March 8, 2016

Selling is complicated

It’s time for another of my quick primers on the enterprise IT business. This one is about sales. First I’ll run through some generalities; then I’ll link you to some previous posts; after that I’ll close with a collection of practical tips.

This is, to put it mildly, an important subject. In particular, there are only two kinds of enterprise IT CEOs:

Every enterprise IT CEO needs to be heavily involved in sales.

Of course, a few tips do not a salesperson make. Selling is a complex process, with many steps. Worse, it’s tough for somebody to explain to you what the process is, in part because there’s a kind of recursion involved — a big part of what you do in the sales process is establish what the process is.

And that’s in both senses of “establish”, namely “figure out” and “bring into being”.

Other inherent difficulties in selling include:

Of course, I’ve written about sales before, mainly in two areas:

In particular:

What I’d like to add in this post are more process-oriented observations. At a high level:

How do you gain this understanding? Well, if you’re an experienced salesperson, you may already know, or be able to find out easily. If you’re not, you probably have to ask very direct questions, early and often.

The key things you need to learn are:

As a final tip, there’s a great question from my stock analyst days that is useful in almost any kind of interview. The phrasing can vary a little depending on context, and indeed it’s often best repeated in slightly different forms, such as:

In a sales context, these questions can be used both to better understand the prospect’s needs and also to identify the ways your sales process could regrettably run off its rails. I suggest that you never forget to use them.

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