Directions on Microsoft has published its list of top ten hurdles for Microsoft in 2006. Here they are in the order they were published with our added commentary:

1-Explain to corporate customers why they should buy Windows Vista without waiting to purchase new hardware first.
a)Explain to ISVs why they should make the investments in Vista given that in many cases Microsoft will be looking to eliminate them from the marketplace. This is a tough sell. Because of massive changes to Windows drivers, and major programming changes from presentation layer -WinPF, networking-WinCF, data storage – WinFS and LINQ, and workflow-WinWF; ISVs will be have to make a lot of changes. But unfortunately they have to do a huge amount of tracking whazzup at Redmond and the best methods to do the programming are changing on the go right now and into the next year (if not two) as Visual Studio and the APIs are still being “fine tuned”. Microsoft will have to do a substantial amount of persuading or perhaps explain to ISVs and partners that, really, maybe they should be VARs for Microsoft technology.
b)Explain to OEMs why to feature Vista in their consumer product lines when the current $500 and under total system package gets broken badly by Vista and its hardware requirements. Selling new-found security and 3D GUI may not be enough to withstand consumer expectations let alone an Appletel challenge.
c)Convince consumers there is more to Vista than “security fixes”.

2-Publish a definitive set of guidelines on developing Windows applications to reduce buggy software and security flaws–and then enforce it.
This is a third call for a Security & Reliability Crusade in Microsoft Country. Given the pronoucements of the Second Trustworthy Computing Crusade and its mixed results including the continuing vacillation and caving-in to a “Just Good Enough” policy whenever market demands dictate (and given a very level stock price, that is quite often lately), this Crusade is best known by its Crooner name -> Hopeless, Hopeless, Hopeless.

3-Communicate its intent for entering into the managed-solutions market, as well as which parts of this business it will leave to its partners.
This is a tough nut. Microsoft will have to fess up to its would-be partners and ISVs. If any market is big or even hints of being big, they would do better to become a Microsoft VAR(but see points 2, 4, 8, and 10 for the VAR downsides). If partners insist on entering the market as an ISV, have a brass ring strategy – buyout by Google or Big Blue … or any Big Sugar Daddy.

4-Quickly distribute to developers the next generation of basic tools to support Vista.
Ouch. We have been forewarned that Microsoft will be switching to Agile Methods in its Tools division. Developers and ISVs would be better served to wait and see how Tom Cruise does it in Mission Impossible III. Fundamental problem – jumping through the Vista Change Hoops and Campus Internecine Warfare are each sufficient to making Agile Methods inoperative.

5-“Gel” its online strategies, such as starting up a new advertising platform and clarifying these offerings to small businesses.
Remarkably, Microsoft has great latitude here and the cash to leverage it; but maybe too much hubris to make the smart plays and buyouts.

6-Make consistent its strategy for enterprise resource planning so its partners can support, sell and transition new customers to its newly named Dynamics product line.
In contrast to the previous point, Microsoft is extremely weak here for two reasons. Its VARS and ISVs have been bruised and beaten by its constant “take aways”. That is the only consistency in strategy. Why not be absolutely brutally frank with partners – be a VAR or else. Second, integration and interoperability are paramount here as well – and with Web Sevices only and on our terms, Redmond is at a distinct disadvantage to its competitors on interoperability. So then they are selling to a Windows primarily market – and that market has a few noses out of joint due to… this is not a winning story line.

7- Move forward on its Dynamic Systems Initiative, potentially a new standard for software that manages other software. Also, document components, such as the Systems Definition Model, and create and promote related developer tools.
No comment.

8-Establish its policy on product releases and show discipline in adhering to it.
See 2-above and Hopeless, Hopeless, Hopeless.

9-Justify the Xbox 360s high price amid pressure from competitors; develop a must-have Xbox game title for consumers; and eliminate the Xbox shortages and glitches that occurred early on.
This is very serious. When South Korea starts disciplining its companies for “pricing below costs” the writing is on the wall. Microsoft cannot continue its below cost monkey business too much longer. Redmond better have an intelligent exit strategy here.

10-Align pricing of its Software Assurance maintenance plan licenses with its actual product release cycles.
Again, see 2 and 8-above. The tune is Hopeless, Hopeless, Hopeless.

(c)JBSurveyer 2005