March 15, 2022

Project Planning: Why It’s So Hard (And How to Get It Right)

Lucy Hitz
Lucy Hitz

You’ve heard the saying that “all good things take time,” but have you heard that about 90% of good things take way too much time? That’s right – it’s not just your imagination that your projects are dragging on forever. Instead, it’s human nature to underestimate the time, costs, and risks of future actions, which means that it usually takes way longer than we think to get a project completed. 

To understand why, let’s take a look at the history of plan-making and the completely human reasons that we struggle to get the timing right. More importantly, I’ll share my three tried-and-true tricks to more accurate planning, so that whether you have a really ambitious project coming up or are trying to make your Fridays less of a scramble, you’ll have better success at getting your projects to come in on time. 

The Iron Law of Megaprojects

The teams who set out to build the Golden Gate Bridge and the Empire State building had incredibly lofty goals. But, because they had clear objectives (build the longest suspension bridge and the tallest building, respectively), they produced stellar results, coming in under budget and on time. Unfortunately, those are the exceptions to the rule.

There’s a long history of poor planning worldwide, which has culminated in what’s now called the “Iron Law of Megaprojects.” There’s even a handbook on it! With 100 years of data informing this law, we can now pretty confidently say that 90% of projects will be “over budget, over time, under benefits, over and over again.” 

The rule doesn’t just apply to government mega-projects, though. It also applies to student projects, IT projects, business projects, and so much more. And it doesn’t just happen to you (and me). Even the founder of planning projects himself – Asana’s Justin Rosenstein – originally predicted it’d take 1 year to launch the company. In reality, it took 3 years. 

So, why does this happen? 

The Planning Fallacy

The planning fallacy (originally proposed by Daniel Kahneman and Amos Tversky in 1979) is a tendency to underestimate the time, costs, and risks of future actions. In other words, it’s a cognitive bias that makes us fall into a trap of overly optimistic planning timelines and budgets. 

It happens because we’re human. More specifically, it happens because of these three human traits:

  1. Optimism. Wishful thinking to focus on the best possible scenario and what we want to happen, rather than what happened in past experience.
  2. Self-serving bias. When something in the past has been successful, we tend to take the credit for ourselves and attribute the positive outcome to our skill. On the other hand, when something has failed, we tend to blame poor outcomes on external forces (or bad luck). This leads us to discount past evidence of tasks taking longer or costing more than anticipated. 
  3. Coordination neglect. We think that when a project starts to go off the rails, bringing in more people will help get things back on track. In reality, it does the opposite.  

The bottom line? Things are almost always going to take longer than you think. So, let’s plan accordingly!


How to Plan Effectively

As the Director of Content and Training at Ally, I’m in charge of building out our training programs. When I first started, I didn’t have any data to go off, so when my boss would ask “how long will it take to complete this training project?” I’d answer, “oh, I guess 1-2 months.” 

Today, after successfully finishing 12 training projects, I can confidently answer that it will take 68 days on average to complete the project. I can also tell you that there are three key things that will help ensure your projects get done on time, and they are as follows:

  1. Focus. There’s a reason we only recommend that organizations, teams, and individuals create 3-5 OKRs at a time. Limiting yourself to only a few key goals, and having a strong planning process to support them, helps filter out distraction and narrow in on the task at hand.
  2. Embrace transparency. You’re more likely to incorrectly predict the time it will take to complete your own projects. That’s why in Ally, we’re all about transparency. Being able to look at everyone’s OKRs gives you a built-in system of checks and balances so you can help each other make realistic plans. 
  3. Be data driven. Don’t blindly make timeline predictions. If you do, you’re extremely likely to fall into the traps of optimism and self-serving bias. Instead, let past data inform your planning so that it’s a realistic reflection of what’s possible.

I hope this helps you plan more effectively in the future, so you have a better chance at hitting your project goals on time.

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