monday 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: 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.

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

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.

Danil Chernyshev: Forged in the Fire—Why the Scrum Master Role Tests Even Experienced Leaders

“From my story, you can probably say that I was forged in the fire.” – Danil Chernyshev

Danil had already climbed the ladder. He started with Scrum in 2010 as a developer, grew into a development manager, and reached executive level, running a department of 70 developers in his home country. Then he immigrated to Canada and had to start his career fresh.

Certified by Scrum.org as both Scrum Master and Product Owner, the first role he landed was Scrum Master—and that’s where the trouble began. He knew the Software Development Lifecycle (SDLC) inside out, he knew how developers think, he knew Scrum from the trenches. What he didn’t know was how to be a servant leader: how to balance serving and leading, how to measure his own success, how to even notice the small wins.

After years at the top, he was suddenly the person who knew the least. In this episode, Danil shares why he stayed in the role instead of walking away—he loves building processes that help teams evolve, and he couldn’t resist a real challenge. His advice to anyone at that same crossroads: be patient, reflect, build a feedback loop, and never stop learning. A certification proves you understand the base theory. Everything that matters comes after.

In this episode, we refer to the Tuckman model of team development, and how the storming phase tests every team—and every newcomer.

Self-reflection Question: When was the last time you were the person on the team who “knew the least”—and what did that teach you about your own growth?

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

About Danil Chernyshev

Danil is a results-driven Scrum Master and Delivery Manager passionate about optimizing SDLC processes and unlocking development teams’ potential. With a keen interest in AI, he empowers organizations to innovate and excel, bridging agile practices with cutting-edge technology for impactful results.

You can link with Danil Chernyshev on LinkedIn.

Alf Dobbert-Baums: The Two-Country Scrum Team and the Rapport That Never Showed Up

“It did not quite go as planned. I was really humbled.” – Alf Dobbert-Baums

Alf was new in the company. His boss walked over with a setup that already sounded like a warning: two development teams in two countries, two locations in Germany, a “difficult” Product Owner — and a quick “do you want to take it?” Alf said sure. Everything happened on video chat. Every meeting, every conversation, every attempt to read the room — through a window that closed the moment the call ended.

The rapport never built.

The PO stayed difficult.

Alf eventually got pulled from the team. Looking back, he saw what the video chat had hidden: the crossed arms, the eyes drifting to email, the small in-between moments that turn coworkers into colleagues. The fix wasn’t a tool — it was a flight. Visit the other location. Run a workshop with a real goal (“how do we want to work together?”, “what’s hard about our setup?”). Build a positive anchor before anything goes wrong, not after. And when you do go, don’t lead with the failures — lead with what could be possible together.

In this episode, we refer to the practice of building team working agreements as a way to create rapport without putting people on the defensive.

Self-reflection Question: When was the last time you saw the people you work with face-to-face — and what conversations are you still postponing because they only happen well in person?

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

About Alf Dobbert-Baums

Alf lives in Berlin. He studied Theater/Religion at the Freie University Berlin. He is a Systemic Organizational Consultant, a Scrum Master and Agile Coach. He has also been a freelancer for Usability and Requirements Engineering for car manufacturers. At “Verti” he led the agile transformation.

You can link with Alf Dobbert-Baums on LinkedIn.