Government contractor here on site at somewhat large gov't facility, we're fully updated to IE11 on Win 7 now. Before that, we had a lot of people on IE9.
Microsoft support end dates are darn helpful. Kicks people into gear.
Yeah... Microsoft standing firm on support dates and actively encouraging people to upgrade seems to have really made a huge difference. I'm sure it also makes them a pretty penny to maintain support contracts for entities that refuse to upgrade past the official EOL.
Microsoft engineer here. I would assert we want people upgraded more than anybody else on the planet. Our extended support contracts were designed to be cost prohibitive to encourage this point and were nowhere near a money-making venture. The engineering matrix (cost) for a fix across old versions was insane: IE6, 7, 8, 10, 10 touch; 32bit, 64bit, ARM; Windows XP, Vista, 7, 8, Server, Mobile, etc.; 5.5/7/8/9/10 browser document modes; etc. A "single" fix often meant weeks of porting work for engineers after the initial fix was written.