Checkout this Planning Falacy post by 37 Signals. It’s an interesting take and for the most part something with which I very much agree. To completely forego planning seems a bit extreme in my opinion. I prefer to make plans and not tell anybody about them… I mean maybe the inner circle. For example, if you publish a schedule/plan for an upcoming software release there are really only two outcomes and both are negative.
1. You could finish late. This one is pretty obvious, it’s what everybody is afraid of. The big dig.
2. You could finish early. This is rare, because basically the team will just slow down. It wastes time. And if pushed to provide a date, any smart person will be as conservative as possible. I think that project would take 2 months, but if we’re going to print t-shirts with the date on them I suppose I better say 6 months to be safe. You pretty much just guaranteed the project would take 3 times as long.
So my plan, is to say 2 months but not really tell anybody. Then when the thing is done in two months you can print the t-shirts and start working on whatever is next.
