Three planning pitfalls (and how to avoid them)

Planning can make the difference between a project that gets done right and on time, and a project that goes down in flames while you wonder what went wrong. The problem is that, because of the way our brains work and the way we communicate now, we’re just not set up for planning success. But once you’re aware of the most common issues, you can avoid them—or at least go into a project knowing that they’re a factor. Here are the top three planning mistakes that even seasoned professionals make and how to fix them:

Bad time estimates

We are really, really bad at creating time estimates. There’s actually a term for this: “Hofstadter’s law,” which states that “any task you’re planning to complete will always take longer than expected—even when Hofstadter’s law is taken into account.”

Part of this is that when we’re working, we’re often in flow state. To put it simply, when we’re fully immersed in our work, we lose track of time. Then, when you try to create a time estimate for a similar project, it might feel like you only spent an hour or two on something, but you actually spent four or five hours on it.

Another factor is that we often don’t break projects down into task lists. We turn it into milestones (“we’ll be 25% done when we have a wireframe for the site”), but don’t break those milestones down into a list of smaller tasks. Since we’re already not great at creating time estimates for a task, the less we break things down, the worse the estimates are—those inaccuracies add up.

How to create better time estimates:

  1. Use the 1.5x rule. Take your time estimate and multiply it by one and a half. Or two, if you want to give it extra padding.
  2. Make sure you’re breaking projects down into their smaller parts. The more accurate your task list is, the more accurate your time estimate will be.
  3. Track your time. The best way to get better at creating time estimates is to know how much time you’ve spent on things in the past. Whether you use the Pomodoro method or an actual time tracking tool (like the one built into Projecturf), knowing where your time is going will let you create more accurate estimates in the future.

Communication struggles

Though the oft-cited statistic about 93% of all communication being nonverbal is probably an exaggeration, it is true that we convey plenty of information with our tone of voice and body language. And verbal communication is often just quicker—a five minute phone call can fix miscommunications and answer questions that hours of email back-and-forth didn’t.

But, especially with remote teams scattered across time zones, a phone call isn’t always an option. Instead, we need to learn how to communicate better with the methods we do have, because miscommunications can throw a project off track and out of scope.

How to communicate better:

  1. Use free tools like Skitch or Jing to communicate visually. A picture’s worth a thousand words, and a video must be worth more. Because of that, these two tools can save you plenty of email time. Instead of trying to explain the process, just show them how to do it.
  2. Re-read each email out loud before you send it to catch potential misunderstandings. This is an old editing trick that works wonders for helping you create clearer emails—sometimes, you just don’t realize how something will sound to someone else until you actually hear it out loud.
  3. Answer questions preemptively. If you aren’t clear on what someone is asking or requesting, don’t send an email back with nothing but a question in it. Instead, ask the question, and then list the potential answers. For example, “Did you mean A or B? If you meant A, then we should proceed by doing XYZ. If you meant B, we should proceed by doing CDE.” That way, the recipient already knows what they need to do next, based on what their question actually was.

Under- or over-planning

When it comes to planning, people typically take one of two routes:

  1. They under plan and don’t break the project down enough. Their time estimates are way off, and the project often goes off the rails because of unforeseen circumstances.
  2. They over plan, creating an exhaustively detailed task list at the start of the project. Then, something changes during the course of the project (sometimes more than once). Each time, they have to re-plan everything, spending a lot of time on the process that could be spent actually working on the project.

How to find the middle road:

  1. First, break the project down into milestones—smaller, but still significant, measures of progress. Four or five is a good place to start.
  2. Plan the first two milestones in detail, then create a less detailed plan for the rest of the project. By breaking up the milestones into smaller parts, you should still be able to get a fairly accurate time estimate (especially if you’ve built in extra padding, as we discussed earlier). And, you still have flexibility in case you need any course corrections.
  3. This process is assuming you have experience with this type of project before. I wouldn’t recommend it if it’s an entirely new project. In that case, err on the side of over-planning, simply because you’re likely to get more accurate time estimates that way.

One of these pitfalls is probably more familiar to you than the other two. To improve your planning processes, give yourself some homework—whether it’s tracking your time diligently for a week, or using visual tools when communicating long distance. You’ll be surprised at how much smoother your next project goes!

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