Hey, boss. None of this stuff you bought actually works.

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I once bought a pair of jeans online.

They didn't fit.

It annoyed me because they were the right (supposed) size, yet they weren't even close to fitting. 

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Worse, I couldn't send them back because I'd bought them on sale.

I'm reminded of my deeply pained feelings on hearing of corporate buying woes. Many companies, it seems, spend far more on IT than I spent on those jeans and feel, if anything, even more unhappy.

I judge this from a torrid survey perpetrated by Gartner.

A fulsome 56% of companies said they feel regret over big IT purchases they've made. And not merely transitory regret, but the big wish-we'd-never-ever-done-that sort of regret.

This may lead you to wonder what the people at these companies thought when they made their purchases.

First, though, it's worth wondering who these people were.

Gartner says that 67% of them weren't actually IT people. I can hear the collective ululation of the world's IT downtrodden, whose stance toward the uninitiated may be: "What the hell do these people know?"

Also: I feared Amazon was always stalking me. The whole truth really hurt

Gartner describes a veritable chasm between those who know what they're doing and buying -- and the majority. The latter may be described as the 'Haven't Got A Clue Club'.

"We need to think about psychographics beyond the motivations for also buying to include how decisions are approached and which groups are driving the strategy," said Gartner's "distinguished VP analyst" Hank Barnes.

He must know what he's talking about. He's distinguished.

Barnes offered another delicious morsel about deep corporate IT purchasing regret.

He said: "The high regret feelings are at their peak for tech buyers that have not started implementation, indicating significant frustration with the buying experience."

It's easy to imagine corporate IT buyers like neophytes walking into Best Buy and thinking: "Ooh, that looks cool. Let's have one of those."

It appears, though, that the fully regretful companies took, on average, 7-10 months more to make their IT purchases than, perhaps, the more savvy types.

There is another aspect to this, however.

What are the salespeople at tech companies thinking? Are they straining their every sinew to help companies buy the right technology for their actual needs? Or might many know a mark when they see one and be motivated only by the glorious maximality of the potential sale?

If you're going to buy these five orange boxes, sir, you'll surely need these three yellow ones.

Buying IT is a costly, time-consuming and often frustrating business. You might think, then, it should be left to those who really, truly know what they're talking about.

Perhaps, though, too many companies think there's too much money at stake to allow that to happen.

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