Scrum Master Toolbox Podcast: Xmas Special — Why Project Management Tools Fail Software Development (and What Works Instead!) Episode aired December 23, 2025 | Host: Vasco Duarte

Episode Overview

In this Christmas special, Vasco Duarte takes listeners on a deep dive into why classic project management tools and mindsets, rooted in industries like railways and construction, do not fit the realities of software development. He argues that successful software is not about delivering a fixed outcome and calling it “done,” but about managing a continuously evolving capability that adapts and provides ongoing business value. Vasco illustrates this with vivid real-world examples—contrasting project management's allure of certainty with the unpredictable, hypothesis-driven nature of modern software. Listeners are left with a strong case for product thinking, learning fast, and iterative delivery as the heart of Agile software development.

Key Discussion Points & Insights

1. The Trap of Project Management Tools in Software (01:11)

• Vasco opens by explaining that while software has become essential societal infrastructure, we continue to manage it using 19th-century thinking—“tools designed for building railways.”
• Quote:
  “Why do we keep thinking in terms of projects... when we know that software is actually never done?” (01:30)

Key Contrasts:

• Traditional projects: Clear start and end, predictable tasks, static requirements.
• Software: “A living capability that evolves with the business that it’s designed to support.” (01:50)

2. History — Where Project Management Came From (02:15)

• Project management arose from industries with finite physical resources (rails, steel) and irreversible decisions (build a track, it stays there).
• Gantt charts, milestones, percent-complete graphs all originate from this world, and provide the illusion of progress and control in software.

Notable Moments:

• Comparing laying railway track (“when the rails meet, the trains can circulate, you’re done”) to software, which is constantly changing.

3. Why Project Management Feels “Right” (03:50)

• Certainty, comfort, accountability: Project tools offer “comforting certainty” with clear milestones and completion graphs.
• Quote:
  “It feels professional, it feels controllable. It feels like we know what we're doing. But does it?” (04:30)

Example:

• Fictional “32 week software plan” impresses leadership and finance, but is a “completely false precision.”
  — Estimates made with little information, requirements misunderstood, etc.

4. Why Requirements-Driven Project Thinking Fails (05:30)

• Requirements and plans give the illusion of progress.
• Real software progress is only measured by “running software and real user feedback.”
• Quote:
  “You don't know if you're right until users interact with it, until you go to production.” (06:40)

Key Insight:

• Our understanding of requirements evolves as soon as users interact with the product. Even unchanged requirements uncover different problems in practice.

5. The “Done” Fallacy and Real Examples (07:40)

• “Done is the wrong goal for successful, living software.”
• The Slack Example:
  If Slack had stopped in 2014, it would have failed. Its continuous value came from evolving (threaded conversations, audio/video calls, automation, knowledge management).
• Quote:
  “Software products evolve because they are successful, and they are successful because they keep on evolving. Projects, on the other hand… end, while products adapt.” (10:25)

6. Five Case Studies in Project Thinking Failure (11:00)

• Recaps five diverse failed software projects (from different countries), all managed with “textbook” project management.
• These projects had detailed requirements, milestones, coordination, audit—but lacked early feedback, iteration, adaptability.
• Quote:
  “They tried to succeed at project management, but ended up failing at both software delivery and in some cases, project management.” (13:45)

7. What’s Needed Instead: Product and Capability Thinking (14:00)

• Shift from “comprehensive planning” to “iteration, constant decision making, and validated hypothesis.”
• Emphasize launching early, learning fast, and adapting.
• Quote:
  “Instead of fixed scope, we need to define problems to solve, not specify the solutions.” (14:45)

Mindset Shift:

• Project thinking: “We’ll build features A, B, C, D and E and we’re done by Q3 of 2026.”
• Product thinking: “We’re solving problem X for users. We’ll start with the riskiest hypothesis, ship a minimal version next week, and learn.”

8. Optimizing for Learning, Not Planning (16:00)

• Software unpredictability isn’t because of bad planning, but because it’s about creating novel solutions to complex, changing problems.
• Quote:
  “The appropriate response to the uniqueness of software isn't better planning, it's faster learning.” (17:00)

Key Takeaway:

• The raw materials are “time and brainpower,” not concrete or steel.

9. Agile as a Societal Shift (17:50)

• Agile isn’t perfect, but recognized the root problem: software changes everything, so must the way it’s made.
• Quote:
  “We must amplify what’s already working and then continue to learn and continue to iterate. You know, being agile about it, right?” (18:30)

10. What’s Next? (18:35)

• Promise for next episode: Examples of what does work—companies successfully delivering software as a “living capability.”
• Festive Sign-Off:
  “Merry Christmas again.”

Notable Quotes & Timestamps

• “Why do we keep thinking in terms of projects... when we know that software is actually never done?” — Vasco Duarte (01:30)
• “It feels professional, it feels controllable. It feels like we know what we're doing. But does it?” — Vasco Duarte (04:30)
• “You don't know if you're right until users interact with it, until you go to production.” — Vasco Duarte (06:40)
• “Done is the wrong goal for successful, living software.” — Vasco Duarte (07:50)
• “Software products evolve because they are successful, and they are successful because they keep on evolving. Projects, on the other hand… end, while products adapt.” — Vasco Duarte (10:25)
• “The appropriate response to the uniqueness of software isn't better planning, it's faster learning.” — Vasco Duarte (17:00)
• “We must amplify what’s already working and then continue to learn and continue to iterate. You know, being agile about it, right?” — Vasco Duarte (18:30)

Important Timestamps

• 01:11 — Main theme opens: why project management tools are ill-fitted for software.
• 02:15 — History of project management and its misapplication.
• 05:30 — False comfort of project plans in software.
• 07:40 — “Done” is the wrong goal for software; Slack’s true story.
• 11:00 — Five international failure case studies.
• 14:00 — Emphasizing product, capabilities, iterative learning.
• 16:00 — Optimizing for learning over planning.
• 17:50 — Agile’s societal shift.
• 18:35 — Preview of next episode: “What’s Already Working.”

Summary & Takeaway

Vasco Duarte’s Xmas special episode is a vivid call to abandon legacy project thinking for software development. He demonstrates, through history, analogy, and modern case studies (notably Slack), that real success comes not from hitting artificial milestones or finishing “projects,” but from treating software as a living, evolving capability. The episode underscores the perils of the “done” mindset and makes a compelling case for Agile’s core principles of early delivery, learning, and iteration. For anyone responsible for delivering or managing software, Vasco’s arguments and storytelling provide both a warning and a roadmap to better outcomes—aiming for adaptability and value, not false certainty.

For more, tune in to the next episode: “What’s Already Working That We Need to Amplify.”