In 2019, foundation evaluation staff and external evaluators came together. As part of the meeting, the facilitators asked all participants to write down what they most wished the other would do differently. The number one request of foundation evaluation staff? Ask harder questions. The number one request by external evaluators? Let us ask harder questions. If we both want the same things, why aren’t we doing better? Clearly, good intentions are not good enough. This brief lifts up six areas that rose to the top as key interventions to change the way the systems of evaluation and philanthropy operate, including implications for increasing the utility of evaluation findings, as well as some specific ways that external evaluation consultants and internal foundation evaluation staff can act together and in their own spheres of influence. This brief is one of five products created as part of the Funder Evaluator Action Network (FEAN) in response to areas of shared interest: Strategy & Practice, Evaluators of Color, Knowledge Sharing, Global Challenges, and Collaboration & Partnership.