How To Stop Using AI Like A Search Engine, with Katelin O'Shea

In this episode of The AIQUALISER Podcast, John Bennett talks to Katelin O'Shea, who is a Project Manager at Dropbox, a Perplexity Business Fellow and has created a consultancy and training business called AI That Works.Katelin saw AI being used in a fintech start-up in 2022, so she was already aware of the possibilities when ChatGPT launched. She put that to good use at Dropbox, where she has built systems that take a project scope from half a day's work to twenty minutes, and freed herself up to actually listen in meetings rather than take notes.She explains what context actually means in plain terms, why rolling out AI to a team is just as much work as building the tool in the first place, and where she draws the line on what AI gets to do.The episode closes with a question Katelin gets asked a lot: if you could only focus on one area of AI right now, what would it be? Her answer is skills, the reusable instruction files that document your processes in a format AI can act on, which can be built without any technical knowledge.In This EpisodeKatelin's introduction to AI before the ChatGPT era, and what working with an early agent taught herWhy people with management experience tend to get better early results from AITranscription, structured folders, and custom AI tools: how Katelin manages projects at DropboxThe difference between using AI as a search engine and using it as a system built around your workWhat context actually means, with examples that require no technical knowledgeWhy AI rollouts fail, and why individual pain points beat company-wide mandatesFiltering LinkedIn noise: building a system that turns saved posts into original contentWhat Katelin will not let AI do without her own voice in the draft firstWhere to start if you have not started yetSkills: reusable instruction files, portable across tools, no technical knowledge requiredChapters00:00 Introduction to Katelin O'Shea03:53 Before ChatGPT changed everything08:29 Inside a project manager's AI workflow20:23 Context isn't technical27:20 Why rollouts fail36:40 Filtering the noise44:00 Keeping the human in the loop48:48 How to get started57:40 Listener question: where to focusYou can find Katelin at aithatworks.io, on YouTube at @aithatworks_kate, on TikTok at @aithatworks, and on LinkedIn at linkedin.com/in/katelinosheaIf you have a question you'd like us to pick up in a future episode, you can get in touch at frmdb.ly/pod