You’re right — listening to customers is holding them back. Tough decision for a company, because these are mostly existing customers (though on the legacy side, considering cloud). The irony is that AWS owes a lot of its success and current product portfolio to listening to customers. The difference is that AWS has customers hell-bent on innovating, whereas Microsoft has customers hell-bent on dragging their feet. The average “we’re interested in Azure” query is probably focused on savings, and doesn’t really understand the whole automation/agility aspect of the cloud. They’re going to forklift everything into Azure — servers, vendors, existing licenses, bloat and even crappy legacy processes.

A year later, they’ll leave “the cloud” for a private cloud option and rave about what a big mistake using public cloud was.

I can’t speak to how well Microsoft does or doesn’t educate its customers, but they’ve told me that customer often isn’t even willing to talk without some legacy IT concessions. The idea is to at least get the customers dipping their toes in, and then perhaps gradually get them educated and willing to adopt the ideas and concepts that scare them with cloud. I think this is a more painful route in the longterm, but Microsoft has different customers, so I think choosing a different path is hard to avoid.