Those of us who have used Microsoft software before are numerous. Those of us who’ve been involved in Microsoft’s licensing before are equally numerous, however, with few exceptions, they require some form of counseling and possibly pharmaceuticals.

Take Microsoft Office, for example. You would think that the question would simply be “what is the easiest way that my company can actually purchase and legally use the software?” Sorry, friends and neighbors, it’s tougher than that. OEM software, retail software, Open License, Open Value, Open Value subscription, Office 365, Office Web apps, Office with Lemon (okay, I’m making that one up).

You get the idea.

It’s fairly routine for us, when working with a new customer, to discover that they have several versions of Office throughout their organization. We refer to these situations as “geological digs.” What ends up happening in these environments is you have people throughout the organization each with their own user experience and user environment. Some might be able to use the new Office document formats, some might only be able to use the new formats, some wouldn’t understand the new format if it bit them in the nose.

On top of all this, consider the support. When someone calls and says “I have trouble with Word” to support we give that person differs dramatically on the version that they’re currently using. So support costs are increased.

At this point in time the flagship products for the stock generation are Office 2003 and Microsoft Windows XP. The problem is, these things work. They work very well. However, these things are also well past their prime. So we’re faced with a dilemma.

The web is full of articles and sites that are aimed at tell you why you should upgrade. They do a much better job than we ever will with that discussion and argument. The question we also run into is WHEN should we upgrade?  Are there certain times where it’s more advantageous than others to invest in new software for the organization?”

The answer there is a lot simpler. The answer is “yes.” And here’s why.

Microsoft, as many of you might know, runs on a fiscal year ending June 30. And like every other public company out there, they want to look good when June 30th rolls around. How do they do this? Simple, they do this through sales.  Yep, Microsoft wants you to buy more stuff before June 30th.

Also they want you to buy their newest stuff. No surprise here, when you think about it. This is why I tell people whenever a new version of a product or new product comes out there’s going to be about a three-month honeymoon period, where Microsoft will create and have incentives for you, the customer, to purchase the stuff.

The simplest way to know about these is, of course the web. Microsoft maintains a site  This shows you the latest incentive program that Microsoft has for organizations purchasing Microsoft software, and it’s updated every month. Microsoft seems to become most aggressive for the software sales during the months of May and June. There are also additional programs usually in the November-December time frame for everybody else’s end of year.

Microsoft Incentives Site

Home Page for Microsoft Incentives Site

This doesn’t mean that Microsoft doesn’t have programs or special deals or the like throughout the rest of the year. There’s always something up on the web from Microsoft. Usually it deals with license programs for new releases. But that’s not always the case.

So how do you keep track of all this? Simple, you don’t. That’s where working with the Microsoft Partner (such as Yours Truly) works to your advantage. Part of our job, part of our livelihood in fact, comes from our relationship with Microsoft. Part of our value to our customers is knowing what our customers are looking to do in the next six months and then developing the best strategy moving forward taking advantage of these incentives and programs. And of course, it’s not just Microsoft. Other vendors, Cisco, SonicWall, others have incentives and programs as well. But from our experience, Microsoft seems to lead the pack in terms of peculiar licensing and peculiar promotions. And, since licensing on the level of your desktop in sheer numbers is greater than most others, special deals and promotions can have a greater impact on your organization’s bottom line.

So here’s the question: if your company has been using the same version of Office and Windows for the last X number of years, and are warm and happy, should you look to upgrade? Again, look to your Microsoft Partner. If they’re worth their salt, the discussion should be based around what the new software and the new licensing can bring to your organization in terms of savings and efficiency. If it sounds like a sales pitch, perhaps you’ve got the wrong partner.