Episodes

  • You Never Forget Your First Time! Stories For The New Manager

    You Never Forget Your First Time! Stories For The New Manager
    Aug 12 2026
    Terrified of taking on your first management role? Don't be. Join us on the week’s episode to learn how you can avoid the biggest trap that new leaders get into, why you need to keep your team moving rather than doing the work for them, and hear our essential reading list for new managers, with your hosts, Squirrel and Jeffrey. Links: - Behind Closed Doors: https://www.jrothman.com/books/behind-closed-doors-secrets-of-great-management/ - High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 - 8 Behaviors: https://www.csu.edu.au/__data/assets/pdf_file/0008/917018/Eight-Behaviors-for-Smarter-Teams-2.pdf - Situational Leadership: https://en.wikipedia.org/wiki/Situational_leadership_theory - Modern Management Made Easy: https://www.jrothman.com/books/modern-management-made-easy-a-three-volume-set/ -------------------------------------------------- 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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    17 mins
  • Jailhouse Talk: Verbal Aikido

    Jailhouse Talk: Verbal Aikido
    Aug 5 2026
    Is it ever okay to manipulate your colleagues? On this episode, Squirrel and Jeffrey discuss Verbal Aikido - a defensive technique borrowed from a Supermax prison doctor. Join us to discover how to redirect manipulative office requests using strategic questions without crossing the line into toxic control. Links: - Verbal Aikido: https://www.jailmedicine.com/verbal-aikido-a-guest-column-by-dr-bill-wright/ - Previous episode on Motivational Interviewing: https://soundcloud.com/troubleshootingagile/motivational-interviewing [Transcript: https://agileconversations.com/blog/motivational-interviewing/] - Previous episode on Active Listening: https://soundcloud.com/troubleshootingagile/active-listening-for-remote-working [Transcript: https://agileconversations.com/blog/active-listening-for-remote-working] -------------------------------------------------- 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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    17 mins
  • Greatest Hits: LLMs & Difficult Conversations

    Greatest Hits: LLMs & Difficult Conversations
    Jul 29 2026
    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 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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    14 mins
  • Single Source of Lies

    Single Source of Lies
    Jul 22 2026
    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 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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    16 mins
  • Speeding Up Agile Hardware Projects with Krunal Patel

    Speeding Up Agile Hardware Projects with Krunal Patel
    Jul 15 2026
    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 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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    23 mins
  • Your Demo Needs a Stakeholder

    Your Demo Needs a Stakeholder
    Jul 8 2026
    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 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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    18 mins
  • Misha and his WorryBot

    Misha and his WorryBot
    Jul 1 2026
    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 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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    25 mins
  • LLMs writing for LLMs: have you tried talking?

    LLMs writing for LLMs: have you tried talking?
    Jun 24 2026
    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/
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    18 mins