The sales profession has used mentoring programs for generations, offering new hires the chance to learn by observing (or “shadowing”) experienced sales reps. These programs tend to follow an informal, ad hoc structure, producing inconsistent results. In their 2004 Harvard Business Review article ““Deep Smarts,”” Dorothy Leonard and Walter Swap pointed out that when experienced workers leave a company, they take their years of knowledge and expertise (i.e., ““deep smarts””) with them. In this brief, we explain how to establish mentoring programs across a sales organization to allow it to maximize and also retain the value of the knowledge, skills, and experience of top sales talent.