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The iPhone as a media event is a wonderful thing but to an IT manager it is Satan Spawned. This is because it is one of those devices and a large number of employees are likely to buy and bring to the enterprise begging, or in the case of executives, demanding support.

But we don’t really take phones as seriously as we should and anything that currently showing the popularity this phone is showing should be taken seriously. If the rumored licensing announcement between Microsoft and Apple on ActiveSync is true (and some argue it is not) this would make a future generation of this device more attractive and you may be able to hold off supporting the first generations of this phone. But, this announcement assures that eventually the iPhone will be coming into the enterprise and you’d better get ready.

What makes this problem visible is the amazing job Apple has done building demand for this phone. But we still have to deal with that demand. Eventually you’ll have to embrace this device, assuming it is successful, and that goes to the core of getting the company to buy one for IT. In the end, this signifies one of the biggest changes since the PC, or Mac was first created and we probably should begin preparing for that change now.

Before we get started, for anyone buying an iPhone, check out the Cell For Cash service which helps find buyers of old cell phones (may help recapture some of the cost).

The Risk of: Amazing Apple Marketing
Now if I were to describe the iPhone on spec but say it was from LG, Sony, or Samsung and not Apple I doubt many would buy it. It would read like this: First generation phone (new OS, new hardware, new applications), costing several times what people currently spend on a phone, lacking a keyboard (folks have historically hated screen phones), made of glass and metal (think what happens if you drop it), with no removable battery (phone batteries generally are good for a year), and requiring a 2 year commitment with only AT&T (a lot of folks truly hate Cingular). Granted it has a nice UI and it is pretty, but so is Paris Hilton and I doubt many of us would want her to move in for 2 years.

But Apple has done a stunning job containing (for the most part) the bad news and focusing us on the eye candy. The Ads are incredibly well done, they appear to have shills all over the blogosphere (even Slashdot appears to have been hit), and the result is demand for this thing that appears to be in line with a video game system.

Something to think about, if you are being asked, or considering buying one yourself, is that the first version of the iPhone is just a mashup of the ideas from Steve Jobs, Product Design, and Engineering with some last minute adjustments for major problems. The second generation will be based on Steve Jobs feedback after having used the phone and the third based on feedback from the market. The ideal phone should be the third generation and this is when Active Sync is should be designed in making this the phone you likely can’t say no to.

While there is some question whether the first generation iPhone will experience the same problem the PlayStation 3 experienced once released (currently Sony is having a great deal of trouble moving the product while demand last December was through the roof), the reality is a lot of folks are going to be buying these things and, if they have a company approved smart phone, a good chunk will likely want to replace it with the iPhone.

I actually suggest IT gets one, or two, but think of it as a firebreak for now.

How to Get Your Company to Buy You an iPhone
Actually this will probably only work for one or two people in each IT shop. But saying no to someone, particularly an executive, is going to be very difficult if you haven’t actually tried to get the iPhone to work. In addition, people are likely to try to access internal and external web services with this phone and the browser isn’t exactly a poster child for IE compatibility. For instance support for things like Java and Flash are uncertain, which could create problems if say a VP of sales (you know your sales guys will likely buy these things) tries to do his or her expense report and it crashes the phone or doesn’t post, they are likely to blame you.

Also, if you have one or two in house you can demonstrate just what kinds of pain employees will experience and make it their problem. This is much easier to do before they buy the phone in the first place and, for most, once they see that the approved smart phone works much better they will likely pass and wait for something better. There is a new iPhone expected in October.

Finally, this gives you a test bed to run against internal and external web resources. I think it would be silly to count Apple out, particularly given the demand the generation one product has and with the rumored Active Sync announcement (if true). And by generation 3 of the phone, if you start looping in testing, you’ll likely have much of the support solved as applications naturally go through updates and improvements without incurring a substantial amount of additional testing and development cost. At the very least it will be a lot less disruptive and expensive than if you had to make fast forced changes in the generation 3 timeline when the phone could actually work.

Until then, however, you are going to want to say no to those wanting to expense and integrate the phone.

Saying No to the iPhone
We had a long podcast on this targeted at telephony administrators earlier this month. (If you click on the link excuse the sound quality I was in an airport when this was taped and the reception sucked).

There are three ways to try to talk an executive or employee out of trying to get you to support it.

1. It is a consumer device, focused on media and entertainment, and not appropriate for corporate use. This is the strongest argument but it won’t hold indefinitely, which is why I suggest you start getting familiar with the device. Since you likely can’t stop it anyway, you may want to say you will evaluate the 3rd generation product that should support Active Sync and likely support that version making this a soft, rather than a hard, no.

2. It is not designed to be compliant with the standards set in the organization. This is a quick way of saying you haven’t tested the device and believe it will have problems with resources that use Java or Flash. Once again this will likely be fixed by generation

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