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The Secret Reason that Development Teams Struggle to Deliver On Time, On Budget, or On…

How long will it take you to run to the store and buy some milk?

You know how far away the store is, you know where they keep the milk, and you know that you’ll probably have to spend a few minutes checking out. But, chances are this isn’t enough information to answer the question.

If you’re like most people, you’re terrible at these kinds of predictions.

You ignore all of the small details. You overestimate your ability to get in and get out. You underestimate the time it will take to get through traffic.

So, whatever number popped into your head–say, 10 minutes?–is almost certainly wrong.

Psychologists call this The Planning Fallacy. It’s a common problem that we all face.

When asked to estimate how long something will take, we always tend to get it wrong. And this leads to a lot of issues in both our personal and professional lives.

So what’s to be done?

First, we must understand the root issues at play when it comes to The Planning Fallacy and then we can start to unravel ways to stop it from happening.

Two Types of Thinking: One is Really Bad at Planning

At a basic level, humans have two “types” of thinking, or systems that we use for different thinking tasks.

System 1 thinking is categorized as being quick, intuitive, and effortless. It’s the system that you use when you look at a string of numbers and see patterns or repetition.

If I ask you to solve 2 * 2, you would, of course, have a quick answer.

Although it probably doesn’t seem like you had to do much thinking, your brain processed the request, understood the pattern, and retrieved the stored answer—that’s System 1 at work.

System 2 thinking is effortful. It’s the kind of thinking that you do when you’re analyzing a large quantity of data or working through a complex math problem.

If I asked you to solve 123 * 48, you could probably do it. But it wouldn’t come to mind quickly.

You’d need to mentally process this problem in a way that feels much more “manual” and less intuitive. This is emblematic of System 2, which usually only engages when your System 1 can’t come up with a quick and intuitive answer.

In his book, “Thinking Fast and Slow”, Daniel Kahneman calls System 2 “lazy”. Or, maybe more accurately, we humans are generally lazy about deploying System 2 thinking because it requires more deliberate effort and concentration.

So, we often defer to System 1–intuition–even when we shouldn’t.

This is why we’re bad at planning.

If I ask you how long it will take you accomplish a task, which kind of thinking will you use?

Almost everyone relies on System 1. They consider the task for a brief second, make a mental approximation, and come up with a response that seems intuitive and reasonable.

Surely it won’t take you more than 10 minutes to run to the store and buy milk, right?

Of course, anyone who has had to make a last-minute run for milk should know—from experience—that it’s almost never as simple as what the intuitive answer would lead us to believe.

Instead, there are nuances we must consider. Like, the fact that there may be only one cashier working at this time, which means you’ll have to wait in line to check out. Or, the fact that there’s construction on Colfax Avenue, which means it will take you 10 minutes to get to the store instead of 5.

This is where System 2 comes in—if we performed a more thorough analysis, these factors would have been considered in our answer. Then it would be clear that it’s much more likely to take 20 or 30 minutes to run to the store instead of 10.

But, we rarely do this when it comes to planning. Why?