Of course he knew he would get them, it doesn’t mean he didn’t want them sooner. What if Caleb’s medicals came back with a problem and then Poles had 3 less weeks to adjust accordingly?
No corporate GM is going to happily sit around waiting several weeks on vital information that will determine the very direction of his company when it’s information he could have today. That is not the way these people operate, and thinking they do operate that way is height of naiveté.
I'm going to guess they had a plan of what they would do if there was some glaring issue with his medicals, which was obviously a longshot from the beginning.
The point is it WASN'T information he could have today. But he almost certainly knew exactly when he would get it, so my guess is he wasn't too worried about Caleb doing fun stuff in the meantime. That's not a guarantee or an assurance because I'm not in the business of projecting my views onto others and guaranteeing they agree, but I have seen no indication anywhere that anyone in Bears organization was particularly worried about the medicals coming at his visit instead of the combine. I've seen you and other people (mostly, surely coincidentally, people who loved Fields and have been weirdly critical of Williams for months before this) complain about it, but nobody who actually is involved.