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The Leader's To-do List

I have been thinking a lot about goals recently. With the month of October, I am coming to the end of my second leadership program of this year. (That doesn't mean that I won't continue to post on the subject, though.) A general rule is that a overarching goal has actions, behaviors, and tasks associated with it. My work to-do tracker of choice (Things) uses the following breakdown: Areas, Projects, To-dos, and then features within a given to-do (checklists, notes, deadlines, etc.) That breakdown works well for me, but there is one aspect that I have realized I don't use very well: scheduling. In addition to deadlines, Things allows you to set an intention for a day during which you will do a certain task. That way, you don't see all the to-dos associated with a given project, only the ones you intend to work on Today. In an ideal situation, the Today view is blank by the end of the day. I have a few thoughts about why this is an important part of the tool, if not the most important part.

The reason I say I don't use the scheduling function of Things well is because I put everything current in the Today view. Current, however, doesn't mean pressing or important, so this is a bad behavior that I need to change. Some resulting problems of the behavior are:

  • I may never get to a blank slate, meaning the next day I come in already feeling behind.
  • I am making the ideal state of "complete" unattainable, meaning I always leave work with something on my mind.
  • I may end the day/week feeling as though I missed the mark no matter how much I actually accomplish.

That being said, a leader's to-do list should always contain things that may not make the cut on a given day, but attempt to be aspirational. So too if something doesn't make the cut, it can be moved to the next appropriate day or week. As long as this doesn't always come with pushing an important deadline, generally speaking it should be fine.

The other piece of the puzzle that this bad behavior has surfaced for me is the deeper notion that not all to-do items are created equal, even beyond the original questions of immediate versus important. Not only am I able to have the Areas and Projects in a specific priority order, but having a to-do that either sits in Today forever or gets consistently bumped to a future date should indicate a level of priority that may mean additional planning action should be taken, be it refactoring, delegating, or outright deleting the to-do item. After all, getting rid of a to-do list item entirely is a state of completion of a sort, as well.

I am not saying that I believe we can always decide to ignore an action item. Depending on its source, it may be something that we actually must do and procrastination gets the better of us. Perhaps the ideal scenario is that the tools we use to track our work help us to better understand what leads us to procrastinate in the first place. Here are some questions (in a bit of a specific order) to ask if you enter a place where your to-do list is getting the better of you in one way or another:

  • Should this to-do item become a project with more attainable steps?
  • Is the (distant) deadline giving me a false sense of security about the amount of work the task entails?
  • Do I need additional guidance from a peer, stakeholder, or manager to accomplish this?
  • Am I the right person to do this work?
  • Would it be good for someone else to attempt this work or work with me on it?
  • Why am I not motivated to complete this task?
  • Would someone else on my team have additional motivation that I lack for this one?
  • Is it possible that this task is unnecessary or unattainable?