With all the hubbub and speculation surrounding Yahoo these days (did you know that employees yodel at the end of their company meetings?), I thought I’d take some time to reflect on the two years I spent in Bing. I was reminded of Bing today during a depressing conversation with a former coworker who soldiers on, nobly, in That Great Darkness. Though it’s been several years since I left, I still remember Bing as the time when I most despaired for Microsoft’s future.

Bing is a madhouse. The inmates are running the asylum, and it’s rotten to the core. The horror! The horror!

And I’m not talking about the product. The search engine itself is solid – in fact, tragicomically, users actually prefer Bing when they’re shown its search results side by side with Google’s, as long as you swap the logos between the companies’ results. That’s right: people prefer the Google logo. All those years of whimsical logo variations – the snowmen, the Einstein homages, the Christmas lights – paid off.

In all seriousness, Bing is solid. But it doesn’t matter because nobody cares. Search is a utility – or, rather, Google by its staidness has reduced web search to a utility – and unless someone does something creative in that space, real soon now, we’re about to get stuck in another decade of Altavista (I date myself).

No, no. When I say Bing is the heart of darkness, that it represents the very worst of Microsoft, I’m not referring to its dismal market share. I’m referring to its people.

[Caveats are obviously needed at this point. Please see (*) paragraph near the end before you start convulsing with rage.]

Bing, more than any other Microsoft team I’ve been in (and I’ve been in a lot: Office, Tablet PC, MSN, Windows, and others), is filled with overly politicized people pursuing Machiavellian schemes to forward their career ambitions. It was a truly odd, odd place to work.

Most Microsoft teams are filled with engineers and leaders that simply love technology. Although every large group of people, whether at work or in social settings, tends to develop some basal amount of “politics” (in quotes because I mean it in the same sense that you read it: disingenuous manipulation of people in pursuit of ulterior motives), the typical Microsoft engineering team tends to be relatively apolitical, instead favoring logic and passion as primary drivers in decision-making.

Not so with Bing. From the outset of my time with Bing, it was filled with people, especially at the topmost levels, who seemed primarily focused on their own ascension. Take, for instance, its former Director of Test, the top leader of Bing’s hundreds of testers. One day his office was simply found inexplicably empty. It turns out that he had accepted a job with Google. Not to worry, though! Within two days, he was back in his office at Bing – not only back, but back in a huge way, complete with a welcome-back party thrown by the General Manager, followed by his passion-filled email to all Bing employees expressing how Bing is the only place to be, how his management really understood the fulfilling rewards he wanted, how they supported him oh-so-well and convinced him that there was, truly, no place like Bing.

No place, that is, unless you plan to go back to Google several days later. Not a joke, not a typo. This man literally joined Google for a day or two, came back to Bing, celebrated at a welcome party enthusiastically thrown by his management, sent a glowing email to thousands of employees about how there was no place on Earth like Bing, no management on earth like Bing’s management, and then went straight back to Google several days later when given a better offer.

At this point you’re about to navigate to some other web site, convinced that I’m throwing out the one oddball outlier anecdote that makes for great conversations at cocktail parties, the one ridiculous case that everyone can chortle at as they politely scan the room for Sergey Brin. But this sort of stuff happened all the time. Like the head of Bing’s front-end engineering: gone to lead IE one day, back the very next day when Bing offered a sweeter deal, then off to eBay as soon as the promotion was sealed. Or the director that spent many of his one-on-one’s with his reports complaining about how he wasn’t being promoted quickly enough, how the management team wasn’t being fair to him, blah de blah de blah. This self-centered behavior pervaded the entire division, affecting its decisions and veritably guaranteeing Bing’s inevitable death unless Google, like most of Microsoft’s previous competitors, summarily shoots itself via a series of disastrous decisions of its own commission. (WordPerfect? AOL? Sun? Too many to name, all undone by their own two hands. Really, Microsoft historically only needed to stay standing long enough for the whole platoon to drop like flies. In order to finish first, you must first finish, etc., etc.)

But none of this is interesting. The rot at Bing has been old news at Microsoft for years. What’s more interesting is the topic I debated with my former coworker today: how exactly does this happen to an entire organization with a company? Do all the political people just find each other, perhaps with some sort of innate Scheme-o-Meter? (Astute observation from a former manager: ‘A’ people tend to hire ‘A’ people, ‘B’ people tend to hire ‘C’ people.) Or do other environmental dynamics foster and encourage self-serving behavior?

I have a few conjectures:

People look out for themselves when there’s nothing to look forward to. I often tell managers to analyze the efficacy of their own leadership if members of their team start asking about career-related topics all the time. Most people, at least most engineers, tend to resort to career last. Engineers mostly want to work on something they believe in, to be part of something that will change the world. When things are going right, career tends to be a side-effect of participating fruitfully in a meaningful project. But many Bing employees simply don’t believe it can be successful. I once witnessed a debate between two leaders in Bing about whether Microsoft network proxies should be modified to redirect all employee traffic targeted at Google towards Bing instead. Never mind that employees were using Google; someone actually thought the way to win was to force them to use Bing. “I know, we’ll make them use it!” Political people recognize and love each other. Lemma: apolitical people avoid political people. This needs no explanation, as I take this to be self-evidently true. Politics are needed when other means are exhausted. Highly talented individuals don’t need politics to be successful. (Now whether those same individuals would be more or less successful with the judicious employment of political maneuvers is both a topic for rigorous debate as well as, I’d point out, a fair indication as to which sort of person you are.) Bing started as MSN Search, during a time when “portals” were all the hotness; a search engine was the price of entry, a rather boring speed bump on your way to collecting the boatloads of display ad revenue you were promised. It’s hard to attract great people to a project that’s perceived as unimportant. Yet the same people who led the 30-person MSN Search team retained key leadership positions in the 3,000-person Bing team. How, exactly, does this happen? Astronomical growth in team size attracts people who love, well, astronomical growth in team size. Bing was on steroids for many years, doubling in size every so often by hiring and acquiring. One coworker who led a team of about 40 people before joining Bing was suddenly, a few years later, managing over a thousand people. Perhaps this sort of growth represents a sort of career gold rush for the ambitious. If enough of those people get together, there’ll be the Good, the Bad, and the Ugly: drama must ensue.

[*] These are merely conjectures, generalizations which are easily disproved by exceptions. Not everyone is overly political in Bing. In fact, I know a bunch of technology-focused, optimistic, apolitical engineers in Bing that just want to do a good job. Bing’s filled with these people, the hardworking, honest people that make every workplace more enjoyable. But there aren’t enough of them to overcome the Cadre of the Cunning, and their numbers are thinning day by day. The Beast Within runs roughshod over innocents.

The hull is breached. Passengers scurry and clamber to the topmost deck. The din of shouts is engulfed by a wave of silence emanating from the crowd’s attention drawn towards three men at the bow. Each man holds guns pointed at the other two; each wants to ensure his own place on the raft. The three are at an impasse and will not move, not even breathe, blocking passengers from the raft that would otherwise save them. The water rises.