When anyone bemoans the prevalence of negative advertising in political campaigns, there’s an easy reply: It works. That’s not always true in the corporate world. Just take Microsoft’s ongoing blitz of attacks on Google, which launched last Thanksgiving under the cutesy tagline “Scroogled!”



The first batch of ads, alleging that Google allows companies to pay for better search results, was roundly criticized as hypocritical and "a joke." (Microsoft's parallel campaign, to convince the Federal Trade Commission that Google had crossed lines in using its search algorithm to favor its own content, was no more successful). The second, which says that Google is "going through your email" in order to better target ads, have been called patronizing, misleading, and "embarrassing." The latest—released on Valentine’s Day—hasn’t taken much of the criticism to heart. Sure, tech pundits aren't the people whose minds Microsoft is trying to change. But by the company’s own objective measure—the number of people who've signed their petition against Google's ad targeting—the campaign is a flop, with fewer than 6,000 signatures worldwide a week after the ads launched.



In trying to cast itself as the company that will protect your privacy, and Google as the greedy snoop, Microsoft may have picked the wrong argument. Though its own surveys and dozens of others by advocacy groups and academics find that people overwhelmingly say they care about safeguarding their personal information, very rarely do people actually base their product decisions around who uses anonymized information to show them ads that are tailored to their interests. In the case of Gmail, it seems like a trivial price to pay for a free service that’s heads and shoulders above the competition.



But the message is only part of Microsoft's misfire. The bigger problem is the whole mentality of the crusade against Google: that of a political campaign.



Negative ads, as much as politicians might decry them, can have a devastating effect when deployed in a tight race, like last year's Iowa Republican primary. Perhaps with this in mind, Microsoft hired ex-Clintonite Mark Penn, who pioneered the practice of micro-targeting ads based on consumer behavior, to work his black magic on Google. Penn, however, seems to not have recognized that there are some fundamental differences between consumer product battles and political campaigns, and mistaking one for the other can render them almost completely ineffective.



For starters, political races have concrete deadlines. When election day comes, voters will make their decisions based on what's managed to stick in their brain about either candidate. On consumer issues, people can decide to adopt a new product at any time in the future, and if one brand doesn't convince them it's worth it, they just won't.



In addition, the bar for buying or using something different is a lot higher than deciding who to vote for. One ballot might play a tiny role in determining who runs the free world, but switching your search engine or email client is a unilateral change to your day-to-day life—both in the ways you conduct business, and the image you project to the outside world.



“You may or may not be labeled by who you're voting for for President,” says Edward Boches, a professor of advertising at Boston University who has designed many campaigns for tech companies. "There's just more at stake [in product choices]. And I think it will be more likely to be effective if there's ways in which I can benefit from another product rather than things that are wrong with the product I'm using." Microsoft's ads don’t make much of an attempt to demonstrate that its own email service is better, and "Outlook.com: We don't go through your email to sell ads"—which the TV spots end on—isn't exactly a rousing slogan.



As much as Microsoft has tried to make this ad blitz about Google, smear campaigns will always reflect on the entities that attach their names to them. In the political world, the bulk of negative advertising actually comes from outside groups with names like "America's Future PAC" or "Concerned Citizens of Wisconsin," shielding the candidate from having to say such nasty things (and even if the campaign did foot the bill, it’s only acknowledged in a perfunctory message at the end). In this case, lacking a viable surrogate, Microsoft takes on the full burden of looking petty and snide. That already comports with public perception—Microsoft doesn't have the nickname the "Evil Empire" for nothing—but there's no need to make the problem worse.



It's not that corporations never talk about their rivals. Alltel did a charming ad making fun of other phone networks set in a high school lunchroom. When it was going up against Microsoft, Apple cut some lovable spots personifying the clumsiness of the IT behemoth. In turn, over the past few years, Samsung has been mocking the fanaticism of Apple fans, and actually seems to be making some headway. Here's what those ads have in common: They're funny, and make light of their competitors' failings, creating the impression of a brand with which a consumer wouldn't mind being identified. In a market that's as much about self-definition as it is about price or quality, that really, really matters.



Deepening the weirdness of Microsoft's Scroogled campaign are the rest of its very expensive ads, which aren't nearly as bad. The Surface spot is mesmerizing, and at least creates the impression of a product that could feasibly fill America's campuses like silver MacBooks now do. Even more tellingly, the website for the new Internet Explorer goes directly up against Microsoft's greatest enemy: its own past. By pre-empting peoples' doubts about a browser they might dimly remember from the dawn of the web, it prompts us to give IE another try. If it's truly a worthy product, the ad accomplishes its goal.



That's the approach Microsoft should be taking with email: Focus on changing the popular memory of Outlook as the rickety, 1990's-era service our workplaces forced us to use before Google introduced something better and free. I hear the new version ain’t bad.



Oh, and fire Mark Penn. Until then, Mountain View will just continue to erupt in giggles every time a new Microsoft ad rolls out.