I think there's something to interviewing a subject and where they are emotionally at that moment. Look at NFL 100, and Bill and Tom were in that moment, and it showed. When Bill was interviewed for the Do You Jobs, they were filmed fairly close to the Super Bowls, and they were all clearly basking in it still. Then there's the layer of trust that Bill has for NFL Films, and you end up with him being very open, because he knows if he says something he regrets, they'll take it out. With this project, he clearly is guarded, he knows the team is not good, and my guess is he's withdrawing even more, trusting fewer and fewer people. The product on the field certainly shows that.
Kraft, same way. At the very least, with Bill's age, he knows the end is very near, even if he's fielding a great team. Bill's not fielding a great team, so Kraft is no doubt looking at it very skeptically. There's gotta be a big tinge of regret too. He didn't meddle in the team, and he has gotta be wishing he kept Tom instead. Not that they would have won more, but maybe he could have done something different as far back as 2018. Who knows?