1. What do I need and want the software to do?
It may seem an obvious question! I would really recommend writing it all down though. It will really clarify what your requirements and expectations are. Getting into the detail early will help you prepare and increase the likelihood of success. When you contact potential suppliers or prospective developers it gives you a great starting point.
Once you have made your full list of requirements, separate them into 'must-haves' and 'nice-to-haves'. There will be some requirements which are absolutely crucial. The sort of thing where you think, if it doesn't do that there there's no point. ...