So far, new Microsoft boss Satya Nadella has tried to have it both ways, with a strategy described as “cloud first, mobile first.” That’s a nice way to say cloud and mobile are equally (and hugely) important to Redmond.

But sometimes it’s just not possible to have something both ways at the same time. Then what happens?

What gives?

Microsoft is a company large enough to devote too many resources to any project(s) it chooses and end up with a Vista-sized mess. Yet, sometimes strategy comes into play and Microsoft must decide. What happens when the who’s-on-first decision can have only one answer?

That question has come up, and been nicely reported by Andrew Orlowski in The Register, who describes the uproar — Cortanagate — created when a Microsoft exec suggested that Cortana, Microsoft’s Siri competitor (and World Cup football tout) might someday land on iOS, Android and Windows, in addition to Windows Phone.

Not surprisingly, Windows Phone fans were upset that their girl Cortana might become friendly with other platforms. Trying the quell the upset, Microsoft’s company line because that wherever else Cortana goes, she will always be best on Microsoft platforms.

It seems impossible that where Cortana is concerned both mobile and cloud strategies can prevail at once.

Microsoft’s dilemma

What should Microsoft do? It depends on how Cortana is supposed to play into Microsoft über alles:

• If cloud is #1, then getting Cortana on every platform, right away, is the best strategy. By using Cortana becomes as a Trojan Horse, the personal assistant can direct her users to other Microsoft services and partners. This strategy uses Cortana to monetize other companies’ hardware sales. A 5-percent adoption rate for Cortana on Android would likely trump 100-percent adoption on Windows Phone sales.

• If mobile is #1, which means Microsoft is considers hardware revenue more important than Cortana-driven services, using Cortana to draw customers to Windows Phone (and only Windows Phone) makes sense.

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If Cortana becomes a super differentiator versus iPhone and Android, Microsoft must decide where she belongs. Is Cortana a global weapon or merely a strategic tool for driving Windows Phone sales?

My recommendation? This is not a right-now decision, except that Microsoft should build the most compelling Cortana possible and start creating ways to drop her onto other platforms. Cortana seems more hardware-dependent than Siri, so that may be an obstacle to overcome.

Cortana would be a great boost for Windows, but it is hard to imagine Apple or Google being quite so welcoming. It may not be possible to bolt Cortana onto these other platforms, though a Bing app would be the likely method of choice. Note how Google brings its features to iOS using apps.

However, if Cortana could be used to hijack iOS and Android devices into Microsoft’s “eco$ystem”, then even if/when Windows Phone bombs, Cortana could bring Microsoft goodness to a world that would remain unwashed otherwise.

Cortana is still not real to users, so it’s too early to anticipate the value Microsoft’s personal assistant will create. The demonstrations look super, but demonstrations usually look super and Microsoft is no slouch.

If Cortana becomes an also-ran, Windows Phone will be in deep trouble. But, if Cortana is considered too valuable not to take cross-platform to Apple and Google, Windows Phone’s troubles could be even worse.

photo credit: Zathraas via photopin cc