This is the difficult question that everyone will be tuning into Digital WPC to find out.

With Microsoft’s now legendary Chairman Bill Gates heading off into the sunset, two men stand at top of Microsoft with clearly different agendas.

First, we have CEO Steve Ballmer known for ruthless acquisition, competition and enhancing shareholder value and customer experience with every move. This is the guy that wanted to buy Yahoo because he was convinced that Microsoft can’t do it on its own.

On the other hand, there is the Chief Software Architect Ray Ozzie, sitting in a role that Bill Gates had newly revealed conflicts with the Steve Ballmer’s direction for Microsoft. So here is my short list of questions:

What proof is there that both Ballmer and Ozzie can coexist, or even work together, to innovate Microsoft past its monopoly-empowered dominance that seems to be crumbling with each passing day?

Which one will take a point to the partners that the software world as we know it now, and the services industry that exists to support it in its current state, will cease to exist?

Who will be the face of the Microsoft accountability to the partners and customers, in the climate in which Microsoft solutions are seen as too expensive, too unreliable, too Vista?

Who will step up into the role of a developer evangelist, to reinvigorate developer community into finding Microsoft’s technology as sexy and unencumbered by the Microsoft’s ever-present need to control everything and flood the system with “me-too” instead of open integration with market leaders?

Where will Microsoft enable me to make money as a partner? If you are pushing for services, will I receive a cut from the subscription fees you will charge your customers to access your cloud service and access my applications for free? Will you be sharing your ad revenues with me to entice me to write applications on your platform instead of the one powered by AWS, Google or Apple? On the services side, will you continue to push solutions direct to our customers (OneCare, Edge services, cloud services) or will you respect the partner boundary and give us the decision making power of making you a platform component instead of a total solution reseller?

These two men are stepping into big shoes and they have big questions to answer, particularly now when Microsoft finds itself far on the tail end of cloud services and online advertising, crumbling monopoly power over the desktop, customer dissatisfaction with Vista, customer confidence of 2003 – 2007 releases of servers and no upgrade intentions.

Microsoft has to convince both the marketplace, the developers and service partners that it is the future of computing and not Google, Apple, Linux and emerging cloud services. Day by day Microsoft loses its status as the best or perceived best solution starting with the desktop but going into mobility, communications, entertainment, services all while flooding the market with me-too products that fail to challenge the dominant solutions in terms of openness, quality, reliability and price (see: XPS, SilverLight, Microsoft Online)

Your move Microsoft. Give us your best sales pitch.

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