Excellence is fragile. Dumb mistakes, in contrast, are more durable than Kevlar. It’s a universal law. For evidence, look no further than Microsoft Outlook.

Try this: Go to July 4th. If Independence Day isn’t already listed as a holiday, enter it as an all day event. Then click Tools/Options, the Calendar Options button, then the Time Zone button. Make sure “Show an additional time zone,” is checked, and set up a different time zone from the one you’re in. Click the Swap Time Zones button followed by Okay until you’re back in Outlook, and guess what: Part of Independence Day occurs on either July 3rd or July 5th, depending on your time zone choice.

Way back when Microsoft first designed Outlook, someone decided it would be clever to treat all-day events and midnight-to-midnight appointments the same way. Every subsequent version has inherited this bonehead design decision, which makes calendar management quite annoying for travelers who schedule events and telephone calls in multiple time zones, and want to show up or dial when they’re supposed to.

But wait. It’s worse! When Palm designed the original Palm Pilot, it ignored time zones altogether. You schedule meetings in local time, change the clock when you change time zones, and that has to do.

For entirely mysterious reasons they designed it this entirely incompatible way, even though they also designed it to synchronize with Outlook. The result? Change time zones in Outlook, the clock on your PDA, synchronize, and your calendar starts to look … wrong. And every subsequent version of the Palm PDA has inherited this bonehead design decision.

You’d think neither Microsoft nor Palm ever figured out that people travel.

I’ve found two PDA-based products that claim to fix the problem. One instructs me to never change the time zone on my PC, only the system clock. And by the way, it’s only reliable if I only enter appointments in my PDA, never in Outlook. No thanks.

The other would be fine if it weren’t for those pesky all-day events, and if it worked. Synchronize a few times and both all-day events and regular appointments act like gerbils — they mysteriously multiply. Make that cockroaches, because sometimes you can’t get rid of them: No matter how many times you delete them they just reappear.

The point of this column isn’t to gripe about Outlook and Palm (well, okay, that’s one point, but there is another, larger one). It’s to encourage you to encourage your managers to encourage everyone who works for you to pay attention to the consequences of their design decisions, because bad design never goes away. Quite the opposite — bad design inevitably creates a cascade of ever-more-fragile workarounds that eventually turns even the finest system into a shambles.

For example: Imagine you start up an on-line clothing store. As part of your systems you implement a customer database. In it you define “customer” as an individual: First name, last name, address and so forth.

After a couple of years you discover that sometimes, more than one customer lives at the same address. You’re selling to households and you never suspected. What to do?

Deadlines are tight and other priorities compete for attention so you take the easy way out — you create a Households table and write a program that sweeps the database once a night, recognizes new households, and populates the Households table accordingly.

Two years later you start selling embroidered clothing to businesses that stock up “trinkets and trash.” Now you also have to handle whole corporations, with multiple contacts, as customers. The pressure hasn’t let up, so you handle this situation much as you handled the Households problem.

The result: Every software change from this point forward has to take these kludges into account, increasing your costs while slowing down your ability to adapt to changing circumstances.

The moral of this story is simple: When you find that some of your design assumptions have changed, in the long run it’s better to adjust the design to your new circumstances than to make the quick fix.

Microsoft’s (and Palm’s) challenge is finding a financial motivation to fix the time zone problem, because it’s hard to see how doing so will sell any more software. Yours is a bit different: While “pay it now or pay it later” is easy for an engineer to understand, pay-it-now dollars are much more tangible than pay-it-later dollars.

Understanding the principle is the easy part. Helping the business make the right decision is a lot harder.

Every week I send Keep the Joint Running to an opt-in list of subscribers. Every week I get a bunch of messages back — autoreplies about travel plans, messages that were undeliverable for one reason or another, and spam managers that ask me to click to confirm it’s a legitimate e-mail.

I also get returns like this one:

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This is an automated message from the mail server at [name withheld because I’m such a nice guy].

An email, apparently sent from you was not delivered because it contains one or more forbidden attachments. It has been placed in temporary Quarantine and will be reviewed by the mail administrator and released to the receipient (sic) if appropriate.

If you have any questions as to why your email was stopped, please call information security at 860-555-5555 begin_of_the_skype_highlighting              860-555-5555      end_of_the_skype_highlighting [actual number withheld for similar reasons]

Please read the summary of the email content to determine why it was stopped.

image/jpeg

forbidden content type

Attachment: image001.jpg

image001.jpg

forbidden attachment

image/jpeg

forbidden content type

[a total of 13 images were listed, one of which was a jpeg of my smiling face]

objectionable content.

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The column in question was “Encouraging adulthood,” (Keep the Joint Running, February 6, 2006). The only possible objectionable content, if you’re wondering, was a reference to the less desirable afterlife alternative.

If Dante had only reserved a circle for the terminally stupid we’d know the ultimate destination of the clever soul who decided to establish this level of security. Because the next step is to ban pens and paper too (to eliminate the risk of nasty doodles), making employees chisel messages in granite. Then the business would be safe from all threats. Except, of course, the threat of employees beating each other to death with memos.

It’s like this: When you eliminate all risk, you eliminate all opportunity. I’m tempted to point out that this is yet another example of optimizing a part (security) at the expense of the whole (getting useful work done) except that we just finally put that subject to bed last week, so never mind.

Corporate America is at risk (get it?) of becoming the League of Frightened Executives. Don’t believe me? How many conversations have you been part of that included the fretful worry, “Someone might sue us!”

Well, yes. There are bottom feeders out there who will sue anyone at the drop of a hat, claiming the hat-fall traumatized their poodle. Does that mean you’ll never remove your chapeau again for fear of litigation?

Among modern corporate executives, the answer, too often, is a proud, resounding “Yes!” And there you are, running IT, trapped in the middle as usual.

The name of the discipline is risk management, not risk elimination. That means IT should be implementing policy, not writing it, and those writing the policy should be clear and explicit about what constitutes the right balance between reducing risk and doing business with as little friction as possible. My bet is that the filter that classified my smiling face as a risk was put in place because there was no policy to follow. Or if there was, it was written by a member of the League of Frightened Executives and stated, “Make sure no spam gets through.”

As a place to start on the path out of the madness, consider the following for your spam filter, which begins with the notion that your employees are adults and you should treat them accordingly: Ask each employee to establish a profile based on their personal preference. Level 1 gives them maximum protection from anything and everything they might find offensive. Level 3 filters out what is clearly spam, but will probably leave in some offensive e-mails they’ll have to deal with manually. Level 2 is halfway between (and if they couldn’t figure that out, it’s time to reconsider your philosophy of employee retention).

Will a setup like this prevent employees from suing you if one of them chooses Level 3, receives something obnoxious, and decides it’s your fault? Of course not. Our legal system needs something equivalent to a Level 3 spam filter but doesn’t have one. There is little or no filtering at the filing level, and probably not enough at the don’t-be-ridiculous level.

You can’t do anything about the risk of being sued. What you should be asking is whether the above policy increases your risk of legitimate lawsuits. It’s a valid question, for which I don’t know the answer.

Besides, if I shared my opinion and it turned out to be wrong, you might sue me.