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As a former music hall dancer in Ankh Morpork, what are the odds that the Duchess has known people who ended up having to beg for their food once they were too old or too ill to work anymore? Probably pretty high. And now she is in a position where she is employing people instead and look at what she does...
(It definitely doesn't make her other behaviour okay, but I think it's an interesting nuance).
Look at the specific words Letitia's uses about the situation and then consider... As a former music hall dancer in Ankh Morpork, it seems quite likely that Duchess saw - and probably knew personally - many people who had to beg for their food at the end of their lives, as well as people who were sacked for being too old or too ill or too confused. And then when she was later given the means to make sure that people who worked for her would avoid that fate, she was motivated to make that happen.
Of course, this doesn't make other aspects of her behaviour okay (such as the way she treats the working servants). But it does make her a more nuanced character.
I think it's the line about Granny looking worried a couple of paragraphs earlier, combined with the part where she says "Blast it. You are a witch. A good witch." that gives me this impression. I see it as Granny wants to insist they help Tiffany, but she knows Tiffany has just as much of the typical witch's pride as Granny herself does so... she doesn't insist, she just raises the possibility.
Maybe I'm completely off base but that's how I read it.
And I'd say FriendofMorn's comment could also apply to my reading ("I think the same person could a) make sure you know help is available, and b) not insist that you accept it if you decide differently. Both actions indicate a respect for the person to whom help is being offered.")
Edited to add because I had another thought:
Also, consider headology - this way Granny can suggest they help her to Tiffany without giving away that Granny herself is thinking that Tiffany might need help. And believing that Granny Weatherwax thinks you're a good enough witch to handle a particular problem is reasonably powerful headology.
(I read this book once many years ago and didn't really get into it - probably something to do with my complete lack of interest in football (or most sports). I've decided to revisit it while Mark's reading it and hopefully gain slightly more appreciation for it. It seems to be working although the sports fanaticism still drags for me).