Calendaring Part 2: Beating Missed Deadlines and Breaking Bad Habits

In Calendaring Best Practices: Seems Simple, but Is It? we talked about calendaring best practices, and establishing a workflow. Today, we will connect some dots and focus on the dreaded missed deadline, bad habits, and improving inefficiencies. Calendaring is critical to your day-to-day operations so don’t take it lightly! If you don’t believe us, keep reading.

The Dreaded Missed Deadline

Did you know that lawyers have a 17% chance of being sued for malpractice every year? 

Addressing the #1 Cause of Malpractice Claims

According to the American Bar Association, nearly a quarter of all legal malpractice claims are based on lawyers procrastinating or failing to calendar.

  • 6% of legal malpractice claims are based on the lawyer’s failure to file documents.
  • 7% are based on the lawyer’s failure to calendar.
  • 9% are based on the lawyer’s procrastination.
  • 8% are based on the lawyer’s failure to react to the calendar.

Crazy, right?! 

If you look at all of these statistics, you will see that they are predominantly related to bad habits and inefficiencies. Let’s take a look at some of the bad habits plaguing the attorneys who are getting hit malpractice suits.

Waiting to schedule deadlines
If you’re not tracking and recording these deadlines as soon as they come in, you could be leaving yourself at risk for malpractice. 

Missing centralized calendars
If someone at your firm loses their calendar, or cannot see deadlines the rest of the firm is trying to meet, the more likely a misstep will occur. A rule of thumb to successful calendaring is transparency and visibility.

Lack of research
If you’re practicing in a new jurisdiction, you need to know the local rules or any rule changes. Even if you’re a new attorney, brush up on the regulations and make sure your bases are covered.

Failure to plan
If you do not have a plan of attack as to how you’re going to meet your deadlines, you will be leaving room to not only procrastinate but to forget about what you have due entirely.

Deadline reassignment
If your staff changes or someone gets sick, those court deadlines won’t change. Your clients should not be on the receiving end of your firms' disorganization when life happens. Always be prepared, and have a backup plan in case your team faces a disruption.

Entering deadlines
It is very inefficient to enter deadlines on a calendar one-by-one. If you have a high volume practice and one person is in charge of entering deadlines, it may take them a few days to enter everything in accordingly. And at that point, you are now a few days into a 10-day timeline, or whatever the timeframe may be. 

Potential Attorney Missteps

According to the American Bar Association, nearly a quarter of all legal malpractice claims are based on lawyers procrastinating or failing to calendar.

There are many things that can go wrong in the span of one case. Many of these things are out of your control, but some are not. Let’s go through some of those examples:

  • Notice of Removal of Federal Court - This is a prominent trap because if you don’t file that notice you can incur attorney’s fees and a whole host of other consequences. 
  • The Certificate of Review (or Professionals in some jurisdictions) - The case can be dismissed without prejudice, and if the statute of limitations expired, you cannot refile.
  • Inadequate or late fact disclosures - This is what it sounds like. You can lose the ability to use evidence at trial if the evidence you’re providing is either past due or insufficient.
  • Hiring an expert - If you hire an expert too late they will either not be allowed on the stand or they will come severely unprepared. You should try your best to prepare to disclose your expert at least 60-90 days prior so that they have a sufficient amount of time to prepare to the best of their ability. 
  • Missing Summary Judgement deadlines - This is really huge. If you miss a deadline, you may be subjected to writing-off a ton of time or worse, a prejudice against your client's case. It should also be noted that your firm's failure to respond to a motion for summary judgment within the time required by Rule 56 cannot be forgiven by reliance on excusable neglect.
  • Notice of Appeal - If you miss this deadline then you miss it. Now you can file a motion to extend the deadline, but doing so also requires you to act in a specific window of time.  

All of these examples severely impact your client. It is worth taking the time to modify and ensure that your calendaring practices are not only accurate but are standardized across the firm. 

Ideal Calendaring Workflow

  1. Calculate your deadlines as soon as they are evident and available
  2. Have another member of the team verify that calculations are done correctly. This initially may seem redundant, but human errors happen.
  3. Schedule deadlines and corresponding reminders at the appropriate intervals and assign those to a second set of eyes 

You may have read those three steps and sighed. That’s a lot of work! But it doesn’t have to be.

Instead of researching deadlines and inputting dates manually, there are ways to automate this process so that you are not only spending less time on it, but you are remaining more accurate and consistent as well.

Practice Management Software

There are a considerable amount of advantages that come with using a practice management software, let’s take a look:

  • You have a centralized calendar that is backed up and will allow you to utilize multiple views along with a matter centric view. 
  • You can sync this calendar with Outlook, Apple, and Google Calendar.
  • Workflows and task management are built into this, so all of the tasks associated with meeting those deadlines can be configured into customizable matter templates that can get layered on depending on what the deadline is. 
  • Organized matters and matter streams that will help you keep track of your last activity. You will have a better idea of when a document has been prepared when tasks have been completed, and you can subscribe to a specific matter feed to get alerts for all things pertaining to that matter. This is great for firms that are collaborative or for firms who have a heavy workload and need help juggling a multitude of tasks.

How to Keep Your Calendaring Head On Straight

Aside from having to meet court and document deadlines, you have regular tasks and everyday to-dos that you have to keep up with. Whether that includes client consultations, new client intakes, progress reports, managing your staff, and not to mention being able to go home and turn off your work brain for a little and enjoy your personal life. All it takes is a plan, and we encourage you to try to implement one of these calendar tips today. 

Take 5-10 minutes at the end of each day to plan out your next day. 

Make sure all your appointments are filled in, check your upcoming deadlines, and ensure you have blocks of time reserved to be able to work towards those deadlines and begin crossing things off your list of to-dos. Also, be thinking about the top 2-3 activities that you can accomplish for that day. You don’t need to write this down, but take mental note of what went well that day, what you're grateful and blessed to have, and what you appreciate. It may seem insignificant, but in this fast-paced, high-stressed industry, it is important to take a moment to acknowledge the good. 

Use 30 minutes on a Friday to plan out the following week.

In addition to looking at your calendar and mentally taking note of everything you have on your plate, try to solidify 3-4 concrete action items or tasks to complete for your work, your relationships, and your personal life. If you already know this, then bear with us for those who don’t. Your work productivity, happiness, and satisfaction with your life are influenced by your relationships and personal life outside of work. 

For relationships, this could be anything from calling your parents to check-in, or writing back to an old friend or old co-worker. Little things like this make a difference and they do matter. For your personal life, this could be as simple as scheduling yourself a lunch. Often times, attorneys and legal teams will get so busy they forget to eat. We aren’t scientists here, but glucose level and productivity go hand in hand. All these things may feel like a distraction at times, but your motivation and the type of work results you produce will correlate in some shape or form with how the rest of your life is going. So take a minute to incorporate those elements into your calendar because they are important.

Create a firm-wide process for scheduling and set boundaries for your time

Sometimes when people have access to a firm-wide calendar, there is a tendency to grab any time they want and book you for things without asking first. All this does is throw you off. If you spent Friday planning out your week and then you find that come Monday there are multiple chunks of your day booked out already without you knowing, you will have to completely adjust what you had planned to do. How do you fix this? You set verbal and transparent boundaries. For example, set specific days for allotted activities. Maybe Tuesdays and Thursdays are when you do your inbound consultations and client calls. So when someone calls your staff requesting your time, they will know to slot them in on either Tuesday or Thursday.

The Pomodoro technique 

The Pomodoro is a proven and popular time management technique. The premise here is that you work in blocks that typically last 25 minutes that are called Pomodoro sessions. You work for 25 minutes straight, focusing on your work with zero distractions then you follow that up with a 5 minute period of rest or a break. The result of this is productivity and higher management of distractions. Now after 4 Pomodoro sessions, you’re supposed to take a longer, 20-minute break to step away from your work, catch your breath and clear your mind. 


Delegate where appropriate and have dedicated time to review with staff. If you’re using practice management software, you will have a way to manage projects at a glance and also get really granular insights into the work your team is doing. This will enhance your firm's productivity overall and the quality of service you are able to provide to your clients. 

If your scheduling regular dates to review your matters and you have specific staff assigned to those matters, pull up the calendar and go through everything that you expect needs to be done or completed by that person. The earlier and more often you do this, the easier it will be to catch mistakes and avoid missed deadlines. Additionally, give these staff members the opportunity to talk about their workload, and give them feedback on the quality of their work. Also, use this time to offer support and constructive feedback; if you don’t like how something is being handled, let them know, or if you are happy with something you should express that as well. 


Calendaring is important. If you walk away with only one thing, it should be that. You may not be able to implement everything we just talked about overnight, but if you can start today, you will only improve company morale, ensure that no task is being forgotten, and you will help foster a system of efficiency and excellence within your firm.

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