Calendar Overload? How to Manage Your Schedule With Calendly’s AI Assistant

Managing meetings and juggling calendar entries is a modern inter-office etiquette nightmare, and it’s arguably worse for freelancers without the cushion of administrative support. (I speak from experience here.) It can also contribute to not-so-subtle power plays among those who consider themselves Very Busy and are reluctant to commit to meeting times.

Once a meeting is set, it’s usually rescheduled several times, often at the last minute. Then there’s the setting of agendas, follow-ups, reminders and that’s before you’ve actually had the meeting. If you’d like to avoid all this, ask an AI to manage your life, or at least your scheduling.

PCMag has tested many of the top calendar apps and I took an AI assistant for a spin in 2016. Many of the firms I freelance for use Google Workspaces, which allows me to book time on execs’ schedules. And while I was wowed by the Google Duplex demo, and gave the Google Assistant a shot, it was not as seamless as I wanted, so I gave up.

Got Calendly? 

Then, about six months ago, someone asked to meet and cheerily suggested that “Calendly can find us time to chat.” I used it and, pleasantly surprised, signed up for my own account.

I’ve been using Calendly(Opens in a new window) solidly since then, and it’s taken the hassle out of juggling a multi-hyphenate career (journalist-ghostwriter-consultant) across five different Gmail profiles with cross-linked calendar apps, a Samsung A03s (don’t judge), and two home/office HP Chromebooks (nope, I haven’t looked back since 2015). 

Started by Tope Awotona in 2013 as a freemium service to bring scheduling into the 21st century, Calendly now boasts 10 million users worldwide, with 50,000 companies as clients and 100+ partner integrations. Awotona started off as a computer science major at the University of Georgia, then switched to management information systems, before working on software sales for IBM, Lexmark, and EMC (before it was sold to Dell).

Last year, Calendly invested in reclaim.ai(Opens in a new window), which integrates into Calendly, then acquired(Opens in a new window) the team productivity app Hugo(Opens in a new window), which builds on scheduling with preparation and follow-up tools, too. 

Overall, Calendly is simple to set up, with a sleek UX that belies the adaptive intelligence through machine learning under the hood. If one is geeky about these things—and I sense I’m among friends here in that regard—it’s cool to watch the software cleverly walk you through setting up rules to “train the AI” to be the perfect assistant.

How to Set Up Calendly

I recently decided to expand my usage of Calendly to another of my business lines and accompanying Gmail profile. If you’d like to do the same, you don’t have to go through all the steps below—there are a lot of options available to configure—but here’s how I set it up.

Go to the Calendly website(Opens in a new window) and click Get Started to set up an account. You can either choose to sign up with your email address or use your Google or Microsoft account. I chose one of my Gmail profiles, which required me to click Allow so Calendly can “see, edit, share, and permanently delete all the calendars you can access using Google Calendar.”

You must then choose a suitable URL, which will be shared with anyone who wants to book time in your calendar. It defaults to the username on your Gmail (or similar), but you can change it.

If you happen to be traveling while setting up Calendly, check that it’s displaying your preferred time zone. I’m on the West Coast, so it was already showing Pacific Time, and I left that option as is. As a European, I also selected the 24-hour clock. But since I live in the US, I stuck to the correct form for month/date/year to avoid confusing everyone. 

On the next page, Calendly confirms what it can do with your existing calendar entries, namely check for conflicts and add events. There is an edit option if you don’t want it to do either; I clicked Continue to keep them both. Now you can set your availability, which is how you start training the AI to protect your time and be helpful.

I work in LA but many of the people I work with are in NYC, London, or mainland Europe. This means I need to set my availability to take into account these different time zones. In order to do that, I shift my hours on specific days. On Mondays and Fridays I work on East Coast time. I allow for (very) early calls on Thursdays to accommodate British and European meetings, but clock off nice and early. Tuesdays and Wednesdays I block out entirely as writing days.

Scheduling this out used to be a nightmare, but Calendly makes it simple. I set these different parameters, and Calendly never shows availability at the wrong time or on the wrong day.

But that’s just the first step. Once you finish the initial setup, you can further fine-tune your availability by clicking the Availability header on the Calendly site. If you have specific responsibilities to attend to, it’s easy to modify availability by day of the week and hours, rather than do a blanket setup for Monday through Friday from 9 a.m. to 5 p.m., for instance. 

The last question Calendly asks you is how you plan to use the product. It’s optional but worth doing, since it leads to a more tailored experience. For example, some people just want to use it to allow others to schedule time on their calendar. Others might want to take advantage of the CRM tools (more on that later). I chose Freelance + Consultant, then clicked Finish. 

How to Schedule an Event

You’re now ready to start getting more granular with Calendly’s functionality. If you clicked Freelance + Consultant, the page is pre-populated with an initial 30 Minute Meeting. You might see additional items on the Event Types page if you selected a different function. However, you can also click New Event Type for more options, such as Group, Collective, or Round Robin.

You can share your calendar with someone by copying your Calendly URL [i.e. Calendly.com/YOURNAMEHERE] and sending it in a text or email. Once they click on it, they’ll see your name and instructions on how to add an event to your calendar.

If you created more than one type of event, you may want to simplify things and send a link to the correct event type. In this case, click the Share button on an event type (or click Copy link) to help people create a specific kind of event on your calendar.

From your link, those who want to book time with you will have access to your calendar. They can select a specific day to open time slots that you have set yourself to be available. They then click a time and hit Confirm to book a meeting with you.

They will be prompted to provide more information, such as their name, email, and any additional notes that may be necessary. There’s even an option for them to add additional guests to the meeting. Once all the details are in, they click Schedule Event. A confirmation screen will then appear with all the meeting details.

You don’t have to do anything. When you check your calendar next, you’ll see a meeting has been scheduled (and a confirmation email will be sent to all parties involved in the meeting). 

Integrations

This has all been a basic setup for you to start scheduling email. However, if you need more functionality, click the Integrations header to find a host of other options, including Firefox, Chrome, and iPhone app integrations.

For instance, if you need Calendly to insert a link to your favorite video conferencing service automatically, there are integrations for Zoom, Google Meet, Microsoft Teams, and more. You can also integrate your Calendly account with PayPal or Stripe, if you charge for meetings. 

One Final Recommendation 

Individuals typically use the free product, but corporations are increasingly shelling out $25 per user, per month, to streamline operations and save precious time. I’m still using the free product, but am considering an upgrade as Calendly does way more than book meetings. The tool also helps with workflow, follow-ups, and more.

And, in case you were wondering, Calendly says that your data is safe(Opens in a new window). It hosts everything in US data centers provided by Google and Amazon Web Services. 

So would I recommend Calendly? Yes. I hate booking meetings and Calendly has been smooth and simple. It has also helped me claw back an enormous amount of time by letting the AI handle my scheduling. Eventually, of course, I’d like to clone myself so my digital doppelganger can handle the meetings themselves.