This article explores issues that had to be confronted over a three-year period in terms of two New York State funded grants for which I was the evaluator. Major, critical challenges are presented, described, and discussed. Specifically, the paper addresses issues related to lack of planning at the grant design stage that resulted in challenges and problems with conducting targeted and meaningful assessments to complete evaluations. This article promotes the concept that evaluators have expertise and competencies that are valuable to grant design and that if an evaluator is involved at the planning/ design stage, many challenges confronted throughout evaluation processes might be prevented or mitigated. The inquiries that were conducted as part of these grants can be regarded as case studies. In the example of one investigation, it was a single-case study of an intervention in a Long Island, New York, district; in the case of the other, it was a multiple-case study wherein a Charter School disseminated an intervention to three New York City schools. Mixed methods were used for data collection. Following my work with these two funded grants, with lessons learned from my experiences with these two grants, I embarked on another journey with another agency where lessons learned from the two previous grants informed my approach to evaluating school programs. Thus, while I was not part of the original design team, we were able to discuss relevant evaluation issues early in the process. My latest experiences will also be briefly discussed at the end of the article in a Postscript.