Will the IT guy learn to love Apple?

iPadWhen you’re listening to music, it’s likely your earbuds are plugged into an Apple device. Making a phone call? One out of every five people buying a smartphone are choosing an iPhone. And Apple’s share of consumer laptop sales jumped to 10.6 percent in the last quarter.

Now here’s the big question: Does your IT department, the guys who think it’s just fine that you’re still using a Windows XP laptop (and P.S., stop whining about it), give a hoot about all this Apple stuff?

Apple executives hope so. The pitch the company has been making in recent months is simple: Employees are already using plenty of Apple products on their own time and like them, and the iPad is a great, lightweight tool for Web-based corporate software. If you thought this was just lip service, Apple is even now working with the decidedly old-school consultants at Unisys to approach big corporate and government customers.

If Apple can make these sorts of corporate inroads, it could be Steve Jobs’ greatest trick yet, because he’s got a lot going against him in the corporate market. As of the third quarter of 2010, Apple sold 1.4 million of the 40.8 million computers sold to commercial customers, according to data gathered by IDC. That’s 3.6 percent of all corporate computer sales.

Blame history…and inertia. Large companies usually have a contract with a Windows-based PC seller, often a third party. Switching contractors could result in higher costs and a lot of hassle, and can also be stymied by an old-school perception among the often conservative IT outfits at large companies that Macs are “toys,” and can’t integrate easily with Windows-based systems. On the mobile side, corporate IT shops long ago became comfortable working with Research In Motion’s Blackberry; supporting the iPhone could add new complexity and potentially more cost to their work. Many people don’t even know Apple sells servers. (It does.) And the iPad? Well, you could argue the touch-screen tablet computing market didn’t exist a year ago.

Andrew Kaiser, a former Apple business sales manager who hawked enterprise systems to companies of all sizes until recently, said often the biggest barriers in selling were opinions formed sometimes decades ago, before Office for Mac, before virtualization, and before Apple switched to Intel chips. “Some had no idea Apple could integrate into a Windows platform,” he recalled.

Employees like Thomas Caleshu, an interactive producer for educational software maker WestEd, have seen that firsthand. Caleshu is an iPhone and Mac user outside of work, and though he said there were no technical issues in getting his company’s IT guys to add his iPhone and MacBook to the network, they were definitely skeptical.

“Some of the established IT people didn’t trust or believe that I could sync my calendar on my phone, and on iCal on my Mac, and in a (corporate) Web interface,” he said. “I had to prove it to them.”

That skepticism is almost always rooted in something real–bad past experiences with Macs before the technology improved, or in times before Apple products were properly compatible with Windows-based hardware. And even though much of that has changed, the features that now are selling points for consumers with the iPhone or the Mac–the focus on design, the cachet of the Apple brand, the idea of a unique experience–doesn’t go over as well with the guy who’s managing that stuff at work.

“IT managers in the past have said, ‘I don’t want unique experiences,'” pointed out Richard Shim, analyst for IDC. For IT department managers, people on different systems often just translates to a huge headache.

Plus, there’s the reality of enterprise applications not being written with the Mac in mind, which is a huge hindrance for companies who’ve invested in software for their employees, Shim added. “Especially because some custom, propriety applications are expensive to create and maintain, as is having to come up with an alternative when people are used to using the old version.” And many people are simply averse to change.

Apple’s recent announcement that it is unlikely to support Java in future versions of the Mac is also sure to irritate plenty of IT folks. Though others might say not that much has changed anyway.

“As far as I’m concerned, they don’t support it today,” said Robert Pickering, vice president of Information Services for the auto club AAA. He expects it will mean his employees will have to patch and update their software on their own, which he says they were already doing because Apple doesn’t support the most up-to-date version of Java anyway.

And of course, there’s a rich tradition of labeling Apple products as unnecessarily expensive.

All of those things amount to big hurdles, but Apple has one very important thing going for it: The end users are often very familiar with their stuff. And with its momentum in mobile devices and the overall “consumerization” of technology, now is the time to make this kind of move.

Apple has sold more than 12 million iPads worldwide in the first six months–for comparison’s sake 170 million PCs shipped worldwide during the same time period. And the iPhone, already a success, has even beaten the workhorse of corporate smartphones, the BlackBerry, in unit sales for the first time ever. IDC counted 12.4 million BlackBerrys sold during the third quarter, compared to 14.1 million iPhones.

The people buying those for personal use have jobs, and like Thomas Caleshu, are increasingly asking their corporate IT folks to connect their new Apple device to their network. And more recently, large companies appear to be complying: Apple COO Tim Cook said recently that two-thirds of Fortune 100 companies are testing or deploying the iPad on their networks, and 85 percent are testing or deploying the iPhone. Those companies reportedly include Citigroup and Bank of America.