Agree, I like Martin Place Bar. The bar inside Regent Place on George Street is swanky, and The Belvedere is simple but functions. Sydney, we're getting spoilt when it comes to the bar scene. Those lane way bars are also something. Helm Bar at Darling Harbour is also good for those after work jam jar cocktails.
Although it's small, Grandma's is great for a smaller group - grab some comfy seats and a cocktail menu and you're set! It doesn't get too busy during the week too (Fridays can sometimes be hectic though)
And although it's nothing special, I kinda like Martin Place Bar for after work drinks. It's right by the station, it's got a bit of an outdoor area and it's just one of those easy bars to hang at.
Well it really depends on what you are after. I know that a lot of the so called "upmarket" places like the Establishment and Hugos have various afterwork promotions like ladies drinks etc but I would favour some of the more out of the closeted away places like Grandmas in Clarence St or Since I Left You on Kent. This new style of bar which more resembles Melbourne's awesome alleyway bar scene is popping up all over Sydney at the moment and they are awesome.
Spring Street Social, Bondi Junction. Serves up cocktails made with duck fat whiskey and served in a relaxing old brown leather chair like your dad had in his study. Think cigar's, long cigarettes, and old school blues. It's the Shady Pines of the east - added with a touch of swank.
I love going to Newtown for the great bars and fun atmosphere to take a night off. Theres a bar called Home Bar that I like. Also, the Courthouse is good! Newtown is just a great area for going out to drink, such friendly and interesting people aswell!
If you're in the rocks area - definitely Cruise Bar near the cruise terminal or Glenmore Hotel for their great view from the rooftop bar. If you're around the CBD, I like Watershed or Ivy. Friday night at Hugos in the Cross is always quite popular
In my opinion you can't go past Grasshopper for a delicious after work cocktail with atmosphere. If it's crowded in there, there are so many other options like The Stitch, Tankstream Way with Marlowe's Way and others right around it, The Arthouse for a more 'pub' like atmosphere, or the classic setting of the Opera Kitchen at Circular Quay and places in the Overseas Passenger Terminal. Going out after work has become MUCH more fun these days in Sydney!