I'm going to note a small thing that persistently bugs me: "Ask for Help" at work costs 3 Energy and gives 3 Career Advancement, but "Helping with workload" costs 4 and only gives 2.
I'm not sure why this is that way.
Helping with workload already tells it's a harder task soo... Makes sense it consumes 4 energy.
I highly recommend you to get high work skills levels for most of them to reach 80-90% chance of success and give you a lot of career XP (Roughly 15-18), especially with max organization + slacking off at half energy
Affection gains are invisible, but you actually gain a lot more affection with a girl for helping her with her workload, than the other way around.
My logic was that a girl helping you is progressing your work, which would improve your career advancement more. Additionally, being helped is easier than helping someone else, hence the energy costs.