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Schuyler Dragoo, Chief Strategy Officer at Kiingo AI on Tech for Founder Podcast with Panida Wayrojpitak, explains why AI is easy to use but hard to use well, and why generic prompts produce generic outputs. Drawing on experiences using ChatGPT as a tool to understand social situations and an art practice of observing and mimicking Boston geese, Schuyler emphasizes that AI misreads users due to incomplete context windows, unstated assumptions, overloaded prompts, and undefined terms. They describe context engineering, structured workflows, documentation, and tools like MCP servers to guide models more precisely. Practical advice includes experimenting to learn a model’s assumptions, iterating based on outputs, building a prompt library, using a role-task-output-context prompt formula, defining good vs. bad responses, providing scenarios and examples, treating AI like an intern who needs onboarding, and starting with low-stakes, repetitive workflows such as email and question-generation.

(00:00) Why AI Misreads You

(00:37) AI Insight

(01:43) Context and Assumptions

(02:24) Fixing Misinterpretations

(03:54) Observing Geese

(05:45) Play to Learn Tools

(06:19) Intention vs Perception

(07:51) Prompt Formula That Works

(09:11) What to Automate

(11:56) Building Translation Systems

(12:52) Treating AI Like an Intern

(15:48) First Simple Workflow

(17:30) Examples Beat Perfect Clarity

(19:33) Wrap Up and Resources

More about Schuyler Dragoo:

Linkedin: https://www.linkedin.com/in/schuyler-dragoo-mfa-a99672333/

Follow for more founder insights:

LinkedIn → https://www.linkedin.com/in/panidawayrojpitak/

Instagram → https://www.instagram.com/panidawayrojpitak/

YouTube → https://www.youtube.com/@PanidaWayrojpitak

Listen on your preferred podcast app:https://podcasters.spotify.com/pod/show/techforfounder

Business inquiries & guest bookings:panida@techforfounder.com

Disclaimer: This podcast provides educational content only and is not a substitute for professional, legal, financial, health, or business advice; we are not liable for any decisions or actions taken based on our discussions.