Steve Ballmer was an underrated CEO

Having spent some time at the Microsoft campus, I can tell you this is basically the consensus view from employees today. Ballmer was not a cool, trendy, or fun CEO who people rallied behind - but he more or less "got the job done". He was the captain of a massive ship with a turning radius the size of a continent guiding it through icebergs.

Azure's success was specifically set in motion under Ballmer. Owed to the fact that it was developed to Microsoft's strengths (enterprise support) that it didn't piss off too many of their partners and sales channels. Same with Office 365 and all of their other successful services. None are glamourous - but all are impressive with how not awful they are given their design constraints.

Even things like Surface, while considered a failure, did its intended job of getting hardware partners to get their act together and make better consumer products.

I remember working with Microsoft as a client in 2000-s, it was awesome. We started as a startup, and enrolled in a BizSpark program. It gave us basically free access to Microsoft tools and with very responsive support.

We later transitioned into volume licensing, that also was simple and straightforward. The business side of Microsoft was a streamlined unstoppable train at that point.

The technical side, not so much. Microsoft was still trying to be the only software company in the world, and it was pushing all kinds of WPF, WCF, and other WTFs. So they completely missed hyperscalers and the growing market of Linux-based servers.

Wow. Microsoft Licensing was the stuff of nightmares.

You could literally get certifications in Microsoft licensing. There were experts whose only job was Microsoft Licensing consultants.

MS’es licensing was so bad you would get different quotes from the same person within a week of asking because almost no one understood it.