Nagging has probably existed since humans developed speech. It is unpleasant and never productive. Being essentially a one-sided activity, it does nothing for relationship building. In some cases it can be actively counter-productive.
SO why is Microsoft doing it? With their endless digital nagging to users of Windows 7 and 8 to upgrade to Windows 10. This has to be one of the most major and ongoing customer experience fails since the introduction of Windows 10.
I have a policy to never upgrade the operating system of my primary laptop. Because I want a stable machine to remain stable and predictable for its entire lifespan. There is another 2 years of life in my current laptop yet thank you very much.
Some of my clients cannot upgrade to Windows 10 - not until key software their businesses rely on have been upgraded to and supported for Windows 10. The constant nagging runs a risk that an employee might be distracted to click Yes. The constant threat that one day soon Microsoft will simple forcefully download and install Windows 10 is a dreadful experience to live with. What this means is that one day out of the blue everyone will turn up to work, discover Windows 10 has magically appeared, and key software is no longer working.
Why such an abysmal customer experience fail Microsoft? Just when I think you are doing a bang-up job with your Surface products too.
I understand what you are trying to do from your internal KPI perspective and towards your own internal goals. But this bully/nagging behaviour goes beyond being customer-centric to active alienation.
Are you nagging your customers? Is it bringing in the results you want? At what cost?
Seriously, every time I see that #$%^@& nagging dialog I make a note to devote even more effort to planning my move away from Windows.