Troubleshooting Agile

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 chann...

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...

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 Co...

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...

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 y...

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...

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 so...

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: - C...

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:...

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_mappi...

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://lr...

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 art...

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 an...

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...

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...

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-s...

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...

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 accou...

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...

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. ------------------...

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.o...

If something feels hard, you might not be the problem, it might be your tools. On this episode of Troubleshooting Agile, Jeffrey shares a skiing mishap, which had him believing he forgot how to ski - until he looked at his feet! Tune in for our thoughts on using the right tools for the right problems, checking assumptions, and the benefits of external perspectives. Links: - Betterism: https://squi...

One time on the podcast, we released the wrong episode - twice! But listener feedback meant we could correct it quickly - and it got us asking, do you know what users think of your software as soon as it’s done? On this re-run episode, which shares the theme of a recent episode, Gliding to Success [see below], Squirrel and Jeffrey show you how daily feedback IS possible and why we’d strongly recom...

Worried non-techy people will expect too much from Vibe Coding? Listener, Tom, wrote to us with his concerns about the actual productivity of AI development. Listen in for Jeffrey’s experience on trivial tools that make a big difference and how to manage expectations, on this episode of Troubleshooting Agile. Links: - Community of Needs: https://snowbirdcollaboratory.org/community-of-needs/ - Firs...

It’s okay to be confused about Vibe Coding! On this episode of Troubleshooting Agile, Squirrel and Jeffrey respond to a listener’s argument from our series with Gene Kim on Vibe Coding and reflect on the question, what stage are we at in the industry when it comes to Vibe Coding and what can we expect for the future? Links: - Community of Needs: https://snowbirdcollaboratory.org/community-of-needs...