difficult conversations Archives - Scrum Master Toolbox Podcast

Wasim Osman: When a Scrum Team’s Silence Becomes a Self-Fulfilling Prophecy

“No team is interested in deliberately destroying their outcome or their team. Nobody does that on purpose.” – Wasim Osman

Wasim’s team was building a SaaS product with real potential. They followed Scrum, shipped features fast—and quietly let the bugs pile up. When customers finally pushed back (“you built five features, four of them have bugs”), the team made a confident bet: one quarter for new features, then one month to fix everything. It didn’t work.

The bug-bashing month revealed deeper, structural problems that demanded refactoring, and the roadmap was already packed. Then the fixes got handed to a single team, who felt demoted from the “prestigious” work of building features. Resentment grew between the teams.

At the height of that tension, the company was acquired by a waterfall-driven parent company. The head of engineering left, the chief architect and two senior engineers followed, and it became chaos. Wasim’s hardest lesson wasn’t about the acquisition—it was about voice.

The engineers assumed waterfall was being forced on them and stopped pushing back; leadership assumed the engineers were fine with it. Nobody said what they actually thought, and the fear became reality. As Wasim puts it, there was “no captain on the ship.”

In this segment, we talk about how even conversations need to be iterative, and how a Scrum Master has to balance speaking up (so the team isn’t rudderless) without speaking so much that the team stops voicing their own opinions.

Self-reflection Question: Where on your team is an unspoken assumption quietly hardening into reality, and what would it take for you to name it out loud first?

Featured Book of the Week: Difficult Conversations by Douglas Stone, Bruce Patton, and Sheila Heen

Wasim’s most-recommended book is Difficult Conversations: How to Discuss What Matters Most. What stuck with him is a deceptively simple model: every hard conversation is really made of three conversations—the “what happened” conversation (the content), the feelings conversation, and the identity conversation (what the situation says about whether you’re competent, good, or lovable). “When I first read it, I thought there can’t be only three types of conversations,” Wasim admits.

“But once you’ve gone through the book, you can put any conversation into one of those funnels.” He found it especially powerful in retrospectives: when the same issue keeps resurfacing, the real conversation is often about feelings, not action items—someone was never okay with an earlier decision, and that’s why the follow-ups never happened.

Self-reflection Question: In your last tense retrospective, which of the three conversations—content, feelings, or identity—was really driving the room?

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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.

Olaitan Fashanu: The Scrum Master Who Tried to Force His Way In—and Got Schooled

“When you want to make things work, you need to find a way to carry people along. Lead, not by forcing your way on the team, because you’re working with smart people, you’re working with professionals.” – Olaitan Fashanu

When Olaitan transitioned from project management into the Scrum Master role, he carried his old habits with him: enforce, push, drive. Then he walked into a team of senior developers. In one retrospective, a team member casually suggested that someone could help set up Jira properly. Olaitan took it personally—wasn’t that his job?

The next day in the daily standup, he called it out publicly. The reaction told him everything. The team member shut down. The PO pulled him aside afterward to say, “We could have had a better discussion around this.”

That moment, Olaitan realized that having no formal authority isn’t a weakness to compensate for with force—it’s the whole point. The job is to influence, to nudge, to coach—even when the conversations are hard. Especially when they are hard.

Self-reflection Question: When was the last time you raised a difficult topic in a way that closed the conversation instead of opening it—and what would it have cost you to bring it up differently?

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

About Olaitan Fashanu

Olaitan Fashanu is a customer-focused professional with expertise in product management, technology, and coaching. He drives digital and agile transformation, builds collaborative cross-functional teams, and delivers high-quality products across markets. Curious and strategic, he explores AI and data intelligence while balancing technical depth, business goals, culture, structure, and long-term vision.

You can link with Olaitan Fashanu on LinkedIn.

Bernard Agrest: Avoiding Hard Conversations—When High-Performing Agile Teams Self-Destruct

Bernard describes how a high-performing, fun-loving team began to unravel when a new member joined who wasn’t delivering on their commitments. Instead of addressing the performance issue directly, team members started picking up the slack, avoiding the difficult conversation that needed to happen. As morale dropped and people checked out, Bernard realized the team was paralyzed by fear of confrontation and assumptions that raising the issue would be ignored. This experience taught him that individual performance problems quickly become whole-team problems when left unaddressed, and that strong relationships require the courage to have honest, supportive conversations.

Self-reflection Question: What difficult conversation are you avoiding on your team, and what assumptions might be preventing you from addressing it?

Featured Book of the Week: The 6 Types of Working Genius by Patrick Lencioni

Bernard recommends The 6 Types of Working Genius by Patrick Lencioni because it helps leaders understand that everyone has specific “genius” areas in different phases of work. When people work outside their natural genius zones, they feel unfulfilled and frustrated. This framework has been invaluable for Bernard in understanding team dynamics—why some teams click naturally while others struggle. By recognizing each person’s working genius, leaders can better position team members for success and create more effective, satisfied teams.

The Scrum Master Toolbox Podcast Recommends…

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About Bernard Agrest

Bernard currently leads a major software implementation at University of Wisconsin—Madison Medical School, serving over 10,000 employees. Previously, he built a PMO and led Data and Learning at Teach For America. His journey began redesigning operations for a Veteran Service Organization, where he co-led national initiatives and launched a new alumni program.

You can link with Bernard Agrest on LinkedIn.

Meena Venkataraman: Building Psychological Safety, lessons from helping an Agile team to share interpersonal feedback

In this segment, Meena shares her experience coaching a team that struggled to take off and was stuck in a cycle. Despite being nice to each other during scrum events, team members were not sharing feedback with each other, and psychological safety was not present in the team. Meena stresses the importance of having hard conversations and discussing the interpersonal topics in the team, and she suggests that teams should have the necessary tools to talk about difficult topics.

By highlighting the value that a team coach can bring to a team, Meena emphasizes the importance of psychological safety and how it plays a crucial role in team dynamics. She suggests that teams should be aware of the small things that can become big things and make sure that they are having hard conversations to address interpersonal issues. Ultimately, Meena’s experience coaching this team shows that building a successful team is not just about being nice to each other but also about creating a culture of openness, trust, and psychological safety.

We also discuss how using approaches such as non-violent communication can help the Scrum Master create an open environment that is also psychologically safe.

Featured Book of the Week: Sooner Safer Happier, by Jonathan Smart

In this segment, Meena Venkataraman recommends the book “Sooner Safer Happier: Antipatterns and Patterns for Business Agility” by Jonathan Smart as a valuable resource for scrum masters. She notes that as a scrum master, it’s important to have a holistic view of agile and to be “T-Shaped” – understanding the various facets of product development. Meena highlights that the book brings the 12 principles of agile to life and is a resource she refers to often.

About Meena Venkataraman

Meena is an Agile & Lean coach who helps organizations and teams transition to Agile ways of working. She is passionate about the neuroscience behind team dynamics and is interested in organizational design and the application of Agile principles across different business domains. Meena enjoys speaking at conferences and is an avid learner.

You can link with Meena Venkataraman on LinkedIn.