Regarding this transfer window, I'm mildly optimistic. I have a strong impression that Williams knows how he wants the team to be as a footballing entity and when asked "How about this guy" will give a useful opinion. Contrast that with,
1. Russell Martin. His first 'must have' import was Fisher, who he had to have so he could build a strong defence around him. The club played over the odds to get him. Who would trust his input on transfers after that?
2. Michael Duff. I was optimistic about Duff (I am usually optimistic, it's more fun) but it became clear he had no vision for his Swansea team and I suspect that for every player discussed he just said yes OK.
Successful transfer business is built around good footballing input and good business management of the transaction. We've been missing the first bit for three seasons.