Please Don’t Be a Calendly Jerk (and Other Thoughts on Scheduling Etiquette)

A connection recently asked her network what they thought about Calendly, and it made me realise—I have some very strong opinions about the subtle power dynamics at play when sharing calendar links.

I should start by saying that I have a Calendly link in my email signature, but I rarely—if ever—share it in response to planning a call or meeting. Why? Because, while scheduling meetings may seem like a small thing, but it’s loaded with unspoken cues about respect, priorities, and power. Getting it wrong can make you seem presumptuous while getting it right shows you’re thoughtful and self-aware. And trust me, people notice these things.

Why?

• Power dynamics exist: Scheduling is just one way these dynamics show up and handling it poorly can leave a bad impression.

• Your words matter: Whether you’re pitching, networking, or job hunting, the way you phrase a scheduling request says a lot about you.

• Brand perception: If you’re part of a company, how you and your team approach something as basic as scheduling can impact your brand image—warm and approachable vs. cold and bureaucratic.

How Not to Share Your Calendly Link

Let’s start with what not to do. If you’re requesting someone’s time, avoid this classic Calendly faux pas:

🚫 “Let’s schedule a call. Here’s my availability.”

This can come across as presumptuous unless you’re close to the person or clearly in a position of authority. It’s like saying, “I’m important, and you should work around my schedule.” Not great!

Better Ways to Share Your Calendly Link

If you use Calendly (or a similar tool), there are ways to share it without seeming entitled.

Try these approaches instead:

• “Do you have a Calendly? Happy to pick a time that works for you.”

• “Should I send over my Calendly if that’s easier? Or let me know your availability—happy to work around you.”

• “I’d love to schedule a call. Would any of these times work for you by any chance?”

• “Here’s my Calendly in case any of these times work, but feel free to share yours and I’ll schedule around you.”

These options strike the right balance between being helpful and being respectful of the other person’s time. They’re polite, warm, and—most importantly—non-presumptuous.

My Personal Rules for Calendly Etiquette

To make things crystal clear, here’s how I approach using Calendly:

• If you’re asking for someone’s time, don’t lead with your Calendly link. Instead, offer a few specific times or ask for their availability first.

• Don’t make the other person do all the work. If you send your Calendly link, make it clear they’re welcome to share their availability or link instead.

• Avoid including a Calendly link in your first outreach email. It feels impersonal and can come across as a power move.

• If you cancel a meeting, don’t make the other person rebook through Calendly. It’s on you to find a new time that works.

Why Politeness Pays Off

Some might argue that these tips make scheduling more complicated. But here’s the thing: politeness pays off. Taking a few extra seconds to write a warm, thoughtful message can:

• Build goodwill

• Show you’re self-aware

• ·Make the other person more inclined to say “yes”

When you’re asking someone to fit into your schedule, it’s worth going the extra mile to make them feel respected. After all, nobody wants to feel like just another calendar slot.

What’s Your Take?

I’d love to hear your thoughts. What’s your go-to phrasing when sharing a Calendly link? Have you ever had a Calendly encounter that rubbed you the wrong way? Let’s swap stories in the comments!