MG, I was just like you in my reservations about asking initially. But eventually I thought "what have I got to lose" so I went to ask the director if it was "appropriate" and she was very supportive and said that it was perfectly OK as long as it was made clear that it was a totally private agreement.
So then I approached Olivia's favourite carer (this was back when Olivia was still in the baby room, but they had all also "got to know" Charlie as he always got passed round for a cuddle at drop off and pick up times as a newborn!). She jumped at the chance, so I wrote down the date and the rate of pay and all our contact details and told her to call me when she got the chance. (I did this to "leave the abll in her court" so that if she was not comfortable about it in any way she could just not ring me IYKWIM?)
Anyway, she rang me and then we took it from there. She then babysat a number of times, and then also babysat Olivia and Charlie on the evening of our wedding (bathed them, put them to bed etc etc and stayed over night in a separate cottage with the children and my matron of honour at the venue where we had our wedding (country house) so that me and DH could have a wedding night as a couple!
Since then she has babysat a lot for us: about once every couple of months at least: I trust her TOTALLY and she has become a really lovely friend to us and the children.
HTH?
My advice would be to check with the director first, just to be "upfront" about it, then take it from there.
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