Selling business software sometimes seems like the worst job in the world, but I’ve come to understand that buying software can be even more difficult.

Software salesmen used to be held in greater contempt than second-hand car salesmen. Indeed, it still seems that a chasm of misunderstanding separates the salesman (even if he is honest) and the buyer. The buyer and the seller each ask questions and answer them in a language couched in their own terminology. Volumes of unspoken assumptions could be written about both.

Which is why selling software gets ever more difficult. The distrust of the buyer (which is not intended to be insulting, isn’t based on the assumption that the salesman will lie) is reasonable. So many projects go wrong, even if both parties are buying and selling in good faith.

Buyers are ever more wary. Long gone are the days when a steady gaze, a firm handshake and a couple of boozy dinners could win you a deal.

But there is risk on both sides of the equation. The buyer risks wasting too much time and money on something that doesn’t do what he wants.  Buying more carefully, at the expense of the seller’s time mitigates this risk. The seller, on the other hand, risks spending vast amounts of time trying to sell, failing, ever more expensively, more often than not.

Which is why the seller must ‘qualify’ every opportunity. If you’re selling software you must always ask yourself:

• Can my software meet the buyer’s requirements?
• Am I talking to the decision makers?
• Is there a clear buying process?
• Does the buyer really intend to buy something within reasonable timescales?
• Does the buyer have a budget for the project?
• Does the list of competitors make sense?

A salesman must be a shrewd psychologist as well as relentlessly inquisitive. He or she must understand the motivation behind each link in the decision-making chain.

So, two trends make selling ever more sorrowful.

The first is the understandable trend of asking the seller to demonstrate the capabilities of his software and consultants more and more extensively. It’s as if the implementation project must be completed before the sale is made. This means prototypes, ‘sandbox’ environments where the buyer can play with the system, and multiple virtual ‘meetings’. These activities close the chasm, narrow the differences between the vocabularies of buyer and seller and they are a very good thing. But for the seller, even more than for the buyer, they are expensive.

The second trend is that all of this is more and more often done remotely, using tools such as GoToMeeting or WebEx. Very often we never meet the people who buy our software, or at least, not until the final stages of a sale or when the project begins.

The trouble with the ‘remote’ approach is that you get to know your buyer less easily and that makes ‘qualification’ very much more difficult. A salesman must make judgements about people, their interests, their ambitions, their credibility and their influence, and this is difficult to do with only an electronic link.

I write this because I spend ever more time building demonstration systems, discussing them with potential users, writing about them, offering them to the buyer to use in secure ‘sandbox’ environment, and failing to sell my software as often as always. These are the sorrows of selling. It gets ever more difficult, ever more expensive.

In one recent case I built several versions of a prototype for a company in India, exchanged at least a hundred emails, attended about ten ‘meetings’ and provided a test environment for the buyer to work with. I was told to expect the procurement process to begin (which means negotiating terms and conditions all over again – often another set of humiliations!). But then they decided that they will widen the scope of the project and start the process all over again. They promise to include us as a potential supplier. True, this isn’t exactly failure, but it certainly feels like it.

You simply can’t know everything you need to know when, as technology now makes possible, you can’t really look the buyer in the eye.