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

Managing meetings and juggling calendar entries is a modern etiquette nightmare between offices, and it’s arguably worse for freelancers without the cushion of administrative support. (I’m speaking from experience here.) It can also contribute to not-so-subtle power plays among those who consider themselves very busy and reluctant to commit to meeting hours.

Once a meeting is scheduled, it is usually rescheduled several times, often at the last minute. Then there’s setting agendas, follow-ups, reminders and that’s before you’ve actually had the meeting. If you want to avoid all of that, have an AI run your life, or at least your schedule.

PCMag has tested several of the best calendar apps and I took an AI assistant for a spin in 2016. Many of the companies I freelance for use Google Workspaces, which allows me to book time on executive schedules . And although I was impressed with the Google Duplex demo and tried the Google Assistant, it wasn’t as seamless as I wanted, so I gave up.

Do you have Calendly?

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

I used Calendment(Opens in a new window) solidly since then, and it’s been easy to juggle a multi-hyphenated career (journalist-ghostwriter-consultant) on five different Gmail profiles with cross calendar apps, a Samsung A03 (don’t judge) and two home/office HP Chromebooks (no, I haven’t looked back since 2015).

Launched by Tope Awotona in 2013 as a freemium service to bring scheduling into the 21st century, Calendly now has 10 million users worldwide, with 50,000 enterprise customers and over 100 partner integrations. Awotona started as a computer science student at the University of Georgia, then moved into 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)which integrates into Calendly, then acquired(Opens in a new window) the team productivity app Hugo(Opens in a new window)which also relies on planning with preparation and monitoring tools.

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

How to configure 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 follow all the steps below – there are plenty of options available for configuration – but here’s how I set it up.

Go to the Calendly website(Opens in a new window) and click Begin to create 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.”

calandly url configuration

You then need to choose an appropriate URL, which will be shared with anyone who wants to book time in your calendar. This is the default username on your Gmail (or similar), but you can change it.

If you happen to travel when setting up Calendly, check that it shows your 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 chose the 24 hour clock. But since I live in the US, I stuck to the correct form for the month/date/year to avoid confusing anyone.

set availability

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

I work in Los Angeles, but most of the people I work with are in New York, London, or continental Europe. This means that I have to set my availability to account for these different time zones. To do this, I shift my hours to specific days. On Mondays and Fridays, I work on East Coast time. I allow (very) early calls on Thursdays to accommodate UK and EU meetings, but clock well and early. I completely block out Tuesdays and Wednesdays as writing days.

days of the week

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

But this is only the first step. Once you’ve completed the initial setup, you can fine-tune your availability by clicking the Availablity header on the Calendly site. If you have specific responsibilities, it’s easy to change availability by day of the week and by time, rather than doing a blanket setup of Monday-Friday 9am-5pm, for example.

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

How to schedule an event

event types page

Now you’re ready to start getting more accurate with Calendly’s features. If you clicked Independent + Consultantthe page is prefilled with an initial 30 minute meeting. You may see additional items on the Event Types page if you selected a different function. 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 your Calendly URL [i.e.] and sending it by SMS or e-mail. Once they click on it, they’ll see your name and instructions on how to add an event to your calendar.

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share meeting link

If you created more than one event type, you can simplify things and send a link to the correct event type. In this case, click on the To share on an event type (or click on Copy link) to help users create a specific type of event in your calendar.

calendar calendar view

From your link, those who wish to reserve time with you will have access to your calendar. They can select a specific day to open time slots that you yourself have set as available. They then click once and hit To confirm to make an appointment with you.

booking details

They will be asked to provide more information, such as their name, email address, and any additional notes that may be needed. They even have the ability to add additional guests to the meeting. Once all the details are entered, they click Schedule an event. A confirmation screen will then appear with all the meeting details.

You have nothing to do. When you next 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 to get you started scheduling emails. However, if you need more features, click the Integrations header to find a host of other options, including Firefox, Chrome, and iPhone app integrations.

For example, if you need Calendly to automatically insert a link to your favorite video conferencing service, 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

Individuals typically use the free product, but businesses are increasingly paying $25 per user, per month to streamline operations and save valuable time. I’m still using the free product, but considering an upgrade because Calendly does so much more than book meetings. The tool also facilitates workflow, follow-ups, etc.

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 was smooth and easy. It also helped me recoup a huge amount of time by letting the AI ​​manage my schedule. Eventually, of course, I’d like to clone myself so my digital doppelganger can handle meetings himself.

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