These 5 AI Scheduling Assistants Can Boost Your Productivity in 2024

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Balancing tight schedules, planning meetings, and managing diverse to-do lists alongside other commitments can be overwhelming. Twenty years ago, it used to be about making time stamps on paper, then came sticky notes—still used today.

But, the past few years have seen the rise of scheduling and time management apps designed to help us manage our schedules better.

With artificial intelligence (AI) now sitting at the epicenter of many software solutions, it’s no surprise AI comes to scheduling assistants — a sector whose market value is projected to reach $400 million by 2030.

To come up with this list, we evaluated a range of AI scheduling assistants based on their features, user ratings, and industry recognition. We focused on tools that offer robust scheduling capabilities, intelligent automation, and seamless integration with popular productivity suites.

Key Takeaways

  • First we had AI, now we have AI scheduling assistants offering streamlined scheduling, conflict resolution, and productivity enhancements.
  • Techopedia evaluates five top free AI scheduling apps based on their features, user ratings, and industry recognition.
  • Trevor AI offers task management and smart scheduling but requires a paid plan for advanced features.
  • Reclaim AI focuses on task allocation and offers customizable schedules, Clockwise automates scheduling preferences, while Sidekick utilizes AI and language processing for meeting scheduling.
  • ClickUp has extensive features and integrations to address challenges in productivity.

What is an AI Scheduling App?

AI scheduling assistants are tools that leverage machine learning (ML) algorithms to help users streamline the scheduling process, manage conflict appointments, and improve productivity by automating the process of scheduling appointments, meetings, and events.

These apps can smartly sync and manage different calendars and rules to recommend the best times for meetings, prevent overlapping appointments, and reduce scheduling errors. Additionally, they can send reminders, handle rescheduling requests, and adapt to changes in real-time (round-the-clock availability), ensuring that users stay organized and on track amidst their busy schedules.

Top AI Scheduling Assistants in 2024

Below are five of the best free AI scheduling assistants, what they do, and their drawbacks.

5. Trevor AI

People can regain control, clarity, and focus in their schedules using this scheduling tool. Trevor AI was founded in February 2016 as an application focused on addressing the disconnect between time management and task management.


This schedule manager comes with features like a task hub, smart planner, unlimited task scheduling, focus mode, predicted task duration, and AI scheduling suggestions that can appeal to anyone looking for an AI scheduling assistant to boost productivity.

One unique capability of this tool is that the app’s smart scheduling function can analyze users’ calendars, habits and priorities to suggest optimal times to auto-assign tasks. The app’s unified-to-do list can also give users a comprehensive view of their daily plans.

While Trevor’s integration capabilities may be on the limited side, it can still integrate with tools like Google Calendar and Outlook & Office360 calendars.

Trevor’s pricing structure starts with a free version, but most of its advanced features are only available on the paid plan, which starts at $3.99 per month or $36 per year.

4. Reclaim AI

Founded in June 2016 and based in Portland, Oregon, Reclaim AI offers an AI-powered calendar assistant designed to help users allocate time more effectively for their desired tasks and objectives.

Reclaim AI is known for blocking flexible time for users, and then automatically pulling in tasks and projects from the platforms they already use.

The application enables users to create customized weekly schedules based on their task priorities. Reclaim AI’s scheduling algorithm analyzes individual calendars, habits, and priorities to optimize scheduling patterns.

The platform can integrate with popular work tools like Asana, Slack, ClickUp, and Zoom.

The product has four pricing plans for its users, including a free version with zero fee and paid plans, which starts at $8 per month.

3. Clockwise

This is an AI scheduling and calendar automation tool that coordinates the way individuals or teams prefer to work. Founded in 2016 and based in San Francisco, Clockwise can allow users to connect to their calendars, set meeting preferences, decide which meetings are flexible, and then automatically optimize their day according to those preferences.

One unique feature of this scheduling tool is its AI Scheduler which helps users manage bulk scheduling requests easily, create space in their week, and find time with a group.

The tool integrates with other platforms like Asana and Slack and has other handy features, including flexible holds, lunch holds, smart meeting breaks, slack status sync, and personal calendar sync.

Clockwise offers a free version for those who only need smart calendar management for a healthier workday. However, the paid version starting at $6.75 per month, offers more functionalities for organizations and larger teams.

2. Sidekick

Sidekick is another notable online meeting scheduling software that is built smarter with AI and language processing. The tool was founded in 2019 and was born out of frustration with existing calendar management tools and the scheduling challenges faced by one of its founders, Nathan Jean.

Sidekick offers several meeting scheduling options, including Sidekick Scheduling, which identifies optimal meeting times for individuals and teams, Forward to Schedule, which schedules meetings through emails, and its custom Scheduling page shared with guests for quick scheduling.

The tool integrates well with many online meeting tools, such as Google Meet, Zoom, Skype, Microsoft Teams, etc.

Sidekick is rated 5/5 on G2 with most users saying that it is a good timesaver schedule app essential to anyone who books meetings with clients every day.

While users can have unlimited scheduled meetings on the Sidekick Hero plan, which is free, their paid plans, starting at $5 per user per month, can offer users more automated features, including meeting stats and team pages.

1. ClickUp

This tool was initially developed in 2017 as an internal tool within the ClickUp productivity platform, headquartered in San Diego, California. It was later released to the public as a cloud-based collaboration and productivity software.

The aim was to solve the issue of fractured productivity caused by the use of multiple tools and separate ecosystems.

The tool offers a free plan and a host of useful features, such as 100+ pre-built prompts and templates, whiteboard templates, native time tracking, AI summary and progress custom fields, voice and video transcription, and Interactive Q&A from anywhere.

Users can integrate ClickUp with over 1,000 third-party applications, including Slack, GitLab, Google Drive, Zoom, and Microsoft Teams. ClickUp can also automate project summaries and progress updates, action items, subtasks planning, and data auto-filling.

ClickUp has received excellent reviews from various review websites, including 4.7/5 stars on G2 and 8.5/10 on TrustRadius.

While its free version provides drag-and-drop scheduling and some other functions for individuals, its paid plan, which starts at $5 per user per month, is better suited for teams and businesses.

The Bottom Line

The productivity landscape in 2024 is ripe for transformation, and AI scheduling assistants present a gateway to new levels of efficiency and productivity.

Among the array of options, these top five free tools stand out for their ability to integrate into workflows, optimize time utilization, reduce scheduling complexities, and connect with popular work management apps.

As we navigate the evolving demands of modern work environments, leveraging AI-driven assistants may be what we all need to keep productivity at the highest level.


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Franklin Okeke
Technology Journalist
Franklin Okeke
Technology Journalist

Franklin Okeke is an author and tech journalist with over seven years of IT experience. Coming from a software development background, his writing spans cybersecurity, AI, cloud computing, IoT, and software development. In addition to pursuing a Master's degree in Cybersecurity & Human Factors from Bournemouth University, Franklin has two published books and four academic papers to his name. His writing has been featured in tech publications such as TechRepublic, The Register, Computing, TechInformed, Moonlock and other top technology publications. When he is not reading or writing, Franklin trains at a boxing gym and plays the piano.