Three Key Behaviours to Master Deadlines

“You may delay, but time will not.” - Benjamin Franklin

‍

Time. Some smart and cheeky person once said it exists so that everything doesn’t happen at once. The problem with it, though, is that it just keeps going forward.

Time is not my strong suit. I much prefer space. On holidays, I’ll gladly do the packing while my wife arranges the travel schedule. However, in my professional life, there is one aspect of time that is unavoidable: deadlines. The very word makes some people sweat.

It used to make me sweat as well, because I knew that it invariably meant pushing hard at the eleventh hour, and sometimes it meant feeling bad about missing the due date. However, stress and guilt don’t have to go with deadlines. The Getting Things Done (GTD) methodology helps me manage anything that comes at me, and everything I commit to do, using time as just one variable in that mix. However, being a bit of a slow learner about time in particular, I have had to think extra hard about the strategies that work best to help me hit deadlines.

The strategies boil down to three simple things for me: recognising commitments at the outset, setting myself up to succeed using calendar and lists, and reviewing my calendar and lists to adjust over time. I think most people who are good with deadlines employ some combination of recognition, structure, and foresight in their own way. Here is how I make those three elements work for me using GTD.

The first biggest key for me has been to simply notice when I have made a commitment to myself or someone else. As soon as I say “yes, I can have that done by such-and-such date”, I recognise that I need to capture that commitment. No matter how important it seems in the white heat of board meeting enthusiasm, I know that if I don’t write it down, I will eventually forget it. Sometimes that starts with a quick jot on a notepad.

Eventually, though, I find that I need more than just a quick jot to really set myself up for success as I march forward in time toward that deadline. I need to think about the outcome, next action, and reminders I would like to see along the way. This is the second big key. I also need to get the results of this thinking input into my trusted GTD system within about 24-48 hours of saying “yes” to the deadline. Typically, I input four different items into my system to handle most types of deadlines:

a) An all-day calendar item on the due date to remind me the project is due

b) One or more reminders anywhere from a few days to a few weeks in advance, usually phrased like “how’s it going on project xyz?”, as a friendly way to check up on myself

c) The project outcome to complete, on my project list, stated in terms of the outcome’s “done state”

d) The very next action, on my action list, in the best context for me to see it in when I’m ready to move it along

The third critical behaviour involves conducting a weekly review. Reminders and due dates on subsequent weeks of my calendar are no good to me if I only ever look at my “this week” view. So, during my GTD weekly review, I look ahead to see the project deadline or reminder coming at me, and potentially renegotiate other commitments early in the week to make sure that I have plenty of time to keep making the right amount of progress on the project. I might block some time out, reschedule meetings, or whatever is needed so I can feel confident that I will make good progress in that coming week.

I still keep the next action and project outcome staked down on my lists as well, because I might get to various next actions much sooner than the day of the due date or reminder–or even finish the project early!–but at least I have that “backstop” of deadline on my calendar, and one or more reminders leading out from there to encourage me along the way. Also, the reminders are not there to say “do this on this day”–they are to check in. The doing happens as soon as I can, and as soon as it makes sense–but the calendar gives me foresight to help me make sure I keep on track.

Far too often people fall into the trap of not staking down project outcome and next action on a list, and thereby create stress for themselves of having to do it all in whatever short span of time there is between the moment they remember it is coming due, and the moment it is actually due. Or, they use the calendared days as the day when they are going to “do it all at once”, but then best laid plans get derailed, or there are unforeseen contingencies or other delays that make “all at once” impossible. This is why consistent forward progress can be safer and more effective for big projects, and the list-based approach gives you the flexibility to work this way.

Not having a naturally easy relationship to time, I had to make this level of tracking routine and mechanical in order to succeed. That way none of it has to stay in my head to stress me out (or worse, not enter my head until the panicked moment just before the clock runs out, and really stress me out!). To accomplish a routine approach, I established three simple new behaviours over time:

1. Recognise whenever I commit to something and write it down.

2. Think through the commitment to flush out the next action, waiting for, calendar item, project, or some combination of these to get into my system to support me along the way.

3. Do a weekly review (weekly!), scanning ahead to see what’s coming at me, including reminders of upcoming events, so that I can engage appropriately, week by week, in advance of the deadline

With these three key behaviours in place, I have found that the rest becomes fairly easy and self-evident in terms of keeping the moving parts moving toward the goal.

Recognise commitments, think them through, reassess once per week. Making these habits has taken the stress out of deadlines for me. In fact, I have found that the kinds of projects I was begging for extensions on previously now often get done early, and the same is true for many of our clients who have applied this approach.

Unlike the Rolling Stones, time may not always be on your side–but you can be on your own side by establishing a few simple habits to support your future self in getting the right things done on time.