Picture this: you’ve got a trial set next January. And littering your calendar between now and then is a ton of deadlines, all of them triggered by that trial date. Dispositive motions. Discovery cutoffs. Pretrial conference.

Then the trial gets continued.

If you’re using Microsoft Outlook as delivered, you’ve really got no choice but to go through your calendar, find each deadline, and re-schedule it relative to the new trial date. (Maybe you’ve been proactive and assigned the case its own Category, making this task easier. Or, maybe not.)

Or, you can extend Outlook with a plugin that will shift all those Tasks and Appointments automatically when you move that trial date.

Unless otherwise noted below, all instructions and screenshots are for Microsoft Office 2010 for Windows.

Price and Features

Smart Schedules is part of a growing category of plug-ins, a piece of software that “extends” the functionality of another piece of software (in this case, Microsoft Outlook versions 2003, 2007 and 2010). Briefly, Smart Schedules allows an Outlook user to use templates to create related Tasks and Appointments (or what Smart Schedules calls “events”) driven either by a trigger date (like the trial date above) or a trigger activity.

At $97, Smart Schedules isn’t one of the cheaper Microsoft Office plug-ins out there (and plug-ins for some of Word’s features like Table of Authorities are far more expensive). But if your law practice is particularly process-driven (for instance, bankruptcy, domestic law, etc.), the ability to automate the creation and shifting of multiple deadlines could prove a huge time-saver. A free and fully-functional 30-day trial is available (and is what I used for this review). It even allows the user to assign Tasks to another user, a boon for anyone who needs to assign work to an associate or paralegal.

This particular plug-in came to my attention as I was searching for a solution to a problem at our office: setting reminders for required case status reporting. One client has a daunting set of guidelines for reports that have to be filed at strict intervals, all based either on the date the case was assigned (initial evaluation due 30 days after assignment, interim evaluation due 120 days after assignment, etc.) or on the date the case is set for trial (a pre-trial evaluation report filed at least 60 days prior).

User Interface

After installation, it only took me a few minutes to set up an entire template (what Smart Schedules calls the group of related events) for handling this client’s future matters. But if you can find something among Smart Schedule’s pre-defined templates that nearly meets your needs, editing a template and its related events is easy.

Once you have a template ready, you can use it to create a set (“project”) of Tasks and/or Appointments (a.k.a. to-do list items or calendar items) for a specific matter. There are three steps: (1) select the template; (2) name the project and select the trigger date/event; (3) review/edit the Tasks/Appointments before creating them in your Outlook file.

Managing the project—revising the trigger date, rescheduling individual items, etc.— is done within the Project Centre, accessible from the toolbar/Ribbon (depending on which version of Outlook you’re using):

The makers of Smart Schedules didn’t forget user training. A training video plus cheat sheets and FAQs are available on their website, and once you download your copy of the software, you’ll begin to receive a tutorial email each day to make the learning curve a little easier to scale.


Overall, the plug-in does what it says it will do and is relatively easy to understand. I did notice, however, that the various wizards (the sets of dialog boxes that guide users through tasks) would “hang” for several seconds before going to the next step. The lack of any sort of status bar or other indicator makes one wonder (for a moment) whether the program has encountered an error.

Also, on the Create a Template Event dialog, the program doesn’t seem to recognize the “weeks” time frames for Reminders, but if you input the same amount of time in days, it’s fine. Where this really becomes annoying is if you have to update the event later, since it re-calculates your “14 days” as “2 weeks,” then suddenly finds its own recalculated reminder time frame objectionable when you try to save a revised version of the event. The workaround here is to re-input “14 days” in the reminder field before saving. Hopefully, this will be addressed in the next update.

Who should buy this?

Any attorney whose practice is highly process-driven and dependent upon close attention to inter-related deadlines should take a look at this plug-in. If you could benefit from a simple project management interface for your practice, Smart Schedules could be a good solution for you.


Smart Schedules for Outlook (version 1.0.760)

Reviewed by Deborah Savadra on .

Summary: A time-saving plug-in for Microsoft Outlook that automates the creation and management of inter-related tasks and appointments.


  • Price and features: 3.5
  • Hardware and design: 4
  • Included software: 4
  • Performance: 4


Overall score: 3.88 (out of 5)


3 responses to “Review: Smart Schedules for Microsoft Outlook”

  1. Lori Muetzel says:

    Deborah, is there a similar solution available for google calendar?

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