Scrum Master Toolbox Podcast: Agile storytelling from the trenches

Prabhleen Kaur: When Team Members Raise Concerns with Clarity, Not Anger
Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes.
 
"My idea of success as a Scrum Master is when you look around, you see motivated people, and when something goes wrong, they come to you not in anger, but with concern." - Prabhleen Kaur
 
Prabhleen offers a refreshing perspective on measuring success as a Scrum Master that goes beyond velocity charts and feature counts. She shares a pivotal moment when her team was in production, delivering relentlessly with barely any time to breathe. A team member approached her—not with frustration or blame—but with thoughtful concern: "This is not going to work out." He sat down with Prabhleen and the Product Owner, explaining that as the middle layer in an API creation team, delays from upstream were creating a cascading problem. 
What struck Prabhleen wasn't just the identification of the issue, but how he approached it: with options to discuss, not demands to make. This moment crystallized her definition of success. When team members feel safe enough to voice concerns early, when they come with ideas rather than accusations, when they see themselves as part of the solution rather than victims of circumstances—that's when a Scrum Master has truly succeeded. 
Prabhleen reminds us that while stakeholders may focus on features delivered, Scrum Masters should watch how well the team responds to change. That adaptability, rooted in psychological safety and mutual trust, is the true measure of a team's maturity.
 
Self-reflection Question: When problems emerge in your team, do people approach you with defensive anger or constructive concern? What does that tell you about the psychological safety you've helped create?
Featured Retrospective Format for the Week: Keep-Stop-Happy-Gratitude
Prabhleen shares her favorite retrospective format, born from necessity when she joined an established team with dismal participation in their standard three-column retrospectives. She transformed it into a four-column approach: (1) What should we keep doing, (2) What should we stop doing, (3) One thing that will make you happy, and (4) Gratitude for the team. The third column—asking what would make team members happy—opened unexpected doors. Suggestions ranged from team outings to skipping Friday stand-ups, giving Prabhleen real-time insights into team needs without waiting for formal working agreement sessions. The gratitude column proved even more powerful. "Appreciation brings a space where trust is automatically built. When every 15 days you're sitting with the team making a point to say thank you to each other for all the work you've done, everybody feels mutually respected," Prabhleen explains. This ties directly to the trust-building discussed in Tuesday's episode—using retrospectives not just to improve processes, but to strengthen the human connections that make teams resilient.
 
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🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥
Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people.
 
🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.
 
Buy Now on Amazon
 
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About Prabhleen Kaur
 
Prabhleen is a Certified Scrum Master with 7+ years of experience helping teams succeed with SAFe, Scrum and Kanban. Passionate about clean backlogs, powerful metrics, and dashboards that actually mean something. She is also known for making JIRA behave, driving Agile transformations, and helping teams ship value consistently and confidently.
 
You can link with Prabhleen Kaur on LinkedIn.

Prabhleen Kaur: How AI Is Changing the Way Agile Teams Deliver Value
Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes.
 
"AI's output is not the final output—it's always the two eyes we have that will get us the best results." - Prabhleen Kaur
 
Prabhleen brings a timely challenge to the coaching conversation: the impact of AI on teams and how Scrum Masters should navigate this transformation. She frames it as both a challenge and an opportunity—teams are now capable of delivering faster than consumers can absorb, fundamentally changing expectations and dynamics. 
Prabhleen has observed her teams evolve from uncertainty about AI to confidently leveraging it for practical benefits. Developers use AI for writing and understanding code, particularly helpful for onboarding new team members who need to comprehend existing codebases quickly. QA professionals find AI invaluable for generating test cases based on story and epic context already captured in JIRA. 
The next frontier? Agentic AI, where AI systems communicate with each other to produce better outputs. But Prabhleen offers an important caution: AI is learning from many conversations, not all of which are reliable. The human element—critical thinking and verification—remains essential. 
For Scrum Masters, this means facilitating conversations about how teams want to experiment with AI, exploring edge cases in testing that AI can help identify, and helping teams navigate the evolving landscape of possibilities while maintaining quality and judgment.
 
Self-reflection Question: How are you helping your team explore AI as a tool for improvement while ensuring they maintain critical thinking about the outputs AI produces?
 
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🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥
Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people.
 
🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.
 
Buy Now on Amazon
 
[The Scrum Master Toolbox Podcast Recommends]
 
About Prabhleen Kaur
 
Prabhleen is a Certified Scrum Master with 7+ years of experience helping teams succeed with SAFe, Scrum and Kanban. Passionate about clean backlogs, powerful metrics, and dashboards that actually mean something. She is also known for making JIRA behave, driving Agile transformations, and helping teams ship value consistently and confidently.
 
You can link with Prabhleen Kaur on LinkedIn.

Prabhleen Kaur: When Lack of Trust Turns Teams Into Isolated Individuals
Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes.
 
"Teams self-destruct despite best efforts when they lack trust." - Prabhleen Kaur
 
Prabhleen observed a troubling pattern while shadowing a team: stand-ups had become a register activity where people reported individual status without any connection to the sprint goal. There was no "we" in the conversation—only "I." 
The team had experienced a missed deadline due to a PR conflict that wasn't merged in time, but instead of addressing it openly, everyone focused on fixing the immediate problem while avoiding the deeper conversation. The discomfort was never voiced, and resentment accumulated silently. 
Prabhleen explains that team destruction is never about one action—it's about the accumulation of unspoken concerns that eventually explode at the worst possible moment. To rebuild trust, she recommends starting with peer reviews that encourage natural collaboration and conversation. 
Scrum Masters must be vocal about challenges in front of the entire team, modeling the openness they want to see. For teams that have completely withdrawn, anonymous feedback and scheduled one-on-ones can create safe spaces for honest communication. The key insight? Trust is rebuilt when people realize they will be heard and understood, not judged.
 
In this segment, we talk about how trust is the foundation of effective teams and how its absence leads to working in silos.
 
Self-reflection Question: When your team experiences a failure or missed deadline, do you create space for open conversation about what happened, or does everyone quietly move on while resentment builds?
Featured Book of the Week: Scrum: The Art of Doing Twice the Work in Half the Time by Jeff Sutherland
Prabhleen recommends Scrum: The Art of Doing Twice the Work in Half the Time by Jeff Sutherland as a foundational read for understanding the spirit behind the framework. "When I actually read the book and understood the nuances of rugby and how the team should be, everything started making sense. I grew beyond the Scrum guide, beyond following rules—it's about how the team operates around you as a collective," she explains. Prabhleen also highly recommends Turn the Ship Around by David Marquet, summarizing its core message as "leaders lead leaders." Both books shaped her understanding that frameworks exist to enable collaboration, not to create compliance. Check out the David Marquet episodes on the Scrum Master Toolbox Podcast for more insights on intent-based leadership.
 
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🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥
Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people.
 
🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.
 
Buy Now on Amazon
 
[The Scrum Master Toolbox Podcast Recommends]
 
About Prabhleen Kaur
 
Prabhleen is a Certified Scrum Master with 7+ years of experience helping teams succeed with SAFe, Scrum and Kanban. Passionate about clean backlogs, powerful metrics, and dashboards that actually mean something. She is also known for making JIRA behave, driving Agile transformations, and helping teams ship value consistently and confidently.
 
You can link with Prabhleen Kaur on LinkedIn.

Prabhleen Kaur: Letting Teams Own Their Process Through Working Agreements
Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes.
 
"It's about coaching the team, not teaching them." - Prabhleen Kaur
 
Prabhleen shares a powerful lesson about the dangers of being too directive with a forming team. When she joined a new team, her enthusiasm and experience led her to immediately introduce best practices, believing she was setting the team up for success. Instead, the team felt burdened by rules they didn't understand the purpose of. The process became about following instructions rather than solving problems together. 
It wasn't until her one-on-one conversations with team members that Prabhleen realized the disconnect. She discovered that the team viewed the practices as mandates rather than tools for their benefit. The turning point came when she brought this observation to the retrospective, and together they unlearned what had been imposed. 
Now, when Prabhleen joins a new team, she takes a different approach. She first seeks to understand how the team has been functioning, then presents situations as problems to be solved collectively. By asking "How do you want to take this up?" instead of prescribing solutions, she invites team ownership. This shift from teaching to coaching means the team creates their own working agreements, their own definitions of ready and done, and their own communication norms. When people voice solutions themselves, they follow through because they own the outcome.
 
In this episode, we refer to working agreements and their importance in team formation.
 
Self-reflection Question: When you join a new team, do you first seek to understand their current ways of working, or do you immediately start suggesting improvements based on your past experience?
 
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🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥
Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people.
 
🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.
 
Buy Now on Amazon
 
[The Scrum Master Toolbox Podcast Recommends]
 
About Prabhleen Kaur
 
Prabhleen is a Certified Scrum Master with 7+ years of experience helping teams succeed with SAFe, Scrum and Kanban. Passionate about clean backlogs, powerful metrics, and dashboards that actually mean something. She is also known for making JIRA behave, driving Agile transformations, and helping teams ship value consistently and confidently.
 
You can link with Prabhleen Kaur on LinkedIn.

BONUS: Conflict Is the Yellow Brick Road to Success — How Embracing Conflict Transforms Teams and Leaders
In this bonus episode, we explore why fear, conflict, and courage sit at the heart of true agility with Dan Tocchini, a leadership catalyst who has spent over four decades helping teams at organizations like ESPN, Disney, and Homeboy Industries break through the human barriers to high performance. Dan shares powerful stories and practical wisdom on how leaders can embrace conflict as a generative force, build trust through vulnerability, and restructure their teams for genuine agility.
The Power of Vulnerability in Leadership
"I'd rather have it on an honest basis, where she knows what I'm thinking, what I'm aiming at, and we're shoulder to shoulder, not head to head."
 
Dan's career-defining moment came when he told a CFO at ESPN — while he was competing against McKinsey for the same contract — that she was the problem behind her department's 75% turnover rate. Rather than sugarcoating or deflecting, Dan chose vulnerability and honesty, even at the risk of losing the contract. This radical transparency became his superpower. The CFO hired him, and within six months, turnover dropped to 15%. Dan stayed with ESPN for eight years. The lesson for Scrum Masters and leaders: you can only truly connect with someone if you're willing to be honest, even when it might cost you.
Listening for Openings, Not Outcomes
"Most people listen for outcomes. I listen for openings."
 
Dan draws a critical distinction between chasing outcomes and discovering openings. When faced with an angry car buyer who felt ripped off, Dan didn't try to close the sale. Instead, he leaned into the conflict, acknowledged the customer's perspective, and opened all the books. The result? A sale with 17% margin — above the dealership average — because the customer chose the price himself. For leaders, this means detaching from your desired outcome and focusing on understanding the opening in front of you. That shift builds trust and often produces better results than pushing for what you want.
Why Team Drama Is a Distraction Strategy
"Whenever there's drama, it's because people don't want you to see something."
 
Drama in teams happens because people are siloed, and they silo because they don't trust each other. They share only the information that serves their position without jeopardizing their role. The drama itself is a distraction — like a child throwing a tantrum so you'll forget what they did wrong. Dan's approach: ask three questions. What are they committed to causing? How much of that are they producing? And what's the story between the two? The problem is never the problem — the problem is how you think about the problem.
Restructuring for Agility: A Restaurant Case Study
"Your way of being needs to be bigger than the structure."
 
Dan illustrates agile restructuring through a top-25 restaurant in Boise where the general manager flows seamlessly between roles — bussing tables, coordinating with the kitchen, and leading the team — without ever pulling rank. The secret? He grounds his team before every shift with genuine connection, shared meals, and open dialogue. When he gives direction, people move — not from fear, but from respect. Structure alone won't solve problems; it only organizes them so you can see them better. Leaders must be committed to what the structure is designed to accomplish, altering it in motion when needed.
Conflict as a Generative Force
"What you're not willing to face will eventually defeat you."
 
Dan's core philosophy centers on embracing conflict rather than avoiding it. When people face conflict, they either seek comfort by avoiding it or realize what's at stake and find a way through. The Stoic principle "the obstacle is the way" applies: to find the path, you must hug the cactus and pull the problem close. In relationships — whether marriage, team, or client — breakdowns should deepen intimacy and trust. Dan reports that 90% of the time, authentically facing into mistakes with clients deepens relationships and keeps contracts alive.
What Keeps Dan Going After Four Decades
"People love to accomplish things they didn't think they could do. To me, that's exciting."
 
After more than 40 years in this work, Dan remains energized by working with people to accomplish challenges they initially thought impossible. He describes his work as akin to family — that same depth of connection and shared purpose. His one-liner: "We turn leadership into leadership." It sparks curiosity and opens conversations about what real leadership transformation looks like.



About Dan Tocchini
 
Dan Tocchini has spent 35+ years working with leadership teams across the spectrum — from ESPN to nonprofits like Defy Ventures — helping them evolve from functional to fully alive. His work focuses on the human systems that make agile succeed… or silently kill it.
 
You can find out more about Dan and his leadership training programs at TakeNewGround.com.