Greatest Hits: Teaching Agile Again and Again and Again

Greatest Hits: Teaching Agile Again and Again and Again

From Troubleshooting Agile by A weekly problem-solving session for all things agile

May 15, 2026 · 20 min

About this episode

The episode discusses the challenges of teaching agile concepts repeatedly and reflects on insights from CITCON 2021.

Do you find yourself covering the same agile lessons over and over again? Back in CITCON 2021, a special guest brought up how he’s been talking about the same problems for 20 years. And five years later, we imagine not much has changed! Listen to this re-run episode for our thoughts on this topic with Squirrel’s analogy on how teaching long division turns out to be surprisingly helpful. LINKS: - CITCON:AI Helsinki: https://citconf.com/helsinki2026/ - Moore, Crossing the Chasm: https://en.wikipedia.org/wiki/Crossing_the_Chasm - Chris Matts, community of needs: https://snowbirdcollaboratory.org/community-of-needs/ - Alistair Cockburn: https://alistair.cockburn.us/ -------------------------------------------------- You'll find free videos and practice material, plus our book Agile Conversations, at agileconversations.com And we'd love to hear any thoughts, ideas, or feedback you have about the show: email us at info@agileconversations.com -------------------------------------------------- About Your Hosts Douglas Squirrel and Jeffrey Fredrick joined forces at TIM Group in 2013, where they studied and practised the art of management through difficult conversations. Over a decade…

People in this episode

Hosts: Douglas Squirrel, Jeffrey Fredrick

Topics covered

  • agile teaching
  • repeated lessons
  • long division analogy
  • CITCON
  • communication in agile
  • management practices

Keywords

  • agile
  • teaching
  • lessons
  • CITCON
  • management
  • communication
  • long division
  • Chris Matts
  • Alistair Cockburn

Mentioned in this episode

Organizations: CITCON

Books & works: Crossing the Chasm

Places: Helsinki

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