Troubleshooting Agile

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

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453

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Oct 2026

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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.

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60 recent

November 12, 202619 min

Don’t Care Too Much

Why are you caring more about the success of a project than your own company does? On this week's Troubleshooting Agile, Squirrel and Jeffrey tackle the frustration of nobody listening to you, why you should write down trade-offs, and how asking genuine questions could save your sanity. Links: - Diogenes: https://en.wikipedia.org/wiki/Diogenes - Everyone is doing their best: https://claude.ai/share/586ddac8-d243-4eb9-a932-ca0ebca1a420 -------------------------------------------------- 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/

October 28, 202612 min

Couples Counseling for Co-Founders

Can you save a broken co-founder partnership over Slack? In this week's episode of Troubleshooting Agile, Squirrel and Jeffrey get into "couples counseling for co-founders." Join us to learn why the act of mapping out strategy in person builds trust, creates shared vocabulary, and beats low-bandwidth remote tools every time. Links: - Alistair Cockburn on communication modalities (see figure 3-14): https://web.archive.org/web/20140329231939/http://alistair.cockburn.us/ASD+book+extract:+%22Communicating,+cooperating+teams%22 -------------------------------------------------- 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/

October 21, 202616 min

The Future of Software is SOUP?

Is your codebase turning into a 500-day perpetual stew? In this episode, Squirrel and Jeffrey dish the dirt on SOUP (Software of Unknown Provenance) and why AI is about to trigger a total tsunami of unexplainable code in your enterprise. Tune in for our tips on how to survive it. Links: - SOUP: https://meddeviceguide.com/blog/soup-software-unknown-provenance-iec-62304-guide - Perpetual stew: https://www.youtube.com/@ZAQ_Makes/shorts - Open AI proof dump: https://tech-insider.org/openai-withdraws-3-math-papers-722-dump-2026/ - Software supply chain attack: https://en.wikipedia.org/wiki/Supply_chain_attack -------------------------------------------------- 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/

October 16, 202632 min

Actually Good Conferences with Misha Glouberman

Are your company meetings and offsites optimized for zero risk, or for actual value? In this week’s episode, Jeffrey is joined by returning guest, Misha Glouberman, to unpack why traditional conferences default to boring lectures, and how you can design gatherings that actually build collaborative relationships. Links: - Actually Good Conferences: https://www.actuallygoodconferences.com/ - Progress Conference: https://rootsofprogress.org/conference - Works In Progress Ad: https://www.actuallygoodconferences.com/wip-ad-text -------------------------------------------------- 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/

October 7, 202614 min

Signals & Levers - Part III with Elisabeth Hendrickson & Joel Tosi

Is your tech team falling for the illusion of control? In this week’s episode, we sit down (again!) with authors of “Signals and Levers,” Elisabeth Hendrickson and Joel Tosi to talk about the events that led up to writing their book. Tune in to the third of our three-part episode where we cover 30-minute exercises you can run TODAY, from listening to non-dashboard "signals" to dissecting organizational illusions. Links: - Signals & Levers: https://signalsandlevers.com/ - Elisabeth Hendrickson previous appearance: https://soundcloud.com/troubleshootingagile/office-politics-and-toxic-behaviors - Tilted Slider Episode: https://agileconversations.com/blog/dont-add-more-metrics/ -------------------------------------------------- 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/

October 2, 202618 min

Signals & Levers - Part II with Elisabeth Hendrickson & Joel Tosi

Are you trying to fix "bad estimates" when you actually have a broken system? In this week’s episode, we sit down (again!) with authors of “Signals and Levers,” Elisabeth Hendrickson and Joel Tosi to talk about the events that led up to writing their book. Tune in to the second of our three-part episode where we discuss Shewhart charts, cycle time, and why aiming directly for predictability always backfires. Links: - Signals & Levers: https://signalsandlevers.com/ - Elisabeth Hendrickson previous appearance: https://soundcloud.com/troubleshootingagile/office-politics-and-toxic-behaviors - Tilted Slider Episode: https://agileconversations.com/blog/dont-add-more-metrics/ -------------------------------------------------- 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 23, 202616 min

Signals & Levers with Elisabeth Hendrickson & Joel Tosi

A pretty whiteboard diagram can’t control your software delivery system! In this week’s episode, we sit down with authors of “Signals and Levers,” Elisabeth Hendrickson and Joel Tosi to talk about the events that led up to writing their book. Tune in to the first of our three-part series where we discuss why complex tech orgs aren't linear machines, why measuring AI with vanity metrics backfires, and how to treat changes as real experiments. Links: - Signals & Levers: https://signalsandlevers.com/ - Elisabeth Hendrickson previous appearance: https://soundcloud.com/troubleshootingagile/office-politics-and-toxic-behaviors - Tilted Slider Episode: https://agileconversations.com/blog/dont-add-more-metrics/ -------------------------------------------------- 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 16, 202611 min

Why Is Everyone Else Wrong? Lessons From One Lane Roads

Ever felt like you’re the only person in a meeting moving at the "right" speed? Well everyone else is probably thinking that too! On this episode, Squirrel uses his example of driving on one of England’s many one-lane roads to make the point of fast and slow communication. Join us to learn his ice-cream incentivised “secret word” strategy to get teams being curious again! -------------------------------------------------- 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 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/