Calendar.help: Automate Meeting Scheduling with AI

Updated on Jun 16,2025

In today's fast-paced professional world, time is a precious commodity. Manually scheduling meetings can be a significant drain on productivity, involving countless emails, calendar checks, and coordination efforts. Calendar.help emerges as a powerful solution by leveraging artificial intelligence to automate and streamline the entire meeting scheduling process, saving valuable time for information workers.

Key Points

Calendar.help is an AI-driven virtual scheduling assistant.

It automates meeting scheduling directly within email conversations.

Research shows information workers spend significant time scheduling meetings

Scheduling meetings is a top task individuals wish they could delegate

Executives often have assistants handling scheduling; Calendar.help aims to democratize this

Complex scheduling scenarios with multiple attendees and time zones are simplified

Personalization based on meeting types and individual preferences are supported

Building trust in AI assistants through understanding automation levels is crucial

The Problem: Time Spent Scheduling Meetings

The High Cost of Manual Scheduling

Research indicates that information workers spend an average of 4.8 hours per week just Scheduling meetings.

This translates to a significant loss of productivity and focus on core job responsibilities. The back-and-forth emails, checking everyone's availability, and managing reschedules all contribute to this time sink. It also shows 13% of employees engaged at work.

Scheduling Meetings: A Top Delegation Target

surveys reveal that scheduling meetings is the number one task that people wish they could delegate to an assistant

. The annoyance of managing multiple schedules, reminding people to respond, and dealing with constant changes makes it a Prime Candidate for automation.

Why is Scheduling so Annoying?

The presenter breaks down exactly why scheduling meetings can be such a burden:

  • Back-and-forth emails: Endless chains to find a time that works for everyone.
  • Reminding people to respond: Following up to get confirmations.
  • Reschedules, cancellations, and updates: Managing constant changes to the schedule. These complexities highlights the need for a intelligent solution that can simplify and automate the whole process. Traditional methods simply can't keep up. The goal is to free up attention and boost productivity by offloading this administrative overhead.

How Calendar.help Solves the Scheduling Problem

Emulating the Executive Assistant Model

Executives often rely on executive assistants (EAs) to manage their calendars and schedule meetings. Calendar.help aims to provide similar support to everyone, democratizing access to efficient scheduling.

This way every employee can delegate the task of scheduling to something and be sure it will be taken care of.

The Traditional (Inefficient) Method

The presenter visualizes the current inefficient method of scheduling with multiple emails going back and forth

. Instead of a linear and focused path, scheduling meetings often involves time consuming discussions, which all amounts to large wastes of time and attention.

Understanding Intent and Extracting Entities

This is at the center of what the AI needs to do. Here's a peek into the complex requirements for intelligent scheduling:

  • Meeting type
  • Duration
  • Attendees
  • Time Zone
  • Location
  • Meeting time and convert to time ranges
  • Handle Negations
  • Resource Booking

Handling Complex Scenarios

The project needs to take into account more specific conditions such as

:

  • More than 1 attendee
  • Rescheduling and cancellation
  • Resource Booking
  • Support for different meeting types

Calendar.help: Weighing the Benefits and Drawbacks

👍 Pros

Significant time savings on meeting scheduling tasks

Increased productivity by freeing up time for core responsibilities

Democratization of executive assistant-level support

Streamlined scheduling within familiar email workflows

Intelligent handling of complex scheduling scenarios

👎 Cons

Reliance on accurate natural language processing

Potential challenges with highly ambiguous or complex requests

Need for user trust in AI decision-making

Dependence on calendar and email system integration

FAQ

What is Calendar.help?
Calendar.help is a virtual scheduling assistant that leverages AI to automate meeting scheduling directly within email conversations, saving users time and boosting productivity.
Why is scheduling meetings such a pain point?
Scheduling meetings manually involves tedious back-and-forth emails, calendar checks, and coordination, consuming valuable time and focus.
How does Calendar.help build trust with users?
Calendar.help utilizes a framework of digital assistant automation levels, mirroring self-driving car automation, to manage user expectations and build confidence in the AI's capabilities .
What key research challenges does Calendar.help address?
Calendar.help addresses three key research challenges: natural language processing for scheduling information, scheduling intelligence for personalization, and human-computer interaction to build user trust .
What is meant by digital assistant automation levels?
It means as the level increases, so does the autonomy and integration of the calendar assistant. The last level even optimizes the schedule for you and organization.

Related Questions

How Does Natural Language Processing Improve Scheduling?
Natural language processing (NLP) empowers Calendar.help to understand scheduling requests expressed in natural language within email conversations. This enables users to interact with the assistant in a conversational manner, eliminating the need for rigid commands or structured inputs. It must be able to perform intent recognition from emails. This allows scheduling tasks to be easier.
What are the Digital Assistant Automation Levels?
The level are: Level 0: Manual - You are in complete control of your calendar. Level 1: Smart on-demand - Requires simple requests. Level 2: Delegate support - Ability to delegate to the assistant. Level 3: Hands-off assistance - All you have to do is specify that the event happens. Level 4: Personalized optimization - Calendar makes choices for you. Level 5: Organizational optimization - Organizes the schedule for the entire organization.
What Happens After Delegating a Meeting?
The following will happen after you delegate to the assistant: The AI reviews the request It determines availabilities from the sender and the invitee(s) An invite is set with the appropriate time and date You are free to manage your time as you see fit