Easy Calendly Hacks: How to Make Your Meetings More Friendly

I used to really make people mad.

I would send them my calendar link all the time.

“Why don’t you book a call here?” I would say.

portrait of Nick pointing at you with a finger, text next to him says 'I want you to book in my calendar!'

I thought I was being nice.

But I’m pretty sure they thought I was a jerk.

See, just sending my calendar link made people feel that I was more busy.

Man standing in a front of calendar filing his nails. Above him 'MR BUSY' banner.

It made others feel like I was plugging them into a system.

Like they were “a cog in the wheel,” not an actual human that I was excited to talk to.

Introduction

I’ll show you how I fixed this problem of people hating my calendar link in two steps:

  1. Never send a cold Calendly link
  2. Offer your Calendly link as a choice

Then I’ll show you exactly how I’ve used Calendly to meet hundreds of new and interesting people for work.

Portrait of 6 new friends Nick made. They are all different characters, male and female from all walks of life.

You’ll learn the three easiest changes you can make to your Calendly settings to make your invites more friendly:

  1. Edit your Calendly profile pics
  2. Personalize the automated messages
  3. Consider shorter meeting times

Plus I’ll give you three extra tips to make all your calls better:

  1. Don’t hide your number
  2. Reply with positive emotion to the confirmation email
  3. You call them (and be explicit about it)

illustration saying 3 easy calendar tips

Even if you only do a few of these things, you’ll be seen as more approachable in business. You’ll add a touch of humanity and enthusiasm to an otherwise automated process.

You might even land some new clients. Or make a few new friends.

Ready?

Here is the first most important rule.

Never send a cold Calendly link

I never send a direct calendar link in these two situations:

  1. Cold outreach (when I’m the one reaching out)
  2. Asking for a favor (when I’m the one asking for the favor)

Why? Because saying:
“Why don’t you book a time in my calendar?”

isn’t too far from saying:
“Why don’t you come clean my kitchen?”

A pile of dirty dishes in the middle of the illustration. A small man waving from behind them. A large script says - Nice to meet you! Below the image - Now, let's clean my kitchen!

It feels like I’m telling you that I’m the most important person, so here’s some work for you to do to get my attention.

NOTE: There’s a distinction between an outbound request (when I am asking for the meeting) and an inbound scheduling request (when someone is asking for a meeting with me). These tips I will share are helpful for both scenarios. But you can be less cautious, or less over-the-top with courtesy, for your inbound requests. Because the duty or responsibility is not on you.

A guy with two paper planes in his two hands. One of them is labeled: inbound - proceed with caution. He holds it very carefully. The other he is about to launch is labeled OUTBOUND, with a speech bubble saying: Careful!

Here’s a simple change that will help you be more tactful.

You might be surprised that most people will still use your Calendly link to schedule time.

Offer your Calendly link as a choice

If I’m proposing a call, I lead with a few open times.

Then I include my Calendly link at the end.

It looks like this:

Hi Noah, I’d love to chat more about that.

Are you free for a quick call? When’s good for you?

I’m open on Tuesday the 25th at 11a, 12p, 1p, or 2p (Eastern).
Also on Wednesday the 26th at 9a, 10a, 3p, or 4p.

My cell is +1-917-635-9967 or send me your number and I’ll call you.

Here’s my full calendar link if it is easier to schedule for you:
https://calendly.com/call-nick/15min

So don’t do this:

Post it saying: Just book time in my calendar! Ps. I hate you!

Instead, do this:

Post it saying: When is good for you? Other postit: Here are some options! Ps: I love you!

Why does this feel better?

Because it gives people the choice to use my calendar. They are in control.

I’ve found that most people (perhaps 70%) will use the Calendly link.

And all people (perhaps 100%) appreciate the choice.

Those two rules:

  1. Never send a cold Calendly link, and
  2. Offer your Calendly link as a choice

are things you can do to make your Calendly invites more human.

There are also three things you can do specifically within Calendly to make your invites more friendly.

Modify these Calendly settings

Here are three easy changes you can make to your Calendly settings to make it feel more friendly.

(1) Edit your profile pics

Make your Calendly look more friendly by using a nice photo of yourself.

You can find this setting to upload your photo in Account → Account settings → Profile

Mine looks like this:

Nick Gray profile photo on Calendly

If you have extra time, make a little logo for yourself that will show up on your call page.

Upload your 440×220 pixels logo under Account → Account Settings → Branding.

My logo looks this:

picture of Nick Gray for Calendly that says PHONE CALLS ARE GREAT text up top

And then my calls page looks like this:

screenshot of Calendly calendar page for Nick Gray

Does it look silly?

A little. But it also looks more friendly and less boring.

(2) Personalize the automated messages

There are a few automated messages that Calendly sends after someone books a call.

You can edit these two messages to add a touch of personality and class.

(2a) Calendar Invitations

This setting is found under Home → Edit One-on-One Event Type → Notifications and Cancellation Policy → Calendar Invitations.

Using the Calendly variables, my settings are here:

screenshot of Calendly settings

(2b) Email Reminders

In the same section, you can edit the email reminder that is sent.

If you only modify one setting in this area, modify this one!

This reminder message makes the most impact. You can share your personality. It is a great way to “break out of the mold” for an otherwise routine and automated system message.

Here’s what mine looks like:

another screenshot from Calendly settings on the reminder message

LITTLE TIP: I set my email reminders to be sent 25 hours before our meeting. Why not 24? Well, I have a hunch that sometimes people schedule calls during “breaks” in their normal day. Sending it 1 hour before that break time is a chance for me to reach them a bit out of pattern. This might be a dumb little hack. But I like it.

(3) Consider shorter meeting times

If this is your first call with someone, or if they are very busy, consider shorter call times.

I like 15 minute calls. Then, if things are going well, we can always extend the call or schedule another time to talk longer.

But how short is too short?

For a few weeks, I tried a test on people that I had never talked to before.

I gave everyone the option in booking either a 10 minute call with me or a 15 minute call.

Every single person picked the 15 minute call.

Call lengths: Generalised summary. 5 mins - Hi. Bye! 10 mins - too short! 15 mins- I like it. 30 mins - I hate you! 60 mins - I hate myself!

A note about 15 minutes: Yes, it can oftentimes be too short. So I always set a 10 minute buffer to give me more time after the call. To collect my notes or extend the call. If you feel 15 minutes is too short, see the Bonus Tips at the end of this article.

A dark haired fellow in glasses is hunching over a large book. Meeting notes i written on the book. He seems very bored. A candle is next to him.

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Don’t hide your number

Be upfront and forward about how to reach you.

Don’t hide your phone number behind the calendar invitation. Don’t wait to give someone your phone number until after the meeting is scheduled.

A post-it saying: Top secret! Nuclear codes, Quant strategy - but not my phone number!

I share my phone number by:

  • Including my phone number in my “When is good for you? Here are some options” message
  • Including my phone number in my Calendly welcome message
  • Including my phone number in my email signature
  • Including my phone number in the Calendly confirmation message and calendar invite

You might be worried that someone will call you randomly now that they have your number.

They probably won’t. And if they do, well, welcome to the big city.

Reply with positive emotion to the confirmation email

When someone schedules a meeting, they’ll get an automated Calendly confirmation as well as a calendar invite. This message gets sent to you, too.

I like to personally reply to these messages with a quick custom note. Calendly sets it so the reply-to address is the person who booked the call.

The illustrations shows a lady with long black hair and a serene facial expression. She is clicking on her phone. From the phone, 3 speech bubbles appear as follows: Excited to meet you tomorrow! New calendar event. Thanks for clicking the link!

For example, here are a few custom replies that I’ve sent after someone has used my calendar link to book a call:

  • Woot!! Thanks for scheduling this call — looking forward to talking party book stuff etc tomorrow afternoon — Nick
  • Thanks for booking w/my calendar link, Britton! Looking forward to chatting on Friday about your new role — Nick

You call them (and be explicit about it)

Be sure the person knows that YOU will call THEM! Then there is no ambiguity.

I think this is courteous. You sent the calendar link, so you should do the work to call them.

  • State it in your signup flow as part of the Event Description: “I’ll call you!”
  • Include it in the reminder message
PRO TIP FOR OVERACHIEVERS: Start to dial the person’s number a few seconds before your scheduled call time. I love it when my phone rings EXACTLY at the scheduled time of an inbound call.

FOR EXTREMELY BUSY PEOPLE: Meetings run late. Unexpected childcare duties pop up. Sometimes we all forget to call. I used to include this line in my reminders and calendar invites: “If you don’t hear from me within 2 minutes of the start time, please call me at +1-917-635-9967.” It was helpful, especially when I was getting a lot of inbound requests. But I’ve removed that line now that my schedule is less busy since I sold my company.

Lots of Bonus Tips

Clickable numbers: Calendly makes it a little hard to click on the person’s phone number in Google Calendar on iOS, as they set their phone number as the meeting location. You can make the phone numbers clickable in your Google Calendar event by adding the LOCATION variable somewhere in the body of the calendar invite. This setting is found in Home → Edit One-on-One Event Type → Notifications and Cancellation Policy → Calendar Invitations.

Welcome message: I customized my Welcome message whenever someone lands on my calendar. You can find this setting to edit your Welcome message in Account → Account settings → Profile. My welcome message looks like this now:

screenshot of Calendly welcome message

Blair Russell sent me a bunch of great Calendly advice for busy people:

  • I’ve gotten 99% compliance by asking people to let me know what times work for them, and then offering my Calendly link. Asking them what time works for them makes me seem really flexible, generous, and available… but it is actually putting the work on them to make a list. They almost always use my Calendly link.
  • Schedule your availability within limited windows. I find the first few hours of the day the best, before I get caught up in other things and the cold calls feel like a burden or distraction.
  • Share your link (or at least one link) publicly in your email signature and/or on your website. I have my 15 minute link on my website and in my email signature labeled “Schedule a meeting with me.”
  • Single use links are your friends when you’re not sure yet if you want that person to have access to your calendar all the time.
  • Put a weekly Calendly update on your to do list. That few minutes will save you a ton of time scheduling and rescheduling around vacations and days off.
  • Inbounds will always pick the longest meeting, so make all meetings 25% shorter than you intend. Then you can either extend the meeting, or followup immediately after and not have to rush to your next meeting. Both make you look good.

Zachary Cohn adds these notes:

  • If you feel that 15 minutes is too short for the type of meetings you want to have, try using 25 or 50 minute meetings instead of the default 30 or 60 minute meetings.
  • What I tend to do that works well is frame the Calendly link as a benefit to them. I say “Pick a time that’s convenient for you.” It’s another way to demonstrate that I’m giving them a choice to pick a time that works well for them.

Conclusion

Phone calls are good.

I love phone calls.

They are authentic and real and raw in a way that emails and text messages can’t be.

Do you take a lot of phone calls?

What do you do to make Calendly or your calls better?

Let me know in the comments.

Or find a time on my calendar 😉

Thanks to Fru Pinter for all the illustrations. Thank you to my friends for edits and suggestions: Zachary Cohn, Blair Russell, Zach Ware, Joshua Dance, Sara Sodine Parr, Joel Runyon, Douglas Widick, Katelyn Donnelly, and more.

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