Troubleshooting Agile

A weekly problem-solving session for all things agile
  • 4.6 (12)
  • Business
  • Updated Weekly

Troubleshooting Agile is a problem-solving session for agile teams. Jeffrey Fredrick and Douglas Squirrel look at common problems agile teams face and provide practical, immediately useful advice for getting back on track.

  1. When shouldn’t you use AI?

    3d ago

    When shouldn’t you use AI?

    Are you treating your AI like an expert consultant or an overly enthusiastic intern? In this week’s episode of Troubleshooting Agile, we’re Live from CITCON:AI in Helsinki, Finland, unpacking the critical boundaries of AI ownership and risk. Join us to learn why AI doesn't create new problems, it just accelerates our old ones, and why you need human "centaurs" to maintain accountability when real money is on the line. Links - CITCON:AI 2026 sessions: https://citconf.com/wiki/index.php?title=CITCONEurope2026Sessions - System 1 vs System 2: https://fs.blog/daniel-kahneman-the-two-systems/ - KYC: Know Your Client: https://www.bitsaboutmoney.com/archive/kyc-and-aml-beyond-the-acronyms/ -------------------------------------------------- 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 later, they remain united in their passion for growing profitable organisations through better communication. Squirrel is an advisor, author, keynote speaker, coach, and consultant, and he's helped over 300 companies of all sizes make huge, profitable improvements in their culture, skills, and processes. You can find out more about his work here: douglassquirrel.com/index.html Jeffrey is Vice President of Engineering at ION Analytics, Organiser at CITCON, the Continuous Integration and Testing Conference, and is an accomplished author and speaker. You can connect with him here: www.linkedin.com/in/jfredrick/

    19 min
  2. Learning From The Lizardmen Questions

    May 20

    Learning From The Lizardmen Questions

    Are you answering questions instead of questioning assumptions? Because you might be missing your biggest product wins! In this episode, Squirrel and Jefrey discuss why the best response to a client or user question is sometimes mu - unasking the question entirely. Join us to hear about Gojko Adzic's "lizard optimization" (and what 4% of the population believing in lizardmen has to do with your software), how the photo-sharing site Flickr was created entirely by mistake, and our own recent user-interface nightmare trying to record this very podcast. Links - “Don’t Answer The Question First:” https://lalitm.com/post/dont-answer-the-first-question/ - Lizard Optimization: https://gojko.net/books/lizard-optimization/ - Lizardman’s Constant: https://en.wiktionary.org/wiki/Lizardman%27s_Constant - CITCON:AI Helsinki: https://citconf.com/helsinki2026/ -------------------------------------------------- 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 later, they remain united in their passion for growing profitable organisations through better communication. Squirrel is an advisor, author, keynote speaker, coach, and consultant, and he's helped over 300 companies of all sizes make huge, profitable improvements in their culture, skills, and processes. You can find out more about his work here: douglassquirrel.com/index.html Jeffrey is Vice President of Engineering at ION Analytics, Organiser at CITCON, the Continuous Integration and Testing Conference, and is an accomplished author and speaker. You can connect with him here: www.linkedin.com/in/jfredrick/

    15 min
  3. Greatest Hits: Teaching Agile Again and Again and Again

    May 15

    Greatest Hits: Teaching Agile Again and Again and Again

    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 later, they remain united in their passion for growing profitable organisations through better communication. Squirrel is an advisor, author, keynote speaker, coach, and consultant, and he's helped over 300 companies of all sizes make huge, profitable improvements in their culture, skills, and processes. You can find out more about his work here: douglassquirrel.com/index.html Jeffrey is Vice President of Engineering at ION Analytics, Organiser at CITCON, the Continuous Integration and Testing Conference, and is an accomplished author and speaker. You can connect with him here: www.linkedin.com/in/jfredrick/

    20 min
  4. Against Product Chatbots

    May 6

    Against Product Chatbots

    Is your chatbot helping your customers or putting them off? In this episode, Squirrel is wound up about the chat-first interface trend in software, which hinders more than it helps. Tune in to get Squirrel and Jeffrey’s thoughts on how you can use “book smarts” vs “street smarts” to determine whether you need a chatbot, and what you should be offering instead. LINKS: - The Dimensionality Problem: https://deadneurons.substack.com/p/why-the-most-valuable-things-you - CITCON:AI in Helsinki: https://citconf.com/helsinki2026/ -------------------------------------------------- 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 later, they remain united in their passion for growing profitable organisations through better communication. Squirrel is an advisor, author, keynote speaker, coach, and consultant, and he's helped over 300 companies of all sizes make huge, profitable improvements in their culture, skills, and processes. You can find out more about his work here: douglassquirrel.com/index.html Jeffrey is Vice President of Engineering at ION Analytics, Organiser at CITCON, the Continuous Integration and Testing Conference, and is an accomplished author and speaker. You can connect with him here: www.linkedin.com/in/jfredrick/

    16 min
  5. Greatest Hits: Why Can’t We Ship Today?

    May 1

    Greatest Hits: Why Can’t We Ship Today?

    Why can’t you ship today? In the run-up to the next CITCON:AI in Helsinki, we re-live this previous episode from CITCON in Ghent, back in 2019, where Squirrel and Jeffrey we’re re-telling three interesting stories from the event, all starting with different answers to Jeffrey's question, "Why can't we ship that today?" LINKS: - Value stream mapping: https://en.wikipedia.org/wiki/Value-stream_mapping - CITCON notes: https://citconf.com/wiki/index.php?title=WarStoriesAndSuccesses - Poppendieck and Poppendieck, Lean Software Development: https://www.amazon.co.uk/Lean-Software-Development-Agile-Toolkit/dp/0321150783 - CITCON:AI in Helsinki: https://citconf.com/helsinki2026/ -------------------------------------------------- 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 later, they remain united in their passion for growing profitable organisations through better communication. Squirrel is an advisor, author, keynote speaker, coach, and consultant, and he's helped over 300 companies of all sizes make huge, profitable improvements in their culture, skills, and processes. You can find out more about his work here: douglassquirrel.com/index.html Jeffrey is Vice President of Engineering at ION Analytics, Organiser at CITCON, the Continuous Integration and Testing Conference, and is an accomplished author and speaker. You can connect with him here: www.linkedin.com/in/jfredrick/

    19 min
  6. Crocker’s Rules

    Apr 22

    Crocker’s Rules

    Is "noisy politeness" slowing your tech team down? In this episode, Squirrel and Jeffrey discuss Crocker’s Rules, which is essentially just the one rule - get to the point. Join us to learn how you and your colleagues can skip the social overhead and get to the data that actually matters. LINKS: - Crocker's Rules: http://sl4.org/crocker.html - Sergei Parajanov's article about the rules: https://lr0.org/blog/p/crocker/ - One Minute Manager: https://en.wikipedia.org/wiki/The_One_Minute_Manager - CITCON:AI in Helsinki: https://citconf.com/helsinki2026/ -------------------------------------------------- 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 later, they remain united in their passion for growing profitable organisations through better communication. Squirrel is an advisor, author, keynote speaker, coach, and consultant, and he's helped over 300 companies of all sizes make huge, profitable improvements in their culture, skills, and processes. You can find out more about his work here: douglassquirrel.com/index.html Jeffrey is Vice President of Engineering at ION Analytics, Organiser at CITCON, the Continuous Integration and Testing Conference, and is an accomplished author and speaker. You can connect with him here: www.linkedin.com/in/jfredrick/

    18 min
  7. Agentic Validation and the Power of Loops

    Apr 15

    Agentic Validation and the Power of Loops

    What’s got Jeffrey - the Founder of CITCON:AI - ruffled about AI?! In this episode, Jeffrey talks about his frustrations with how organisations approach AI rollouts without learning any lessons from the change-management initiatives that have gone before. Join us to get our take on when to hand over reporting to LLMs, when not to, and how to use ‘agentic validation.’ LINKS: - Alistair Cockburn article: https://ameyakarve.wordpress.com/2012/07/22/characterizing-people-as-non-linear-1st-order-components-in-software-development-cockburn-us/ - IMVU post: http://timothyfitz.com/2009/02/10/continuous-deployment-at-imvu-doing-the-impossible-fifty-times-a-day/ - CiTCON 2026: https://citconf.com/helsinki2026/ -------------------------------------------------- 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 later, they remain united in their passion for growing profitable organisations through better communication. Squirrel is an advisor, author, keynote speaker, coach, and consultant, and he's helped over 300 companies of all sizes make huge, profitable improvements in their culture, skills, and processes. You can find out more about his work here: douglassquirrel.com/index.html Jeffrey is Vice President of Engineering at ION Analytics, Organiser at CITCON, the Continuous Integration and Testing Conference, and is an accomplished author and speaker. You can connect with him here: www.linkedin.com/in/jfredrick/

    21 min
  8. Disagree and Commit - Part II

    Apr 8

    Disagree and Commit - Part II

    Are you starting from the bottom of the ladder? In the second episode of a two-part series on the practice of disagree and commit, Squirrel uses the ladder of inference to quiz Jeffrey on the reasoning behind his involvement in the sport of deer hunting, with the aim to demonstrate how two people with opposed beliefs can still find common ground on which they can move forward. LINKS: - Disagree and Commit: https://en.wikipedia.org/wiki/Disagree_and_commit - Test-Driven Development for People: https://itrevolution.com/articles/test-driven-development-for-people/ - The Ladder of Inference: https://douglassquirrel.com/LadderOfInferenceHandout.pdf -------------------------------------------------- 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 later, they remain united in their passion for growing profitable organisations through better communication. Squirrel is an advisor, author, keynote speaker, coach, and consultant, and he's helped over 300 companies of all sizes make huge, profitable improvements in their culture, skills, and processes. You can find out more about his work here: douglassquirrel.com/index.html Jeffrey is Vice President of Engineering at ION Analytics, Organiser at CITCON, the Continuous Integration and Testing Conference, and is an accomplished author and speaker. You can connect with him here: www.linkedin.com/in/jfredrick/

    22 min
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Ratings & Reviews

4.6
out of 5
12 Ratings

About

Troubleshooting Agile is a problem-solving session for agile teams. Jeffrey Fredrick and Douglas Squirrel look at common problems agile teams face and provide practical, immediately useful advice for getting back on track.

Information

  • Creator
    A weekly problem-solving session for all things agile
  • Years Active
    2017 - 2026
  • Episodes
    432
  • Rating
    Explicit
  • Copyright
    © All rights reserved
  • Show Website
    Troubleshooting Agile

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