Why Most Work Plans Fail Despite Showing Promise

why work plans fail

Plans don’t fail because they suck. They fail because their execution sucks.

Here’s a common scenario: A team gets together to discuss a new initiative or project. Members brainstorm for hours to document expected goals and outcomes.

An insane number of meetings follow, each of which is a discussion on new strategies or tactics to “perfect” the planned strategies. More people get added to the meetings. More suggestions follow. More tasks get added to the to-do list.

In all this, talking turns into a proxy for taking action. The team gets caught in a vicious loop of asking and answering the same question: “What more can we do?” And before they realize, the deadline is upon them.

Suddenly, people feel overwhelmed with the quantum of tasks on their hands. Juggling everything keeps them busy, but it also results in mediocre outcomes. Or people get so exhausted by the incessant debates and discussions that they simply want to get done with the project. And projects like exploring new technologies or product lines that don’t have deadlines get sent to pilot purgatory: instead of scaling up to provide long-term ROI, they get put on the back-burner indefinitely.

“You’ve worn me down” is an awful decision-making process. It’s slow and de-energizing. — Jeff Bezos

I’ve experienced plenty of such moments. Clients brainstormed half-a-dozen iterations for a single article draft. The back-and-forth was exhausting to the level that we either abandoned the article or put out something for the heck of it. (If they fussed so much over a single article, what must they be doing for bigger projects?)

But doing “something” is as good as not doing anything at all. It makes us do what we already know and stay in the same spot despite running as hard as we can. It leads to zero progress. Not to mention how de-energizing it is.


How We Make Plans Work

Growth doesn’t come from talking. It comes from taking action, learning, and applying our lessons.

At Content Sutra, we focus on just two or three important goals at once. Then we break them down into subgoals. We work backward to create smaller, achievable tasks and milestones and set deadlines for each of them. Then we periodically connect to check their status, address obstacles, and move things forward.

We ship when we’re 70 percent satisfied. We collect feedback, return to the drawing board, and refine our plans for the next time. Rinse. Repeat.

In theory, most leaders agree with this approach. But in practice, they obsess over the question: “What if we fail?”

That’s the wrong question to ask. You fail only when you give up. When you take action, you test your assumptions and learn from the outcomes. When applied, these learnings increase your chances of success in the future, which means you don’t fail until you give up.

Action and learning also provide people with psychological inspiration and meaning—things everyone craves for. Driven people give their best at the workplace and turn it into an enjoyable playground instead of a bloody battlefield.


Final Thoughts

Progress is not linear like an assembly line that just moves forward. It’s a never-ending Plan—Action—Feedback flywheel. The faster your flywheel spins, the more momentum it generates, and the faster you move.

Your company is not much different from a car. We cannot steer a stationary car. To do that, you have to put it in gear, press the accelerator, release the clutch, and let the flywheel build momentum. Then use the steering wheel to keep the car in the right lane and direction.

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