We outline our work on evaluating robots that assist older adults by engaging with them through multiple modalities that include physical interaction. Our thesis is that to increase the effectiveness of assistive robots: 1) robots need to understand and effect multimodal actions, 2) robots should not only react to the human, they need to take the initiative and lead the task when it is necessary. We start by briefly introducing our proposed framework for multimodal interaction and then describe two different experiments with the actual robots. In the first experiment, a Baxter robot helps a human find and locate an object using the Multimodal Interaction Manager (MIM) framework. In the second experiment, a NAO robot is used in the same task, however, the roles of the robot and the human are reversed. We discuss the evaluation methods that were used in these experiments, including different metrics employed to characterize the performance of the robot in each case. We conclude by providing our perspective on the challenges and opportunities for the evaluation of assistive robots for older adults in realistic settings.