Evan Schuman's StorefrontBacktalk

It has been said that CIOs at large companies today have limited direct power and?more than almost any other C-level executive?need to push the IT/business agenda by persuasion and by maintaining good relations with other stakeholders.

Taking that to heart, the CIO of Overstock.com recently sent off a note to key business partners taking the heat for a wide range of technologies that weren’t working out.

The letter from CIO Shawn Schwegman?which was signed “Humbly”?did not mince words.

“I’ll start by saying that the vast majority of system problems we have are problems related to updates,” Schwegman wrote. “These update problems have been manifesting themselves as inventory update failures, missing orders, missing images, incorrect status synchs, etc.

“At the end of the day, all of these problems boil down to Overstock’s failure (read, my failure) to architect a system that can handle real-time updates properly,” Schwegman wrote.

“I cannot apologize enough for both the number of problems you all have had to deal with and for the length of time you’ve been plagued with these problems. I consider this one of my greatest failures over the last two years and I am terribly sorry.”

Schwegman went on to describe problems with the interactions of the Oracle database and a Vcommerce database, an effort that he labeled “horribly architected.”

“In the current system, inventory updates, orders, image data, status changes, etc., are all written to small files which are then sent back and forth between systems.

“The sending system writes and sends the file and automatically assumes that the receiving system processed the file,” he wrote.

“This ‘fire and forget’ approach is killing us. In reality, a file might not send properly, become corrupted in transfer or produce errors when the receiving system attempts to process it. In most cases, we don’t know when we have problems. The architecture is horribly architected.”

Schwegman then said the one thing every company wants to hear from its distributor’s CIO.

“It’s critically important that I prepare you for the worst,” he wrote as he described a major Oracle upgrade and added that he “expects it to get worse in the short term,” and better eventually.

Shortly after the letter leaked, much to the displeasure of Schwegman, he said that a lot of the memo was simplified because he was writing “to a bunch of non-technical people,” and that simplifications may have been misleading.

That letter was written a few weeks ago and the Oracle major upgrade that he was dreading has been completed, Schwegman said, and his worst fears were not realized. Thus far, he said, it has been been “a huge success.”

I find this incident fascinating in the way that it illustrates the communication challenges that a CIO has to deal with, especially when one’s employer is publicly held.

Technology veterans are, by nature, pessimistic. Present any detailed plan to an engineer and the engineer will quickly project every way it could glitch and start figuring out ways to prevent that glitch.

It’s like the mentality bred with the new homeland security approach. Law enforcement agents are supposed to be creative and anticipate any way that terrorists could strike.

IT directors and CIOs must often have the same mental approach. After all, who other than them will be able to anticipate problems when two wonderful programs suddenly decide to conflict?

CEOs, COOs and CMOs (chief marketing officers) are the opposite.

In the same way the CIO can be considered the ultimate programmer (the best programmer would care about business objectives and design accordingly), the CEO, COO and CMO are the ultimate salespeople.

A good salesperson is genetically disposed to optimism in the same way that a good programmer is disposed to pessimism.

The conflict comes when those communications go external.

Schwegman is not only the CIO, but he’s also a senior vice president. Partners interpret senior executive comments in a certain way and the kind of raw candor that Schwegman’s letter used can be, to say the least, discomforting.

So when IT projects go astray, should a CIO publicly fall on his sword?

I’m envisioning the original “Saturday Night Live” shows and can see John Belushi as Samurai CIO. (Personally, I’d have paid good money to watch a “Samurai CIO Gets Angry At The Bad Product Demo” skit.)

I might feel differently if the confessional correspondence had suggested specific things the partners could have done to protect themselves.

As it was, the letter pretty much came down to: Bad things have happened and worse things are probably going to happen. Sorry about that. Carry on.

As comedian Robert Klein said about the air raid drills at his elementary school, the message the children took away was, “the siren means disaster. It’s too horrible to think about. Don’t even try to save yourselves.” And then, “they had the wisdom to sound a siren every day at noon.”

Non-technical partners rarely want the unvarnished truth when it comes to technology projects.

They want to know that their problems are being heard, but they also want to hear that responsible adults are taking care of the matter and that all will be fine.

In the true tradition of Dilbert, CIOs tend to be honest to a fault and to volunteer problems and possible problems.

When communicating externally, it’s probably best to curb those tendencies.

As our elected officials say: Honesty is a powerful concept. Use it only as a last resort.