Collaboration is a large and growing part of the landscape for community development work. Often it makes sense and leads to good results. Yet the timing is not always right, nor the ingredients in place for a successful collaborative effort. Although there’s no foolproof way to predict the outcome of any undertaking that involves people and organizations working together, a few basic checkpoints can be quite revealing. And if you’re already involved in a collaborative effort, these same checkpoints can help your group recognize strengths and work on weaknesses. This paper provides 20 factors that can make or break any group effort.