As leaders plan for their organizations’ optimal mix of remote work, this article suggests they will need to revisit decisions in two main categories: 1) company policies that set expectations of a dispersed workforce and 2) management practices and behaviors that enable remote or a hybrid work environment. The authors provide ten questions that leaders can ask as they make these decisions. On company policy, questions range from what is the right mix of remote work for our organization, which HR policies will need to be updated, are we ready to consider a work from anywhere (WFA) policy? Concerning management practices and behaviors, leaders should consider questions such as how can I help employees manage competing work and life priorities, how can we consciously engage employees, and how do we create a sense of psychological safety? Each question includes a few recommended practices. For example, leaders can foster psychological safety by showing vulnerability (e.g., sharing experiences where they made a mistake) and inviting all team members’ participation (e.g., on a call asking someone ‘what do you think?’ Firms can use this framework to proactively consider company policies and management practices to transform their remote workforce.