A weekly problem-solving session for all things agile

Troubleshooting Agile

Business EN ↓ 438 episodes

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.

Author

A weekly problem-solving session for all things agile

Category

Business

Podcast website

agileconversations.com

Latest episode

Jul 8, 2026

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Episodes

Things You're Allowed to Do 26.06.2024

You’re allowed to do much more than you think, including working outside your team, disappointing others (helpfully), or learning things that aren’t on your business card. On this episode, we continue our theme of agency with inspiring ideas from a listener email. Links: - Things You're Allowed to Do: https://milan.cvitkovic.net/writing/things_youre_allowed_to_do/ - Stone Soup: https://agileconver...

Learning Agency, Part II 19.06.2024

Successful experiments with negative results are a vital part of learning to have agency. Discover how to fail for success on this episode of Troubleshooting Agile with our guest. Sammy Hath: Links: - https://hath.blog/posts/hire/ - https://hath.blog/posts/cultivating-destroying-agency/ - Failing for Success: https://failingforsuccess.substack.com - Taleb’s Antifragile book: https://en.wikipedia.o...

Learning Agency, Part 1 12.06.2024

"Agency" "empowerment" "accountability" can be empty promises to your tech team, or real skills you can learn. In this episode, Squirrel and Jeffrey are joined by “competent minion” Sammy Hath to discuss how to solve difficult problems. Links: - https://hath.blog/posts/hire/ - https://hath.blog/posts/cultivating-destroying-agency/ - Message to Garcia episode: https://soundcloud.com/troubleshooting...

Learning from Prediction Markets 05.06.2024

Fast feedback to executives on whether executing the HiPPO (Highest Paid Person's Opinion) actually made your software more profitable. Get answers on how and why "prediction markets" speed up learning, on this episode of Troubleshooting Agile, with Douglas Squirrel and Jeffrey Fredrick. Links: - Manifest prediction markets conference: https://www.manifest.is/ - Previous episode on predictions and...

Get Your Reps In 29.05.2024

Frequent repetition and practice doesn't constitute micromanagement, if done well: it reinforces accountability and alignment. Tune in to this episode of Troubleshooting Agile to find out how and why you and your tech team need daily rehearsal and feedback, with your hosts, Squirrel and Jeffrey. Links: - Toyota Kata Practice Guide: https://theleanthinker.com/2017/12/21/mike-rother-the-toyota-kata-...

Keeping Score With Cash 22.05.2024

Getting users to love your product isn't enough. Somebody needs to give you rectangular pictures of kings and presidents in exchange for it. Join your hosts, Squirrel and Jeffrey for product pitfalls and how to avoid them, on this episode of Troubleshooting Agile. Links: - Squirrel's tweet: https://twitter.com/douglassquirrel/status/1791438669070426526 - Rectangular pictures of the king: https://w...

Farming not Gardening 15.05.2024

If you or your tech leaders are exhausted from tracking an overwhelming number of individual tickets, features, or products, you're gardening when you should be farming. On this episode of Troubleshooting Agile, Squirrel and Jeffrey give their insights on how to manage whole "flocks" of engineers and customers. Links: - Briefing and Back Briefing : https://soundcloud.com/troubleshootingagile/brief...

Root Causes 08.05.2024

You've never been in a plane crash because accident investigations are blameless, but do you know how to run a blame-free postmortem? Timelines, timeboxes, and more ways to learn from disasters before they happen, when you join Squirrel and Jeffrey on this episode of Troubleshooting Agile. Links: - Airline Safety article - https://asteriskmag.com/issues/05/why-you-ve-never-been-in-a-plane-crash -...

War and Peace 01.05.2024

When disaster looms and results are immediate, joint design really shines by driving informed, prompt, unpopular decisions. Learn how to keep your decision process when all about you are losing theirs, with your hosts, Squirrel and Jeffrey, Links: - Horowitz on wartime vs peacetime: https://a16z.com/peacetime-ceo-wartime-ceo/ - Squirrel decisiveness story: https://twitter.com/douglassquirrel/statu...

Message to Garcia 24.04.2024

Is your timid tech team constantly seeking direction and second-guessing themselves? Improvement is possible - if you create frequent accountability. Discover how your team can get a "message to Garcia", by tuning in this episode of Troubleshooting Agile. Links: - Patrick McKenzie tweet: https://twitter.com/patio11/status/1781424185094402558 - Sammy (Patrick's EA) on agency: https://hath.blog/post...

Falsifying for Fun and Profit 17.04.2024

The Imperial Japanese Navy and Borland Software made the same strategic mistake: testing hypotheses but ignoring negative results. Join your hosts, Squirrel and Jeffrey to discover what they missed and how you can make falsification work for you on this episode of Troubleshooting Agile. Links: - Shattered Sword: http://www.shatteredswordbook.com/ - Borland: https://en.wikipedia.org/wiki/Borland -...

Working With Eeyore 10.04.2024

Do you have an "Eeyore" in your technology team, for whom it's all thorns and no roses? Can you help them to be more Tigger.. and would you even want to? Join Squirrel and Jeffrey as they discuss pessimism and burnout on this episode of Troubleshooting Agile. Links: - Eeyore & Tigger: https://en.wikipedia.org/wiki/List_of_Winnie-the-Pooh_characters - Previous episode on burnout: https://agileconve...

Why Didn't They Just... 03.04.2024

Mistakes are only obvious looking backwards, looking forwards, they seem like good ideas. On this episode of Troubleshooting Agile, Squirrel and Jeffrey discuss why they encourage meaningful errors that lead to learning and how a negative result is a sign of a successful experiment. Links: - Retrospective Coherence: https://www.chriscorrigan.com/parkinglot/retrospective-coherence-and-the-road-not-...

Agile is Dead? 27.03.2024

Agile is dead, but does anyone care? Cynefin tells us that we should be watching the slope of improvement, not aiming for a mythical "best practice". Squirrel and Jeffrey discuss why agile is irrelevant, on this episode of the (ironically named) Troubleshooting Agile podcast. Links: - Ubiquitous Language: https://martinfowler.com/bliki/UbiquitousLanguage.html - Cynefin: https://en.wikipedia.org/wi...

The Agile Software 20.03.2024

Has "adopting Jira" become the definition of "being agile"? If so, Squirrel says he’ll find another line of work! Tune in to hear Squirrel and Jeffrey's discussion on using the right tools for certain and uncertain environments, on this episode of Troubleshooting Agile. - Squirrel’s Jira tweet: https://x.com/douglassquirrel/status/1767536165790376281?s=20 - Chris Matts on Needs and Solutions: http...

(De)Centralisation Dilemmas 13.03.2024

Build centralised, standard structures for your tech only when you're sure the terrain isn't moving under your feet and stable software is no guarantee against market avalanches. This week’s episode is all about centralisation and decentralisation, with your hosts, Squirrel and Jeffrey. Links: - Wardley Mapping: https://en.wikipedia.org/wiki/Wardley_map - Pioneers, Settlers, Town Planners: https:/...

The Async-First Playbook 06.03.2024

Cancel your standup and record your decisions in writing, not conversations. This week on Troubleshooting Agile, Collaborations Expert and Author, Sumeet Moghe joins Squirrel and Jeffrey to explore "async-first" software development. Links: - Sumeet Moghe: https://www.linkedin.com/in/sumeetmoghe/ and https://www.asyncagile.org/ - The Async-First Playbook: https://www.thoughtworks.com/en-gb/insight...

Classic Blunders 28.02.2024

Go ahead and bravely demand the next feature right after the completion of the last! This week on Troubleshooting Agile, Squirrel tells us why he likes to be more demanding than Kent Beck. Links: - Kent Beck: https://en.wikipedia.org/wiki/Kent_Beck - Tidy First: https://tidyfirst.substack.com/p/tidy-first-in-one-page - Extreme Programming: https://en.wikipedia.org/wiki/Extreme_programming --------...

Greatest Hits: Learning Loops 21.02.2024

This week on Troubleshooting Agile, we bring you a bumper edition of 2022’s Summer Shorts - Learning Loops. Taking iterative development to heart, Squirrel and Jeffrey discuss six learning loop topics in less than five minutes each. Join us to learn about: - Basic daily learning loops - Weekly planning - Elephant Carpaccio - Walking the board - Retrospectives - OKRs -------------------------------...

No Vehicles in the Park 14.02.2024

"Scope" and "requirements" for software rely on a common understanding of basic concepts like "vehicles" or "names" but humans have no idea how to nail down those ideas. Join your host Squirrel and Jeffrey to find out why, and what to do about it, on this episode of Troubleshooting Agile. Links: - No Vehicles in the Park game: https://novehiclesinthepark.com - Keith Braithwaite: https://twitter.co...

Tindallgrams 07.02.2024

One guy you've never heard of kept the Apollo moonshot on track - by holding great meetings and taking super notes. Do your ADRs and Notion pages measure up? We’re talking Bill Tindall and the Tindallgram on today's episode of Troubleshooting Agile with your hosts, Squirrel and Jeffrey. (Some editing snafus mean no intro/outro music this week, but the same juicy words as always!) Links: - Tindallg...

Teal Data Science 31.01.2024

How can your organisation be simultaneously fast and collaborative? Foster willingness to fail successfully and collaboratively, while applying strong leadership and accountability. Find out why and how on this episode of Troubleshooting Agile with your hosts, Squirrel and Jeffrey. Links: - Teal Organisations book: https://en.wikipedia.org/wiki/Reinventing_Organizations ---------------------------...

One- and Two-Way Doors 24.01.2024

How can you do risky experiments even in the most risk-averse organisations? Find the answers on this week’s episode as Squirrel and Jeffrey discuss the value of two-way doors and reversible decisions for your tech team and your product. Links: - Jeff Bezos on Doors: https://www.inc.com/jeff-haden/amazon-founder-jeff-bezos-this-is-how-successful-people-make-such-smart-decisions.html - Feature Flag...

Practical Slowification 17.01.2024

You know investing in skills or tech advancements will speed you up, but how to make it happen? Convincing your boss is all kinds of wrong! On this week’s episode of Troubleshooting Agile we discuss why and what works better, with your hosts Squirrel and Jeffrey. Links: - Gene Kim, Wiring the Winning Organization: https://myresources.itrevolution.com/id006657164/Wiring-the-Winning-Organization - S...

Butterfly Ideas 10.01.2024

Use a shared language to ensure good ideas for your product or team aren't crushed before they get a chance to live. Inspired by Elizabeth Van Nostrand’s article, Jeffrey and Squirrel discuss the concept of “Butterfly Ideas,” on this episode of Troubleshooting Agile. Links: - Butterfly Ideas: https://acesounderglass.com/2022/02/04/butterfly-ideas/ - Wiring the Winning Organisation, Gene Kim: https...

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