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September/October 2021

Hot Buttons: Defensive Calendaring

Catherine Sanders Reach

Do you feel as if your calendar is under constant bombardment with meetings, client consultations, events and to-do’s? Do you know how to use calendars such as Google Calendar or Microsoft Outlook to free up time? Apply defensive calendaring techniques so you can allow people to schedule meetings with you themselves, effectively coordinate meetings with multiple parties and leverage artificial intelligence so you’re not wasting time negotiating availability.

First, Do You Need to Upgrade?

You may still use a paper calendar, which may work if you are a true solo, but if you want to get help from a virtual assistant, let people book time on your calendar or send invitations to someone to participate in a videoconference, you need an electronic calendar. While there are other options, the most extensible electronic calendars are the Google Calendar and the Microsoft Outlook calendar. If you are using Microsoft Outlook simply for connecting an email account and you do not use the Exchange server (hosted, local or through Microsoft 365), you may consider upgrading to get all the functionality of the calendar. With the Exchange server, your calendar will synchronize with most any other application including apps, add-ons, practice management applications, videoconferencing platforms and more.

What Problem Are You Trying to Solve?

Do you need to stay on top of tasks and appointments, make it easier to share time within the firm, reduce back and forth negotiations for meetings or reduce no-shows/no-calls with clients? All of the above? Do you mix your work and personal schedules? Current best practices suggest that you should be able to see all the meetings and activities for your day so you can better manage available time. Even if you keep a family calendar in Google and a work calendar in Outlook, you can use your smartphone calendar app to sync with both and see all appointments and activities in one place. There are many ways to use one or more calendars, but first you will need to decide your priorities and work from there.

Schedule Time for Deep Work

Are you blocking time on your calendar for deep work so you can (attempt) uninterrupted time to get things done? If you are using Microsoft 365, you probably get a daily email from Cortana suggesting that you schedule “quiet” time. Insights in Microsoft makes the same suggestions. Perhaps there is something to this? Of course it is aspirational, but if you do not make it a habit of reserving portions of your day to get work done, you may find yourself falling behind with a full calendar. While it is not always possible, build in breaks as much as you can.

Your Work Calendar

Your calendar should be available on every device you have and available through the browser. If you’re a Microsoft 365 user, get the Outlook app for your smartphone. If you’re a Google Workspace user, get the Calendar app. You should be able to have bidirectional synchronization so that no matter where you are and on what device, you can see and edit your calendar. This synchronization should include apps like your practice management system and anywhere else you need to access your calendar and see the same version of reality no matter how you access it. If you must manually synchronize your calendar with another app or on your phone, you should look into ways to flow all the calendar information from one place to another so you can update or edit anywhere and your change is reflected everywhere.

Sharing Your Calendar Internally

Calendars designed for business users have the advantage of letting you delegate and give permission to others in your firm to see your calendar and add appointments as needed. For instance, in Microsoft Outlook’s calendar with the Exchange server, you can choose your calendar, right-click and give different people permission to view specific information and even edit your calendar. You can give someone permission to edit or choose “delegate.” Because you can mark items in your Outlook calendar as private, you can choose whether the delegate can see details for private events. Of course, people can send you appointment requests, but these permissions will let you go beyond viewing free/busy time.

Reply With a Meeting

In Microsoft Outlook, you can convert an email to an appointment with one click on the “Reply with Meeting” button. There is similar functionality to move messages from Gmail into your Google Calendar. Do not wait on someone who says, “I’ll send you an appointment request.” Move the email into your calendar to ensure the time is blocked out and you do not inadvertently double-book. This is especially important if you are using a tool like Calendly or Acuity to let people outside of the firm book time on your calendar.

See Other People's Schedules

If everyone in the firm is effectively using their online calendar, you can use yours to see your colleagues’ and support team’s availability. In Microsoft Outlook if you want to see if someone is available, set up a meeting with your preferred time and date in the calendar, add the participants and then click on the Scheduling Assistant tab. You can see availability for people in your firm for multiple days and easily choose a time that works for everyone without having to send an email or place a phone call. There is even an AutoPick option, so you don’t have to look at a lot of options—which is especially useful if there are multiple people involved.

Scheduling Meetings With Multiple People

If you need to schedule mutually agreeable time with parties inside and outside the firm, consider FindTime if you are a Microsoft Outlook user and Doodle Premium for Google Calendar. FindTime is a free add-on for Outlook that lets you create a poll so people can click on the times they are available. It then tallies the responses and sends out a meeting request. FindTime is especially useful because it will first show availability for internal users in the firm, so you have a fighting chance of picking times that work for your team before you send the poll to people outside your firm. When you set up the meeting in FindTime, you can enter a location, such as your office, or add a Zoom link, and turn on and off options like requiring attendees to verify their identity. FindTime has a dashboard so if someone is not being responsive, you can just ping that person or drop them from the attendees list. There are other options with FindTime, including blocking all the times you send in the poll as tentative on your calendar so that you don’t accidentally book over a time while the poll is out. Doodle is a tool that is free to use and much like FindTime. However, the free version does not include integration into your calendar and is full of ads, which is not very professional. Doodle Premium for one user is $6.95 per month, paid annually. In addition to integrations with Microsoft Outlook/Exchange/ Microsoft 365, it has integrations with Google Calendar and offers apps. The paid version of Doodle also provides features like a scheduling assistant and lets you set up meeting reminders. There is a 14-day free trial. Whether you use FindTime or Doodle, do not suggest a whole lot of optional times in the poll. It is overwhelming and difficult for the respondents to participate. Just pick five or six times, and if those don’t work, try again.

Scheduling Assistants

One of the best reasons to practice defensive calendaring is that it allows you to leverage automated scheduling tools. Products like the aforementioned Doodle Premium, plus Calendly, Acuity,, Bookings and more, will let you send or share a link via email or on your website and allow people to book time on your calendar. Some of the products, like Calendly, are free for limited use, so if you want to see how it works, you can start with a free account. You set it up with your Google or Outlook calendar, and all it sees is free/busy time. When you’re setting up a scheduling assistant, you can set up multiple types of meetings for different time durations, even for only certain hours. For instance, if you do 30-minute free consultations on Thursday, you can set up a meeting type to handle bookings for those appointments. You can exclude certain times and weekends for other types of appointments. You can also set restrictions to keep from getting overwhelmed, especially if you make the link to your scheduler publicly available. For instance, you can limit your availability to a certain number of meetings a day, so you won’t find yourself with an overloaded calendar. You can also set the amount of time between meetings, so you can keep from having all your meetings back to back. You can restrict how far into the future someone can schedule an appointment. These tools give you many ways to provide the convenience of DIY for those who want to meet with you, while helping you “protect” your calendar so you’re not overwhelmed. Other features in many of the scheduling assistant tools include reminders via email or text to reduce no-shows, rescheduling links, automated feedback/follow-up emails and more. Many of these tools also let you set up online payments in advance of a meeting. Of note, some people may be a little put off depending on how you approach them with the option to book an appointment on your calendar. While most people see it as a convenience, some may think it impersonal or want a “human” touch. If you send a link to your scheduling assistant, consider how you phrase it. A nice note with a “find a time that works with your schedule here:” will seem friendlier than “book now.” Context is important, and the same approach may not be right for all the people you meet with in your practice. One rather unique scheduling assistant is In addition to the calendar integration common to these tools, gives you an artificial intelligence (AI) bot to help negotiate availability. If you have clients who may want that personal attention, you can ask Amy or Andrew to help set up a meeting. Amy (or Andrew) are nonhuman AI assistants. They can “see” your calendar and help schedule a meeting if you provide the right prompts. For instance, respond to a client, copy Amy and write, “Would next Friday at 2 p.m. for an hour at my office work for you? Amy can help get that scheduled.” Amy will set up the meeting on your calendar and send the appointment request to the other person. can also help set up meetings with multiple parties. The AI is capable of taking some cues and can handle some options, but do not expect it to hold a conversation with your client. is free to try, and the paid version has some extra bells and whistles like putting the AI bots on your domain, designating VIPs and storing favorite locations.

Videoconferencing and Your Calendar

While many lawyers had participated in a webinar here and there, the pandemic made it a way of life. Post-pandemic, it is likely that webinars and videoconferencing will still dominate lawyers’ calendars. They are convenient and help reduce travel time and expenses. Most videoconferencing tools, whether through your Voice over Internet Protocol provider, through Microsoft 365 Teams, or via stand-alone products like Zoom or Webex, have calendar integrations. There are several reasons to take advantage of these integrations. One, when you set up a videoconference, you will never have to tell someone that you’ll send the link later (and forget until the last minute). Two, it will immediately block the time on your calendar. Three, you can adjust meeting settings like waiting rooms/lobby, allow/disallow chat and more directly from the calendar plug-in so you do not have to remember to get those things set up in different meetings. Zoom and Teams also integrates with many of the meeting scheduling tools, ensuring that everyone has everything they need to participate and on their calendars. The Zoom integration is so good you can even set up a Zoom videoconference from the Outlook app on your smartphone!

Legal-Specific Rules-Based Calendaring

If your firm handles matters that include a lot of court appearances and deadlines, you can take advantage of subscription rules-based calendaring products. These tools integrate with your online calendar and will help calculate the deadlines on your calendar based on the court rules for that jurisdiction. Some practice management applications have rules-based calendaring included in the subscription, and some include the rules for an additional subscription fee. There are also standalone products that integrate with your calendar, your practice management application and more, including LawToolBox, and Calendar Rules.

The Best Defense is a Good Offense

Lawyers and their teams are busy people. The more you can block time, share availability, interact with products you already use, get out of the way of scheduling meetings and take advantage of the technology, the more control you will have over your day. Or at least you will be able to see what is coming.

Catherine Sanders Reach


Catherine Sanders Reach is director of the Center for Practice Management at the North Carolina Bar Association. Formerly she was director, Law Practice Management and Technology for the Chicago Bar Association and the director at the American Bar Association’s Legal Technology Resource Center. She served on the ABA TECHSHOW Board from 2007-2009 and 2014-2016, and was co-vice chair in 2019 and co-chair in 2020. [email protected] 

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