scrum master Archives - Scrum Master Toolbox Podcast

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?

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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: The Scrum Master as a Router, Redefining Success Through Efficient Communication

“A big part of the Scrum Master role is to work as a router—handling a lot of conversations with a lot of different devices, even though the internet is coming in through one cable.” – Wasim Osman

For Wasim, success as a Scrum Master looks like a router in a house: many conversations, many stakeholders, all flowing through one point that has to prioritize, schedule, and stay on time. If the router slows down, everything downstream stalls—and the Scrum Master becomes the blocker.

Early in his career he was overwhelmed juggling three or four engineering teams, so he built himself a personal Kanban board and ran his own quick standup every morning and again at the end of the day, just to see what moved, what stalled, and why. Getting organized with himself is when the work started to feel satisfying, because he stopped being the bottleneck. But he’s honest about the hardest part: people rarely tell you to your face when you’re slowing them down.

The feedback is already there—you’re just not hearing it. So you have to ask for it, react well when you get it (or people stop offering), and sometimes name the awkward truth first: “Our meetings used to be better—what happened?” That opening gives everyone permission to be honest.

Self-reflection Question: If you’re the “router” for your teams, where are you quietly becoming the bottleneck—and who would tell you if you were?

Featured Retrospective Format for the Week: What Went Well / What Went Wrong / Outliers + Open Discussion

Wasim’s go-to retrospective is deliberately bare-bones: what went well, what went wrong, and—the part that makes it his own—what were the outliers, followed by open discussion.

He added the “outliers” question years ago after noticing that team members kept raising points that weren’t clearly good or bad, but were still significant enough to discuss. Outliers give people “a bucket for sharing information that has no polarity”—an early signal about the future, a quiet concern, something that doesn’t fit the other two columns but matters.

He sometimes pairs it with lightweight metrics: sprint completion rate, or tickets that sat too long in review or QA, surfacing patterns the team wouldn’t otherwise notice.

Self-reflection Question: What “outlier” signal has your team been sitting on—neither a win nor a problem yet—that deserves an open conversation before it becomes one?

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.

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

You can link with Wasim Osman on LinkedIn.

Havva Sevay: Success Is Feedback, Not Metrics—And the Power of Standing in Someone Else’s Shoes

“My success is not metrics or numbers—that was my controller past. I measure myself through feedback, and through team satisfaction.” – Havva Sevay

As a former project controller, Havva could have defined success in numbers. Instead, she measures it through feedback and team satisfaction. As long as people keep talking to her—telling her how she can be a better Scrum Master—she considers that success, and she treats even hard feedback as learning. But the most striking part of her definition is the discipline of standing in someone else’s shoes.

When a developer suggested she’d give better advice if she understood programming, she took the Scrum Developer training—the hardest training she’s ever done—just to feel the team’s daily reality. Vasco connects it to coaching a team that builds tools for other teams: the role isn’t to produce the system, it’s to make the other teams’ lives easier.

Havva’s takeaway for every Scrum Master: put your shoes in a different position. Understanding the work from the other person’s perspective is what drives team success.

Self-reflection Question: How do you measure your own success as a Scrum Master—and when did you last experience your team’s work from their perspective?

Featured Retrospective Format for the Week: The Mario Kart (Gamified) Retrospective

Havva’s favorite retrospective format is gamification—she believes in the magic of playing, because it lets everyone relax, open up, and step out of the daily stress. Her go-to is a Mario Kart–inspired retrospective. Team members choose their character (Mario, Luigi, Peach, Bowser), then map the sprint onto the game: the star and speed mushroom for successes and who helped them, the bad mushroom for impediments, another icon for the solution. They praise each other by handing out stars, and close with a “Mario checklist” of action points for next time.

Havva also adapts to the team—asking their favorite Nintendo game, board game, or even pen-and-paper RPGs like The Dark Eye (Das Schwarze Auge). The point: make the retrospective something people genuinely enjoy, and the honest reflection follows.

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

About Havva Sevay

Havva is a people-focused organizational development expert with a Master’s in Business Administration and certification as a Scrum Master. She empowers teams and leaders through agile methodologies, modern leadership, and a strong feedback culture, fostering psychological safety and collaboration. Passionate about HR initiatives, Havva shapes people strategies, enhances employee experience, and drives inclusive, high-performing workplaces built on trust and engagement.

You can link with Havva Sevay on LinkedIn.

Havva Sevay: When Doing Your Best Isn’t Enough—The Scrum Master Lesson That Changed Everything

“I didn’t really acknowledge that the team is important, or what a team needs. I thought I was only focusing on getting the job done.” – Havva Sevay

When Havva took her first Scrum Master job, she knew the framework cold and she was highly motivated. So she did exactly what the framework told her to do—and failed.

Frustrated, she kept asking herself the same question: why did I fail? I really did my best. The turning point came from a mentor who asked her something she hadn’t considered: did you ever think about what the team needed? In this episode, Havva walks us through the slow, honest work of realizing she had been judging instead of listening, pushing instead of stepping back. Her mentor introduced her to active listening—writing down what people actually said, not her interpretation of it—and to the discipline of silence.

Becoming a better Scrum Master, she learned, is an everyday process that takes its time. We also explore how she stayed grounded: taking courses outside her bubble, networking, and learning from other people’s experience.

Self-reflection Question: When you face a team problem, are you observing what is actually happening, or are you already judging and rushing to the next step?

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

About Havva Sevay

You can link with Havva Sevay on LinkedIn.