There are two quotes from Peter Drucker that are well worth remembering when planning.
“The planner must be right in his timing of 10 or 20 separate developments, all of which must arrive at the same point at the same moment lest the whole plan collapse. The planner stakes all on an unbroken series of 20 rolls of seven.” — The New Society
This first quote warns us that each additional date in the schedule exponentially increases the risk of variations in the schedule. This is not a call to reduce the number of deadlines.
“Unless we build expectations into the planning decision in such a way that we can find out early whether they are actually fulfilled or not – including a fair understanding of what are significant deviations both in time and in scale – we cannot plan. We have no feedback, no way of self-control from events back to the planning process.” — Management: Tasks, Responsibilities, Practices
Targets are control points. Monitoring and managing deviations to the schedule requires that there enough control points to catch the deviations as they happen. This is one of the objectives of breaking down the deliverables for the WBS.
Identify the real issues — Understand the context and analyze the issues objectively.
Set realistic time frames — Monitor dates in the schedule, adjust dates when the schedule changes and remember to check for effects on the dates of related deliverables.
Align the work streams — Watch the dependencies between deliverables. A smooth running project has the nail ready when it’s time to shoe the horse.
Look beyond the indicators — Project health indicators are often trailing indicators telling you how well the project has performed until now. Look for leading indicators that will tell you how the project will perform from now.
Manage the expectations — Set realistic expectations from the start of the project and continue managing them by communicating project changes;
Seek objectivity — Find experts from outside the project and review the project with them.