Executive coaches will be more effective if they understand how their clients think and experience emotions. They have to be skilled at detecting and evaluating the psychological strengths and challenges that can help or hinder a client's development as a leader. What will be helpful in their work is when they take a more holistic approach to the information clients present, which means considering information from both their waking and dreaming life. This article suggests that, to help executives with their journey into their own interior—working with an additional source of information—executive coaches could also pay attention to their clients' dreamtime. The dreams that occur during their clients' “night journeys” can offer useful clues about their main preoccupations and concerns. Reflecting on how the feelings in their clients' dreams relate to what's happening in their waking life can help executive coaches and their clients better recognize and address their internal struggles and challenges, and figure out what is most on their minds. Making sense of dreams can be a very powerful problem-solving and inspirational tool, offering a pathway to out-of-awareness preoccupations. This relatively unexplored territory is the main focus of this article. I will also take into consideration various theories about dreaming, and make a number of observations on the kind of training that executive coaches need to be able to practice working with dreams.