Willy’s humiliating interview with Howard sheds some light on his advice for Biff’s interview with Oliver. This advice clearly has its roots in Willy’s relationship with his boss. Despite being much younger than Willy, Howard patronizes Willy by repeatedly calling him “kid.” Willy proves entirely subservient to Howard, as evidenced by the fact that he picks up Howard’s lighter and hands it to him, unable to follow his own advice about such office boy jobs.
Willy’s repeated reminders to Howard that he helped his father name Howard illustrate his psychological reliance on outmoded and insubstantial concepts of chivalry and nobility. Like his emphasis on being “well liked,” Willy’s harping upon the honor of bestowing Howard’s name—one can draw a parallel between this naming and the sanctity and dignity of medieval concepts of christening and the dubbing of knights—is anachronistically incompatible with the reality of the modern business world.
Willy seems to transfer his familial anxieties to his professional life. His brother and father did not like him enough to stay, so he endeavors to be “well liked” in his profession. He heard the story of Dave Singleman’s success and exaggerated it to heroic, mythical proportions. Hundreds of people attended Singleman’s funeral—obviously, he was a man who was “well liked.” Dave Singleman’s story hooked Willy as the key to emotional and psychological fulfillment. However, the inappropriateness of Willy’s ideals reveals itself in his lament about the loss of friendship and camaraderie in his profession. Willy fantasizes about such things, and he used to tell his sons about all of his friends in various cities; as Willy’s hard experience evidences, however, such camaraderie belongs only to the realm of his delusion.