Comment by kettlecorn

It was always going to be difficult, but classic Microsoft blunders and extreme arrogance set back Windows Phone dramatically.

They basically couldn't stick to a strategy and alienated every potential audience one by one. I was trying to make a Windows Phone app back then and for developers they forced them to go through an extremely difficult series of migrations where some APIs were supported on some versions and others on other versions and they were extremely unhelpful in the process.

They had a great opportunity with low-end phones because Nokia managed to make a very good ~$50 Windows Phone. Microsoft decided there was no money in that after they bought Nokia they immediately wanted to hard pivot to compete head-to-head with Apple with Apple-like prices. They then proceeded to churn through 'flagships' that suffered updates that broke and undermined those flagships shortly after they released thus alienating high end users as well.

Having worked at Microsoft I think the greatest problem with the culture there is that everyone is trying to appeal to a higher up rather than customers, and higher ups don't care because they're doing the same. I think that works out OK when defending incumbency but when battling in a competitive landscape Microsoft has no follow through because most shot callers are focused on their career trajectory over a <5 year time frame.