Calendar overload? How to manage your schedule with Calendly’s AI assistant

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

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

PCMag has tested many of the top calendar apps, and I tested an AI assistant in 2016. Many of the companies I freelance for use Google Workspaces, which allows me to book time into executive schedules. And while I was impressed by the Google Duplex demo and gave Google Assistant a try, it wasn’t as perfect as I wanted, so I gave up.

Do you have Calendar?

calendar calendar

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

I have been using Calendly(Opens in a new window) solidly on ever since, and eliminated the hassle of juggling a multi-hyphenate career (journalist-ghostwriter-consultant) across five different Gmail profiles with interlocking calendar apps, one Samsung A03s (don’t judge), and two home/office HP Chromebooks (no, I haven’t looked back since 2015).

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

Last year, Calendly invested in in a new window)that integrates with Calendly, then acquired(Opens in a new window) the Hugo team productivity app(Opens in a new window)which is also based on programming with preparation and monitoring tools.

Overall, Calendly is easy to set up, with an elegant user experience that belies adaptive intelligence via machine learning under the hood. If you’re geeking about these things, and I feel like I’m among friends here in that regard, it’s great to see the software deftly guide you through setting up rules to “train the AI” to be the perfect assistant.

How to set up Calendly

calendly welcome screen

I recently decided to expand my use of Calendly to another of my lines of business and the accompanying Gmail profile. If you want to do the same, you don’t have to go through all the steps below, there are many options available to configure, but this is how I configure it.

Go to the Calendly website(Opens in a new window) and click Start to set up an account. You can 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 “view, edit, share, and permanently delete all calendars you can access using Google Calendar.”

calendar url configuration

Next, you need to choose a suitable URL, which will be shared with anyone who wants to reserve time on your calendar. By default it is the username in your Gmail (or similar), but you can change it.

If you’re on the go while setting up Calendly, make sure it shows your preference time zone. I’m on the west coast so it was already displaying pacific time and I left that option as it is. As a European, I also selected the 24-hour clock. But since I live in the US, I followed the correct month/date/year form to avoid confusing everyone.

set availability

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

I work in Los Angeles, but a lot of the people I work with are in New York, London, or continental Europe. This means that I need to set my availability to account for these different time zones. To do that, I change my hours on specific days. Mondays and Fridays I work East Coast time. I allow (very) early calls on Thursdays to accommodate UK and European meetings, but I do leave nice and early. Tuesdays and Wednesdays I completely block as writing days.


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

But that is only the first step. Once you finish the initial setup, you can further adjust 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 making a general setting of Monday through Friday from 9am to 5pm, for example.

The last question Calendly asks is how you plan to use the product. It’s optional but worth doing as it leads to a more personalized experience. For example, some people just want to use it to let others schedule time on their calendar. Others may want to take advantage of CRM tools (more on that later). I chose Independent + Consultantthen clicked To finalize.

How to schedule an event

event types page

Now you’re ready to start getting more granular with Calendly’s functionality. if you clicked Independent + Consultantthe page is pre-populated with an initial 30 minute meeting. You may see additional items on the Event Types page if you selected a different feature. However, you can also click New type of event for more options, such as Group, Collective, or Round Robin.

new type of event

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

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share meeting link

If you’ve created more than one event type, you may want to keep things simple and send a link to the correct event type. In this case, click the Share on an event type (or click copy link) to help people create a specific type of event on their calendar.

calendly calendar view

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. Then they click on a time and press Confirm to book a meeting with you.

Details of the reserve

They will be asked to provide more information, such as their name, email, and any additional notes that may be required. 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 appear with all the meeting details.

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


integrations for calendly

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

For example, 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 last recommendation

People often use the free product, but corporations are increasingly spending $25 per user, per month to streamline operations and save precious time. I’m still using the free product, but I’m considering an upgrade, since Calendly does so much more than just schedule meetings. The tool also helps with workflow, follow-ups, and more.

And, in case you were wondering, Calendly says your data is safe.(Opens in a new window). Host 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 gain 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 double can handle meetings himself.

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