listening skills Archives - Scrum Master Toolbox Podcast

Sara Di Gregorio: When Teams Lose Trust—How Scrum Masters Rebuild It One Small Change at a Time

“I continue to approach this situation with openness, positivity, and trust, because I truly believe that even the smallest changes can make a difference over time.” – Sara Di Gregorio

Sara faced one of the most challenging situations a Scrum Master can encounter—a team member who had lost all trust in change, creating a negative atmosphere that weighed heavily on the entire team. She remembers the heaviness on her shoulders, feeling personally responsible for the team’s wellbeing. The negativity was palpable during every meeting, and it threatened to undermine the team’s progress.

But Sara refused to give up. She started experimenting with different approaches: one-to-one conversations to understand what was happening, bringing intentional energy to meetings, and trying new facilitation techniques in retrospectives. She added personal check-ins, asking “How are you today?” at the start of stand-ups, consciously bringing positive energy even on days when she didn’t feel it herself.

She discovered that listening—truly listening, not just hearing—means understanding how people feel, not just what they’re saying. Sara learned that the energy you bring to interactions matters deeply. Starting the day with genuine interest, asking about the team’s wellbeing, and even making small comments about the weather could create tiny shifts—a small smile that signaled something had changed.

Her approach was rooted in persistence and belief: she continued approaching the situation with openness, positivity, and trust, knowing that even the smallest changes can make a difference over time. For Sara, reestablishing a good environment wasn’t about quick fixes—it was about showing up every day with the right energy and never giving up on her team.

Self-reflection Question: What energy are you bringing to your interactions with the team today, and how might that be shaping the team’s atmosphere?

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 Sara Di Gregorio

Sara is a people-centered Scrum Master who champions trust, collaboration, and real value over rigid frameworks. With experience introducing Agile practices, she fosters empathy, inclusion, and clarity in every team. As an Advanced Scrum Master, she helps teams grow, perform, and deliver with enthusiasm and purpose.

You can link with Sara Di Gregorio on LinkedIn.

Shawn Dsouza: The Database Migration Disaster— Why Software Development Teams Need Psychological Safety

Shawn worked with a skilled team migrating a database from local to cloud-based systems, supported by a strong Product Owner. Despite surface-level success in ceremonies, he noticed the team avoided discussing difficult topics. After three months of seemingly smooth progress, they delivered to pre-production only to discover 140 critical issues. The root cause? Unspoken disagreements and tensions that festered beneath polite ceremony facades. The situation deteriorated to the point where a senior engineer quit, teaching Shawn that pausing to address underlying issues doesn’t cost time—it builds sustainability.

In this segment, we refer to the episodes with Mahesh Jade, a previous guest on the Scrum Master Toolbox podcast.

Featured Book of the Week: The Advice Trap by Michael Bungay Stanier

Shawn discovered this transformative book when he realized he was talking too much in team meetings despite wanting to add value. The Advice Trap revealed how his instinct to give advice, though well-intentioned, was actually self-defeating. The book taught him to stay curious longer and ask better questions rather than rushing to provide solutions. As Shawn puts it, “The minute you think you have the answer you stop listening”—a lesson that fundamentally changed his coaching approach and helped him become more effective with his teams.

Self-reflection Question: When working with teams, do you find yourself jumping to advice-giving mode, or do you stay curious long enough to truly understand the underlying challenges?

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

About Shawn Dsouza
Shawn, a Mangalore native and Software Technology postgraduate from AIMIT, brings 8+ years of IT expertise, excelling as a Scrum Master fostering innovation and teamwork. Beyond technology, he leads SPARK, a social service initiative, and pursues his passion as an aquarist, nurturing vibrant aquatic ecosystems with dedication.

You can link with Shawn Dsouza on LinkedIn.

Shawn Dsouza: When Scrum Masters Forget to Listen – A Team Trust Crisis in Agile Implementation

Shawn shares a powerful lesson about the importance of listening before implementing. Working with a young, talented team drowning in firefighting, he rolled out Scrum in “full” without taking time to understand the team’s context. Going through the motions of Scrum ceremonies without genuine team ownership led to dropping energy levels and lost trust. The turning point came when Shawn realized the team had lost faith in his approach, prompting him to rebuild the process collaboratively with team ownership at its core. This story highlights how good intentions can backfire when we prioritize frameworks over people.

Self-reflection Question: Before implementing any new process or framework, how do you ensure you truly understand your team’s current challenges and context rather than jumping straight to solutions?

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

You can link with Shawn Dsouza on LinkedIn.