Although throwing your tag team partner through a plate glass window is a great way to get heat, Shawn Michaels didn't yet know who his character really was beyond, "Bad guy." Everybody could see that he had way more potential than Marty Jannetty, but I'm not sure if anybody really knew where it was going. But he kept getting time, first with his interview show, The Heartbreak Hotel, but even then he was a little stiff. The most important thing that happened to him was when Macho Man left, and he was allowed to take over commentary on Raw for several weeks.
When he first started on commentary, he knew to take the heel perspective but didn't quite know how to talk it out. Vince McMahon may have been shitty at commentating wrestling matches, but he was always willing to set up his broadcast partners. Now some, like Rob Bartlett, took the ball and ran it into his own end zone, laid down, and shit his pants. But, Shawn Michaels slowly warmed up to talking during the matches. It started as the bad is good, good is bad trope that is easy and predictable, but he went from arrogant bad guy to conceited, self-absorbed, sex symbol bad guy, and the latter led to a very long shelf life.
I think that people remember Shawn Michaels as a great talker from his career, but that was never his greatest strength. I mean, it's not like you remember any great HBK lines outside of the lyrics to his song (which was written by Jimmy Hart). Where his real strength lied was in reacting to things as he was always comfortable giving the proper reactions whether it be with words or looks. Too many people in wrestling will agree with the guys on their side and disagree with the guys against them, but Michaels actually used some nuance. Him, Diesel, and Undertaker were going to tag together against Yokouzuna, Owen Hart, and British Bulldog. They had a promo together and Shawn and Diesel are keeping things lighthearted, and Undertaker takes it to a way darker place, and HBK gets a WTF look on his face, and then Undertaker finishes, and he goes into the "Yeah, what he said," reaction. It's subtle, but it makes him relatable instead of a caricature of how a person would react.
Although I still frequently listen to Sexy Boy, I'm not the biggest mark for HBK. Still, he had one of the ten most successful wrestling careers of all time, and that never would have happened had he not been given the chance to fail. He wasn't great at first, and had he not been able to refine his act subtly during commentary, he may never have caught on like he did.
WWE usually uses one wrestler to do commentary for one segment during Raw each week. Letting different guys take over an entire show and helping them find their voice may lead to some awkward moments, but it could also help WWE uncover the next great superstar.