In this podcast episode host Jason Rome and guest David Brown talk about the crucial role of "confidence" in effective planning. They explore how organizations can honestly assess certainty and uncertainty in project estimates, distinguishing between confidence in "what it'll take to do" and "what this thing will do." The discussion highlights the importance of early, honest conversations about risks and major assumptions, emphasizing that overconfidence can be detrimental. The conversation provides valuable insights into how to build a culture of honesty and clear communication in planning, ultimately aiming to mitigate risks and ensure that projects are not only feasible but also truly desirable for users.