Troubleshooting Agile

Are you using AI to avoid difficult conversations, or to prompt better ones? In this episode, Squirrel and Jeffrey are joined by Misha Globerman, who tells us about the WorryBot he built to spot and prevent weaknesses in his systems, track missed accountability and guide real conversation with his team. Links: - Previous episode on LLMs: https://soundcloud.com/troubleshootingagile/llms-writing-for-llms-have-you - Misha Glouberman’s website: https://www.mishaglouberman.com/ - Misha Glouberman’s Substack: https://mishaglouberman.substack.com/ - Misha Glouberman’s X: https://x.com/mishaglouberman -------------------------------------------------- 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

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

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, an

Are your software tests a beautiful work of fiction? In this episode of Troubleshooting Agile, Squirrel and Jeffrey question the obsession with "shift left" and instead make the case for shifting right i.e. testing right in production where the real world happens. Join us for a discussion on AI logging, Etsy's continuous real-world tests, and why keeping your code in a sterile sandbox is costing you money. Links: CITCON 2026 Discussion “Why shift-right is a great approach for testing” https://citconf.com/wiki/index.php?title=Why_shift-right_is_a_great_approach_for_testing - CITCON: https://citconf.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

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 -------------------------------------------------

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 An

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 Host

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 diffic

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

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

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 -------------------------------

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/ -------------------------------------------------- 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 practis

Do you know how to disagree and commit? Clue - it’s not the same as “just shut up and get on with it!” In the first episode of a two-part series, Squirrel and Jeffrey discuss the practice of disagree and commit, why so many teams get it wrong, and what happens when you know how to stop discussing and start doing - even when you don’t agree with the outcome. LINKS: - Disagree and Commit: https://en.wikipedia.org/wiki/Disagree_and_commit -------------------------------------------------- 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 growin

Are you forgetting to ask the question? A lot of people lead with stories, but what Squirrel really wants to know is, “What’s the question?!” In this episode, Squirrel and Jeffrey discuss why the most efficient teams ask the question first and then give context. As always, real-world examples and practical tips aplenty! SHOW LINKS: - Rubber Duck: https://en.wikipedia.org/wiki/Rubber_duck_debugging - 7 Habits of Highly Effective People / Habit 2: Begin with the end in mind : https://www.franklincovey.com/courses/the-7-habits/habit-2/ -------------------------------------------------- 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

Are you talking about what you’re working on or what you should be working on? On this episode of Troubleshooting Agile, Squirrel and Jeffrey discuss “walking the board,” with real world examples of organisations doing it well - and not not so well, and why you need to bring the cards to the board, not the people. SHOW LINKS: - Walking the board: https://www.audiodog.co.uk/blog/2017/12/10/better-stand-up-by-walking-the-board/ - Cards come to the standup: http://www.exampler.com/blog/2007/11/06/latour-3-anthrax-and-standups/ - CITCON 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 stu

Want to join Squirrel on his anti-AI protest? CITCON has had a rebrand to CITCON:AI, which Squirrel is in equal parts excited and cynical about. On this episode, CITCON founder, Jeffrey, and enthusiast, Squirrel, discuss what you can expect from the 20th anniversary of the “anti-conference” in Helsinki on 22nd & 23rd May 2026. SHOW LINKS: - CITCON Helsinki: https://citconf.com/helsinki2026/ - "The future is here, it's just not evenly distributed": https://sqdc.st/s/G5eZioC -------------------------------------------------- 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 rema

If taking accountability scares you, you’re doing it wrong! In this episode of Troubleshooting Agile, Squirrel and Jeffrey talk about the background of the final chapter of their book, Agile Conversations, including Jeffrey’s “Aha” moment watching a Kent Beck speech, why the idea of accountability teaches us to lie as kids, and what really happens when we ditch the fear and hold ourselves to account. SHOW LINKS: - XP Explained book: https://www.goodreads.com/book/show/67833.Extreme_Programming_Explained - Rapid Development book: https://www.goodreads.com/book/show/93892.Rapid_Development - Dynamics of Software Development ("don't flip the bozo bit"): https://www.goodreads.com/book/show/1416996.Dynamics_of_Software_Development - Nurtureshock: https://www.goodreads.com/book/show/6496815-nurtureshock - Greenshifting: https://soundcloud.com/troubleshootingagile/greenshifting - Kent Beck Ease at Work: https://www.infoq.com/news/2007/04/beck-ease-at-work/ and https://www.youtube.com/watch?v=yeA4CBInqKo - The Art

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 un

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. Squ

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 stud