March/April 2021

Product Watch: Your Artificial Assistant

Heidi S. Alexander

I recall the launch of in 2014. It generated much hype through a waiting list of beta testers. I remember thinking, “Could an artificial intelligence (AI) scheduling assistant really solve all my scheduling woes (something I’ve expressed in this column before)?” At that time, the product was amorphous, at least to the general public. Soon after, I received an email with a meeting request from a friend with similar interests in legal technology. He cc’d his assistant “Amy” to find a mutually convenient time. Without hesitation, I responded directly to Amy, treating her as a member of his team and providing her with my availability. Amy then responded with potential dates and times, and then confirmed with an invitation for a meeting. It was not until a later date that I realized I was corresponding to my friend’s AI assistant and not a human. It was then I understood how this AI assistant worked. It was only a matter of time before I too was accepted off the waitlist and could test out

The Core Product

At its core, reduces the time and tedium of scheduling. Like other tools, it links to your calendar to determine your availability. But, in a detour from other products, the way works is by cc’ing the assistant on an email and providing simple instructions for to then coordinate a time that works for all guests included on the email. For example, an email might look something like this: “Hello Client. Let’s find a time to discuss your matter. Scheduler, please schedule a two-hour call via Zoom at the end of next week and call the meeting ‘Client Check-in.’” will find a convenient time by communicating directly with your parties and then schedule the meeting in your calendar and send out a calendar invite to all parties. And, there you have it, an AI scheduling assistant at work!

In its infancy, provided only “” or “” as assistants working exclusively over email. Since then, the product has developed by leaps and bounds. In January of 2020, I’m happy to report that added a nonbinary assistant, “” Not only do I appreciate the inclusivity of this option, but I’ve always found it strange to refer to Amy or Andrew as if they were humans. Something about that felt misleading. To avoid that, I would typically write “my AI scheduler Amy or Andrew,” wishing there were another option. The addition of “scheduler” is a positive step.

Let me walk you through some of the useful features of this tool.

The Setup 


To begin, I connect my accounts and calendars, and then set scheduling defaults. I can choose when guests book meetings (e.g., 9:00 a.m. to 5:00 p.m. on weekdays). I can add specific options by day (e.g., 8:00 a.m. to 3:00 p.m. on Tuesdays only). I can set the default meeting duration and require to avoid scheduling meetings back to back. Furthermore, I can set a default location (e.g., Zoom). All my one-off meetings use these default settings.


One of the most beneficial and unique features of this product is its automated follow-ups to guests who have not confirmed a date and time. You no longer need to remember to repeatedly reach out until the recipient responds.’s default follow-up schedule is dynamic, which, in true AI fashion, will determine when to follow up.

Reminders sends reminders of your meeting. You can choose how many days, hours or minutes before the meeting you’d like to send the reminder. And, you can add as many reminders as you choose. You can customize the reminder subject and email to your heart’s content.

The Scheduling Process

As noted above, the foundational product feature is the ability to let take the reins and schedule a meeting for you and others via email. With recent product enhancements, this works in a few ways.

The first method was described above. It is the most basic and least human-directed version. To recap, if I want to schedule a meeting with another individual(s) and have do all the work, I would send an email to these individual(s) and copy my scheduler ( and in the body of the email provide certain parameters for to schedule (e.g., during a certain time, via a certain venue and with a specific title). Almost immediately after sending the email, I will receive a confirmation email from to confirm my instructions. After confirming, does all the work behind the scenes, corresponding with my invitees until a convenient time is found. I then receive an email from with the scheduled meeting and the meeting is automatically added to my default calendar.

The second method allows more human control over the process. Through its app and webpage, you can set up your own meeting with parameters, add invitees by their email addresses and create a one-time link to send to your invitees. Think: Doodle. But this goes a step beyond. Now, rather than copy “scheduler,” which still seems to cause confusion with my invitees, I send a link and ask them to provide their availability. Following that first email, will again work behind the scenes to find a date and time that works for all.

The third method is similar to other services, such as Calendly (a product I’ve written about in the past). provides you with a customized calendar homepage URL. Mine, for example, is You can further customize the appearance of the calendar homepage and title.

The fourth method enables you to send specific availability during a certain time frame. For example, say I receive an email from someone requesting a meeting at the end of this week. I can choose to copy and paste times from my calendar for Wednesday, Thursday and Friday. When I paste the formatted text into my email, it creates a simple image with my three days with times that the recipient can then click on to confirm.


As with many legal tech products, price has evolved along the way. Initially, charged $39/month for individuals and $59/month for teams. Now, pricing is $8/month for individuals and $12/month for teams. for teams provides additional functionality for multiple users, enabling additional calendars, payment collection, scheduling with multiple team members and round robin fashion, administrative features, conference rooms and many customizations.

Final Thoughts

I’ve been on a mission to find the best calendaring tool for some time now. I’ve tested many. I find that each serves a certain purpose. I still love Calendly for its simple and user-friendly format, great support and reliability. My only gripe is that it does not allow you to schedule with multiple people. For that reason, I fell back on Doodle, a known service for scheduling with large groups of people. Doodle also has its place. I still use it for scheduling with large groups, especially when I’m worried about the technological sophistication of all the invitees, since most people are now familiar with Doodle. Now, most days, I use only But it is not flawless and I wouldn’t purport it to be so. I nearly left the service multiple times when discovering bugs that needed to be fixed by developers. Each time I discovered a flaw, support came to the rescue. In fact, when writing this piece I discovered a feature that could be enhanced and have since written support about it. They wrote me back the next morning to tell me that they understood the problem and that they had provided the feedback directly to their developers to make further updates. Based on past experiences, I believe that they will incorporate this modification. In my experience, this company is highly responsive to its users.

For now, I’ll stick with as my primary calendaring tool and look forward to future features and product enhancements. Is this tool for you? Maybe. It certainly has some unique features that you won’t find elsewhere (as far as I’m aware). Take a look at 


Heidi S. Alexander


Heidi S. Alexander is Massachusetts’ first director of the Supreme Judicial Court Standing Committee on Lawyer Well-Being. She is the author of Evernote as a Law Practice Tool, past co-chair of ABA TECHSHOW and founder of the ABA’s Women of Legal Technology initiative.