Maybe more than one, as I have 2 issues right now.
A little background: DD is about to turn 2 has never slept anywhere but in my bed and I'd like it to stay that way. I lay with her for both naps and bed until she falls asleep and then leave the room. We nightweaned about 2-3 months ago. She doesn't nurse to sleep at night but often falls asleep that way at nap just because she is so ready. I take her to work with me everyday as a Nanny and Household Manager. The family I work for has a little girl that is about to turn 3 (hard core sleep trained so I put her in her bed, for naps, say good night and that is it). They are having another little girl in March. It used to just take about 5 minutes to put my get my daughter down and that was about as long as I spent reading to the other little girl so I felt like that worked out. She sleeps in their guest bedroom which is as far away from me in this huge house as possible and has a TV on a shelf, eliptical etc so I really need to stay with her until she falls asleep. She has been giving me a hard time going down lately, mostly waking up as I am trying to sneek out of the room! So, I was thinking that I need to bring a chair into the room that I can sit in and nurse her before laying her down. Then I can slowly move the chair each day or week until it is no longer in the room while she falls asleep. I don't know what else to do but am open to suggestions. She is a very bright and verbal 2 year old but if I try to leave the room while she is awake she just goes ballistic and always comes screaming after me. When my boss is home on maternity leave and when I have a newborn to care for our current arrangement is not going to work for sure. She often wakes between 45-1 hour after going down and loses her mind. Sometimes, I can get her back down for another hour sometimes it is hopeless. AT home, I lay with her she falls asleep and then comes out to get me 2 hours later - no harm no foul!
My second issue is the middle of the night has now become a time when she wakes up and screams at me for milk. This really didn't happen when we nightweaned or passed pretty quickly. She is wide awake and will often pull at my clothes or even hit me. If I turn over or otherwise ignore her she really goes crazy. When she finally calms down she will ask me to hold her and when I do she says "no hold me" and starts these manipulative games. I have tried everything to avoid it getting this bad every night but it seems to be just getting worse.
What doesn't work with her is this: "if you don't stop screaming Mama's going to have to leave" she says "mama leave" but then of course when I do she goes crazy. It is that way with everything "if you don't do x, y is going to happen" she'll say "y" (and sometimes why? too) so no amount of logical consequences seems to work at this point.
I think sitting in the chair and slowly trying to move it away from her is probably your best bet for naptime at work.
I don't have any advise for your nighttime issues, if it were me I'd probably cave and nurse her, so idk.