Ben Haines knows about cloud transitions because he’s lived them. An IT veteran with a resume including Red Bull and Pabst projects, Haines told Den about what he’s learned on making cloud transitions (which he did with Pabst), and the insights a public cloud company like Box has to offer.

As Den put it in his diginomica writeup on his interview with Haines:

Haines argument for cloud is a little different to most. He says that it is all about moving at the speed of business. He says that while IT may have been brought up in an era that worships the server farm and keenly anticipates two year projects, he has no use for that approach. Why? Because the legacy way is very costly for little value by the time projects are delivered. “They deliver on the value originally envisaged but inevitably the business has moved on,” he argues.

Some other highlights from the interview:  Cloud has also forced a change with the longevity of projects. Haines actually banned two year projects because by the time they had been completed, the value they need to deliver has likely changed. Now, Haines only approves projects that take a maximum of 3 months to go-live.

If today’s organizations want to prosper, Haines recommends they look at SaaS companies because they provide a high level of security and agility for the business. Security may not be the point you’d expect Haines to emphasize as a positive for SaaS providers, but as he points out, cloud companies like Google must put huge resources into avoiding outages and data breaches – far more than a typical IT manager can allocate.

The two main steps Haines outlines for businesses to work their way to the cloud are: Know your businesses objectives, and look at your strategic IT operation. In other words, it’s not just a tech project – you have to start with the business needs and issues.

Haines doesn’t mince words on this point:

After you understand what your company is trying to achieve, then you look at your strategic IT operation. People say they have a cloud strategy, but that’s not right – you don’t have a cloud strategy, you have to have a business strategy, and cloud can enable that.

Sometimes the use cases are obvious, due to the sunk cost of a legacy landscape. As Den wrote:

Off camera, he told me about a Microsoft Exchange landscape he inherited where the annual cost of running it were the equivalent of eight years subscription to Google Apps. Faced with that, making the switch was a no brainer.

Haines doesn’t sugar coat the cloud to transition, especially for companies with legacy infrastructures. He warns it’s a long process to move operations to the cloud, but the long term benefits are, in his experience, well worth the effort. But each time, a use case must be carefully established. For Haines, cloud is never an excuse to avoid due diligence.