In a very general sense, there is no “right” amount of planning or organizing you can do prior to starting a project. However, by identifying what “too little” and “too much” are, you can hope to find something that works.
On the “too much” end of the spectrum:
- Speculating about situations that may or may not ever arise far down the road is usually a waste of time. Better to dig in and start creating.
- Drafting a 100 page design document that multiple parties sign off on is usually a waste of time. People are generally thinking of slightly different things when they read about functionality—over the course of a large document these differences add up.
On the “too little” end:
- Don’t just start work on a project without covering at least a few general questions. What’s the goal? How can it be accomplished? What might cause it to fail and how can we avoid those things? How will it make money?
- Avoid “hand waving” issues away. For example, if you don’t have widget X in place yet and the person building widget Y needs X before they can begin, don’t use “X is available” as an assumption in the project timeline. A lot of “hand waving” will lead to a group of people who can all claim to not be responsible for a failed project.