speaking so much that the team stops voicing their own opinions.

Self-reflection Question: Where on your team is an unspoken assumption quietly hardening into reality, and what would it take for you to name it out loud first?

Featured Book of the Week: Difficult Conversations by Douglas Stone, Bruce Patton, and Sheila Heen

Wasim’s most-recommended book is Difficult Conversations: How to Discuss What Matters Most. What stuck with him is a deceptively simple model: every hard conversation is really made of three conversations—the “what happened” conversation (the content), the feelings conversation, and the identity conversation (what the situation says about whether you’re competent, good, or lovable). “When I first read it, I thought there can’t be only three types of conversations,” Wasim admits.

“But once you’ve gone through the book, you can put any conversation into one of those funnels.” He found it especially powerful in retrospectives: when the same issue keeps resurfacing, the real conversation is often about feelings, not action items—someone was never okay with an earlier decision, and that’s why the follow-ups never happened.

Self-reflection Question: In your last tense retrospective, which of the three conversations—content, feelings, or identity—was really driving the room?

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

About Wasim Osman

Wasim Osman is a seasoned Agile Coach and a Product Owner at Orkestra SCS. He launched his agile career at a Silicon Valley startup based in New York, then spent years coaching teams across Canada, helping organizations transform how they deliver value. Wasim brings a rare blend of agile discipline and product thinking. He’s passionate about building technology that drives real business impact.

You can link with Wasim Osman on LinkedIn.

Junaid Shaikh: How Scrum Masters Can Measure Their Own Impact, Practical Self-Assessment Metrics

On defining success as a Scrum Master, Junaid starts with a Peter Drucker quote: “You cannot improve something you cannot measure.” He proposes several practical self-assessment metrics:

First, the Agile Team Maturity Index — a spider graph that shows where the team stands across multiple criteria, making gaps visible and actionable.

Second, track retrospective action items. Create tiger teams for specific issues, run small iterative experiments, and measure in the next retrospective whether the trend is improving.

Third, watch for shared sprint goals. Junaid once saw a team with nine sprint goals for a two-week sprint — those weren’t goals, they were individual tasks. A real sprint goal should be something multiple team members work together to achieve.

Fourth, self-organizing teams. If the team falls apart when the Scrum Master is absent for a sprint, there’s a problem. Coach teams to self-organize, and their ability to function independently becomes a success metric.

Fifth, communication patterns. Too many emails flying around can signal hidden conflicts or trust barriers. If communication happens through the right channels — dailies, direct interactions — you’re likely in good shape.

Sixth, Scrum event health. If events get canceled too frequently, the team may be reverting to traditional ways of working.

Featured Retrospective Format for the Week: What Went Well, Not So Well, What Could Be Improved?

Junaid’s favorite retrospective format? The vanilla: what went well, what could have gone better, what to do better next. He’s tried many formats — the Three L’s (liked, learned, lacked), the Three Little Pigs, the sailboat retrospective — but the core principle is always the same. His practical advice: stick with a consistent format so the team gets better at the process itself rather than constantly adjusting to new concepts.

One addition he insists on for any format: an appreciation component. In the rush to analyze processes and outcomes, teams often skip acknowledging how another team member, PO, or Scrum Master helped during the sprint. That appreciation builds trust, respect, and openness that feeds into subsequent sprints.

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

About Junaid Shaikh

Junaid Shaikh is an energetic Agile Coach with a natural flair for Agile and Scrum, shaped by recent experiences at software giants like Ericsson and hardware leaders ABB. In his work, he champions collaboration, curiosity, and continuous improvement. Beyond coaching, he brings the same passion to cricket, table tennis, carrom, and his newest sporting obsession — padel.

You can link with Junaid Shaikh on LinkedIn.

Sara Di Gregorio: Facilitating Deeper Retrospectives—When to Step In and When to Step Back

“When they start connecting and having an interesting discussion, I go to the corner, and I’m only trying to listen.” – Sara Di Gregorio

Sara faces a challenge that many Scrum Masters encounter: teams that want to discuss too many topics during retrospectives without going deep on any of them. The team had plenty to talk about, but conversations stayed surface-level, never reaching the insights that drive real improvement. Sara recognized that the aim of the retrospective isn’t to talk about everything—it’s to go deeper on topics the team genuinely cares about.

So she started coaching teams to select just three main topics they wanted to discuss, helping them understand why prioritization matters and making explicit which topics are most important. But her real skill emerged in how she facilitated the discussions. When she saw communication starting to flow and team members becoming deeply connected to the topic, she moved to the corner and listened. She didn’t abandon the team—she remained present, ready to help shy or quiet members speak up, watching the clock to respect timeboxes.

But she understood that when teams connect authentically, the Scrum Master’s job is to create space, not fill it. Sara learned to ask better questions too. Instead of repeatedly asking “Why? Why? Why?”—which can feel accusatory—she reformulated: “How did you approach it? What happens?” When teams started blaming other teams, she redirected: “What can we influence? What can we do from our side?” She used visual tools like white paper, sharpies, and sticky notes to help teams visualize their discussion steps and create structured moments for questions.

Sometimes, when teams discussed complex technical topics beyond her understanding, she empowered them: “You are the main expert of this topic. Please, when someone sees that we’re going out of topic or getting too detailed, raise your hand and help me bring the communication back to what we’ve chosen to talk about.”

This balance—knowing when to step in with structure and when to step back and listen—is what transforms retrospectives from checkbox events into genuine opportunities for team growth.

Self-reflection Question: In your facilitation, are you creating space for deep team connection, or are you inadvertently filling the space that teams need to discover insights for themselves?

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

About Sara Di Gregorio

Sara is a people-centered Scrum Master who champions trust, collaboration, and real value over rigid frameworks. With experience introducing Agile practices, she fosters empathy, inclusion, and clarity in every team. As an Advanced Scrum Master, she helps teams grow, perform, and deliver with enthusiasm and purpose.

You can link with Sara Di Gregorio on LinkedIn.