agile coaching Archives - Scrum Master Toolbox Podcast

Deborah Colombari: When Agile Principles Became a Fight With the System

“I was trying to go against the system, but you cannot go against the system.” – Deborah Colombari

Deborah Colombari’s Scrum Master journey started with a sense that Agile gave her permission to work differently. After early project management work, a year in Canada exposed her to Agile, and the Scrum Master role soon “felt like a glove.” But her failure story starts when a supportive leader left and a more command-driven manager arrived. Deborah pushed back hard, trying to protect the Agile practices she believed were right: dailies, burn-down and burn-up charts, transparency, and team focus.

The problem was that she was fighting the manager instead of first understanding the system around him. That conflict spilled into the team and damaged morale. Looking back, Deborah says she would now sit down with the manager first, understand the goals and pressures behind the change, and look for compromise before escalating into resistance. Her key learning was pragmatic: Scrum Masters need principles, but they also need diplomacy. The work is not only helping the team inside the Agile bubble, but also translating between that bubble and the wider organization.

In this episode, we refer to ITIL, the Dunning-Kruger effect, and Thinking in Systems by Donella Meadows.

Self-reflection Question: Where are you fighting the system before you have understood the pressure it is trying to respond to?

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About Deborah Colombari

Deborah is an Enterprise Agile Coach with a decade of experience championing Agile principles across organizations. Passionate about collaboration and continuous improvement, Deborah genuinely loves what she does—empowering others to work smarter, deliver value, and thrive in dynamic environments.

You can link with Deborah Colombari on LinkedIn.

Sheik Meeajaun: Scrum Masters Must Learn by Experimenting When AI Joins the Agile Team

“Never be afraid to admit you don’t know something.” – Sheik Meeajaun

Sheik brings a current challenge that goes beyond one team: the gap between Scrum theory and real work when the context changes faster than the playbook. His example is AI. Scrum Masters are now asked to help teams where AI agents contribute to delivery, but no certification course can fully prepare us for that. Sheik’s starting point is humility: say “I don’t know,” learn the domain, run small experiments, and reflect quickly.

In one team, two human developers worked alongside several AI agents. They could not run a normal standup with Claude, so the team created a status report and reviewed it with the human team members. Sheik framed the agents as junior developers: useful, fast, and still requiring clear instructions, review, and guardrails. That framing helped experienced developers see AI collaboration as coaching and oversight, not as magic productivity. The key lesson is practical empiricism: try, inspect, adapt, and keep learning as the work changes.

In this episode, we refer to Scrumling’s AI Product Owner course and the need to adapt Scrum practice to AI-enabled work.

Self-reflection Question: What new reality is your team facing where the honest Scrum Master answer should start with “I don’t know yet”?

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

About Sheik Meeajaun

Sheik is a seasoned product and Agile leader with over 20 years of experience scaling innovative, customer-centric digital solutions. A certified Scrum and Agile expert, he bridges strategy and execution, driving high-performance teams at enterprises like Rabobank and citizenM. As a hands-on builder, Sheik created Scrumling—a free, interactive Agile training platform—and ScrumJobs.net, a niche job board for Agile professionals. His passion lies in transforming theory into impactful, real-world results.

You can link with Sheik Meeajaun on LinkedIn.

You can also explore Scrumling, ScrumJobs.net, and Simatech.

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: When Your Agile Enthusiasm Creates Resistance, Start With Trust

“Don’t assume they’re as enthusiastic about Agile and Scrum as you are.” – Joshua McDonald

Joshua McDonald starts the week with a failure story many Scrum Masters will recognize: stepping into a team and assuming the role, the expectations, and the Agile conversation were already understood.

The team had worked with a hands-off Scrum Master before, so Joshua’s attempts to facilitate events, talk about metrics, and bring more structure were received as interference. The pushback grew so strong he sensed people were talking to his manager about removing him. The turning point came when Joshua stopped leading with Scrum language and started rebuilding social equity through one-on-ones.

He asked what he could have done differently, acted on the feedback, and reminded himself and the team to assume positive intent. His lesson is direct: when we join a new team, trust is the work before the work. Go slow, understand how people operate, and bring suggestions through relationships before bringing them to the whole room.

Self-reflection Question: When you join a new team, what do you do first to understand their relationship with Scrum before you suggest changes?

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

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.

Maria Skvortsova: When Agile Labels Hide Waterfall Reality — A Scrum Master’s Wake-Up Call in SAP Migration

“I realized that even if I like Scrum and Agile, and I think they are really good ways of thinking, some areas cannot adapt them because they are completely different from the mindset and ways of working.” — Maria Skvortsova

Maria came to Agile with the fire of a true believer. After a decade as a C++ developer, she’d found something that matched how she thought and felt about building software — something that went beyond controlling budgets and roadmaps. When a boutique SAP consulting company hired her as an Agile coach to transform their entire organization, she was all in. She built what she describes as a “really good” training for senior management, designed to sell them on Agile ways of working.

But when she stepped out of the PMO role and into a real SAP migration project as delivery manager, the ground shifted beneath her. The iron triangle — fixed cost, fixed scope, fixed time — ruled everything. Teams ran “sprints” that were really just boxed iterations with no feedback loops, no value delivery, just a march toward a go-live date.

Maria realized she was putting Agile labels on a fundamentally waterfall process. The hardest part wasn’t the discovery — it was accepting that she needed to redirect her energy to environments where Agile could genuinely take root, rather than forcing it where the mindset simply didn’t exist. Her advice: recognize when labels don’t match reality as quickly as possible, and have the courage to choose environments that align with how you want to work.

Self-reflection Question: Are you putting Agile labels on processes that are fundamentally waterfall? How quickly would you recognize the mismatch — and what would you do about it?

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

About Maria Skvortsova

Maria is a Delivery Manager and Agile Coach who thrives in complexity, bringing clarity to chaotic environments. With a decade in C++ development and a background in professional opera, she blends technical precision with human empathy, helping enterprise teams move beyond task execution to collaborate seamlessly and perform like a synchronized, high-impact orchestra.

You can link with Maria Skvortsova on LinkedIn.