I just finished reading Baseline Selling by Dave Kurlan, a book my sales coach Rick Roberge recommended I read.  There are several lessons the book teaches, and that Rick echoes, but one I've taken to heart is to "Go Negative" with the prospect - frequently and quickly.  This isn't called out exactly as such in the book, or even by Rick, but it's my simple way of remembering to qualify a prospect well.   

Why is this the most important tip to me?

One thing I've realized is that most products are NOT a good fit for a given prospect.  Unless you're selling mass market consumer products it's likely that your specialized product is not a fit for the average prospect.  Looking at typical lead conversion ratios in most organizations you probably would see that 9 times out of 10 your product isn't a good fit.  What you want to do is find out as quickly as possible if the prospect you're talking to is in the 90% that don't fit or the 10% that do fit.  And one of the best ways to do that is to ask tough questions that challenge the idea that your product is useful for your prospect.  The sooner you find this out the faster you can move on to the 10% that are a good fit and work on those opportunities.

I realize that the phrase "go negative" may be more traditionally used in a reverse-psychology sense; i.e., to reject the prospect and have them "beg" for your solution.  Indeed, going negative reminds me of that infamous book The Game that advises how guys can use somewhat questionable reverse psychology to land a member of the opposite sex (don't judge me; was received as a gift and if anyone saw my "game" it'd be clear I learned nothing from the book).  

However, when I say "go negative" that isn't what I mean.  I simply mean that you should be willing to challenge your prospect on if it's really worth both parties engaging in this deal.  Often people are too nice to reject you outright and if you don't ask questions that challenge them it may be a long time before you can rule out the poor fit prospect.

At the heart of this approach is the realization that even with a good fit it's likely that both parties need to put in some work to implement the product.  Asking people to do this is only fair if it really moves the proverbial needle for both parties, otherwise why bother?  And to figure out if it moves the needle means asking tough questions around revenue goals, consequences of not hitting goals, resource and time constraints etc.

Of course, there's a risk of going too far with this approach.  Do this too soon before you bulid trust and you might irritate, or worse alienate, your prospect who may in fact be a good fit.  You could also end up disqualifying too fast, not allowing your prospect to think through their challenges and possible solutions, which might then make them realize you are what they really need.

I am by no means a master of this skill, or probably any other sales skill for that matter, but going negative seems to be serving me well so far.  Readers - what do you think?  Is this a strategy you've used and like or dislike?  Are there other tactics you rely on more as your default?