In this BONUS episode, we explore what AI changes for software leaders, and what it leaves firmly in human hands. Mateo Bervejillo, CEO of Xseed Solutions and author of Back to Basics, brings the view of a manager of managers: AI can help us process information faster, but leadership still happens through clarity, judgment, and relationships.
From Attorney to Software CEO: Clarity as a Leadership Skill
“What are we building? Why are we building it? What’s the benefit for the client? What’s the business value?”
Mateo started his career as an attorney, then moved through operations, vendor management, business development, and finally into software company leadership. That path gave him an unusual advantage in technology: an obsession with clear definitions.
In law, unclear scope creates risk. In software, unclear scope creates waste, frustration, and products that miss the point. For Mateo, leadership starts before execution, with crisp answers to simple questions: what problem are we solving, why does it matter, and what would success look like?
AI Removes Busywork, But It Does Not Replace Leadership
AI is changing the work of software teams, but Salima Bhimani argues that the bigger question is not only what AI can automate. In this BONUS episode, Salima shares what she learned inside Alphabet’s moonshot ecosystem, why breakthrough ideas may be hiding in plain sight, and how more people can become moonshot makers when technology meets lived intelligence.
“Invention is something that is always happening in relationship to something that’s in the world.”
Salima traces her view of invention back to a family history of migration, adaptation, and rebuilding under constraints. Her roots go from India to East Africa, where her family had to learn new languages, new land, and new ways to survive. That experience shaped a practical view of innovation: invention is not only the work of a lone genius in a lab. It often starts in friction, necessity, and the daily encounter between people and the systems around them.
AI becomes useful when it moves from generic answers into the daily work of solving real problems. In this BONUS episode, William Davis shares how he started building his own AI-assisted project management tools, what went wrong when the code grew too fast, and how Scrum Masters can use AI more carefully at individual, team, and project levels.
When AI Stops Being a Curiosity
“I really need to get a handle on how to productively use AI in my job.”
William’s shift started with a familiar problem: release plans are full of uncertainty, but stakeholders still need to understand what might happen and when. Instead of handcrafting uncertain delivery ranges in Excel, William used AI to build a desktop application that created probabilistic Gantt charts. In his work, these were not traditional command-and-control schedules. They were release plans that showed stakeholders a realistic range of possible delivery dates, making uncertainty visible instead of hiding it behind a false promise.
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 dive into the journey of Toni Ala-Piirto, a seasoned software leader with 15 years of experience designing and implementing distributed systems. Toni opens up about pivotal lessons from his leadership career, balancing tech strategy with business goals, and the nuances of scaling engineering teams during rapid growth. Whether you’re a CTO, a team lead, or a tech enthusiast, this conversation is packed with practical insights.
The Evolution of a Leader: A Journey, Not a Single Moment
“Leadership isn’t built in a single defining moment but shaped by many experiences.”
Toni recounts a key challenge early in his career involving a major performance issue for a customer. This experience taught him the importance of viewing systems holistically rather than focusing solely on individual contributions. His “boring” leadership style—marked by forward-thinking and crisis prevention—emphasizes preparation and identifying risks without over-engineering solutions.
Aligning Tech and Business: The Power of Collaboration
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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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.