When 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.

Apple is pitching the iPad and iPhone as corporate productivity tools, and more and more companies are beginning to try them out.

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.

Apple is pushing the Mac Pro Server for business customers, now with the help of contractor Unisys.

"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.

More employees asking for Macs Now it looks like the Mac is starting to make inroads too. The Enterprise Desktop Alliance, a group of enterprise software companies that integrate Mac and Windows systems for businesses, said that during its recent survey of more than 460 IT administrators that more and more employees are asking their IT departments for Macs.

Pickering, who manages all employee computers at AAA, said there's been a noticeable change in the nature of employee requests just this year. "This is the first year, based on four years of supporting Macs, that we've received requests for Macs from what I would consider 'non-standard' Mac users," he said.

The Mac's stronghold in commercial sales has traditionally been to graphics and marketing departments, and that's long been the case at AAA. "But also now my membership department, which doesn't have a traditional reason for having a Mac other than they like the hardware" wants them, said Pickering. The travel department is now asking too.

"Our executive vice president for travel wants it mainly for the form factor," added Pickering. "He wants a MacBook Air."

That's not a unique story: Executives are frequently the reason Macs become an option at all for some companies.

"High-level people will have a Mac at home and they say I need to connect it here, and they have a wake that pulls other people (like the IT department) into providing the option," said T. Reid Lewis, president of enterprise software company GroupLogic, and of the Enterprise Desktop Alliance.

When people in the executive suite make a request they usually get it, no matter the cost. But now even regular employees are getting the choice of something besides a PC, as the idea of Macs being more expensive may also be fading. AAA's Pickering, who reports to his company's chief financial officer, says he and his boss are increasingly taking a longer view of the money they're putting down on computers for their workers. They don't mind paying a little more money up front for a Mac, a computer that, he says, doesn't require as many support resources dedicated to it over the years.

Ben Hanes, a senior systems analyst for Children's Hospital Oakland Research Institute, echoed that attitude. He says his department doesn't focus on the initial cost. Rather, "it's on over time how much it's going to cost us on support. We spend a lot more time supporting Windows OS than Mac OS," he said, pegging it to about three times as many man hours used supporting a PC as a Mac. So Hanes finds the initial investment worth the extra cash they spend at the beginning.

As these attitudes have begun to change, the Enterprise Desktop Alliance is predicting that Macs will climb from 3.3 percent of all systems at companies last year to 5.2 percent in 2011. That's still small, but it represents sizable growth: between 2009 and 2011 one of every four new systems added at companies will be Macs, though much of that will come from companies already deploying Apple machines, according to the IT administrators they surveyed.

But to make some real headway, Apple is going to have to convert non-believers too. That's likely where Unisys comes in. Unisys' contract to sell and support Macs and other "iDevices" to large enterprises and governments could be an experiment for Apple, a testing of the waters. But the timing is good as the commercial market for computers is finally starting to rebound after a couple years of spending cutbacks driven by a weak economy.

But how much heft Apple will put behind this over the next few years is still a big question. This is, after all, a traditionally consumer-focused company, and the projects that Jobs himself is interested in--like the iPad--get the most attention internally. It's not clear how energized Jobs might be about the comparatively stale subject of commercial sales. But there are some signs that will indicate in the next months and years how Apple is viewing this business, said IDC's Shim.

"What will ultimately determine how dedicated they are to this space is what sort of applications they commit to it. That's what we learned in the consumer space: What differentiates you is a unique experience, and they nailed it on the consumer side," he said. "They've done better than anyone else. The question is, how do you do that on the commercial side or on the large enterprise side"