“Developers and QAs know each other very well, but they don’t trust anybody else.” – Danil Chernyshev
This week’s coaching conversation starts with a hard situation. A subcontractor’s developers—people who had always worked isolated from the business, with no plans and no communication—were brought back inside the “mother firm” as part of a digital transformation. Overnight they faced new teams, Scrum, SDLC, CI/CD, and full transparency.
The developers and QAs trusted each other completely and trusted no one else: not the Scrum Master, not the Product Owner, not the BAs. Forced to estimate with story points, every story came back as a 3 or a 5, with no conversation. When Danil asked why, the answer was always “we’ll discuss internally and tell you tomorrow”—he suspected a second, hidden daily Scrum without him. As he and Vasco unpack it, the real issue is transparency itself: a team used to hiding now feels exposed and doesn’t know the consequences of being open.
Vasco offers an experiment—build a “trio” of the Product Owner, the Scrum Master, and one friendly insider from the team to prepare refinements together. The Product Owner is always the outsider; pairing them with a trusted insider lets ideas and experiments spread faster. Before you can improve the Scrum, you first have to bring the outsiders in.
Self-reflection Question: Where on your team is trust the real bottleneck—and who is the “insider” who could help an outsider earn it?
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 Danil Chernyshev
Danil is a results-driven Scrum Master and Delivery Manager passionate about optimizing SDLC processes and unlocking development teams’ potential. With a keen interest in AI, he empowers organizations to innovate and excel, bridging agile practices with cutting-edge technology for impactful results.
Welcome to the 2025 Xmas special – a five-episode deep dive into how software as an industry needs to transform. In this opening episode, we explore the fundamental disconnect between how we manage software and what software actually is. From small businesses to global infrastructure, software has become the backbone of modern society, yet we continue to manage it with tools designed for building ships in the 1800s. This episode sets the stage for understanding why software development must evolve into a mature discipline.
Software Runs Everything Now
“Without any single piece, I couldn’t operate – and I’m tiny. Scale this reality up: software isn’t just in tech companies anymore.”
Even the smallest businesses today run entirely on software infrastructure. A small consulting and media business depends on WordPress for websites, Kajabi for courses, Stripe for payments, Quaderno for accounting, plus email, calendar, CRM systems, and AI assistants for content creation. The challenge? We’re managing this critical infrastructure with tools designed for building physical structures with fixed requirements – an approach that fundamentally misunderstands what software is and how it evolves. This disconnect has to change.
The Oscillation Between Technology and Process
“AI amplifies our ability to create software, but doesn’t solve the fundamental process problems of maintaining, evolving, and enhancing that software over its lifetime.”
Software improvement follows a predictable pattern: technology leaps forward, then processes must adapt to manage the new complexity. In the 1960s-70s, we moved from machine code to COBOL and Fortran, which was revolutionary but led to the “software crisis” when we couldn’t manage the resulting complexity. This eventually drove us toward structured programming and object-oriented programming as process responses, which, in turn, resulted in technology changes!
Today, AI tools like GitHub Copilot, ChatGPT, and Claude make writing code absurdly easy – but writing code was never the hard part. Robert Glass documents in “Facts and Fallacies of Software Engineering” that maintenance typically consumes between 40 and 80 percent of software costs, making “maintenance” probably the most important life cycle phase. We’re overdue for a process evolution that addresses the real challenge: maintaining, evolving, and enhancing software over its lifetime.
Software Creates An Expanding Possibility Space
“If they’d treated it like a construction project (‘ship v1.0 and we’re done’), it would never have reached that value.”
Traditional project management assumes fixed scope, known solutions, and a definable “done” state. The Sydney Opera House exemplifies this: designed in 1957, completed in 1973, ten times over budget, with the architect resigning – but once built, it stands with “minimal” (compared to initial cost) maintenance. Software operates fundamentally differently. Slack started as an internal tool for a failed gaming company called Glitch in 2013. When the game failed, they noticed their communication tool was special and pivoted entirely. After launching in 2014, Slack continuously evolved based on user feedback: adding threads in 2017, calls in 2016, workflow builder in 2019, and Canvas in 2023. Each addition changed what was possible in organizational communication. In 2021, Salesforce acquired Slack for $27.7 billion precisely because it kept evolving with user needs. The key difference is that software creates possibility space that didn’t exist before, and that space keeps expanding through continuous evolution.
Software Is Societal Infrastructure
“This wasn’t a cyber attack – it was a software update gone wrong.”
Software has become essential societal infrastructure, not optional and not just for tech companies. In July 2024, a faulty software update from cybersecurity firm CrowdStrike crashed 8.5 million Windows computers globally. Airlines grounded flights, hospitals canceled surgeries, banks couldn’t process transactions, and 911 services went down. The global cost exceeded $10 billion. This wasn’t an attack – it was a routine update that failed catastrophically. AWS outages in 2021 and 2023 took down major portions of the internet, stopping Netflix, Disney+, Robinhood, and Ring doorbells from working. CloudFlare outages similarly cascaded across daily-use services. When software fails, society fails. We cannot keep managing something this critical with tools designed for building physical things with fixed requirements. Project management was brilliant for its era, but that era isn’t this one.
The Path Ahead: Four Critical Challenges
“The software industry doesn’t just need better tools – it needs to become a mature discipline.”
This five-episode series will address how we mature as an industry by facing four critical challenges:
Episode 2: The Project Management Trap – Why we think in terms of projects, dates, scope, and “done” when software is never done, and how this mindset prevents us from treating software as a living capability
Episode 3: What’s Already Working – The better approaches we’ve already discovered, including iterative delivery, feedback loops, and continuous improvement, with real examples of companies doing this well
Episode 4: The Organizational Immune System – Why better approaches aren’t universal, how organizations unconsciously resist what would help them, and the hidden forces preventing adoption
Episode 5: Software-Native Organizations – What it means to truly be a software-native organization, transforming how the business thinks, not just using agile on teams
Software is too important to our society to keep getting it wrong. We have much of the knowledge we need – the challenge is adoption and evolution. Over the next four episodes, we’ll build this case together, starting with understanding why we keep falling into the same trap.
Vasco Duarte is a thought leader in the Agile space, co-founder of Agile Finland, and host of the Scrum Master Toolbox Podcast, which has over 10 million downloads. Author of NoEstimates: How To Measure Project Progress Without Estimating, Vasco is a sought-after speaker and consultant helping organizations embrace Agile practices to achieve business success.
In this BONUS episode we explore the remarkable transformation journey at Omniva with CEO Martti Kuldma. From traditional postal services to innovative logistics solutions, we explore how a 100+ year old company embraced product thinking, DevOps practices, and agile transformation to become a competitive force in modern logistics.
Omniva’s Digital Evolution—IT as a Revenue Center
“We innovated the parcel machine business for a few years, and software has been an area of investment for us – software as a separate vertical in our business.”
Omniva represents a fascinating case study in organizational transformation. While many know it as Estonia’s post office, the company has evolved into an international logistics powerhouse with significant revenue streams beyond traditional postal services. Under Martti’s leadership, the organization has reimagined software not as a support function but as a core revenue driver, positioning itself for the dramatic shifts expected in logistics delivery over the next five years.
The Vision: Physical Mailing as the Next IP Network
“The Vision: physical mailing as the next IP network – this will give us a lot more freedom to adapt to changes in delivery demand.”
Martti’s strategic vision extends far beyond conventional logistics thinking. By conceptualizing physical delivery networks similar to internet protocols, Omniva is preparing for a future where logistics companies leverage their physical infrastructure advantages. This approach addresses the fundamental challenge of fluctuating demand in e-commerce and traditional logistics, creating opportunities for crowd delivery solutions and gig economy integration that capitalize on existing network effects.
In this Substack Week episode, we explore how artificial intelligence is transforming product management with Toni Dos Santos, co-author of The Product Courier newsletter. From automating routine tasks to enhancing strategic decision-making, Toni shares practical insights on leveraging AI to build better products faster and more efficiently.
From Music to Banking to AI Product Management
“I wanted to work in that area to find ways to put innovation to service to the consumers, and making it as invisible as possible.”
Toni’s journey into AI and product management began in an unexpected place – the music industry. After working as a music producer, his interest in innovation led him to banking, where he discovered the untapped potential of data analytics. His experience working with machine learning and deep learning in banking laid the foundation for his current work with generative AI in product management. The launch of ChatGPT in 2022 sparked his deep dive into applying AI to product management challenges.
Revolutionizing User Story Creation with AI
“User stories are a big pain for many product managers, particularly junior ones… The idea is that you provide the AI with a PRD or description of the product, and it’s going to write user stories based on best practices.”
Toni explains how AI can transform the process of writing user stories by automating the initial drafting while preserving the essential collaborative aspects. He emphasizes that while AI can handle the mechanics of writing, the real value comes from using it as a springboard for deeper discussions with the team. The technology can suggest edge cases, highlight potential gaps, and provide a structured foundation for further refinement.
AI as a Tool for Understanding User Needs
“Use all the transcripts, the feedback from user interviews that I have, feed it to AI and retrieve from it the key pain points, the major patterns that it identifies.”
Aria recounts his involvement in a top-down, multi-layered agile transformation in a company with five teams. Despite management’s drive for change, the transformation faced resistance from the teams on the ground. After six months, it became evident that morale and engagement had plummeted, and the desired outcomes were not met. Aria attempted widespread training, but this approach backfired. He learned the importance of focusing on one major change at a time, prioritizing people, and fine-tuning direction for successful transformations. The episode serves as a valuable guide for navigating complex organizational shifts.
Want to Improve Your Change Management Results? Discover the Lean Change Management Approach Today!
As Scrum Master we work with change continuously! Do you have your own change framework that provides the guidance, and queues you need when working with change? The Lean Change Management framework is a fully defined, lean-startup inspired change framework that can be used as the backbone of any change process!You can buy Lean Change Management the book at Amazon. Also available in French, Spanish, German and Portuguese.
About Aria Omidvar
Aria has 4+ years of experience serving as Scrum Master, Product Owner, and Agile Coach (CSM, A-CSM, CSPO) from single teams to multiple teams and the whole software organization. He’s a Software Engineer turned Software Developer turned Peopleware Developer and Agilist.
Enter e-mail to download a clickable PO Cheat Sheet
This handy Coach Your PO cheat-sheet includes questions to help you define the problem, and links to handy, easy techniques to help you coach your Product Owner
Enter e-mail to download a clickable PO Cheat Sheet
This handy Coach Your PO cheat-sheet includes questions to help you define the problem, and links to handy, easy techniques to help you coach your Product Owner
Enter e-mail to download a checklist to help your PO manage their time
This simple checklist and calendar handout, with a coaching article will help you define the minimum enagement your PO must have with the team
Enter e-mail to download a checklist to help your PO manage their time
This simple checklist and calendar handout, with a coaching article will help you define the minimum enagement your PO must have with the team
Internal Conference
Checklist
Internal Conference
Checklist
Download a detailed How-To to help measure success for your team
Motivate your team with the right metrics, and the right way to visualize and track them. Marcus presents a detailed How-To document based on his experience at The Bungsu Hospital
Download a detailed How-To to help measure success for your team
Read about Visualization and
TRANSFORM
The way your team works
A moving story of how work at the Bungsu Hospital was transformed by a simple tool that you can use to help your team.
Read about Visualization and
TRANSFORM
The way your team works
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners. Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners. Access three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners.
Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
FREE! Audiobook Chapters: Overcome Team Resistance and Gain Leadership Buy-In
Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
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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!
Danil is a results-driven Scrum Master and Delivery Manager passionate about optimizing SDLC processes and unlocking development teams’ potential. With a keen interest in AI, he empowers organizations to innovate and excel, bridging agile practices with cutting-edge technology for impactful results.
Vasco Duarte is a thought leader in the Agile space, co-founder of Agile Finland, and host of the Scrum Master Toolbox Podcast, which has over 10 million downloads. Author of NoEstimates: How To Measure Project Progress Without Estimating, Vasco is a sought-after speaker and consultant helping organizations embrace Agile practices to achieve business success.
As Scrum Master we work with change continuously! Do you have your own change framework that provides the guidance, and queues you need when working with change? 
Aria has 4+ years of experience serving as Scrum Master, Product Owner, and Agile Coach (CSM, A-CSM, CSPO) from single teams to multiple teams and the whole software organization. He’s a Software Engineer turned Software Developer turned Peopleware Developer and Agilist.