Coding Chats

AI, management and situational leadership in software engineering

Coding Chats

Show Notes

Coding Chats episode 37 - John Crickett and Simon Copsey explore the intricate relationship between technology, management, and leadership in software engineering. They discuss the limitations of technology, particularly AI, emphasizing that while it can be a powerful tool, it is not a one-size-fits-all solution. The importance of soft skills, situational leadership, and understanding organizational dynamics is highlighted as essential for effective management. They also delve into the significance of learning from mistakes and the need for psychological safety in decision-making processes.

Chapters 00:00 Technology: Necessary but Not Sufficient 02:49 AI: The Shiny Object Syndrome 05:38 The Role of Collaboration in Software Engineering 08:09 Management vs. Engineering: A Different Skill Set 10:33 Understanding Team Dynamics and Cooperation 13:28 The Importance of Systems Thinking 16:13 Identifying Underlying Causes in Organizations 18:58 Creating Paths of Least Resistance 21:37 The Impact of Metrics on Team Behavior 23:54 The Role of Systems in Organizational Success 26:00 Balancing Individual Uniqueness and Organizational Needs 31:53 Leadership Models and Situational Context 34:20 Bureaucracy vs. Creativity in Leadership 37:37 Command and Control vs. Intent-Based Leadership 42:35 The Importance of Psychological Safety 45:18 Learning from Mistakes and Decision-Making 48:51 Sociocratic vs. Democratic Leadership 53:11 The Role of Assumptions in Decision-Making 56:37 Adapting Leadership Styles to Team Contexts 01:00:49 The Importance of Asking Why in Leadership 01:04:34 Summary of Key Insights 01:09:37 Outro Final Coding Chats.mp4

LINKS Talk by Simon: From Diapers to Delivery: Parenting Lessons for Management - https://www.youtube.com/watch?v=HBCLoklUZMg

References: The Goal (Book, Eli Goldratt)Necessary But Not Sufficient (Book, Eli Goldratt) Technical debt is a myth (Article, Noah Cantor) Management in Small Doses (Book, Russell Ackoff) The New Economics (Book, W. Edwards Deming) Thinking for a Change (Book, Lisa Scheinkopf)

John's Links: John's LinkedIn: https://www.linkedin.com/in/johncrickett/ John’s YouTube: https://www.youtube.com/@johncrickett John's Twitter: https://x.com/johncrickett John's Bluesky: https://bsky.app/profile/johncrickett.bsky.social

Check out John's software engineering related newsletters: Coding Challenges: https://codingchallenges.substack.com/ which shares real-world project ideas that you can use to level up your coding skills. Developing Skills: https://read.developingskills.fyi/ covering everything from system design to soft skills, helping them progress their career from junior to staff+ or for those that want onto a management track.

Takeaways Technology is necessary but not sufficient for success.AI should be applied to specific problems, not as a blanket solution. Management is a distinct career path from engineering. Soft skills are crucial in software engineering. Mistakes are essential for learning and growth. Situational leadership adapts to the context and team dynamics. Understanding the system is key to solving organizational problems. Effective decision-making requires psychological safety. Disagree and commit fosters a culture of learning. Assumptions should be documented to facilitate learning.

More from Coding Chats

Oct 22, 2026

Coding Chats Episode 83 - In this episode, VB from OpenAI’s developer experience team explains why he thinks plan mode is obsolete and how coding agents have shifted from step-by-step instructions to outcome-driven, long-running work. We cover how to write a good agents.md, why tests still matter when agents write the code, spec-driven development, and why cloud agents may be the future of dev tooling.

Oct 15, 2026

Coding Chats Episode 82 - John talks with Dave Westgarth, head of delivery at a Databricks consultancy. Dave shares his path from a psychology degree and McDonald's into tech, and they discuss why the Scrum Master role is so misunderstood, how it differs from a delivery manager, and whether either needs to be technical.They also look at how AI is changing delivery work. Faster code just moves the bottleneck upstream, John argues there's no AI-specific skill you can't learn in a day, and engineering fundamentals are what make AI useful.

Oct 8, 2026

Coding Chats Episode 81 - Ben Howdle talks to John Crickett about being a first time CTO in a start-up. Ben, author of The First CTO, shares what changes when you move from building technology to leading a technical team: the pressure, the trade-offs, and the realization that writing code is only part of the job.Drawing on startup experience and lessons learned the hard way, Ben discusses how to balance quality against runway, manage people, and communicate technical decisions in terms that founders and other non-technical stakeholders can understand. He also explores why resourcefulness, resilience, and comfort with ambiguity matter so much—and why CTOs often spend more time selling ideas than they expect.Whether you’re stepping into your first CTO role or leading a technical team at an early-stage company, this conversation offers candid insights into the realities of technical leadership.

May 28, 2026

Coding Chats Episode 80 - start-up advisor Alexander Berkovich shares his expertise on building successful start-ups, hiring strategies, CTO roles, and the importance of communication between technical and business teams. Discover practical tips for navigating the challenges of early-stage companies and how to align technical excellence with business goals.

May 21, 2026

Coding Chats Episode 79 - Richmond Alake, Director of AI Developer Experience at Oracle, joins John to discuss agent memory — how AI agents store, retrieve, and adapt to information. He argues that developers building memory on flat files are naively reinventing the database, and that once you factor in concurrency, security, and scalability, a proper database is inevitable. The conversation covers the full memory stack and how Oracle's AI database keeps embeddings and data together without shipping sensitive information to external providers.

See all episodes →