Microsoft: Misery sure loves this company

Compared to Apple’s news that Siri will soon be able to talk you out of traffic tickets, Microsoft’s headlines for the start of the week are a serious downer. Another flagrantly missed market opportunity, a tepid product enhancement, default promotions, and executive departures are countered by only one semi-positive announcement in Forbes’ annual list of who amassed the biggest money pile.

For starters, take Apple’s new CarPlay, surely the next trend to which Microsoft applies its tried-and-true innovation strategy: watch others invent it and succeed, then build a sad version 1 competitor, and year after year thereafter, slowly crawl into the No. 2 or No. 3 spot with the ever-present lotto-luck possibility of leading the segment for a few minutes.

[ Microsoft is saved! But the CEO sweepstakes rage on ]

To be fair, Microsoft tried the concept of smarter cars first via Microsoft Sync, a deal brilliantly predicated on an exclusive relationship with Ford. Both companies claim the platform is a huge success, though Ford doesn’t market it much and people tend to forget Microsoft even offers it. However, insiders claim that more than 50 people are actively using it. In fact, the deal has been so successful, Ford is considering dropping Microsoft in favor of technology from a robust and promising leader in the mobile market: BlackBerry.

Siri, what is a winning strategy?

Apple, on the other hand, foolishly made an open deal with multiple car companies (including Ford), had tied its product to a successful brand and technology (iOS), and even made sure you buy more of its products by relegating CarPlay solely to compatibility with the iPhone 5. I think Microsoft should watch this segment because it sounds like a real loser for Apple. It should be supereasy to dominate a few years from now.

In other product news, the SharePoint team is announcing Project Oslo this week at its conference in Las Vegas. Oslo is another exciting technology that Microsoft says will promote the wonderfully vague goal of “enhanced collaboration and team building.” It’s a supposedly benign Big Brother for the workplace that’ll watch the work you do, with whom you do it, and which Microsoft tools you use to “get things done,” so it can “better connect you” to the people and information you need the most.

If you’re wondering why this not only gives you a headache but also sounds familiar, it’s because Microsoft used the same marketing message for on-premises SharePoint Server 2013. Now, Oslo aims to bring it to the off-premises Office 365 version because as Microsoft VP Jeff Teper puts it in clear, buzzword-free language, “We’re optimizing on the cloud.” I’m sure there are absolutely no Office 365 product managers in Vegas trying to get hammered enough to forget the shambles their professional lives have become.

Redmond’s revolving door

Speaking of Microsoft professionals, let’s move on to exciting executive news. Continuing its trend of promoting from within to engender fresh changes in Microsoft culture and leadership, Redmond announced it’s promoting Mark Penn to a clearly defined gig: head of strategy. Penn has been at Microsoft for several years and is responsible for the “Scroogled” campaign that everyone (read: no one) thought was a huge success. Prior to Microsoft, Penn held the undoubtedly techno-savvy job of political strategist, the high point of which was when he helped Hillary Clinton’s 2008 presidential bid crash and burn. Shortly after that he joined a big technology company — undoubtedly not at all related to his success in politics.

Meanwhile, as a probable consequence of Penn’s ascension, Microsoft loses two executives who were both passed over for the same gig. Actually, Microsoft delisted one of them, Tony Bates, not only for head of strategy, but also for CEO, losing to Microsoft longtimer and email poet, Satya Nadella. However, analysts agree that bypassing Bates for both jobs was the right thing to do now that Microsoft is looking for new leadership perspectives. Think about it: He came to Microsoft a dejected, beaten man whose only accomplishment was making a huge success out of Skype and selling it for a massive profit — mostly for himself.

I’ve never heard of the other soon-to-fly exec, Tami Reller, though her long anonymity despite holding senior leadership positions speaks well of her big-corporate political talents.

That old Gates magic

All in all, the only really positive Microsoft-related announcement so far this week is that Superbrain Emeritus Bill Gates has reclaimed the top spot as world’s most ridiculously wealthy man in Forbes’ annual “Who’s the Fairest Billionaire” competition. His reported net worth of $76 billion would have been beaten by Flappy Birds inventor Dong Nguyen, if he hadn’t folded under pressure, and only narrowly exceeded the growing wealth of Justin Bieber’s legal team. If Bieber manages to avoid rehab in 2014, I think his group has a great chance in 2015.

My guess at what spiked Gates’ fortune this past year? I’m pretty sure he invested in Apple.