In this LinkedIn Live episode, host Kelsey and Todd discuss how to improve AI workflow results by moving beyond vague prompts like “write me a marketing email” and using an iterative approach. Todd shares the CRIT framework (Context, Role, Interview, Task), recommends prompting AI to ask clarifying questions one at a time, and stresses specifying desired outputs such as a Word document, table, or executive summary. They demo a prompt-building tool called Prompt Cowboy and discuss using screenshots or PDFs to extract, simplify, or reformat information, including translating legal documents into plain English. The conversation highlights governance concerns such as AI memory, paid vs. unpaid tools, and avoiding sensitive data like PII, employee information, financials, and health details. Todd also mentions agents for specialized compliance use cases and a voice tool called Whisper Flow for capturing ideas while away from a keyboard.

00:00 Welcome and Setup

00:55 Why Prompts Fail

01:49 CRIT Prompt Framework

04:10 Handling Complex Requests

05:50 Prompt Cowboy Demo

07:58 Iterative Prompting Tips

10:32 Screenshots and Privacy

16:23 Everyday Business Use Cases

19:04 Saved Prompts Debate

26:44 Agents and Compliance

27:53 Wrap Up and Voice Tools

30:05 Outro and Next Episode