Sun Tzu wrote:
I. LAYING PLANS
26. Now the general who wins a battle makes many
calculations in his temple ere the battle is fought.
The general who loses a battle makes but few
calculations beforehand. Thus do many calculations
lead to victory, and few calculations to defeat:
how much more no calculation at all! It is by attention
to this point that I can foresee who is likely to win or lose.
Whether performing a routine upgrade or making a massive infrastructure change, if you haven’t performed the appropriate amount of planning you will most likely fail. The more planning you perform the more likely you are to succeed, and the more likely you will be prepared for any problems you encounter.
When you make plans your imagination must be fully engaged. Visualize the tasks ahead of you, re-arranging them in time and space, step forward and backward through the process. In this way, you will recognize potential pitfalls and devise methods to avoid or mitigate against them.
As the plans solidify in your mind, document them in written form (Wiki, text document, paper, anything). Use this document to engage the opinions and imaginations of people you trust. Their experience and alternate view of the situation will help bring to light anything you may have missed. Use this information to refine your plans, incorporating their advice.
For small projects, a miniature version of the above process will suffice. You may not even need to write anything down for a small enough project, but don’t neglect planning. When scaling up for larger projects, make sure to build in some checkpoints for re-assessing your plans and dealing with anything which may have cropped up. As projects grow in complexity it becomes more import to build in extra flexibility.
No matter what the time frame, make sure to take time for planning. You will not regret it.