Specifically: in a company of five, don't hire a customer service person if you haven't done customer support yourself at least a bit. Don't hire a database person if you yourself (or somebody internal) hasn't already tried [and presumably failed].
Experience and Failure are important guide-posts to help you look for the right person to fill that role. Where are they better than you? Then you have to mentor them so they get to be better than themselves so they can make your next hire(s).
Experience and Failure are important guide-posts to help you look for the right person to fill that role. Where are they better than you? Then you have to mentor them so they get to be better than themselves so they can make your next hire(s).