Coaching Product Owners from Isolation to Collaboration | Sara Di Gregorio

Sara Di Gregorio: Coaching Product Owners from Isolation to Collaboration

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The Great Product Owner: Using User Story Mapping to Break Down PO Isolation

"One of the key strengths is the ability to build a strong collaborative relationship with the Scrum team. We constantly exchange feedback, with the shared goal of improving both our collaborating and the way of working." - Sara Di Gregorio

Sara considers herself fortunate—she currently works with Product Owners who exemplify what great collaboration looks like. One of their key strengths is the ability to build strong collaborative relationships with the Scrum team. They don't wait for sprint reviews to exchange feedback; instead, they constantly communicate with the shared goal of improving both collaboration and ways of working.

These Product Owners involve the team early, using techniques like user story mapping after analysis phases to create open discussions around upcoming topics and help the team understand potential dependencies. They make themselves truly available—they observe daily stand-ups not as passive attendees but as engaged contributors. If the team needs five minutes to discuss something afterward, the Product Owner is ready. They attend Scrum events with genuine interest in working with the team, not just fulfilling an attendance requirement. They encourage open dialogue, even participating in retrospectives to understand how the team is working and where they can improve collaboration. What sets these Product Owners apart is their communication approach. They don't come in thinking they know everything or that they need to do everything alone. Their mindset is collaborative: "We're doing this together." They recognize that developers aren't just executors—they're users of the product, experts who can provide valuable perspectives.

When Product Owners ask "Why do you want this?" and developers respond with "If we do it this way, we can be faster, and you can try your product sooner," that's when magic happens. Great Product Owners understand that strong communication skills and collaborative relationships create better products, better teams, and better outcomes for everyone involved.

Self-reflection Question: How are your Product Owners involving the team early in discovery and analysis, and are they building collaborative relationships or just attending required events?

The Bad Product Owner: The Isolated Expert Who Thinks Teams Just Execute

"Sometimes they feel very comfortable in their subject, so they assume they know everything, and the team has only to execute what they asked for." - Sara Di Gregorio

Sara has encountered Product Owners who embody the worst anti-pattern: they believe they don't need to interact with the development team because they're confident in their subject matter expertise. They assume they know everything, and the team's job is simply to execute what they ask for. These Product Owners work isolated from the development team, writing detailed user stories alone and skipping the interesting discussions with developers. They only involve the team when they think it's necessary, treating developers as order-takers rather than collaborators who could contribute valuable insights.

The impact is significant—teams lose the opportunity to understand the "why" behind features, Product Owners miss perspectives that could improve the product, and collaboration becomes transactional instead of transformational. Sara's approach to addressing this anti-pattern is patient but deliberate. She creates space for dialogue and provides training with the Product Owner to help them understand how important it is to collaborate and cooperate with the team. She shows them the impact of including the team from the beginning of feature study.

One powerful technique she uses is user story mapping workshops, bringing both the team and Product Owner together. The Product Owner explains what they want to deliver from their point of view, but then something crucial happens: the team asks lots of questions to understand "Why do you want this?"—not just "I will do it."

Through this exercise, Sara watched Product Owners have profound realizations. They understood they could change their mindset by talking with developers, who often are users of the product and can offer perspectives like "If we do it this way, we can be faster, and you can try your product sooner."

The workshop helps teams understand the big picture of what the Product Owner is asking for while helping the Product Owner reflect on what they're actually asking. It transforms the relationship from isolation to collaboration, from directive to dialogue, from assumption to shared understanding.

In this segment, we refer to the User Story Mapping blog post by Jeff Patton.

Self-reflection Question: Are your Product Owners writing user stories in isolation, or are they involving the team in discovery to create shared understanding and better solutions?

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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.