Now You're Thinking With Portals

This case study addresses the challenge of how product teams and companies should approach AI integration beyond superficial improvements. Casey Winters argues that most teams are still using AI tools to make incremental improvements to existing workflows rather than leveraging them to accomplish previously impossible tasks - what he calls "thinking with portals" (referencing the video game Portal).

Winters introduces a framework of three tiers for AI adoption: "the old way" (manual processes), "the half measure" (AI-assisted existing workflows), and "the one shot" (AI-native solutions that fundamentally change how work gets done). He illustrates this with data retrieval: from writing SQL queries manually, to using ChatGPT to help write SQL, to having AI tools like Cursor automatically generate Python scripts. He warns entrepreneurs against building products that are merely "half measures" without a path to becoming "one shot" solutions, calling these "escalators to nowhere."

Key takeaways for product managers include: prioritize building AI-native experiences that enable previously impossible outcomes rather than just optimizing existing processes; avoid investing heavily in "half measure" solutions that don't sequence toward owned "one shot" capabilities; and recognize that AI adoption is existential - companies must successfully become AI-first or risk being displaced by competitors who do. The framework helps PMs evaluate whether their AI features represent genuine step-changes or just incremental improvements that competitors can easily replicate.