Maria Skvortsova: The Yes-Man Product Owner and the Scrum Master Who Became a Proxy for the Proxy

In this episode, we refer to User Story Mapping and the MoSCoW prioritization method.

The Great Product Owner: Structure Over Gut Feeling — When a Well-Shaped Backlog Speaks for Itself

“The indicator of a good product owner is a well-shaped backlog — with priorities, with values, with efforts. You definitely know that you pull from the top, and it is the most valuable thing you should work on.” — Maria Skvortsova

For Maria, the best product owners she’s worked with share one trait: they bring structure. Not rigidity — structure. They use techniques like user story mapping to make priorities visual for everyone. They use value-effort matrices instead of gut feelings.

They apply methods like MoSCoW to give the backlog a clear, unambiguous order. The result? A developer never has to ask “what should I work on next?” — the answer is always at the top of the backlog. Maria, drawing on her decade as a C++ developer, knows firsthand how frustrating it is to chase down a BA or PO just to figure out what to build next.

A well-ordered backlog doesn’t just help the team move faster — it also makes it easier for the product owner to communicate with the business, because every decision has data behind it, not just intuition.

Self-reflection Question: Could a new team member look at your product backlog right now and immediately know what to work on next — and why that item is the most valuable?

The Bad Product Owner: The Yes-Man Who Sank the Ship — When Saying Yes to Everything Means Delivering Nothing

“He was always saying yes. And this led to the scope that grew and grew, until we realized we were not capable of delivering what we committed to.” — Maria Skvortsova

Maria returns to her SAP migration experience for this anti-pattern. The team had a team lead acting as product owner — someone technical who saw everything as important.

Every new requirement got a “yes.” The scope ballooned while the iron triangle held firm: fixed cost, fixed time, no room to breathe. The team reached a breaking point where they had to admit, to each other and to the client, that delivery was impossible. Maria stepped in as what Vasco called “a proxy for the proxy” — she helped the team lead build a user story map on Miro, then facilitated a workshop with the business.

Her question was disarmingly simple: “If we don’t deliver this by go-live, will your product still function? If yes, it goes to release two.” That reframing — not “no” but “yes, later” — gave the client clarity without triggering defensiveness. The team lead learned that business stakeholders aren’t the enemy; they just need someone to help them make honest trade-offs. And saying “not now” is infinitely more useful than saying “yes” to everything and delivering nothing on time.

Self-reflection Question: When was the last time you or your product owner said “not now” to a stakeholder — and did it feel like a failure or a strategic decision?

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 Maria Skvortsova

Maria SkvortsovaMaria is a Delivery Manager and Agile Coach who thrives in complexity, bringing clarity to chaotic environments. With a decade in C++ development and a background in professional opera, she blends technical precision with human empathy, helping enterprise teams move beyond task execution to collaborate seamlessly and perform like a synchronized, high-impact orchestra.

You can link with Maria Skvortsova on LinkedIn.

Sara Di Gregorio: Coaching Product Owners from Isolation to Collaboration

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?

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 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.

Irene Castagnotto: The Risk-Aware Scrum Master: Preventing Problems Before They Happen

Irene defines success for Scrum Masters as helping teams anticipate and manage risks before they become unexpected problems. She focuses on ensuring teams don’t face surprise risks during sprints and don’t start work with missing requirements. Her approach includes using user story mapping with Product Owners to visualize potential risks and maintaining team happiness as a key success indicator. For Irene, creating a positive team environment is a crucial deliverable that Scrum Masters must actively work on. She emphasizes the importance of listening to team feedback and regularly assessing whether the team feels supported and engaged.

In this segment, we refer to W. Edwards Deming, and his famous quote “a bad system will beat a good person, every time!”

Featured Retrospective Format for the Week: The Good/Bad/Risk Retrospective

This retrospective format works particularly well with younger teams and uses humor to help teams discuss emotionally challenging topics. The format focuses on three key areas: what went well (Good), what didn’t work (Bad), and what potential risks the team sees ahead (Risk). Irene recommends this approach because it helps teams surface risks that aren’t visible to anyone else, creating opportunities to address potential problems proactively. By incorporating the language of risk into everyday conversations, teams become more aware of potential challenges and can plan accordingly. The humor element helps reduce the emotional intensity that often accompanies difficult discussions about team performance and challenges.

In this segment, we refer to the book “How to Make Good Things Happen: Know Your Brain, Enhance Your Life” by Marian Rojas Estape.

Self-reflection Question: How comfortable is your team with discussing risks openly, and what techniques could you use to make these conversations more approachable?

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 Irene Castagnotto

Irene, a Gen Z Italian Scrum Master, began her Agile journey at a young age. With a positive and passionate approach, she aims to help her generation navigate the world of work with confidence and serenity, while supporting teams in unlocking their full potential.

You can link with Irene Castagnotto on LinkedIn.

BONUS: The Art Of Crafting User Stories with Christopher Lee

In this episode, we talk with Christopher Lee about his latest book, “The Art Of Crafting User Stories” (available on Amazon). Christopher shares the fascinating origin story of his book and how principles of product management were applied to its creation.

Product Development Insights

Christopher draws intriguing parallels between software development and book creation, highlighting two key concepts that apply to both realms. He introduces the concept of “debugging for books” and shares essential tips, like the importance of having multiple content reviewers and utilizing the technique of “Rubber Duck Debugging” for authors. The examples he uses also clarify how his approach to Product Management can help you with software products.

Learning To Empathize With The User

Continue reading BONUS: The Art Of Crafting User Stories with Christopher Lee

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