How to Plan Properly with Deadlines and Milestones

Proper use of deadlines and milestones will help keep your project moving, even with an unrealistic boss and a daunting project plan.

Stever Robbins
4-minute read
Episode #484

image of hourglass symbolizing planning with deadlines

Today we’re going to explore how to deal with falling behind on a project. Once, we all lived blissfully in nature. We wandered from tree to tree and ate fruit, took down an occasional saber-toothed tiger, and generally feasted on whatever nature provided. Life was good! It was also short. Very short. Too short. Something had to change.

And something did. The ancient Babylonians invented science. Specifically, sun dials. At last, we could keep track of time and coordinate our activities in ways never before possible. We could build pyramids, and make sure that the little pieces at the top arrived when we were ready, after we’d already put in place the pieces at the bottom. Life was good (at least, if you were the Pharoah).

And of course, the crowning achievement of our newfound ability to control time is that for the first time in human history, we could miss a deadline. That opened up the human race to a new range of emotions, ranging from shame to anger, despair, and dismay. The human experience was growing by leaps and bounds.

You can keep yourself from drowning in the shame of missed deadlines with a few simple project management tricks.

Make Sure Your Plans Are Realistic

You can only fall behind if you have set a milestone in the first place. Presumably, you have a deadline because your planning process included a careful consideration of what needed to be done to reach your deliverable. If you plan to knit your shmoopie some exciting underwear for their birthday, the underwear better be done by the time the birthday rolls around.

When you’re scoping out your project, make sure you’re choosing realistic deadlines. If you’ve never managed to knit exciting underwear in less than two months, plan to get started at least that far in advance.

Set Intermediary Deadlines

Along with your final deadline, choose a few milestones that will let you know you’ve made progress. Four weeks in, you should have completed the waistband and one leg of the underwear. If you miss that deadline, you’ll know early that you need to crank those knitting needles into high gear. 

Unrealistic Deadline? Fail Early!

This sounds fine and dandy. But just between us, your pointy-haired boss probably makes schedules without actually consulting anyone who knows how long things actually take. They demand impossible results with unrealistic deadlines. 

So set an intermediate milestone for the soonest time you believe you’ll be able to demonstrate that the schedule was absurdly, ridiculously unachievable. That way, your boss will be forced to confront the unrealistic schedule as early as possible, while there’s still time to figure out something realistic to do.

Check in Often to Minimize How Far Behind You Fall

Not only should you set deadlines at major milestones, but it’s best to have some kind of deadline about twice a week, even if it’s only self-imposed. 

Milestones are when you take stock of your progress. If you check in once a week, you could potentially lose an entire week’s worth of work before you notice how far behind you’ve fallen. If you check in twice a week, you’ll notice things are slipping when they’re only two or three days behind.

Catch up...If You Can

This sounds pretty innocuous, right? It’s only a three-day slip. How long could it possibly take to catch up? For years, some part of my brain thought, “it will take three days to catch up from a three-day slip.” Er, no. That’s totally wrong.

Let’s assume you decide to work 25% overtime—ten hours instead of eight— until you’ve caught up with the missed work. Each day you still have to do that full day’s work, and then you do 1/4 of a missed day’s work. It takes four days of overtime to make up for one day of slippage. If you slipped three days, it will take 12 days (almost three work weeks) to catch up. That’s why it’s nice to have check-ins every two to three days. If you waited a week before noticing slip, it could take an entire month of overtime to catch up, assuming you can even work that much overtime and stay sane.

If You Can’t Catch Up, Change Your Scope

Of course, we both know that putting in 25% overtime for a month isn’t actually going to happen. Even if you put in the hours, you’d be as fried as a Charleston pickel by the end of the day. Your work would suck. And besides, you have a life to live, and exciting underwear you need to knit! You can’t afford to crumble into an anxiety-ridden bundle of insecurities just because a pointy-haired bozo boss refuses to listen to reality. 

And that is why you scheduled your “soonest time you know it’s too late” milestone. When that one slips, it’s time to sit down with the boss. Explain the situation, and propose that you rescope the rest of the project, only this time, with a more realistic timeframe. Faced with incontrovertible evidence that the schedule was unrealistic, your boss will relent and restore your project plan to sanity.

In the extremely unlikely event that your boss still refuses to face reality, it may be time to take matters into your own hands. The ancient Babylonians invented more than just sundials; they also invented human sacrifice. You’ve got knitting needles. Maybe it’s time to call your boss in for a more intense, “heart to heart” conversation.

The pyramids may have been completed according to schedule, but since then, nothing else has been. Don’t stress it. Set deadlines and major milestones so you can monitor your progress. Set mini-deadlines every two to three days for yourself, so you never fall too far behind without noticing it. Small slips require big work to recover. If your boss gives you unrealistic goals, make sure you have a milestone for the first moment when you’ll be able to prove to your boss that the project needs to be rescoped. And then, sit down with your boss for that heart-to-heart and take matters into your own hands. Your shmoopie is eager for their exciting underwear, and that’s one deadline you won’t want to miss.

I’m Stever Robbins. Follow GetItDoneGuy on Twitter and Facebook. Want great keynote speeches on productivity, Living an Extraordinary Life, or entrepreneurship? Hire me! Find me at http://SteverRobbins.com

Image of hourglass © Shutterstock

About the Author

Stever Robbins

Stever Robbins was the host of the podcast Get-it-Done Guy from 2007 to 2019. He is a graduate of W. Edward Deming’s Total Quality Management training program and a Certified Master Trainer Elite of NLP. He holds an MBA from the Harvard Business School and a BS in Computer Sciences from MIT.