Why is anyone still hesitant about moving their email services to the cloud?

I've worked on email technology since 1980, and I've seen a lot of changes.  It's hard to keep up with the evolution of a technology that is only a utility for your business, not a core competence.  As email has grown more complicated, the fact is that it's incredibly hard to find a company that manages its own email as well as it would be managed by an outsourced and/or cloud service.

In the 1980's, having any kind of email made you a pioneer, and it was all DIY.  In the 1990's, companies began setting up their own email systems using Microsoft Exchange, Lotus Notes,  or a host of short-lived competitors. Bandwidth limitations meant that they typically had no choice but to set up a mail server at each site, and then get them to work together.  

They also had no chioce but to learn how to deal with the evolving complexities of email.  As quantities of spam rose, no company could afford to ignore it, so they found themselves running a bewildering and ever changing variety of products that fought spam and viruses.   As email became more central to business, they had to bring in and administer archiving solutions.  As email became subject to various legal regulations, businesses had to acquire and administer projects that tried to keep their email systems in compliance.  As email became critical to business, they had to worry about disaster recovery and continuity.  Through all of this they had to keep up with the ongoing evolution of email itself.  As long as the net was slow and couldn't be counted on, businesses had no choice but to run their own ever-more-complex email systems.

The first hint that things wouldn't just keep getting harder and harder for business was the debut of Hotmail and other webmail.  These services placed all the complexities of email in what we now call the cloud.  With the advent of webmail, almost no individual has run their own mail system for years.

Individuals can generally tolerate an occasional outage, but critical business email is another story.  Businesses kep running their own systems, and the gap between the complexity of business email and the simplicity of personal email steadily widened.  The success of webmail for personal use didn't automatically transfer to business use.

Of course, many entrepreneurs saw the problems and sought to make a business of outsourcing complexity.  Businesses might or might not retain their own Exchange servers, but they left its operation to someone they hoped knew what he was doing.

I can't point to a single moment when the cloud became reliable enough for business use.  In fact it was probably a different moment for different businesses with different needs.  But by today there is no room for doubt:  a rapidly increasing number of businesses have shown that cloud-based email gave them more reiability and less in-house work.  It is now on-premise email systems that are likely to raises eyebrows.

Accordingly, I have raised my own substantial eyebrows, and I'm trying to understand why some companies still fear the cloud.

I think it all comes down to perceived risk.  Many businesspeople understand how critical email is to their companies and they fear two things:  Internet connectivity failures, and loss of control over critical infrastructure.  What they may not understand, especially if they've had years of experience with email in the pre-cloud Internet, is that the balance of factors have changed, and the risks have migrated from cloud to on-premises solutions.

Internet connection failure has become far less frequent, but will always remain a concern.  However, its worth noting that on-premises systems might keep internal mail running, but not external mail.  Moreover, entrepreneurs have devised cloud-based solutions that actually do a better job,such as, for example the way Mimecast kept up  Blackberry email access for its users when the entire Blackberry network went down.  To the extent that cloud providers take the problem of Internet outages seriously, which they do, they can offer fallbacks that make the internet connection failure scenario a reason to move to the cloud, not to stay away from it.

Loss of control is a bit harder to address, because it is so subjective.  I will say only that you probably  have less control than you think you do.  A highly responsive customer service team can usually meet your needs more quickly than an in-house employee with less specialized expertise.  There's inevitably a leap of faith involved, but by now there are enough examples of similar companies moving to the cloud that it's not a very big leap.

In the last 30 years, email has progressed from a cool new thing to a vital business tool to a dauntingly complex set of services.  The next step is to pass those complexities off to a cloud provider.  Email can finally be a straightforward utility that someone else takes care of, like electricity, water, and telephone.  What business would want to get heavily involved in the details of all of those things, when they could simply pay the experts and demand excellence from their provider?