I planned my transition at work beginning a year in advance with the HR department. By the time I actually transitioned and came into work as a female, everyone at work already knew weeks in advance. The company had two big meetings where the entire staff of my department (there are many 1000's who work there) were told about my impending transition, and were offered the chance to talk to HR or a counsellor about any misgivings they had about the subject.
Plus, as there was quite a social group within my department, who used to go out for a meal, drinks and clubbing once a month, they invited me (pre-transition) to attend as "her". So I did, and it was a great icebreaker and helped immensely and also helped my confidence too. In fact, thinking back to a funny moment, we had agreed to all meet up at a certain pub/bar in 'town'. So I arrived (all glammed up) a little early, and as I approached the bar there were only one or two other people from my work who were there. I recognised one person at the bar and went up and started chatting with him. After a while, he mentioned that he was waiting for some other friends from where he worked to show up, as they were all waiting to meet a colleague who was having a 'sex-change', and everyone was going to meet 'her' for the first time. It was at this point that I realised that he hadn't recognised me! He then asked me where my husband was, because as it transpired he thought I was the wife of another guy from work, who was joining him for drinks after work!!!!! As if on cue, this other guy turned up, and the man I had been chatting to called over to him and said:
"Hey, I've been chatting to your wife for ages, was wondering when you were going to turn up, because 'xxxx' (my name) is going to turn up soon, dressed as a woman!"
It was at this point that this other guy informed the person I had been chatting to, that I wasn't his wife, but was actually 'xxxx'. Luckily they both saw the funny side, and it actually became the major talking point for the evening. As well as being a confidence boost for me.
But going back to my original point (eventually), as I had been taking hormones and also having facial hair removal for at least 18 months before I transitioned, it got to the point in the end that I was only really 'going through the motions' as a guy at work by the end. I was even stopped as I entered the guys toilet by someone who thought I was already female, because of how I looked by then.
So yeah, it was all a big charade at the end, and quite difficult to keep going, that when I did return to work as a female, so many people commented that it was the right decision for me, and it was "about time" that I started living as "who I was supposed to be", which was all really nice comments to hear.
I guess I was just very very lucky in this respect.
But I did do a great deal of planning and preparation over many months in advance, to get to that point in my life.
You might ask, how did I get hormones so long before I transitioned, well I was a naughty girl and self-medicated (don't do this!!!) for a couple of years before I began supervised/prescribed HRT as part of my 'real life test/experience'.