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Episode 543: Catch Project Trouble Early and Protect Your Delivery

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Episode Summary

Subtle problems often start long before a project shows obvious signs of distress. Leaders feel the pressure to deliver momentum, teams shift toward activity over outcomes, and stakeholders slowly fade as competing priorities pull them away. In this conversation, Matthew Oleniuk brings his experience from overseeing large public sector projects and highlights seven early indicators that signal when a project is heading toward trouble. He explains why these issues are easy to ignore, how they quietly compound over time, and why strong leadership vigilance matters more than any dashboard color. He also describes how patterns like output beating outcome, performance theater, and risk box ticking show up in real projects and why they are so harmful when left unchallenged.

Matthew shares examples from large government programs, multi-year initiatives, and everyday delivery environments to show how project culture and infrastructure can create blind spots. He also explains why people naturally lean toward positive reporting and how even well intentioned leaders slip into habits that mask the truth.

The discussion closes with practical guidance on rebuilding transparency, protecting meaningful testing, anchoring to clear outcomes, and strengthening leadership behaviors. Matthew emphasizes that project drift, unclear roles, weak accountability, stakeholder fade, and generic risk lists are not signs of bad people but signs of systems that need stronger leadership habits. His final recommendation centers on objective self-assessment so project managers can identify trouble early and adjust course with confidence.

In This Episode, You Will Learn:

  • Why subtle early problems often go unnoticed and slowly grow into major delivery threats.
  • How outcome clarity prevents teams from drifting into activity rather than value.
  • Why performance theater happens and how culture influences honest reporting.
  • How stakeholder enthusiasm fades over time and what project managers can do to maintain engagement.
  • Why rushed or limited testing creates hidden failures that surface too late.

Resources Mentioned

Quotes from This Episode

  • "Busyness always trumps idle creative thought." - Matthew Oleniuk
  • "Every single day of a project is a day closer to its expiration." - Matthew Oleniuk
  • "Nothing went wrong is extremely different from everything went right." - Matthew Oleniuk

Connect with Matthew Oleniuk

Time-Stamped Show Notes

  • [00:00] - Opening remarks and introduction to the theme of early warning signs.
  • [00:57] - Introduction of guest Matthew Oleniuk and overview of his work.
  • [03:00] - Why leaders miss subtle problems that grow into major failures.
  • [09:00] - Red Flag 1: Output beats outcome and why teams drift toward activity.
  • [14:10] - Red Flag 2: Project drift and how long timelines increase risk.
  • [20:10] - Red Flag 3: Performance theater and the culture behind always reporting green.
  • [26:20] - Red Flag 4: Stakeholder fade and how to keep engagement meaningful.
  • [30:17] - Red Flag 5: Tangled roles and why responsibilities blur during delivery.
  • [37:28] - Red Flag 6: Hollow testing and the danger of validating only what works.
  • [44:13] - Red Flag 7: Box ticking risks and why generic risk registers fail.
  • [50:00] - The one leadership habit that helps catch project trouble early.
  • [53:25] - Closing thanks and details on claiming PDUs.

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Cornelius Fichtner
Cornelius Fichtner
Cornelius Fichtner, PMP, CSM, is the host and the author at The Project Management Podcast. He has welcomed hundreds of guests and project management experts to the podcast and has helped over 60,0000 students prepare for their PMP® Exam. He has authored dozens of articles on projectmanagement.com and PM World 360. He speaks at conferences around the world about project management, agile methodology, PMOs, and Project Business. Follow him on Twitter and connect with him on LinkedIn.

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