Hindsight is 20/20 but I favored the hiring of Ted Thompson at the time because I thought Harlan made a mistake in promoting Sherman to the VP/GM job. Harlan's master stroke IMO was making the decision in '91 to have one "football man" in charge of all football operations with as little interference from the executive committee and board as possible. That corrected the structure of the organization in my view: One man was to oversee football operations who could hire and fire the HC and take a long-term view regarding personnel.
However, Harlan "loved" Sherman so much he went away from that formula. IMO Sherman is a very good person who appreciated the history of the Packers as much or more than any other HC since Lombardi. And I think he was a decent HC but he had never trained to be a GM. In my view it wasn't Sherman's fault he accepted the promotion, but because of his inexperience (and had another full time job as HC) he was set up to fail. Look at his "mortgage the future" forays into free agency and even more telling, look at his record drafting: He had almost the exact same scouting and personnel departments that Thompson has used and look at the dramatic difference in results. (At the time, I was very surprised Thompson didn't bring a single scout or personnel guy when he became GM.)
As we all know, in 2005 Harlan came to the conclusion (again) that the GM and HC jobs were too much for one man and one man should be in charge of all football operations. (Harlan has said it was how much time Sherman was spending as GM with the Mike McKenzie situation that convinced him Sherman was over his head.) So Harlan determined to hire a GM and again split the jobs. At the time I thought he made a mistake in requiring that the new GM would have to agree to keep Sherman on as HC, but that was a minor error on the way to making a huge correction. When he "stole" Thompson back from SEA I was delighted, not only because Thompson had spent more than a decade training to be a GM, but because he was mentored by the great Ron Wolf.