15 Thoughts on Meeting Deadlines

I love deadlines. I love the whooshing noise they make as they go by.
~ Douglas Adams

I’ve been managing work and people for 20 years. These are things I’ve learned about deadlines and being accountable. They apply equally in the workplace, life and to personal writing projects. I still suck at most of them.

#1. Give a damn. If you don’t care about the deadline, you won’t make it. Invest in the ‘why’. Make it personal. Make it a priority.

#2. Write your commitments and deadlines down. All of ’em. If you live digitally, put them on your phone. If physical, put them near the fridge. Do both. Trust me– you’ll see ’em.

#3. Communicate a clear deadline with whomever the deadline is for. Be specific. Neither later this month nor by the end of summer are deadlines. March 30th and Friday by 4pm are. See the difference? Set clear start and end dates.

#4. Build in a buffer. I call this the ‘Montgomery Scott School of Engineering Estimates.’ Multiply all effort estimates by 4. I’m not joking.

#4 a. Humans suck at estimating how much time something will take. We’re very good at comparing stuff though. A realistic estimate should be based on a similar activity you’ve done before.

#4 b. Multiply by 4.

#5. Have a clear definition of ‘done’. If you don’t know what done looks like and all parties don’t share the same definition of done, then you’re hooped.

#6. Break the work down into smaller sub-tasks. It makes them seem more ‘complete-able’ and not so overwhelming. Estimates are easier too. Give the sub-tasks start and end dates.

Then you can do the things one step at a time. If you’re competitive, crossing stuff off is quite satisfying.

Personal story time! My bride makes a ridiculous number of cat toys for a rescue. If she’s making a hundred catnip fish bones, she’ll break the task down: heads, spines, ribs, stuffing and assembly. And then she’ll do them in batches of five-to-seven for each phase of work. She plots out her daily production targets in her calendar. The check marks keep her rolling.

#7. Focus on the specific activity in front of you. One step at a time. All that matters is what you have to do right meow. You’ve already planned the work. It’s time to just do the thing. Let the rest go. You got this.

#8. Calendars are curiously useful things. We tend to put meetings and appointments in them, but never schedule our work. We do a very good job of scheduling our interruptions. Weird, huh? Schedule time to do the work. Block it off. Make yourself busy for that period of time and get to it.

#9. Communicate your progress. If someone is waiting on you or even if it’s yourself. Be accountable. If you’re falling behind or things are going sideways, peeps need to know.

#10. Don’t make promises you can’t deliver on. Over-committing will crush your soul and sully your reputation. If you plan your work, you’ll know what available capacity you have to do the work. Saying ‘yes’ to everything is what puts the dead in deadline.

#11. If you screw up and miss a deadline, apologize and learn. Take some time to reflect on how you could have avoided the train-wreck. From failure comes growth.

#12. Sometimes you have to lean-in to the work and get it done. That will occasionally mean sacrificing sleep. Get over it. If you committed to a deadline, sometimes this is just where you’re at.

#13. Ask for help. Seriously. Don’t be a hero. Heroes die.

#14. Renegotiate your commitments and set a new deadline. The earlier you do this, the better. Otherwise, see #12

#15. Get started already. Procrastination is the worst villain. It will undermine all your good intentions. If you’re planning well, then getting started looks just like the first step. Do that one step. If you haven’t planned, then you can still climb the mountain. Just start with one step forward.

A goal is a dream with a deadline. ~ Napoleon Hill

Now, get back to work. That project won’t do itself. 


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