How does Willy's inability to deal with technology connect to his lack success as a salesman in Death of a Salesman?
Willy has failed to adapt to changing times. This evidences especially in his sales techniques and professional attitude. His difficulties with technology are emblematic of this failure to change - a characteristic of larger significance with Willy when seen in light of his unwavering and unhealthy fixation on a false vision of success. This vision takes hold of Willy and he is powerless to free himself of it; to change.
[Willy] cannot face the reality that he has misdirected his energies and talents chasing a dream that never had any chance of materializing.
Willy is frustrated by his sense of failure and frustrated by the treatment he receives at work. He is aware that he can no longer continue to be successful "out on the road" as a salesman, but his boss will not offer Willy a change of position.
Howard answers that there are no openings to be a salesman in the store. “[W]here am I going to put you, kid?”
Part of Willy's response to this rebuff is to say that all the personality has been taken out of business. As Howard fawns over his recording device, demonstrating his interest in progress, Willy proves he is obsolete, harping on the past.
The result of this conversation is Willy's dismissal. He is fired by Howard after embarrassing himself, shouting, and demanding what he feels is his due. Howard does not feel that the company owes Willy anything. His worth and his value to the company are measured by his ability to sell, not by his years of service in the company.