[The Office] Stanley was trying to help Ryan on the sales call in season 3.
In season 3 episode 13 "Traveling Salesmen", Stanley tries to strike out on his own when he is assigned to travel. When Michael tells him he can't do that, he sighs and says he'll take Ryan. While this may seem like it's because Ryan is the least annoying person, I think it's because Stanley was trying to help Ryan.
Ryan had not made a sale prior to that episode (possibly due to his visible anxiety when trying to make a sale), so I think when Stanley dropped Ryan in a situation outside his comfort zone (all black salesmen who know Stanley well), it was a form of immersion therapy. Stanley knew the clients liked him, so he wouldn't lose the account even if Ryan bombed.
Granted, Stanley is later seen laughing at Ryan's failure, but I think this is because Stanley doesn't want to be seen by Ryan as a mentor. He's too lazy to present himself as a permanent resource for Ryan.
TL;DR: Stanley gave Ryan a worst-case scenario, and showed him it wouldn't be all that bad.
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