failure 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: The Scrum Master Who Let Standups Stay Silent Until the Team Took Ownership

“You can’t fix something until it breaks.” – Sheik Meeajaun

Sheik Meeajaun’s Monday story, is a story about silence, escalation, and the uncomfortable work of helping a team own its own communication. He stepped into a hybrid team where the previous Scrum Master had led the Daily Scrum like a status meeting. When Sheik stopped driving the conversation, the team simply stopped speaking.

For two weeks, the standups were painfully quiet. The Product Owner tried to take over, managers escalated complaints, and Sheik had to explain that the silence was exposing the real problem: the team had learned to wait for someone else to lead.

The breakthrough came when one quiet team member finally spoke up and said what she was working on. Sheik asked her to pass the conversation to the next person, and the team slowly built the habit of talking to each other. His lesson is clear: sometimes the Scrum Master must resist rescuing the team long enough for the team to see what needs to change.

Self-reflection Question: Where are you stepping in so quickly that your team never has to build the muscle of ownership?

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.

Arun Parameswaran: The Scrum Master Mistake of Fixing Trust With Process

“Don’t confuse activity with progress.” – Arun Parameswaran

When Arun Parameswaran stepped into one of his first Scrum Master assignments, he joined a distributed team where everything looked normal from the outside. Meetings were happening, Jira was updated, and work appeared to be moving. Underneath that surface, knowledge was unevenly shared, communication between locations was weak, and trust was not yet strong enough for people to speak openly.

Arun’s first instinct was to add more structure: more meetings, more activities, more process. Looking back, he saw the real mistake. He was creating activity, not progress. The shift came when he stopped trying to provide answers and started listening through one-on-one conversations.

He learned where people were struggling, what they expected from him, and what the team needed to own for itself. In this episode, Arun shares why Scrum Masters must understand people before changing the process, and why the best coaching often starts by asking better questions.

Self-reflection Question: Where are you adding process today because the real issue feels harder to talk about?

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

About Arun Parameswaran

Arun is an Agile delivery leader at Bosch Global Software Technologies who builds high-performing, data-driven ecosystems. He blends flow metrics, Jira analytics, Power BI, and applied AI to turn delivery into a transparent, predictable system.

You can link with Arun Parameswaran on LinkedIn.

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.

Wasim Osman: From Finance to Scrum Master, a Deliberate Career Pivot

“The homework should start a lot earlier than that. The person looking for a particular role should already be moving in that direction before they even start the journey.” – Wasim Osman

Wasim never planned to become a Scrum Master. He trained in finance and stock markets in the UK, but the pull toward software—and even 3D animation—had been there since he was young. When he realized the finance world wasn’t for him, he made a move that looked like a detour and turned out to be a runway: he joined the people team at a tech company in Bangladesh, a branch of a New York-based firm.

He didn’t have the leverage to be picky, so he took the opportunity, learned how the engineering teams actually worked, and made himself useful. When the company started shifting from waterfall to agile and hosting Scrum certification events, Wasim was in the room organizing them. One day the head of engineering asked a “random question”—would he consider becoming a Scrum Master? For Wasim, it was an easy yes, because it was the direction he’d quietly been aiming at all along.

He shadowed a senior engineer for a quarter, then took over a team of senior-most engineers who were patient with his mistakes. That patience built his confidence, and his willingness to keep his prior curiosity alive made the transition feel organic rather than forced.

Self-reflection Question: What direction are you quietly moving toward right now, and what “homework” could you start today so the next opportunity feels organic instead of accidental?

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.