The Innovation of Litigation.

How to Stop Doing that One Work-Chore You Really Hate Doing

You know that one task in your work-life you hate doing the most? Most people can immediately think of something. You might occasionally ponder if there is a better way, but you’re busy. We all are. You don’t have time to fix every inefficiency in the system, right? In this article, I’ll give you a process for systematically eliminating those tasks you hate the most.

For me, it was scheduling meetings. I don’t just dislike scheduling meetings, I loathe scheduling meetings with a burning passion of a thousand suns. First, I check my calendar to see when I’m available. Then, because I am frequently pulled in many directions in my job, I engage in a quasi-mystical process of divining which slots are least likely to get bumped. I send an email copying several other stakeholders and suggesting dates and times. I wait to get emails back. Sometimes it’s easy and everyone can agree to meet during one of my suggested dates and times–often, there is a tedious back and forth before we all agree on a day and time that works for everyone. Sometimes, just getting answers back is like chewing nails.

This task is one of the most unbearable chores of my work-life, and yet, it is unavoidable. I depend on regularly meeting with a variety of teams of diverse professionals throughout the week and if I–or they–fail to show up, things go off the rails, often quickly. So for many years, I did what most people do when they hate doing a necessary but arduous task: I gritted my teeth and put up with it for the good of God and country.

Enter If you click the link, you’ll see a slogan that reads like a chorus of angels ringing in my ears: “Scheduling sucks.” Ahem. You have my attention.

The focus of this article isn’t on, so I’ll keep it brief, here. (Also, I should note that I am receiving no benefit for using this service to illustrate my point.) For a few dollars a month, gives you a machine-learning-powered, digital scheduling assistant. When you need to schedule a meeting, you send an email to the invitees and you copy the assistant. The assistant understands natural language and can figure out when and where you want to schedule the meeting, check your calendar, and do all of the back and forth ping-pong of figuring out a time that works for everyone. The best part? After that first email, you rarely see another part of that negotiation until all parties have decided on a day and time that works with your schedule. Usually, the next thing I see after sending that first email is a calendar invite where everyone has agreed upon the place and time.

To someone who abhors the chore of scheduling meetings, this result feels like magic. It feels like living in a future where we all have flying cars and can move things with our minds.


As I reveled in the glory that was eliminating my least favorite work-chore from my life, I realized that there was a broader and more important lesson, here. My experience with eliminating this work-chore I hated doing offers a blueprint on how to start improving processes that annoy and slow down productivity. Here’s what to do.

Look for any process in your work-life that is:

  1. Irritating,
  2. Necessary,
  3. Routine,
  4. Highly repetitive, and
  5. Doesn’t involve customer-facing activities*

*Now would be a good moment to confess that I do not use to schedule meetings with say, a prospective new client that I’m trying to pitch. In that limited circumstance, it’s worth my time to put my human touch on setting up the meeting. Sometimes customer-facing tasks are great for automation, see self-checkouts for example, but tread carefully. Automating an annoying customer-facing activity may improve your life to the detriment of your customers.

Any time you find yourself annoyed with doing a chore that checks these boxes, a red flag should run up in your brain and you should ask yourself: is this the sort of thing that can be automated? If the process checks these boxes, then there’s a good chance the answer is yes.

Here is the point I’m trying to impress upon you: in an environment when you are busy and feel like you have no time to think about process improvement within your company or law firm, identifying processes that can be automated is half the battle. Learn this checklist, internalize it, keep notes on when you encounter processes that fit within these parameters.

If a process irritates you, chances are good it irritates others, too. If it irritates others, there’s a good chance someone has already thought of a great solution to automate the process. If that is the case, beg, steal, or borrow a solution that works best for you. If no one has solved the process, but it’s a universal irritant that meets this criteria, then congratulations, you may have stumbled upon the next great idea for a successful startup.

The bottom line is that by internalizing this checklist and being purposeful about noting when you find these processes, you’ll position yourself to continually improve the quality of your work-life and the work-life of those around you. By improving tedious and repetitive chores, you’ll free yourself up to spend more time focusing on productive output where you are most valuable.

Have a work-chore you hate doing? Share it with us! Let’s brainstorm how we can automate the chores you hate the most.

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Trial by Tech is a blog brought to you by Baylor Law’s Executive LL.M. in Litigation Management—the first program in the nation designed exclusively for lawyers who aspire to direct effective litigation strategy, control electronic discovery, leverage technology, manage a team, and lead their company’s or firm’s efforts to manage a high-volume, high-stakes docket.

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