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Can an AI Calendar Assistant Really Organize Your Calendar

Can an AI Calendar Assistant Really Organize Your Calendar

Alyssa Towns
April 25, 2024
Updated on:

Can an AI Calendar Assistant Really Organize Your Calendar
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Having an AI calendar assistant to handle your calendar automatically is like having your own personal Jarvis, reminiscent of Tony Stark's ever-efficient AI assistant in the Marvel universe, except this time, it's not fiction. Sure, Jarvis did it all—tackled chores, provided advice, and managed online systems—and the right AI calendar assistant, even if not as complex and well-rounded as Jarvis, can become your trusty digital sidekick.

AI calendar assistants blend artificial intelligence with scheduling mastery, promising a future where forgetting appointments, wasting time scheduling them, and missing deadlines are no longer. In this post, we cover:

  • What an AI calendar assistant is (+ how it can benefit you)
  • How AI calendar assistants work (with real scenarios) 
  • Potential drawbacks (or considerations) before adopting an AI calendar assistant 
  • 5 AI calendar assistant tools to explore

What is an AI calendar assistant?

To understand the added value of an AI calendar assistant, we must distinguish between a smart calendar and an AI calendar assistant. While a smart calendar and an AI calendar assistant may seem synonymous, a smart calendar makes suggestions and optimizes calendars using algorithms. 

Put simply, developers build software programs that enable users to input data and receive outputs based on that data. For example, I tell Clockwise to hold a 30-minute lunch block for me between noon and 2:00 pm, and it does that for me. It also recognizes when I have two or more hours of uninterrupted work time and slaps a Focus Time block on my calendar. Ultimately, the smart calendar functionality optimizes my schedule based on the information I provide. 

An AI calendar assistant is a more powerful companion that does more than optimize schedules. AI calendar assistants use machine learning (ML) and natural language processing (NLP) to learn patterns. They get to know your schedule, process your daily event information, and adapt and make changes over time as they learn from experience. 

For example, an AI calendar assistant like Clockwise can help me schedule a meeting with five of my teammates during working hours, not during my lunch or my boss’ Focus Time, or on the day my colleague takes off early to pick up his kids, and not during our unstated preferences either. The best meeting time might require rescheduling other meetings, but that’s no problem because the AI tools can reschedule those. I give the AI scheduler a specific task, and it does all of the heavy lifting, finding more than just a blank white space that may or may not work best for everyone.

AI calendar assistants offer a more personalized experience, understanding individuals' habits, workstyles, and working patterns to find the best time to do the work that matters most. The best AI calendar assistants help users organize their calendars, reschedule conflicts, tackle complex scheduling needs, and, most importantly, provide users with a quick and easy way to do all of the above (such as through a simple chat request).

What are the benefits of AI calendar assistants and schedulers?

AI calendar assistants and schedulers address many challenges modern-day workers face—not enough time to work, too many meetings, and far too much time spent comparing calendars to find time to meet. The primary benefits of AI calendar assistants include: 

Scheduling capabilities for all (not just the C-Suite)

As a former executive assistant, I deeply understand the incredible amount of magic sprinkled with pain when effectively managing complex calendars, busy schedules, and endless priorities. It’s essential work, and while AI calendar assistants can’t and won’t fully replace executive assistant capabilities (you still need a human to help manage relationships, get work over the finish line, and be a strategic partner), they extend the magic of assistant-level calendar management magic to all. You don’t have to be a CEO to get the help you need to manage your time anymore—AI can help.

Better work-life integration & time budgeting

The term “work-life balance” can be off-putting to some, but work-life integration might even be necessary as the world of work changes (especially in the land of distributed work). A recent study by Gallup found eight in ten remote-capable employees work hybrid or fully remote. The modern workplace evolution forced an integration of environments, which also brings an integration of how we allocate our time.

So you might need a break to get up and walk your dog or take a walk to remove yourself from a screen-filled existence. And these needs might serve you best during “traditional” working hours. Our environments have changed (and continue to), and we must change with them. AI calendar assistants help protect time for the work-life integrations you want and need.

Less burnout (leading to better overall work quality)

Constructing—and perhaps, more importantly—sticking to the workday schedules we build without letting unexpected or last-minute meetings and requests take over continues to challenge many workers today. According to Microsoft’s 2023 Work Trend Index Annual Report, 68% of people don’t have enough uninterrupted focus time in their workday. Without a proper amount of time to focus, innovate, and do quality work, it’s no surprise many workers shut their computers down at the end of the day feeling drained, exhausted, and dreading doing more of the same tomorrow. 

Workplace burnout is at the forefront of today’s workplace challenges, and fortunately, AI calendars can help. An AI scheduler will honor your workday preferences—so you can decide how many hours you need for deep work, when you need to take a lunch break, and when you might not be in the best headspace to participate in a meeting—and handle scheduling on your behalf. Feeling exhausted from too many meetings back-to-back and need a break? You can ask your AI calendar to reschedule your next meeting for you with ease. 

How does an AI calendar assistant work?

AI calendar assistants marry your workday calendar with NLP, ML, and artificial intelligence technologies to help you manage your schedule. You, the user, can ask your AI-powered assistant to complete specific scheduling tasks for you:

  • Schedule a meeting next Monday at 3 pm MT with Kacy 
  • Cancel all of my meetings tomorrow because I’m sick 
  • Find time for me to sync with the CEO, CMO, and CPO today before 2 pm MT 

Your tool will do some automated scheduling magic so you can get back to work with the reassurance that your trusted sidekick has your back. 

Depending on the AI-powered calendar assistant you choose, your tool might also be able to reschedule meetings for you to address scheduling conflicts, send automated emails throughout the scheduling process, generate templates to help you send emails, and more. Below are some of the best features you might search for in an AI calendar assistant: 

Booking meetings with AI (instead of manually) 

AI-powered calendar assistants are automatic schedulers. They remove the hassle of back-and-forth emails, Slacks, Google Calendar browsing (talking about you, Find a Time feature), and overall frustration by scheduling your meetings for you. 

With some tools, you provide it with the details for your meeting (who needs to attend, for how long, and when you want to have it), and the tool will take care of the rest. With others, you might prompt the assistant with meeting details and ask for a few meeting options. 

Rescheduling meetings as needed

You’ve seen the calendar filled top to bottom day in and day out with group meetings, Focus Time, one-on-ones, status updates, lunch breaks, time to walk the dog, and more. Fortunately, when you need to squeeze an ad hoc meeting in, a scheduler can not only get the meeting on the calendar for you, but it’s a huge boon when it can also reschedule meetings that might stand in the way of the ideal time. 

For example, with Clockwise, you can mark meetings as flexible, so when you ask the AI Scheduler to help book a meeting, it can return meeting conflicts and provide recommendations on how best to move your flexible meetings to accommodate. 

Drafting and responding to emails that support scheduling

Some tools, like Clara, can draft and send emails throughout the scheduling process, so you don’t have to. For individuals in email-heavy roles or organizations, an AI calendar assistant with this feature can come in handy to not only streamline scheduling but also reduce the time spent managing your inbox.

How can an AI calendar assistant organize my calendar?

Let's revisit a few everyday use cases for these tools to get a feel for how AI calendar assistants can organize your calendar, using Clockwise as an example.

Searching for whitespace to schedule the impossible

Are you scheduling a large meeting? Do you need to pull together a cross-functional team for a quick sync by the end of the week? Are you setting up a weekly project meeting to share and gather updates with a handful of folks? 

I don’t know about you, but I can feel the rainbow of colors in Google Calendar appearing thinking about these scenarios. One by one, you pull up each calendar only to realize one thing: there isn’t any whitespace available for the meeting. Not today. Or this week. And certainly not regularly. 

That’s where scheduling assistants can help. For example, you can use Clockwise’s AI Scheduler to find a time to meet (while simultaneously clearing the way and rescheduling meetings as needed). No more asking people to move their meetings, opening Slack messages from your colleagues explaining that they can’t make that meeting time, or wasting precious minutes scouring calendars when you could instead be wrapping up the report due today. 

Tackling last-minute meetings with ease

Ad hoc meetings (even if they are the bane of your existence) will always arise in some form. When you need to schedule a last-minute meeting, the best thing you can do is minimize disruptions and cause chaos for others. But you aren’t a mind reader, so how can you avoid blocking a meeting smack in the middle of Courtney’s focus time or during John’s lunch break that he can’t move because of other back-to-back meetings?

Your AI calendar assistant—particularly Clockwise’s AI Scheduler—has your back. It will find the time (or create it by rescheduling other meetings) so you don’t have to. 

What are the drawbacks of using AI to organize my calendar?

Automating processes and parts of our workday tends to excite some people, leaving others a bit queasy. Changing how we work can be challenging, and inviting technology to help brings new challenges and considerations. Call these drawbacks, considerations, or "things to be aware of" when using AI to organize your calendar.

You release control of your calendar

For those who love managing all of the details of their calendar and time, using an AI calendar releases some sense of control. You sync your calendar with your AI calendar assistant and let it do its job so you can return to yours. 

While your calendar will always fully be yours (with some external pressures due to expectations and commitments, of course), leveraging an AI calendar assistant gives part of your control away. It’s important to accept that a tool might not get it right 100% of the time or might not choose the same free time slots you would. 

Eliminate some opportunities to connect personally

Even though automation can save us time and energy, it can remove some opportunities to connect and lean into our relationships as humans. Let’s be clear—chatting to get meetings scheduled might not be helping you build connections and solid relationships with your coworkers (in fact, some folks might find it annoying), but what about when you’re setting up a meeting with someone new for the first time? Or how about interacting with a hot lead that you hope to convert?

Automatic scheduling can feel more “cold” when scheduling meetings with external vendors, leads, or other people you might not interact with regularly or have a pre-existing relationship with. This isn’t always the case, but it’s essential to supplement automation with the irreplaceable human elements—your personality, authentic relationship-building, and connection.  

Potential concerns around data privacy

Privacy issues are (almost always) top of mind when considering AI solutions. This might not necessarily be a drawback, but it’s always worth researching how the tools will use your data when looking at AI calendar assistants (and other AI-powered tools). 

What are the top AI calendar assistants?

There are many AI calendar assistants to explore depending on your role, needs, budget, and current workday tech stack. When searching for the best tool for you, you might consider: 

  • Where do you want to leverage a calendar assistant? Are you looking for a separate app? Do you need help coordinating meetings with internal team members? Are you externally focused and need help scheduling appointments via email? Do you need a scheduling link to share?
  • What integrations will make your life a breeze? What tools do you currently use and are non-negotiable to you? For example, browsing through tools that only work with Outlook doesn't make sense if you use Gmail. 
  • What do you want the experience to feel like? Prioritize a friendly user experience, easy setup, and solid customer service if you know you’ll need assistance and guidance along the way. 

Choose Clockwise for your AI calendar assistant 

Clockwise is an AI scheduling and calendar automation tool that calculates the best time for deep work, meetings, and other tasks based on your preferences. 

Think of it as your trusted personal assistant, allowing you to create your ideal workday and setting you up for success in doing your best work. Clockwise’s AI Scheduler is an AI-powered conversational assistant that rearranges meetings to simplify team scheduling, finds time for last-minute syncs (and moves flexible meetings that might be in the way so you don’t have to), and helps you book and modify multiple events at the same time. 

With Clockwise, you can add flexible holds to your calendar (for important tasks, routines, etc.), Focus Time for uninterrupted work, meeting breaks between back-to-backs, travel time, and more. As a result, you’ll have more time for your to-do list and can reclaim your workday.

Get started for free, and check out our pricing plans, which start as low as $6.75/user/mo billed annually to regain control of your workday.

Clockwise AI Calendar Assistant
Clockwise AI is a robust AI-powered scheduler 

4 other top AI calendar assistants

In addition to Clockwise, we added a few other top scheduling tools for your exploration below, listed in alphabetical order. Happy calendaring! 


Clara is an AI scheduling assistant you can CC on any email thread, and Clara will handle the scheduling and back-and-forth required to coordinate. Once a meeting time is confirmed, Clara sends calendar invites to all recipients to reserve the time on calendars. Clara works 24/7 and is attentive, sending timely responses and follow-ups to unanswered responses. Read more about Clara’s history, key features, and more in this thorough review by Huda Idris.

Clara AI Scheduling Assistant
Add Clara to your emails for automatic scheduling | Image source: ClaraLabs


  • Human-like assistant that responds to emails to coordinate meetings (just like a human executive assistant would) 
  • Easy to use—add Clara to your emails via CC 
  • Clara will follow up if the person on the other end of your email thread doesn’t respond or forgets to 


  • Email scheduler (so it only works in your inbox)
  • It is expensive compared to some of the other tools available


  • Clara’s website says new pricing is coming soon; you can join the waitlist for the Clara 3.0 beta here
  • Previous pricing structures (on G2) start at $99/user/month for a Personal plan and $199/user/month for a Professional plan


Mayday is a little different from the other tools mentioned in this list. It’s a robust all–in–one calendar, task manager, and scheduling assistant for iOS, Mac, and iPad devices only. Mayday combines your workday patterns and productivity best practices to schedule your tasks and meetings at an ideal time that works best for you. There are many additional features for effective time management, including FYI events (events you can minimize) to declutter your calendar, Smart Tags for calendar organization, buffer time placeholders for before and after events, and more. 

AI Scheduling with Mayday
Mayday is an AI scheduling assistant for Mac & iOS | Image source: Mayday


  • Additional calendar management features on top of scheduling assistance for better organization (Smart Tags, FYI Events, Time Windows, and more)
  • Supports Google Calendar, Microsoft Outlook, Google Meets, Microsoft Teams, and Zoom
  • Free right now


  • Only available on iOS, Mac & iPad
  • Reviews indicate the tool doesn’t function as expected (beta functionality is subpar)


  • Currently free (monthly subscription pricing coming soon according to the FAQs

Sidekick Ai

Use Sidekick Ai to choose how you want to schedule meetings using one of three options: forward to schedule (email forward to Sidekick), scheduling pages for manual booking, or Sidekick scheduling for finding a time that works for everyone across teams. Sidekick Ai sends reminders before meetings, creates calendar events automatically, and sends invites out to all attendees. You can use it to book virtual meetings with Microsoft or Google products.

Sidekick AI Scheduler
Sidekick Ai is meeting scheduling software | Image source: Sidekick Ai


  • Users can take advantage of a free plan
  • Tons of integrations—Gmail, Google Calendar, Outlook, Zoom, Teams, Google Meet, Office 365, and more 
  • There are multiple ways to take advantage of the tool through its various scheduling options 


  • Some reviewers noted that the tool is great overall, but more integrations would make it even better


  • A free plan is available that provides access to most features
  • $5/month to upgrade to a paid plan

Trevor AI

Trevor AI is an intuitive planner and task-scheduling app for time blocking. Unlike some of the more robust and complex tools on this list with fancy bells and whistles, Trevor is simple. It isn’t designed for rescheduling meetings or automating the meeting scheduling process. Instead, you connect your calendar to see all your scheduled events and then use Trevor to drag and drop your tasks from your task list to your calendar. Trevor will learn about you and suggest the best task times to help you build your schedule. 

Trevor AI Scheduler
Trevor AI is an AI-powered task scheduler | Image source: Trevor AI


  • Great workload planning tool for individuals with a heavy emphasis on task management 
  • Auto-scheduling for personal and work tasks in one convenient place 
  • Super intuitive and easy to use due to its drag-and-drop functionality 


  • Integrations are currently limited (integrates with Todoist, Google Calendar, Outlook & Office365 calendars)
  • If you want a tool to help automate meeting scheduling, Trevor AI isn’t a good fit


  • Free plan available with limited functionality 
  • Pro plan is $3.99/mo or $36/year

Read next: AI Scheduling for Outlook Calendar

About the author

Alyssa Towns

Alyssa Towns has written productivity and time management content for Clockwise for several years. Early in her career, she dove into time management strategies to effectively manage her workday calendar and 10+ C-Suite officers' calendars across various organizations. She uses her training in change management to write time management, the future of work, and career content that helps people change their behaviors and habits. In addition, she writes about artificial intelligence (AI) and other technology for G2's Learn Hub. When she isn't writing, Alyssa enjoys trying new restaurants with her husband, playing with her Bengal cats, adventuring outdoors, or reading a book from her TBR list.

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