In 2009, two Hamilton multi-sector collaborations—the Hamilton Roundtable for Poverty Reduction (HRPR) and the Jobs Prosperity Collaborative (JPC)—undertook an evaluation process. The evaluation, conducted by Dr. Arnold Love, surfaced a number of lessons and questions. Drawing from the evaluation report, the HRPR and JPC have produced this short working tool, in the hope that it will be useful to other collaborative efforts. Five key lessons are highlighted here. They are just a few of the many that arose during the evaluation process.