For most of the history of software engineering, we’ve built systems around a simple and comforting assumption: Given the same input, a program will produce the same output. When something went wrong, it was usually because of a bug, a misconfiguration, or a dependency that wasn’t behaving as advertised. Our tools, testing strategies, and even our mental models evolved around that expectation of determinism. AI quietly breaks that assumption. As large language models and AI services make their way into production systems, they often arrive through familiar shapes. There’s an API endpoint, a request payload, and a response body. Latency, […]

The following article includes clips from a recent Live with Tim O’Reilly interview. You can watch the full version on the O’Reilly Media learning platform. Addy Osmani is one of my favorite people to talk with about the state of software engineering with AI. He spent 14 years leading Chrome’s developer experience team at Google, and recently moved to Google Cloud AI to focus on Gemini and agent development. He’s also the author of numerous books for O’Reilly, including The Effective Software Engineer (due out in March), and my cohost for O’Reilly’s AI Codecon. Every time I talk with him […]

Think about what happens when you onboard a new employee. First, you provision them tools. Email access. Slack. CRM. Office software. Project management software. Development environment. Connecting a person to the system they’ll need to do their job. However, this is necessary but not sufficient. Nobody becomes effective just because they can log into Salesforce. Then comes the harder part: teaching them how your organization actually works. The analysis methodology your team developed over years of iteration. The quality bar that is not written down anywhere. The implicit ways of working. The judgment calls about when to escalate and when […]