In Seth's recent post (Fear of Apples) he talks about how fear impacts buying. People don't want to do things that scare them and for some the threshold is low (buying the wrong apples).
"Whatever you sell, there are two big reasons people aren't buying it:
1. They don't know about it.
2. They're afraid of it."
Unfortunately, software development (one of the things we do) fits into this category big time. This is why business people often want to bring their IT people with them to a meeting... what if you say something they don't understand and make them look foolish.
Unfortunately some industries have rightly or wrongly been pigeon-holed into the scary realm.
Getting the right tools and help in front of business owners and managers should not be a scary prospect. If you are selling a high "fear" product or service you will have a longer sales cycle. If the price is high often perceived risk is higher too.
You need to build trust and consider starting with something a little smaller. As the trust goes up you can move to the more complex offerings.
As a (small) business owner you need to address any fears you have about important aspects of your business. Find a trusted partner to help you with things like information technology, human resources and business optimization... focus on what you do best.
In an ideal world, it would be easy to make sure people know about it and you would choose something to sell that no one (in the mainstream) is afraid of.
In reality there may be no such thing. If people are afraid of buying the wrong apples then anything more complex is going to have some perils for someone.
I think the key is to make sure there are "enough" people who are in the no or low fear (innovator/early adopter) category to support your offering while you are Crossing the Chasm (Geoffry Moore) into the mainstream; and whether or not it is even possible to make that jump.
For ourselves, we are constantly striving to make software development easier for our customers. Success breeds word of mouth and more success. But we are also making it easier for customers to try us out by offering more low risk "packaged" software products in the future.
What is your business doing to address the fear of buying?