“Pity The Fool” Award Goes To Microsoft Manager.

Can you imagine being lectured by Bill Gates on how to secure your Windows PC? Or, the value in Oracle’s Larry Ellison telling you what kind of relational database you need for your company (hint: Oracle)?

Just recently, a Microsoft manager told Apple how to handle security issues. Seriously. It was all over the news. I didn’t know whether to laugh or cry.

Regardless, Microsoft’s Stephen Toulouse wins our “Pity The Fool” Award for March (or, whenever we award such things; it’s not a regular even around here).

Most of the Mac360 crew believe strongly in freedom of speech. Most. Tera’s not afraid to edit articles, comments, and forum postings from time to time. Of course, you can’t yell “fire” in a crowded theatre when there’s no fire, but you get the point.

We need to be tolerant and accepting of the point of view of others, even when said view is ridiculous, silly, a poorly constructed sentence, or comes from The Commander in Chief.

The world of computing as we know it has four major operating systems. Microsoft Windows, Mac OS X, Linux, and the various flavors of UNIX. Of them, it’s arguable that Windows has the most security problems.

It’s also arguable that the other three are rather far down the list of security issues to be concerned about.

By “security problems” I mean issues of OS security that affect the end user.

Regarding that, there are very few end user security problems for Mac OS X, Linux, or the UNIX flavors, but there are plenty of such for Microsoft’s Windows.

So, why would a Microsoft manager scold Apple about security? Chutzpah? Kahones? Stupidity? Diversionary tactic?

At about the same time as the little tirade against Apple’s security efforts, Microsoft announced that Windows Vista, delayed since about 2003, now won’t make it out the doors until 2007.

This Microsoft manager works for the same company that owns, pushes, sells, defends an operating system with more security holes than Las Vegas has sand (I live in Las Vegas, so I know; it gets into everything), yet desires to sell security products to customers.

So, what did poor fool Stephen Toulouse say that’s such a pity? Indeed, what could a Microsoft manager say that would make headlines in eWeek?

How’s this for starters?

“Look, the only way you can tackle security issues is by getting out ahead of them and clearly communicating to your users the threat, and the clear guidance on how to be safe.”

Remember, this is coming from a Microsoft employee. Maybe I should give him benefit of the doubt, and recognize the value of what he says on its face, right?

“Here’s the reality, for the next couple of years the Mac OS will experience increasing security threats and mark my words, the company will have to seek outside expertise in the form of a head of security communications in the next 12 months...”

We’ve gone from advice and recommendations to prophecy in just a few sentences.

MacDailyNews had a wonderful take on this pityfool situation: “What’s next? Rob Glaser (former Microsoft employee, head of Real Networks, eater of many doughnuts) lecturing Jack LaLanne (Google it) on physical fitness?”

On the surface, any authoritative recommendation to Apple regarding how to improve security problems and communication to customers is welcome. The key is “authoritative.”

A recent blog by a so-called Microsoft insider revealed startling views of Microsoft employees and what they think of security, Windows Vista, and Microsoft in general:

“Being a 10+ year [Microsoft] vet I feel ashamed and sad. This company is a mess on so many levels.”

“Compare this to OS X, where people fall all over themselves trying to get the newest version running on their old hardware because there’s actual value in the new features. So Vista has its guts ripped out, slips, and we wait another 5 years for a potentially insipring version of Windows, meanwhile Apple ships another 3 updates to OS X.”

“I wonder how many employees at PC hardware companies are wishing they had some way to call up Apple and license OS X for Intel. They could have 10.4 “Tiger” on PC hardware in a matter of weeks.”

Not all is well with Microsoft as a company, and that’s reflected by Microsoft’s employees. I want Apple and Mac OS X to succeed because I like the company, the products, the attitude. I also want Apple to pay attention to security problems, issues, and communicate better to customers.

But I have to laugh when it’s Microsoft’s employees telling Apple how to do it.