Calendar Etiquette: Why You Should Not Send Booking Links

Booking links were meant to make scheduling easier. In practice, they often do the opposite — especially when used indiscriminately.

If you’ve ever hesitated before sending a Calendly link, or felt a slight power imbalance when someone dropped one into your inbox, that instinct is right. Calendar etiquette still matters, even in a world of automation.

And it goes beyond etiquette. It’s about how quickly decisions get made, deals move forward, and work actually gets done. Scheduling is an operational layer, and when it’s handled poorly, everything downstream slows.

1. Booking Links Shift the Cognitive Load — to the Wrong Person

When you send a booking link, you’re not solving scheduling.

You’re outsourcing it.

The recipient now has to:

Scan your availability
Cross-check their own calendar
Infer which slot is appropriate

That’s work. And it’s work you’ve delegated without asking.

Good etiquette minimises the effort required of the other person — especially if they’re senior, external, or doing you a favour.

People remember how easy (or awkward) it felt to meet you. They remember whether scheduling felt thoughtful or transactional.

2. They Flatten Context and Priority

A booking link treats every meeting the same.

A quick intro call
An investor conversation
A customer meeting

All reduced to identical 30-minute rectangles.

The best scheduling interactions acknowledge constraints.

Booking links are unable to capture this nuance.

“She’s in London this week”
“He prefers mornings”
“Let’s avoid back-to-back meetings”
“This needs to happen quickly”

Scheduling with important stakeholders involves subtle sensitivities and negotiation, not just availability. A booking link is often too simplistic for this.

Many people realise this soon enough and end up taking on scheduling themselves over email (till it becomes overwhelming…)

3. It Slows Business Down — and Creates Follow-Up Hell

Booking links feel efficient in the moment.

You send one email, drop a link, and move on.

But what actually happens next is rarely efficient.

When recipients are faced with too many available slots, decision-making slows. They postpone choosing, leave the tab open, or plan to “get back to it later.” Meetings that should take hours to schedule stretch into days — or never happen at all.

What looked like time saved upfront turns into follow-up work downstream.

You end up nudging:

“Just checking if you saw the link”

“Let me know if none of the times work”

“Happy to reshare availability”

Now you’re back in the inbox anyway — except later, with more context switching and less momentum.

A Better Standard for Business-Critical Scheduling

Experienced executive assistants optimise for outcomes, not convenience. They don’t maximise choice; they minimise delay. By proposing a small number of sensible, context-aware options — and following up proactively — they keep deals moving and decisions unblocked.

Carrie is built to deliver that same outcome, automatically.

You CC Carrie on an email thread, and she handles the entire workflow: narrowing options, managing time zones, following up at the right moment, and confirming the meeting — without exposing your calendar or sending booking links.

Real efficiency isn’t how fast you send an email.

It’s how fast the meeting happens — and what it unblocks next.

Try Carrie at getcarrie.com.