[Editor’s note: Joachim Kempin is a former top Microsoft executive and author of a new memoir, Resolve and Fortitude: Microsoft’s 'Secret Power Broker’ Breaks His Silence. This is Kempin's third column on Microsoft for ReadWrite. See his earlier contributions here and here.]

When I saw a TV ad using this strange word scroogled, I wasn't quite sure what it meant, so I looked it up in the Merriam-Webster online dictionary. I got this reply: “The word you've entered isn't in the dictionary.”

Frustrated, I thought maybe the dictionary hadn’t been updated recently. So l pursued an alternative way of exploring the word’s usefulness: Microsoft Word. The software redlined the word, meaning scroogle is not a genuine word.

I don't Google. As a loyal ex-Microsoft employee, I use the all-knowing Bing. So I challenged the oracle-engine from Redmond to find out what this mysterious word without meaning (or, should I say, meaningless word) stands for.

I soon discovered that “scroogled” is the centerpiece of an advertising campaign in which Microsoft warns Internet users of ugly consequences if they don't let go of their despicable habit of Gmailing. It soon dawned on me that the word must have been invented by somebody who wanted to avoid saying “scr(ew G)oogle” in public.

(See also: Undeterred By Failure, Microsoft Vows To 'Scroogle' Google Some More)

A dirty word indeed, so my kids will definitely be forbidden to use it in school. But I decided to add it, just for fun, to my Word vocabulary.

What Is Microsoft Thinking?

That Microsoft is using this silly word in TV and online ads nevertheless remains a conundrum. I'd thought the company had stopped nastily smearing competitors right after its painful antitrust experience. Now I'm wondering if this inexplicable little word is just a simple faux pas, or a sign that the company is returning to its innately competitive, if not exactly pleasant, roots.

I broke my own rules and turned to Google’s search engine to dig deeper. I was surprised to find a richer and more revealing trove of information than Bing had offered me.

I learned that Microsoft’s ad campaign is designed to lure Gmail customers into the realm of Microsoft’s recently launched and updated Outlook e-mail system. (This is a replacement for its old Hotmail product, which I've  used for eons.)

Mark Penn, Idea Man

The person behind the ad campaign is Mark Penn, who made his mark as a political operative and is best known for his involvement in Hillary Clinton’s unsuccessful 2008 presidential campaign.

He joined Microsoft last year because its CEO, Steve Ballmer, was reportedly impressed by Penn’s novel ideas of how to present Microsoft’s products to the public. I'm surprised the company hired him, knowing from a most trusted source that he was one of the most useless consultants Microsoft hired during its antitrust trial. He apparently believes that where search engines are concerned, “people these days are making a choice, just like they’re making a political choice.”

So here we have it. What works well in politics should, according to him, work as well for Microsoft in the 21st century. The notion of this software-driven company resorting to politics is nothing novel. The only surprise for me is that its latest target is now its current and former customer base.

(See also: Incoming! Microsoft Launching Another Pathetic Smear Campaign Against Google)

Smearing a competitor might work in politics, as we witnessed again in the last presidential election, because in that universe the word truth does not hold a lot of water. The software business is quite different. Ease of use, performance and affordable prices have long been the foundation for success. In short: Better products eventually win.

In Software, It's All About Products

Remember how Microsoft once beat another fierce competitor called Netscape? Its browser, Navigator, reigned supreme for nearly three years until Internet Explorer caught up and the development community and the pundits eventually regarded Explorer as superior. Only then did its public usage increase, and only then did Netscape lose the race. This is a lesson Microsoft needs to recall.

To retain customers, companies often build marketing campaigns around FUD — that is, by spreading Fear, Uncertainty and Doubt about competitive offerings while promising future improvements for their own. It’s pretty nasty when you're on the receiving end, but if you have an inferior product this tactic can work by delaying customer defections, buying you time to beef up your offering.

But the Scroogled campaign doesn't follow this well-known pattern. It seems to be built solely on fear. Has Microsoft’s obsessive-compulsive disorder spread so far that it can’t get past fear to uncertainty and doubt?

Oh, no! Google has the audacity to match ads to words found in a machine search on customer emails! Therefore Microsoft wants Gmail users to believe that their privacy is endangered. My Google search, however, quickly discovered what Microsoft states in its own usage policy:

Information about your past online activity, or the activity of others using this computer, might be used to help predict your interests and to select the ads that you see. But you’re in control and can opt-out of receiving personalized ads at any time.

Google allows its customers to opt-out as well. So what is there to fear?

If Microsoft could match Google’s smarter technology, the word scroogle would have never been invented. A couple of years ago, Microsoft bought an Internet-wide advertising platform by buying aQuantive for $6.3 billion, but then couldn’t make it work properly to beat Google and subsequently wrote off nearly the entire value of the acquisition.

Now, guided by a political smear artist, the company has to resort to a fear campaign where very little fear exists. If you're the sort to worry that the postal service knows where you live, then you might be scared about the ads Google derives from your email content. The government, under the Patriot Act, snoops way more intensely — and for uglier reasons.

Outlook Is Actually Better!

Even more disturbing, when you compare the new version of Outlook with Gmail, Outlook already wins. Instead of designing a campaign designed to stir up privacy anxiety among Gmail users, the energy should have been directed towards making Outlook usage most desirable. Microsoft could have challenged its marketing folks to create additional incentives for switching to Outlook, instead of wasting between $30 million and $90 million of shareholders’ money on useless slander.

Consumers make their product decisions in private, helped by their friends’ recommendations and information derived from the Internet. Most seem to consider Google to be a couple of notches less evil than the bully from Redmond, which is why Microsoft’s scare tactics won't work.

There's another reason Microsoft’ energy is totally misdirected. Neither Microsoft nor Google represent a political party. The process of choosing the right software isn't really comparable to voting in political elections, where fiscal or social principles in general determine the outcome.

Therefore I will keep the ugly word scroogle in my dictionary just to remind me what not to do in sales and marketing. A company and a CEO that resorts to a political smear campaign to promote its products and services has most definitely seen better days.

"OK, people, listen up. Seymour, pay attention. Elsie, turn on your hearing aid. It's time to move your Hotmail accounts to Outlook.com. Hey! No, stop complaining. Don't use that language, Ethel, it's un-ladylike."

Yes, the the time has come - the hundreds of millions of email users who are currently using Hotmail will be migrated over to Outlook.com by this summer, Microsoft said Tuesday. For many of Microsoft's long-time customers, this will be their first experience with the Windows 8-styled "Metro" user interface that Microsoft is propagating around its properties.

(See also Outlook.com: Take A Tour Of Microsoft's Hotmail Replacement.)

"We've been very excited by the adoption of the preview and how it's delivering on our promise of a new, reimagined email service," David Law, director of product management for Outlook.com, said in a blog post on Tuesday. "Throughout the preview, we learned a tremendous amount from seeing how people used the service.  Early adopters have told us what they liked, what they'd like to see next, and what we needed to do to make more people switch. And we've used that to add new features and fine-tune the services to scale.  Now that Outlook.com is coming out of preview, we'll be kicking off a huge push across a number of countries around the world to drive even greater awareness and adoption of Outlook.com."

Last July, Microsoft reworked its email system and unveiled Outlook.com, a beta of a dramatically improved email client that it said at the time would eventually replace Hotmail. The Windows 8 style "Metro makeovers" eventually reached SkyDrive, the new Office Web Apps, and a revamped MSN, among other Microsoft propertiess. Although Hotmail and Outlook.com share several elements - social connections to Twitter and Facebook, for example, and the ability to put rich media - including videos - within the client itself, Outlook.com is a bold reimagining of the Web email client in the Windows 8 vein.

The Dad Problem

The problem, unfortunately, is Dad.

My father, like many fathers, is a wonderful man. But even though he's an engineer, he despises technology. He hated beepers. Cell phones. ATM cards. Computers. Since I convinced my mother that a DVR could record Oakland A's games or St. Mary's basketball games, they've added a (standard-definition) video recoreder, which collects dust under their 27-inch Sony Trinitron CRT television. To their credit, we were one of the early families to adopt the microwave, which still resides in our kitchen, waiting for me to reset the clock in the event of a power failure.

My father has an AOL account.

My father quite logically points out that he has no need for an additional email address, since that AOL account is now embedded deep in the list of contact of their friends. And, cheapskate that he is (a compliment, in our family) he quickly bailed out of AOL's dialup service when a better ISP deal came along.

But there is no way on God's green earth that my father wants Windows 8. He's quite happy with Windows XP, thank you, which chugs along on his old Dell PC. I'm pretty sure he would still be on an ancient version of Internet Explorer had I not upgraded him for fear of him getting hacked.

No, my father does not have a Hotmail account, but I suspect that there are plenty of people just like him who do. Shifting from Hotmail to the Outlook.com environment is definitely going to blow some minds. I suspect that after glimpsing the Windows 8 style interface, some people may never venture upon the Internet again.

Easing The Transition?

I kid, of course.

Honestly, I'm sure some users will be blown away by the look and feel of Outlook.com, and the wealth of new features it offers. Some may even feel comfortable enough to upgrade their PCs to finally enter the 21st Century. And give credit where credit is due: Law and Microsoft are definitely trying to make the transition as easy as possible:

"Everything from their @hotmail.com email address, password, messages, folders, contacts, rules, vacation replies, etc. will stay the same, with no disruption in service," Law wrote. "When upgraded, they'll also get all the benefits from the redesigned Outlook.com experience - a fresh and intuitive user interface, lots of new features and better performance. And we won't ever make you switch your email address to an @outlook.com address if you don't want to."

But when I read all that, I still can't help but think of this quote:

"I used to be with it, but then they changed what *it* was. Now what I'm with isn't *it,* and what's *it* seems weird and scary to me. It'll happen to you..." Abe Simpson, The Simpsons: "Homerpalooza"

Image source: Flickr/pauldwaite.