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Unless you are hiring someone for a VP type role, your new hire likely isn't going to step in and know exactly what they should be doing everyday to achieve the goals you have laid out for them.

So you have to try it all out yourself first and figure out what makes someone in this role successful, what makes them not successful, and how to create a process or blueprint that your new hire can follow to success.

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).

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