ChatGPT is (a little too) good at having difficult conversations, but use it with caution! On this episode of Troubleshooting Agile, we revisit a previous conversation, first recorded at the beginning of 2024, where Squirrel and Jeffrey share their thoughts on how you can use AI language models to learn how to have difficult conversations with colleagues and disappoint them helpfully. Links: Roger Schwarz's Ted and Paula conversation: in cdn.csu.edu.au/__data/assets/pdf…arter-Teams-2.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 [email protected] -------------------------------------------------- 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/

Are your top leaders arguing over basic status data? In this episode, Squirrel and Jeffrey discuss the executive trap of arguing over facts that can be easily settled. Join us to learn why you should be agreeing on a “single source of lies” not chasing a "single source of truth." -------------------------------------------------- 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 [email protected] -------------------------------------------------- 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/

Are you committing massive resources before testing reality? In this episode, Squirrel is joined by guest, technical program manager, Krunal Patel, who explains how he developed an exciting new car feature in less than a third of the time of a typical waterfall cycle, using cheap prototyping and rapid feedback loops. Join us to learn how you can use “soft-tooling” for your software. Links: Krunal Patel on LinkedIn: https://www.linkedin.com/in/krunalpatel1860/ -------------------------------------------------- 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 [email protected] -------------------------------------------------- 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/

Are your daily software demos an absolute snore-fest? Good. That’s exactly why you should be holding them! In this week's episode, Squirrel and Jeffrey react to listener feedback on the fear of daily demos. We explore how exposing raw back-end outputs can act as an "unfreezing event" that forces middle management to get out of the way and lets you build true team cohesion. Links: - Our slack channel: https://agile-conversations.slack.com/archives/C012TKN2X42 - Previous episode on The Fear of Daily Demos: https://soundcloud.com/troubleshootingagile/the-fear-of-daily-demos - Action Learning: https://en.wikipedia.org/wiki/Action_learning - Kurt Lewin: https://en.wikipedia.org/wiki/Kurt_Lewin -------------------------------------------------- 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 [email protected] -------------------------------------------------- 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/

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 [email protected] -------------------------------------------------- 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/

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 [email protected] -------------------------------------------------- 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/

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 [email protected] -------------------------------------------------- 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/

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 [email protected] -------------------------------------------------- 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/

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 [email protected] -------------------------------------------------- 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/

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 [email protected] -------------------------------------------------- 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/