You should be smiling during your sales conversations. You should be nice. You should be happy. You should be caring. That does not mean you should be weak. Robert Herjavec on Shark Tank famously says “I’m a very nice guy, but don’t mistake my kindness for weakness.” Asking questions which challenge your prospect to think hard about what is not working and determine how relevant their problems are to address is where you become effective, while still being nice and empathetic. The two are not mutually exclusive. Be nice. but challenge.