Watch a good manager in the final minutes of a tight match and you will notice they are rarely surprised. A player goes down. A goal goes in against the run of play. A red card reduces them to ten men. And the response, more often than not, is not panic but a substitution already half-decided, a shape already rehearsed, a plan that was made for exactly this. The best teams do not merely hope things go well. They plan, in detail, for the moment things go wrong. And that habit — planning for failure as carefully as for success — is one of the most underrated disciplines in any kind of delivery.
It runs against a certain optimism that projects encourage. We are taught to sell the vision, to rally the team around the goal, to believe. Planning for failure can feel like disloyalty to that, like admitting defeat before you have begun. I want to argue the opposite: that planning for failure is the most confident thing a team can do, because it is what lets you keep your nerve when failure actually arrives.
Hope is not a plan, and optimism is not a method
The weakest projects I have seen all shared a quiet assumption: that things would basically go to plan. Not stated, of course. Nobody writes “we are assuming nothing goes wrong” into a schedule. But it is there in the absence of slack, in the single supplier with no alternative, in the timeline that only works if every task finishes on time and nobody is ever sick. The plan describes the version of events where everything cooperates, and quietly stakes everything on it.
Reality does not cooperate. It never has. A team that has built its entire delivery on the assumption of smooth conditions is not really planning at all; it is hoping, with a Gantt chart for cover. The good football side knows that the opponent gets a say, that the weather gets a say, that luck gets a say, and it builds for a match in which not everything goes its way — because no match ever does.
Planning for failure is what buys you calm
Here is the part people miss. The value of planning for failure is not mainly that you have the contingency ready, though that helps. The deeper value is what it does to you in the moment of crisis. When the thing you feared actually happens, the team that planned for it does not freeze, because it has already thought the thought. The decision was made in the calm of preparation, not the heat of the moment, and that is worth more than any document.
I have watched two teams hit the same setback and respond completely differently, and the difference was almost entirely composure. The team that had war-gamed the failure absorbed it almost without breaking stride; the decision was already taken, so the only thing left was to act. The team that had not war-gamed it lost a day to shock and argument before it even began to respond. Same problem. Same capability. The gap was preparation, and preparation showed up as calm.
The pre-mortem: imagining the failure before it happens
There is a simple practice I keep coming back to, and it is the most useful single habit I know for this. Before the work begins, gather the team and ask them to imagine it is over and the project has failed. Not might fail — has failed, completely. Then ask them to write down why. What killed it.
The effect of this is remarkable. Asked to predict success, people are vague and polite. Asked to explain a failure that has already happened, they become specific and honest, because the framing gives them permission to name the things they were quietly worried about. The supplier nobody trusts. The dependency everyone is hoping will hold. The decision that keeps getting deferred. A pre-mortem surfaces, in twenty minutes, the failures the team already half-saw coming, while there is still time to do something about them. It is the structured version of what the good manager does instinctively: rehearse the disaster, so that the disaster, if it comes, is familiar.
Depth is a form of planning for failure
One reason great football teams survive setbacks is that they are built with depth — a bench, cover in every position, players who can do more than one job. The squad is designed on the assumption that some of the first eleven will be unavailable when it matters, because they always are. The depth is not extravagance. It is failure-planning made physical.
Projects need the same, and rarely have it. The plan that depends on one irreplaceable person is one illness away from collapse. The delivery with a single supplier and no alternative has handed its fate to that supplier. Building depth — cross-trained people, a second source, knowledge that lives in more than one head — costs something up front and feels redundant right up until the moment it saves you. The teams that plan for failure pay that cost willingly, because they know the first eleven never makes it through intact.
What to carry into your own work
Planning for failure is not pessimism, and it is not a lack of belief in the goal. It is the discipline that lets ambitious things survive contact with a reality that was never going to cooperate. A few ways to build the habit:
Run a pre-mortem before you start. Imagine the project has already failed and ask the team why. Then fix what they name while you still can.
Find the single points of failure. The one person, the one supplier, the one assumption everything rests on. Build depth behind each of them before you need it.
Decide in the calm, not the crisis. The point of planning for failure is to make the hard decisions when you are clear-headed, so the moment of trouble is execution, not deliberation.
Treat composure as an output of preparation. The team that stays calm under pressure is usually not braver. It has simply already thought the thought.
The best manager is not the one whose plan never meets trouble. No such plan exists. The best manager is the one who has already imagined the trouble, decided what to do about it, and can therefore meet it with a substitution rather than a panic. Plan for the match in which not everything goes your way. It is the only kind of match there is.
This piece sits alongside Risk Management at World Cup Scale and How World Cup Organisers Manage Fixed Deadlines.
Ben Webb is a Sydney-based project leader and former Australian Project Manager of the Year, sharing practical lessons from major projects, events and complex stakeholder environments.
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