Troubleshooting Agile

Hosted by A weekly problem-solving session for all things agile

BusinessExplicit

Website RSS feed

Episodes

444

Latest episode

Aug 2026

Language

About the show

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.

Listen to episodes

60 recent

September 9, 202616 min

Bug Blindness

Are you suffering from bug blindness? This week, we dive into Dan Luu's article on how entire teams grow blind to obvious software bugs, Squirrel shares how their brilliant QA broke their system with a simple negative number, and Jeffrey ponders the reality that bug blindness isn't an accident; it's a cultural choice you make upstream. Links: - Dan Luu: https://danluu.com/bug-blind/ - Steve Jobs on MobileMe: https://daringfireball.net/2025/03/something_is_rotten_in_the_state_of_cupertino - Bill Gates on Movie Maker: https://www.techemails.com/p/bill-gates-tries-to-install-movie-maker -------------------------------------------------- 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/

September 2, 202614 min

Life Finds A Way… To Cheat!

Are your teams quietly cheating your software controls to get their actual job done? In this episode of Troubleshooting Agile, Jeffrey and Squirrel tackle the "normalization of deviance," rogue AI agents sharing cheat sheets, and why human (and bot) workarounds reveal your real systemic problems. Links: - Dianne Vaughn: https://en.wikipedia.org/wiki/Normalization_of_deviance - Open AI / HuggingFace incident: https://thezvi.substack.com/p/huggingface-attack-postmortem-fleshing -------------------------------------------------- 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/

August 26, 202612 min

Bozo the Client? Managing In A Consultancy

Do you want to be right or do you want to be helpful? Choose carefully, because insisting on being "right" usually just makes you poor! On this week’s episode, Squirrel and Jeffrey tackle the classic consultancy challenge: dealing with boneheaded clients. Join us to learn how to use the LEAP method (Listen, Empathize, Agree, Partner) to find common ground, ship workable results and keep your consultancy clients playing you! Links: - “I’m Right, You’re Wrong, Now What?” (The LEAP Method) by Dr Xavier Amador’s https://www.xavieramador.com/books - “I am Not Sick, I Don't Need Help!” by Dr Xavier Amador: https://www.xavieramador.com/books - LEAP Institute: https://leapinstitute.org/ -------------------------------------------------- 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/

August 12, 202616 min

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

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/

August 5, 202617 min

Jailhouse Talk: Verbal Aikido

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/

July 29, 202613 min

Greatest Hits: LLMs & Difficult Conversations

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/

July 22, 202616 min

Single Source of Lies

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/

July 15, 202623 min

Speeding Up Agile Hardware Projects with Krunal Patel

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/

July 8, 202618 min

Your Demo Needs a Stakeholder

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/

July 1, 202624 min

Misha and his WorryBot

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/