Troubleshooting Agile
by A weekly problem-solving session for all things agile
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On the show
From 14 epsHosts
Recent guests
Recent episodes
LLMs writing for LLMs: have you tried talking?
Jun 24, 2026
Unknown duration
The Fear of Daily Demos
Jun 19, 2026
Unknown duration
Why You Should Shift-Right Your Testing
Jun 4, 2026
19m 32s
When shouldn’t you use AI?
May 27, 2026
18m 47s
Learning From The Lizardmen Questions
May 20, 2026
15m 03s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/24/26 | ![]() LLMs writing for LLMs: have you tried talking? | Are you token maxing or actually learning? Squirrel and Jeffrey have observed a wild new trend where AIs write specs, AIs summarize them for engineers, and AIs write the code. Nobody is actually talking to each other! Join us as we make the case for human-to-human collaboration, not just bots collating text for other bots, on this week’s episode of Troubleshooting Agile. Links - Our book, Agile Conversations: https://agileconversations.com/ - The Tenerife Airport Disaster: https://en.wikipedia.org/wiki/Tenerife_airport_disaster - Crew Resource Management https://en.wikipedia.org/wiki/Crew_resource_management -------------------------------------------------- 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/ | — | ||||||
| 6/19/26 | ![]() The Fear of Daily Demos | Is your tech team reluctant to show you daily progress? It’s because they’re scared of failure! Listen to this episode of Troubleshooting Agile to learn how leaders can use emotional intelligence and universal demoing to break down the "status report" paranoia and unlock rapid delivery, with your hosts Squirrel and Jeffrey. -------------------------------------------------- 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/ | — | ||||||
| 6/4/26 | ![]() Why You Should Shift-Right Your Testing✨ | shift-right testingproduction testing+3 | — | EtsyCITCON+1 | — | shift-righttesting+4 | — | 19m 32s | |
| 5/27/26 | ![]() When shouldn’t you use AI?✨ | AI ownershipAI risk+3 | — | CITCON:AI 2026TIM Group+1 | Helsinki, Finland | AIconsultant+5 | — | 18m 47s | |
| 5/20/26 | ![]() Learning From The Lizardmen Questions✨ | questioning assumptionsproduct development+3 | — | FlickrTIM Group+2 | — | lizardmenassumptions+5 | — | 15m 03s | |
| 5/15/26 | ![]() Greatest Hits: Teaching Agile Again and Again and Again✨ | agile teachingrepeated lessons+4 | — | CITCONCrossing the Chasm | Helsinki | agileteaching+7 | — | 20m 14s | |
| 5/6/26 | ![]() Against Product Chatbots✨ | chatbotscustomer experience+3 | — | TIM GroupION Analytics+3 | — | chatbotscustomer service+3 | — | 16m 27s | |
| 5/1/26 | ![]() Greatest Hits: Why Can’t We Ship Today?✨ | shipping challengesagile practices+3 | — | CITCONLean Software Development | HelsinkiGhent | shippingagile+3 | — | 19m 07s | |
| 4/22/26 | ![]() Crocker’s Rules✨ | Crocker's Rulescommunication+3 | — | TIM GroupCITCON:AI+2 | — | Crocker's Rulesnoisy politeness+3 | — | 17m 35s | |
| 4/15/26 | ![]() Agentic Validation and the Power of Loops✨ | AI rolloutschange management+3 | Jeffrey | CITCON:AIIMVU+2 | — | AIchange management+5 | — | 20m 35s | |
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| 4/8/26 | ![]() Disagree and Commit - Part II✨ | disagree and commitladder of inference+4 | — | TIM GroupAgile Conversations+3 | — | disagree and commitladder of inference+5 | — | 21m 38s | |
| 4/1/26 | ![]() Disagree and Commit - Part I✨ | disagree and committeam dynamics+3 | — | TIM GroupION Analytics+2 | CITCON | disagree and commitagile+3 | — | 14m 18s | |
| 3/25/26 | ![]() Question First!✨ | agile methodologyteam efficiency+3 | — | Rubber DuckTIM Group+3 | — | agilequestions+5 | — | 12m 58s | |
| 3/18/26 | ![]() Executives Walking the Board✨ | walking the boardagile management+3 | — | TIM GroupCITCON+3 | — | agilemanagement+5 | — | 14m 48s | |
| 3/11/26 | ![]() The Bots Take Over Helsinki✨ | AICITCON+4 | — | CITCON | Helsinki | CITCONAI protest+5 | — | 21m 17s | |
| 2/26/26 | ![]() Leaders are Accountable Too✨ | accountabilityfear+3 | — | Agile ConversationsXP Explained+7 | — | accountabilityAgile Conversations+5 | — | 18m 46s | |
| 2/18/26 | ![]() What the Fuck?! | Ever been in a meeting wondering “Why are we talking about this?” but not said anything? In this episode, Squirrel talks about a meeting where his client admitted he was thinking “What the fuck?” Join us for our thoughts on why people don’t challenge this pattern and practical tips on how to speak up and embrace productive conflict. Links: - Parkinson's Law: https://en.wikipedia.org/wiki/Parkinson%27s_law - Bikeshedding: https://en.wikipedia.org/wiki/Law_of_triviality -------------------------------------------------- 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/ | — | ||||||
| 2/11/26 | ![]() Check Your Dipstick, Continuously! | Are you maintaining your software team management like you do your car? In this week’s episode of Troubleshooting Agile, Squirrel and Jeffrey use their car maintenance issues to help explore the concept of continuous monitoring versus manual checks and ask about the impact of alert fatigue. Join us to learn how you can create effective monitoring systems to prevent major issues. -------------------------------------------------- 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/ | — | ||||||
| 2/4/26 | ![]() Beginner's Mind on the Ski Slope | Being good at something doesn’t make you good at teaching it! Following on from last week’s episode about forgetting the fundamentals of skiing, Jeffrey and Squirrel discuss the importance of using a beginner’s mindset when teaching new skills and how you can use creative techniques, like Squirrel’s Squirrelmobile, to explain ideas more effectively. Links: - Beginner's Mind: https://en.wikipedia.org/wiki/Shoshin - The Squirrelmobile: https://squirrelsquadron.substack.com/p/the-squirrelmobile-the-insanely-profitabe - Wax On Wax Off: https://www.youtube.com/watch?v=-P11Bcpyw4g -------------------------------------------------- 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/ | — | ||||||
| 1/28/26 | ![]() Learning You're Wrong on the Ski Slope | If something feels hard, you might not be the problem, it might be your tools. On this episode of Troubleshooting Agile, Jeffrey shares a skiing mishap, which had him believing he forgot how to ski - until he looked at his feet! Tune in for our thoughts on using the right tools for the right problems, checking assumptions, and the benefits of external perspectives. Links: - Betterism: https://squirrelsquadron.substack.com/p/stop-improving-your-product-squadron - The Checklist Manifesto: https://atulgawande.com/book/the-checklist-manifesto/ -------------------------------------------------- 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/ | — | ||||||
| 1/21/26 | ![]() Fixing a Mistake with Immediate Feedback | One time on the podcast, we released the wrong episode - twice! But listener feedback meant we could correct it quickly - and it got us asking, do you know what users think of your software as soon as it’s done? On this re-run episode, which shares the theme of a recent episode, Gliding to Success [see below], Squirrel and Jeffrey show you how daily feedback IS possible and why we’d strongly recommend it. Links: - Previous episode on the Glidepath Indicator: https://soundcloud.com/troubleshootingagile/gliding-to-success - Glidepath Indicator: agileconversations.com/blog/glideslope/ -------------------------------------------------- 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/ | — | ||||||
| 1/14/26 | ![]() Vibing Isn't for Everyone, Part II | Worried non-techy people will expect too much from Vibe Coding? Listener, Tom, wrote to us with his concerns about the actual productivity of AI development. Listen in for Jeffrey’s experience on trivial tools that make a big difference and how to manage expectations, on this episode of Troubleshooting Agile. Links: - Community of Needs: https://snowbirdcollaboratory.org/community-of-needs/ - First episode of the podcast series on Vibe Coding: https://soundcloud.com/troubleshootingagile/gene-kim-on-vibe-coding-part-i -------------------------------------------------- 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/ | — | ||||||
| 1/7/26 | ![]() Vibing Isn't for Everyone, Part I | It’s okay to be confused about Vibe Coding! On this episode of Troubleshooting Agile, Squirrel and Jeffrey respond to a listener’s argument from our series with Gene Kim on Vibe Coding and reflect on the question, what stage are we at in the industry when it comes to Vibe Coding and what can we expect for the future? Links: - Community of Needs: https://snowbirdcollaboratory.org/community-of-needs/ - First episode of the podcast series on Vibe Coding: https://soundcloud.com/troubleshootingagile/gene-kim-on-vibe-coding-part-i -------------------------------------------------- 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/ | — | ||||||
| 12/31/25 | ![]() Gliding to Success | Are you using the Glidepath Method? On this episode of Troubleshooting Agile, Squirrel and Jeffrey talk about how the method of landing a plane - something Jeffrey’s done - can be useful in effective project management. Join us to learn how you can navigate uncertainty and complexity in your projects - no plane landing experience necessary! Links: - Printed glidepath booklet: https://douglassquirrel.com/resources.html - The Squirrel Squadron: https://squirrelsquadron.com -------------------------------------------------- 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/ | — | ||||||
| 12/24/25 | ![]() Gene Kim on Vibe Coding Part III | How do you get the best out of AI tools when you don’t have the talent that understands them? In the final of a three part series with guest, Gene Kim, we look at the misconceptions of AI for non-techy people, what happens when you don’t have industry-leading talent to discuss leaf nodes and whether vibe coding really means switching your brain off. Links: - Gene Kim: https://itrevolution.com/author/gene-kim/ - Vibe Coding book: https://itrevolution.com/product/vibe-coding-book/ - Claude code: https://www.claude.com/product/claude-code - Erik Meijer: https://en.wikipedia.org/wiki/Erik_Meijer_(computer_scientist) - Vibe Coding podcast: https://www.youtube.com/@VibeCodingWithSteveandGene -------------------------------------------------- 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/ | — | ||||||
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