No matter how many courses you attend, there are things that, as a Scrum Masters, you only really learn the important lessons on the field. Doing the work.
One of the reasons I don’t think certification courses are enough for Scrum Masters that certifications courses very often focus on the rules and regulations of the job,but not on the problems, the hardships and the obstacles we face, day-in, day-out when we try to do a good work as a Scrum Master.
So, what can we do when courses aren’t enough? Read on!
“They started to separate and call each other out, which is definitely not Agile.” – Joshua McDonald
Joshua shares the story of a 17-person distributed team spread across time zones, cultures, and communication styles. Some team members were direct and ready to challenge problems in public. Others preferred quieter, one-on-one conversations.
Over time, those differences created a blame environment where people stopped asking for help and started hiding problems. Long-running work was closed and replaced with follow-up stories, then part two, then part three, until the real issue disappeared under Jira housekeeping.
The result was not better flow, but delayed learning, missed upskilling opportunities, and a stressful team environment where quieter people stopped speaking in standups and retrospectives. Joshua explains what he would do differently now: split the team by communication patterns, listen to what each group needs, act as a mediator, and only bring the whole group together once people feel heard.
Self-reflection Question: What signals tell you that people are hiding problems because the team environment does not feel safe enough?
Featured Book of the Week: Never Eat Alone by Keith Ferrazzi
Joshua recommends Never Eat Alone by Keith Ferrazzi because it reframed networking as a relationship practice, not a transaction. The book helped him see that staying connected with people creates learning, support, and a safety net over time.
He also mentions the Bible as a daily source for reflecting on respect, peace, and conflict resolution, especially because Scrum Masters often need more than process knowledge to help teams work well together. For Joshua, both recommendations point to the same deeper idea: our work improves when we treat relationships as something to maintain before we urgently need them.
Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters
Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today!The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!
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.
“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
Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today!The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!
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.
The Great Product Owner: The Absolute User Who Works Two Quarters Ahead
“The Product Owner needs to be the absolute user of the software—the user’s journey so well defined in their mind that every engineer’s question already has an answer, with context.” – Wasim Osman
Wasim’s best Product Owner works ahead of the team without doing the team’s work. Their product roadmap is well-defined at least two quarters ahead of the development cycle, so nobody is panicking against tomorrow’s deadline. Designers and product people work on concepts months before development starts, which gives them room to show early ideas to engineers and gather feedback while there’s still time to change course.
Crucially, this PO is the absolute user of the software—so completely inside the user’s journey that when an engineer asks “how does this connect to that module?”, the answer is ready, with context. Wasim connects this to how his team uses AI today: the PO can run ahead, spin up prototypes, and iterate on the ideas without burdening the team with building throwaway work—while staying the voice of the customer.
Self-reflection Question: How far ahead of your team is your Product Owner really working—and could they answer an engineer’s design question today without going back to the drawing board?
The Bad Product Owner: When Optimism Overrides the Data
“They were optimistic without any data. We had the data—they were just being wishful.” – Wasim Osman
The worst anti-pattern Wasim has seen is the Product Owner whose optimism overrides the evidence. In one company, a customer asked for a delivery estimate, and the product team promised an aggressive date—”optimistic without any data,” even though the data existed. When the engineering team sat down with the numbers, it was obvious the date was impossible, but that gap never reached the customer.
The product team stayed disconnected from both the engineers and the customer, so expectations kept drifting from reality. Wasim, who held the data, finally bridged the two and told the product team the real timeline was several months later. They “lost their minds”—but by then it was too late to renegotiate gracefully.
The deeper anti-pattern: features handed down without enough depth, so the moment engineering hits real questions mid-development, the PO panics and rushes back to the drawing board while development is already in motion. As Wasim says, “optimism just took over too much.”
Self-reflection Question: When was the last time optimism—not evidence—set a delivery date on your team, and who had the data that should have been in the room?
Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters
Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today!The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!
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.
“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
Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today!The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!
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.
“It’s like my own software has a voice now. It’s telling me—okay, you’re going to build me like this? Have you considered this?” – Wasim Osman
Wasim’s biggest current challenge is one nearly every team shares: how AI is reshaping software development. He sees a clear split—developers rapidly adopting AI-driven development, and others “not downright rejecting it, but still taking their time.” His warning is blunt: even when AI hallucinates and generates garbage code, it lets you deliver an order of magnitude faster, and the quality is only going to improve.
The early adopters are heading somewhere the late adopters won’t be able to reach. In practice, the resistance shows up as questions no one can answer: if I used to get every requirement nailed down before writing code by hand, what do I do with AI—just ask it for a one-liner and hope? Leadership often can’t help, because they lack AI experience themselves. At Orkestra SCS, the head of engineering did holistic research into how companies (like AWS, with its AI-Driven Development Lifecycle) are reshaping the process, documented it, and shared it with every team.
Feedback sessions and hands-on experiments followed, until they built a tailored version that fit how they actually work. The mindset shift that unlocked it: treat AI as a partner. Wasim describes his software “having a voice”—asking it questions he’d never think of, the way a pair-programming partner would, so the team explores the solution space instead of guessing at it.
Self-reflection Question: Is your team treating AI as a threat to write around, or as a pair-programming partner that surfaces the blind spots you’d never find alone?
Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters
Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today!The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!
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.
Enter e-mail to download a clickable PO Cheat Sheet
This handy Coach Your PO cheat-sheet includes questions to help you define the problem, and links to handy, easy techniques to help you coach your Product Owner
Enter e-mail to download a clickable PO Cheat Sheet
This handy Coach Your PO cheat-sheet includes questions to help you define the problem, and links to handy, easy techniques to help you coach your Product Owner
Enter e-mail to download a checklist to help your PO manage their time
This simple checklist and calendar handout, with a coaching article will help you define the minimum enagement your PO must have with the team
Enter e-mail to download a checklist to help your PO manage their time
This simple checklist and calendar handout, with a coaching article will help you define the minimum enagement your PO must have with the team
Internal Conference
Checklist
Internal Conference
Checklist
Download a detailed How-To to help measure success for your team
Motivate your team with the right metrics, and the right way to visualize and track them. Marcus presents a detailed How-To document based on his experience at The Bungsu Hospital
Download a detailed How-To to help measure success for your team
Read about Visualization and
TRANSFORM
The way your team works
A moving story of how work at the Bungsu Hospital was transformed by a simple tool that you can use to help your team.
Read about Visualization and
TRANSFORM
The way your team works
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners. Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners. Access three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners.
Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
FREE! Audiobook Chapters: Overcome Team Resistance and Gain Leadership Buy-In
Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
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No matter how many courses you attend, there are things that, as a Scrum Masters, you only really learn the important lessons on the field. Doing the work.
Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today! 
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.
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.