Working Backwards from the Outcome: A prompting workshop for people doing real work

​Working Backwards from the Outcome, led by Ashwin Jaiprakash.

​A prompting workshop for people doing real work: care, community, commerce, and the next job.

​AI can produce anything. Prompting is how you stop it from doing that.

​This is a hands-on session for people who use AI like a search engine — one line in, first answer out — and want to use it like a director instead. You'll learn OSCAR, one habit built from five questions: Outcome, Success, Constraints, Assumptions, Reference. Same five questions, every task.

​We'll work through real examples from three crews: care and community staff writing benefits appeal letters, shop owners drafting a week of Instagram captions, and job seekers tailoring resumes to real postings. You'll leave having run OSCAR on a task from your own week — not a hypothetical, something you'll actually use Monday morning.

​Phones out for a 10-minute mini lab. Leave with a master prompt and a habit you can repeat.

​Generously hosted by Whitman-Walker (https://www.whitman-walker.org/) at the Max-Robinson Center in Congress Heights.
Registration closes July 31. Please bring photo ID.

​Bio:
Ashwin Jaiprakash is an AI Strategist, GTM Leader, and Forward Deployed Engineer who helps organizations activate their ecosystems and partnerships through data-driven interventions. His work sits at the boundary between companies, reducing the friction that slows down joint missions and building the connective tissue that allows people to work better together across organizational lines.

​He currently leads customer strategy, product, and engineering for applied intelligence at GTM Fabric, where he translates complex signals into actionable strategies that move partner and customer ecosystems forward. He brings that same practitioner mindset to prompt engineering, treating it less as a technical skill and more as a design discipline for human-AI collaboration.