When the Plan Fails: 5 Things to Do When it All Falls Through

There’s the plan, and then there’s what actually happens. Sometimes one resembles the other, but many times not. What do you do when you find an enormous gap between the two and everything seems to be falling apart?

Today we’ll look at a high-risk plan that failed badly, see what the people involved did about it, and come up with five things we can do when it inevitably happens to us.

It Seemed Like a Good Idea…

Imagine having a great plan to achieve some important organizational goal. Thousands of people are committed, millions of dollars of equipment and resources are involved, years of training have gone into making it work out.

Yet at the critical moment, everything seems to go wrong. Half your leaders are suddenly out of the picture. You can’t communicate, the weather is not cooperating. The great scheme seems to be shattered into a million pieces with no hope of recovery.

That’s what happened in Sicily in 1943. The Allied forces had planned to re-take the island from the Nazis during World War II. Part of the plan was to do an amphibious landing on one of the beaches.

In support of that effort, thousands of paratroopers were to drop onto the island the night before the landing. Their job was to seize critical objectives and prevent a German counterattack against the vulnerable forces on the beach as they came ashore.

This was to be the first major use of paratroopers by the Allies. The best minds available put together the plan, and it seemed viable. They hoped to drop large groups of soldiers in a few key areas. They would quickly assemble and mass their forces to seize a few key objectives and prevent the Germans from interrupting the landing.

It’s Not Looking Good…

But things went wrong from the moment the planes took off. Winds were twice as high as expected, blowing the aircraft off course. Many pilots never saw a critical navigational beacon on Malta and didn’t make it to Sicily at all.

Others made it to Sicily but were so disoriented, they found themselves approaching from the wrong direction. Most could not accurately identify the specific drop zones they were assigned. Making their best guess, they turned on the green jump lights, and the Soldiers jumped out into the night.

When they landed, they were widely scattered across the island. Some ended up as far as 60 miles from their objectives. And instead of gathering together in large formations to take their objectives, they found themselves isolated in small groups.

They didn’t know where they were, they couldn’t communicate, leaders were separated from their men. Almost nothing had gone according to plan.

When one of the senior leaders boarded his plane, he was in command of thousands of men. Now he had only 20. It was a disaster.

Do the Best You Can…

What did the paratroopers do? Well, getting back up in the airplanes and going home was not an option, and just because the plan was a mess didn’t mean that the mission had changed.

There was no chance for a ‘take back’ or a ‘do over’ or to waste precious time blaming someone else for their current situation. They knew they had to keep their eye on the ball. They did what Teddy Roosevelt would have suggested: “Do what you can, with what you have, where you are.”

They did their best to find each other in the dark, banding into small elements that later became known informally as LGOPs (Little Groups of Paratroopers) and they put that advice into action.

They knew that the goal for them was to disrupt the Germans and keep them away from the beach. So for the next several days, that’s what they did. They cut telephone lines interrupting communications. Seized bridges. Attacked vehicles, ambushed patrols, blew things up. They sabotaged anything and everything they could, wreaking chaos all over the island. LGOPs were everywhere.

At the German headquarters, reports started flooding in from all parts of the island. Allied paratroopers suddenly seemed to be everywhere. According to Radio Rome, they estimated somewhere between 60,000 and 120,000 paratroopers had landed on the island. The real number was closer to 7,300, but the effect they had was all out of proportion to the size of their actual force.

All these reports left the German leadership unable to respond cohesively and decisively. As Clay Blair describes in Ridgway’s Paratroopers: The American Airborne in World War II, they had no way of knowing that the parachute drop had gone terribly wrong. They had to assume it had been well-executed and that the countryside was crawling with well-organized and led Allied forces.

When the landings began on the beach, the Germans attempted to counterattack with two tank-led forces from the Hermann Göering Division, but ultimately both failed, stopped by unexpected attacks from the paratroopers.

Despite all that had gone wrong, because of their continuing efforts to do something, anything, that could contribute to accomplishing their mission, no matter how small each individual act may have been, cumulatively, it was enough to stop the Germans.

When the Plan Fails – The Takeaway

The plans we make often look good at the outset. But if there is one thing you can guarantee, it is that when it comes time to execute, it will not turn out exactly as envisioned. The larger the operation and the more complex the parts, the more likely that something significant will go wrong.

Thinking about the actions of the Allied paratroopers on Sicily, we can draw several lessons worth keeping in mind for the next time you put your plan into action:

Be clear about the vision and goals. When everyone down to the parking lot attendant and the dishwasher understand and believe in what you are trying to achieve, you have equipped them to make smart choices about what to do when the plan starts to fail.

If you have no vision of yourself in the future, then you have nothing to live for.

Les Brown

Encourage leadership and initiative at every level. Once your vision is crystal clear to all, give your team the latitude to find ways to make it happen. More than just motivating, leadership is all about empowering people to act toward achieving a common goal.

Leaders instill in their people a hope for success and a belief in themselves. Positive leaders empower people to accomplish their goals.


Don’t waste time with recrimination. It’s not productive, doesn’t get you anywhere, and when you are done pointing the finger, you are no better off for it. Use your energy to take action to fix the problem.

The way we see the problem is the problem.

Stephen R. Covey

Focus on the positive. Figure out what you CAN do and do that. Good leaders make the most of the situation they find themselves in, not wishing that things were better or the plan had worked out.

The successful warrior is an average man, with laser-like focus.

Bruce Lee

Recognize the impact. Even small efforts can cumulatively have great effects. Whether it’s a simple act of goodwill, a little extra customer service, or going the extra mile to be sure that you have met your responsibilities, if everyone is doing their best at these things, the plan stands a better chance of succeeding.

Make incremental progress, change comes not by the yard, but by the inch.

Rick Pitino

The plan in Sicily may have failed, but the mission was a success because the paratroopers focused on finding some way to make it happen. You may not be storming beaches or jumping out of airplanes today, but you’re probably following some kind of plan. And if there’s one thing you can say about plans, it’s that something will probably go wrong. That’s when you find out who the real leaders are.

This article has been adapted from RapidStart Leadership, where it first appeared.


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