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Almost every project comes in a little bit late and a little bit over budget.

Part of the reason for that, says entrepreneur Seth Godin, is that in proposing the project we made our best guess and predicted the predictable. If we didn’t, the project would probably never get approved. But hiccups and mishaps will occur. “When things break, the breaks are rarely lucky ones,” he warns.

But we can’t escape formulating project plans and budgets. Software engineer Jacob Kaplan-Moss notes that in his field if you avoid estimation and don’t learn how to give timelines you won’t rise to top positions, and it’s the same in other fields. But if that’s scary, he counters that project estimation is not magic. It’s a skill, and can be learned and improved.

His own five-step approach, which he shared on his blog, revolves around the two key characteristics of project planning: capturing time and uncertainty.

It starts by breaking the work down into tasks based on complexity. He places them in four categories: small (one day); medium (three days); large (five days); and extra-large (two weeks). Use real hours, not idealized hours. People don’t actually work full out for eight hours a day, so he assumes, for example, a programmer will produce code for four hours in an actual day.

Even with that caution, don’t be overly optimistic. “If something probably will take three days, but take one if you get lucky, call it medium. On the other hand, don’t be overly pessimistic,” he says. Don’t upgrade a medium task to a large just to be safe. Aim for the expected time and leave it for the next step to capture uncertainty.

Since coming in early won’t be a problem, he doesn’t worry about that in his calculations. Instead, he applies an “if-things-go-wrong” multiplier to his estimates, based on the level of uncertainty, to come up with a worst-case scenario for the project. For low uncertainty about his estimate of a task, he multiplies by 1.1; for moderate, 1.5; for high, 2; and for extreme, 5.

“Just like with the time estimates, the specific labels and multipliers are arbitrary. I find these multipliers to work well, but different ones are fine,” he says, as long as you have a system. “Also like the time estimates: You should be aiming to have low uncertainty. Too many high and extreme uncertainty estimates are a sign you might want to iterate and refine your estimate.”

Now do the math. Your initial estimates before multipliers are the expected situation. The multipliers provide the worst-case scenario.

If the difference between them is too large, you may have to go back and refine the estimates. Looking at the task list, it should be immediately obvious where the uncertainty comes from. It’s common to have a very long timeline dominated by a few high-complexity (extra-large) tasks. Break those into smaller tasks and see if you can reduce the uncertainty. “Of course, if this was easy to do, you would have already done it: Those big tasks stay big because breaking them down isn’t obvious; those risky projects stay risky because of unanswerable questions,” he notes.

The final step is to track your accuracy, so you can improve at project estimation down the road. Look at the variance in specific tasks so you can understand the nature of the work and uncertainty better. “You’ll learn where your team tends to get stuck and where they blaze through the work,” he writes.

If you mess up don’t make the mistake he did at one firm, which led to him being edged out in what he calls a “not-quite-firing.” He waited too long to inform the bosses his estimate was wildly wrong. He warns that late projects stay late – indeed, they usually get later, and adding more people will only compound lateness. Communicate lateness early by communicating status regularly.

Quick hits

  • Share a meaningful piece of information in your out-of-office message that can be a conversation starter next time you are talking to somebody, says researcher Michelle Gielan. It’s a delayed honeymoon, a dream visit to a certain city or a chance to be with your favourite cousin for a week.
  • If self-doubt leads to timidity in sharing your ideas in a meeting, leading to you being ignored, executive coach Sabina Nawaz suggests creating space and drawing attention by announcing your intention, such as, “Let’s look at this from the customer perspective.” Before sharing your thoughts, give your point of view a name. And then outline the skeleton of the idea before delving into details.
  • Self-deception begins when you tell yourself the things you aren’t doing are easy, observes leadership coach Dan Rockwell.
  • Strengths are context sensitive. A strength can work well for you in one setting and hurt you in another, says consultant Julie Winkle Giulioni.
  • Almost everything in life can be learned faster, insists habits expert James Clear. Most people learn passively, waiting for insights to come to them. Instead, speed things up by actively searching for useful ideas. One pathway is to ask top people what they do and adopt their best practices as your baseline.

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