This document describes small group activities to help participants assess a youth program's readiness for outcome-based measurement. The activities focus on a case study of a program called New Possibilities Youth Services that provides leadership and employment skills development for newcomer youth. Participants discuss questions about the clarity of the program's description and theory, the realism of its strategies and intended outcomes, and key elements of a measurement plan for the program, including anticipated challenges in implementation. The goal is to help participants evaluate if a program's design supports outcome-based evaluation and determine appropriate outcome measures and indicators.