I tell anyone I work with, or who works for me, to keep talking to me. Tell me how you are doing. Tell me if you think it will be late, or over budget, or the wrong colour. Set my expectations correctly as soon as you can. The truth is that we will all mess up or get caught by circumstances beyond our control, at some point. I know that. But I want to know about it as soon as possible – not at the eleventh hour. Please! This way, you see, I can help, or get others to help. And at a minimum, I can adjust my stakeholder’s expectations.
This is the key to project success. If the original plan has to be adjusted, this is fine. The earlier the better. And the earlier, the better chance that the new plan becomes THE plan.
Bottom line is that no one wants to be surprised. No one.
And about the planning… don’t try to plan low and deliver high. It looks terrible to the well educated, and eventually it will get you where you don’t want to be. Ouch!
Plan the work and work the plan and find a simple, easy way to keep everyone in the project on top of the progress. No surprises!