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Why I use Calendly to schedule my meetings

Vivek Nair
Vivek Nair
Jan 2, 2020 - 5 min read
Why I use Calendly to schedule my meetings

I was exhausted to see another one of these emails.

The content of the email wasn’t too noteworthy. I had just messaged another founder to grab coffee a few days earlier, and we were scheduling times to chat.

But, what was noteworthy was the number of back and forth clarifications I had with him: three full iterations. Here’s a simplified transcript of the events.

Vivek: “Do you want to sync up and chat marketing next week?”
Founder: “Sure - does Tuesday 9 AM or Wednesday 1 PM work?”
Vivek: “Doesn’t work for me unfortunately :/ How’s next week on Monday 10 AM or Friday 11 AM?”
Founder: “Monday 10 AM works! See you then”

Founder sends a calendar invite with the wrong timezone

Vivek: “Looks like you sent it for 7 AM PST. Are you based in EST?”
Founder: “Whoops, yep I am. Can you do 1 PM EST (10 AM PST) tomorrow instead?”
Vivek: Yep, works for me! Talk soon.

Founder sends the correct invite

Here’s the worst part of the whole situation. I wasn’t even available at the final time that he proposed.

I was so tired of the scheduling process that I decided to cancel my haircut that was scheduled for the same time. Of course, I don’t blame him for the scheduling fiasco. Manual scheduling is inherently a wasteful process. But after receiving that last email, I was so frustrated that I signed up for Calendly that afternoon.

If you don't know already, Calendly is a simple scheduling application that integrates with your calendar to help recipients find and schedule times that work for you. Here are a few reasons why Calendly is a game-changer for your productivity.

#1 No more toggling between applications

Before Calendly, my scheduling workflow was a mess.

  1. I open Gmail and read a meeting request
  2. I open Google Calendar and find a couple times that work for me
  3. I send her those times in Gmail
  4. She sees the message in Gmail
  5. She validates in her Google Calendar that she has availability amongst those times
  6. She sends me a confirmation in Gmail
  7. I see the message in Gmail
  8. I copy her email into the calendar event in Google Calendar
  9. She accepts the request in Gmail or Google Calendar

Even in this easy scheduling situation, we both are constantly toggling back and forth between Gmail - the communication medium - and Google Calendar - the scheduling medium.

With Calendly, my workflow is dead simple.

  1. I open Gmail and read a meeting request
  2. I send her my static Calendly link
  3. She opens the Calendly link and selects a time

I don’t need to manually verify whether the times work for me. I've already given Calendly guidelines for determining my availability. So long as I trust the guidelines, I know that I can attend the meeting.

By bridging the communication and scheduling mediums with Calendly, I immediately simplified the scheduling process for everyone involved.

#2 Less context switching

Every minute I spend manually scheduling is dead time that I could have spent on something way more important like building product or hanging out with friends.

Furthermore, scheduling fragments my focus time and stops me from achieving deep work - times when I’m operating at my most productive. Here’s a visual timeline of my correspondence with that founder.

With every disruption, I needed at least 15 minutes to get back into my “deep work” mindset again. So in total, I lost 1 hour of deep work time just to schedule a meeting. 🤦

Calendly allows me to send a simple link at the start and never think about the meeting again until it starts.

#3 Reschedule within the app

I understand when people have to reschedule. Heck, I had to reschedule two meetings last month because of customer fires. But honestly, it does suck to restart the whole scheduling workflow.

On the flip side, people often feel pressured to attend meetings that are no longer ideal for them at the risk of bothering me with a reschedule request. It sucks that they feel that way.

Calendly has a rescheduling feature built into the product, and it’s awesome.

Simply click on the rescheduling link and select a new date and time that works for you. Calendly automatically removes the original event and sends all participants new events.

#4 More optionality

When I pick out availability times, I’m often:

  1. Picking a subset of the times that I can actually meet, often to save keystrokes and not overload the person with a long email
  2. Guessing dates and times that work for the recipient

Since we’re reducing the set of options, we could miss out on the most ideal meeting time for both of us. But, by using Calendly to show all available times and dates, I’m providing her optionality.

Maybe she prefers to meet in the evening versus the morning or the weekend versus the weekday. She would have never known that I had availability at those times unless she had access to the exhaustive set of options.

Side Note - Addressing adoption challenges

Not everyone uses Calendly, and some might wonder why you’ve sent them a link and why they should use it rather than just scheduling with you directly. Others might just be used to the human element of scheduling. Here’s my script whenever I send over a Calendly link to make the other party more comfortable with this new way of scheduling.

I'm more than happy to meet. What's your availability for this week?

Alternatively if it’s easier for you, feel free to grab some time from my Calendly with the link below. That might save us some time in scheduling!

The copy is effective for two reasons:

  1. I’m giving the recipient the option of manually scheduling if she really wants
  2. I’m suggesting that using Calendly will save us both time

Concluding thoughts

I’m sure you wish you didn’t have to go through endless back-and-forths to schedule meetings. I certainly did. Give Calendly a try and we can help each other keep our minds and inboxes cleaner.

What’s Pesto?

I’m a founder of Pesto, a virtual office for remote teams. If you’re running a remote team and waste tons of time fumbling with Zoom links or typing out long Slack messages, try out Pesto for free today!

Also if you have any questions, feel free to reach out to me on Twitter.

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