Troubleshooting Agile
A weekly problem-solving session for all things agile
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.
Episodes
Mentioned books

13 snips
May 6, 2026 • 16min
Against Product Chatbots
A critique of chat-first interfaces and why they often frustrate real users. A concrete failure story about a chat UI that made a simple task harder. Discussion of when AI should work behind the scenes and when deterministic guidance is better. A contrast between textbook knowledge and expert, high-dimensional judgment.

5 snips
May 1, 2026 • 19min
Greatest Hits: Why Can’t We Ship Today?
A lively replay of three war stories centered on the provocative question, why can’t we ship today? They explore value stream mapping to expose hidden waits and long idea-to-cash lead times. Team-level mapping reveals automation opportunities to speed releases. Stories contrast quick patches, full releases, and minimal solutions that won back customers.

8 snips
Apr 22, 2026 • 18min
Crocker’s Rules
A brisk take on cutting through workplace small talk to get straight to the facts. They explore how ‘noisy politeness’ like long Slack greetings bogs teams down. Practical scenes include phone-first onboarding, incident reporting with clear technical context, and using concise feedback to speed improvement. The episode discusses when and how to invite direct communication as a team norm.

12 snips
Apr 15, 2026 • 21min
Agentic Validation and the Power of Loops
They debate organisations rushing AI rollouts without learning change-management lessons. They explore when to automate status reporting with LLMs and when that misses the point. They introduce agentic validation for documenting predictions and checking outcomes over time. They unpack monitoring-driven rollouts, rollback safeguards, and iterative AI loops that experiment and refine results.

8 snips
Apr 8, 2026 • 22min
Disagree and Commit - Part II
A lively dive into productive disagreement using the ladder of inference. They unpack how differing values shape arguments and test assumptions step by step. A real-world hunting example shows how to find common ground and negotiate commitments. Practical tips on reflecting back someone’s reasoning and treating conversations like test-driven development.

7 snips
Apr 1, 2026 • 14min
Disagree and Commit - Part I
They unpack how 'disagree and commit' is often misused as a silencing tactic and why the disagreement step truly matters. They explore when urgent compliance is appropriate and when objections surface crucial information. They talk about spotting endless debate and knowing when to stop discussing and move forward.

7 snips
Mar 25, 2026 • 13min
Question First!
They argue for stating the question first to cut through vague stories and get straight to the point. Examples show how a clear question helps people find their own answers and sharpens fuzzy problems. Practical habits like rubber-ducking and targeted context make conversations and meetings more efficient. Tips extend to product discovery and meeting design.

7 snips
Mar 18, 2026 • 15min
Executives Walking the Board
A conversation about using the board to drive focus and better standups. Practical contrasts between card-centered and person-centered status updates. How executive meetings can use boards to expose misalignment, side projects, and accountability gaps. Tips for building the habit and handling resistance to change.

9 snips
Mar 11, 2026 • 21min
The Bots Take Over Helsinki
A frank preview of a Helsinki unconference celebrating its 20th year and pivot to AI. They explain the open-space format and how topics get chosen. The conversation covers who shows up and why the crowd is unusually diverse and experienced. They debate the surge of AI in development and promise contrarian sessions and lively skepticism.

7 snips
Feb 26, 2026 • 19min
Leaders are Accountable Too
A lively conversation about what accountability really means and how fear teaches people to hide mistakes. They revisit a pivotal Kent Beck insight that reframes accountability as explaining your choices. The discussion covers leadership responsibility, how optimistic reporting masks problems, and practical communication practices like briefing and back-briefing.


