I just read an Joel's article about Microsoft's breaking change (non-backwards compatibility) with dot net's introduction. It is interesting and explicitly reflected the condition during that time. But now almost 10 years has passed.
The breaking change
It is mainly on how bad is Microsoft introducing non-backwards compatibility development tools, such as dot net, instead of improving the already-widely used asp classic or VB6. As much have known, dot net is not natively embedded in windows XP (yes in vista or 7), so in order to use the .net apps, you need to install the .net framework of over 300mb (it's big that day).
However, as we see that nowadays many business use .net as their main development tools, with asp.net or mvc as their web-based applications. C# nowadays be one of tops programming languages (the most questions in stackoverflow). The more interesing part is, win32api still alive even there is newer technology out there (and still widely used).
Imagine if microsoft does not introduce the breaking change, there will many corporates still uses asp classic or vb-based applications (there still is, but not that much). There are many corporates use additional services such as azure or sharepoint (beside how expensive is it).
Please note that I also know there are many flagships applications (maybe adobe's and blizzard's) still use C-based or older language and not porting to newer high-level language.
How can Microsoft persuade the users to migrate their old applications into dot net? As we have known it is very hard and give no immediate value when rewrite the applications (netscape story), and it is very risky. I am more interested in Microsoft's way and not opinion such as "because dot net is OOP, or dot net is dll-embedable, etc".
This question may be constructive, as the technology is vastly changes over times lately. As we can see, Microsoft changes Asp.Net webform to MVC, winform is legacy now, it is starting to change to use windows store rather than basic-installment, touchscreen and later on we will have see-through applications such as google class. And that will be breaking changes.
We will need to account portability as an issue nowadays. We will need other than just mere technology choice, but also migration plans. Even maybe as critical as we might need multiplatform language compiler, as approached by Joel's Wasabi. (hey, I read his articles too much!)