The 7 best AI scheduling assistants in 2023

Productivity starts with your calendar—but sometimes it ends there too. No one wants to reprioritize an entire week after an emergency, or play calendar Tetris to land a meeting with that busy lead sometime in the next two days. This is where an AI scheduling assistant can help: instead of working on your schedule, you can let AI calendar apps do it for you.

The 7 best AI scheduling assistants in 2023
The 7 best AI scheduling assistants in 2023

I’ve been playing around with all sorts of AI tools recently. For this article, I considered a couple dozen AI calendars and did in-depth research and testing to find the best AI scheduling assistants that can sort out the tricky bits for you.

Ready? Block a few minutes on your calendar, and let’s dive in.

The best AI scheduling assistants

  • Reclaim for protecting your habits

  • Clockwise for syncing team calendars
  • Motion for AI-assisted project management

  • Clara for having a human-like AI virtual assistant

  • Trevor for a simple, free AI solution for task management
  • Kronologic for following up with more leads
  • Scheduler AI for managing meetings for busy teams

Smart calendars vs. AI calendars

The best AI scheduling assistants help place your tasks on your calendar, reschedule conflicts, schedule 1:1s with ease, and group most of it into time blocks, so you do less context-switching. But should you move to a new app if you’re already using a smart calendar or smart meeting scheduler? Here’s a brief comparison to help you distinguish one from the other.

Smart calendars use deterministic algorithms—fixed rules built by developers—to make suggestions and optimize your calendar. It will always bring up the same results if you input similar data. For example: a developer may add a rule that says whenever a user adds a task called “jogging,” schedule that task at that same time on every following day.

Calendar AI is more powerful: it can recognize patterns, make decisions, and learn from experience. When it starts processing the data on your calendar, it’ll be able to adapt and make more relevant changes over time. For example, it may figure out how long you take to tackle a specific task and adjust the estimated time to complete it in the future. It can discover at which time in the day you’re more productive and slot higher priority tasks there. It’s dynamic, and it provides a more personalized result to each user.

AI for scheduling: What to look for

Ready to go from smart to AI-powered? Here’s what I looked for in every AI scheduling assistant I tested:

  • Great user interface. You’ll be looking at your schedule assistant app throughout the day—it’s your calendar, after all—so it needs to be functional, intuitive, and easy to use.
  • Easy to set up and offers a good set of integrations. It should take you less than five minutes to go through onboarding, which includes connecting your calendar of choice. I also prioritized apps that have integrations with other popular apps, so you can save time generating those Zoom meeting links, for example.
  • More than a smart calendar. As I tested each scheduling assistant app, I was looking for true AI features. Where it was unclear if there was actual AI at work, I reached out to the support team to ask what kind of technology was running behind the scenes and learn more about the AI scheduling algorithms.

  • Insights and tips. Each AI scheduler app listed here has tooltips, articles, and videos outlining how they work, so you can understand what’s going on when your calendar is suddenly reorganized.
  • Extras. I was looking for any innovative AI appointment scheduling features that could be game changers for the way you schedule and work through your day.

To test, I first made sure it was actually AI at work. After that, I signed up for each AI scheduling app and added my schedule, making some changes to see how the platform adapted as I did. I set up meetings with myself (via a bunch of separate calendar accounts) and rearranged events over the course of a week. I explored the settings, tried out all the available features, and watched the robots create my schedule for me. Based on all that experience researching and testing these tools, here are the best AI calendar apps.

The best AI scheduling assistants at a glance

Best forStandout featurePricing
ReclaimProtecting your habitsManages recurring events wellFree plan available for 2 calendars, 3 habits, and limited integrations; paid plans start at $8/user/month
ClockwiseSyncing team calendarsThorough onboarding experienceFree plan available for basic features; paid plans start at $6.75/user/month
MotionAI-assisted project managementHigh visibility for tasksIndividual plan for $34/month; Team plan for $20/user/month
ClaraA human-like AI virtual assistantVery flexible, really seems like a human assistantPlans start at $99/month
TrevorSimple, free AI solution for task managementIntuitive, simple controls to schedule and manage tasksFree plan available; paid plan is $3.99/month
KronologicFollowing up with more leadsCaters to sales teams but can also replace CalendlyPlans start at $6/month
Scheduler AIManaging meetings for busy teamsWorks well for all kinds of meetingsPlans start at $25/user/month

Best AI scheduler for protecting your habits

Reclaim (Web)

Reclaim pros:

  • Manages recurring events well
  • Quickly reschedules and adjusts your calendar when conflict is detected
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Reclaim cons:

  • Native task management is clunky

Strengthening habits is all about consistency, and Reclaim.ai is a great AI calendar assistant to help you build that consistency. It looks good, works even better, and it has the right balance between power and complexity.

During onboarding, you set up your work hours, weave in your habits, and choose the way the AI engine should prioritize your to-dos. It does a great job explaining what’s going on behind the scenes, so you’ll never wake up to a completely different calendar and wonder what happened (that confusion was pretty common with a lot of other apps I tested).

All the action is on the Planner screen. It has a calendar view in the center with three lists on the right side: priority habits, open tasks, and low-priority habits. You can keep track of what’s left to do with just a glance, great to keep your focus as you work.

I also loved the customization options available for each habit: in addition to the start and end times, you can pick an ideal time and set how defensive the AI engine should be when rescheduling. If you set it to Always free, it’ll let Fred from accounting grab those 30 minutes easily; if you set it to Busy, it won’t let even the president in.

You can enter all the tasks you have to tackle manually, and Reclaim will start dropping them on your schedule on its own. Better yet, you can integrate a wide range of task management apps and turn on sync, automating the whole process. As it populates your near future, it’ll keep an eye out for deadlines, defending the time needed to complete critical tasks from an out-of-the-blue 1:1. Speaking of 1:1s, Reclaim empowers your weekly catch-ups by rescheduling any recurring meetings if someone has to cancel, finding the best time slot for both and sending the appropriate notifications.

If you’re having a hard time sticking to your morning meditation or that brisk afternoon walk, Reclaim will get you back on track easily, without scheduling headaches.

Reclaim.ai price: Free plan available for 2 calendars, 3 habits, and limited integrations and features; paid plans start at $8/user/month for unlimited calendars, unlimited habits, more integrations, and more advanced features.

Best scheduling AI tool for syncing team calendars

Clockwise (Web, Chrome and Firefox extensions)

Clockwise pros:

  • Thorough onboarding experience

  • Plenty of in-app context and explanation

Clockwise cons:

  • Can only be used with a Google Workspace account

Clockwise’s #1 objective is to create time for you by putting together more focused blocks, reducing conflicts when scheduling meetings with others, and providing stats to help you see how you’re doing.

Clockwise has lots of knobs and levers—it’s definitely the most customizable engine on this list. The onboarding experience lets you fine-tune the balance between meetings and focused work. When I finished setting up my account, Clockwise blocked three hours of continuous focus work every day and two hours of fragmented work time. My 45-minute lunch break hovers somewhere between noon and 3 p.m., depending on meetings and deadlines. Where will it land? Who knows. And there’s one special treat you get your first week with the app: Clockwise organizes your time better, freeing up a 30-minute break you can use to have a cup of coffee.

If you want to revisit these settings at any time, click Your ideal day on the dashboard, and set everything from when you should have lunch to how much travel time to reserve for a meeting away from the office.

While Clockwise feels strong for a solo player, it’s meant for teams. When you connect it to Slack, it updates your status based on what’s on your calendar and prevents non-urgent messages from pinging you. And the Asana integration lets you assign tasks to your calendar, so you can go there to fill up your plate and come back to Clockwise to bite it bit by bit.

Unsure if it’s actually doing anything for your productivity? Visit the Analytics dashboard, with a count of all schedule assists, meeting conflicts resolved, and a breakdown of focus hours created. If you want to implement a no-meeting day, there’s a specific setting you can tick on to try that out.

One big drawback: you can’t join with a regular Google email address—you need a Google Workspace account. Microsoft 365 users will have to sit tight too: the integration is “coming soon,” but you can hop on the waitlist and see if you’re lucky.

Clockwise price: Free plan available for basic features; paid plans start at $6.75/user/month for advanced features, team productivity tools, and more security and support.

Best AI schedule assistant for project management

Motion (Web, iOS, Android)

Motion pros:

  • High visibility for tasks
  • Great task priority controls

Motion cons:

  • A bit too complex

Motion is an AI calendar that crashed into a solid project management app. The result? A great scheduling engine coupled with advanced task tracking, making sure you never miss a deadline.

The user experience suits productivity lovers, keeping all the critical information accessible. On the left, you have a list of all your upcoming tasks, scrollable deep into the future. The bulk of the screen contains the calendar with day and week views. Need to schedule something quick? Click and drag anywhere on the calendar to slot that emergency. If it lands on top of any event, Motion will shuffle your to-dos to make everything fit neatly, but be patient: once you’re done with the major changes, you’ll have to wait a minute to let the engine sort everything out.

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Clicking on the Projects & Tasks tab lets you create your workspace. With that done, be sure to invite your team over, add your projects, and start assigning tasks. You can see everything in a list or in a Kanban view. Anything you add here ends up on your calendar automatically, as expected. If you’re not a manager, this dashboard will look simpler: click on My Tasks, and lose yourself in deep work.

What surprised me here was the settings you can pick for each task. You can assign four types of priorities, from ASAP to Low, which will determine how early the task will appear on your calendar. You can also set if the task has a soft or hard deadline, letting the engine be more strict or lenient as the date approaches. If you ever lose your rhythm, the dashboard will display a warning showing the number of tasks at risk of missing their due dates, prompting you to change the task details or to pick up the pace—whatever makes the most sense.

The project management features extend a bit further into task notes, sub-tasks, task labels, and an activity feed where you can leave comments for your team to pick up. Another thing I liked was the possibility of adding project and task templates—which, considering how many controls there are for both, really helps speed things up.

While Motion campaigns for fewer meetings on the app’s marketing pages, it still lets you create meeting templates and assign a priority for each type of meeting, with the more urgent ones having more power to displace everything. This makes it a pretty complete scheduling assistant.

You can do even more with Motion by connecting it to Zapier. Automatically create new Motion tasks from Slack messages, emails, and any other tool you use at work. Here are a few examples to get you started.

Motion price: Individual plan for $34/month; Team plan for $20/user/month (with steep discounts for paying annually).

Best AI scheduling tool for having a human-like virtual scheduling assistant

Clara (Web, your inbox)

Clara pros:

  • Very flexible
  • Really seems like a human assistant

Clara cons:

  • Expensive

Clara is unlike any other tool on this list. After you finish setting it up with your email account and calendar, you land on the dashboard and… it seems there’s nothing else to do. That’s because the real magic happens elsewhere: when you want to meet someone, head to your inbox, compose a new email, and add Clara’s email as a CC. Say something like:

“Hey Clara, I want to find time for me and John this week.”

Somewhere between five and 20 minutes later, Clara will take a look at your schedule and respond with something like this:

“Hi Miguel,

Happy to help find a time for you and John to talk.

Does speaking at one or more of the following work for you:

  • Thursday (Jan 26) at 11am GMT
  • Thursday (Jan 26) at 2pm GMT
  • Friday (Jan 27) starting between 9am and 10:30am GMT
  • Friday (Jan 27) starting between 1pm and 2:30pm GMT

If these don’t work, feel free to suggest other times.

Best,

Clara”

You may think it breaks with a few curveballs, but no, Clara’s on top of it. Endless rescheduling? Cancellations? No one replied? Clara’s got it. Just keep it CC’d and the event will land on your calendar eventually.

It’s not just AI at work here. Most of the heavy lifting is artificial, but there’s also human intelligence at play with what Clara Labs calls human-in-the-middle: at some point, one of your emails will end up in the eyes of one of Clara Labs’ experts in case Clara is having a hard time divining the meaning of the content. Shortly after, seamlessly, the appropriate email will fire, and your elusive industry contact will definitely come out for that promised cup of coffee.

The paid plan lets you name Clara whatever you wish, with an email address ending with your domain name. Your invitees won’t know if they’re talking to a flesh-and-bone or silicon-and-chrome assistant. Way to run an impromptu Turing test, right?

Clara price: Plans start at $99/month

Best AI calendar for a simple, free solution for task management

Trevor (Web)

Trevor pros:

  • Very intuitive
  • Simple controls to help you schedule and manage tasks

Trevor cons:

  • Requires a bit too much interaction

Trevor is simple. It won’t reshuffle your entire day for emergencies, and it doesn’t have advanced controls, but it does have a streamlined user experience that makes a lot of sense and a set of AI features that help you put your tasks in the best calendar slots.

Start by connecting your calendar. Trevor picks up the events you already have scheduled, but it won’t mess with those. Instead, it creates a separate calendar where it adds your tasks separately. You can tick it on or off when accessing it from within Google Calendar. This means that it won’t reorganize all your events, so you can keep a degree of control over your scheduling but still leverage the benefits of AI.

Next, it’s time to add your tasks to the list on the left. They get categorized with the hashtag #inbox, but you can create other categories by clicking on the three-dot menu. When you have all your tasks ready, click and drag each task to the calendar. Trevor will suggest the best times to schedule each activity by outlining the place in time where you should drop that task. It learns as you use it to build your schedule, getting a little better every time.

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There’s a bit of a zen experience here. It has to do with the soft colors and the way you add all your tasks first, drag them to your schedule, turn on the day view, and forget about everything else that’s not there. I used it for an entire day and time got a little lighter, helping me reach the end of my day with a feeling that I spent less energy.

This is my subjective opinion, of course, so try it out and see if it fits your workflow. The free plan is quite generous, and if you want Trevor to learn faster and be more accurate, there’s an inexpensive paid plan for that. If you value simplicity and losing yourself in your tasks, Trevor will put you on the path to deep work, minus the monumental effort.

Trevor price: Free plan available; paid plan is $3.99/month.

Best AI scheduling assistant for following up with leads

Kronologic (Web)

Kronologic pros:

  • Automated meeting scheduling
  • Can replace Calendly

Kronologic cons:

  • Parts of the UI could be better

Kronologic is on a different plane when compared with the rest of the tools on this list. It’s built to help sales teams schedule more calls with interested leads, increasing conversion rates across your sales pipeline. To fully explain what it does, I’ll walk you through a few situations.

I’ve been testing software for a while. Most of it involves self-service registration, leading to a free trial or a free plan. But every now and then, there are a few apps that require filling out a form and waiting for a phone call to schedule a demo. And that’s the beginning of the touchpoint roulette: Will they call me in five minutes? Two days from now? Will it take one phone call? Three? It’s impossible to know.

After having a sales team from a CRM app call me at 2 a.m. in the cold British morning, I wish these apps would use Kronologic. Instead of filling the form and putting that lead on a queue, so a sales rep can pick it up whenever they can, the app automatically schedules a date and time when both parties are likely to be available. If the lead objects via email, Kronologic’s natural language processing features will detect if there’s a rescheduling intent and, if so, will update the invite to match. Sales team involvement during this process? If you want, zero.

This is the beginning of what Kronologic’s AI engine can do. Let’s imagine you’ve put together a list of 200 interested leads. It’d be great to schedule a call with them as soon as possible, right? But do you want to get your sales team in a frenzy trying to get hold of everyone?

Within the app, you can create the meeting type with the email template, and set the AI behavior to High-density scheduling. Emails will start going out to these leads, inviting them to a meeting at a specific time and date within a time period. Most of these meetings will overlap, but since the app keeps track of conversion rates over time, it knows your specific percentage. So even though you sent out 200 invites for 200 meetings in three days, not all of them are actually interested, so you can identify and get to talk to all the leads that are.

While Kronologic is a great fit for sales teams and larger companies, it now offers pricing tiers and features for both individuals and small businesses, along with a Calendly-style scheduling flow if your leads prefer to block a slot in your calendar.

Kronologic price: Subscriptions start at $6 per month.

Best AI scheduling assistant for managing meetings for busy teams

Scheduler AI (Web)

Scheduler AI pros:

  • Great for all kinds of meetings
  • Includes meeting troubleshooting for group meeting scheduling

Scheduler AI cons:

  • Not a lot of controls available on the dashboard yet

Scheduler AI is another app where the action happens in your emails and messages, not so much on the dashboard. With it, you’ll be able to schedule 1-on-1s or group meetings, and quickly book demos and discovery calls sourced from your website or landing page. It works great both at an individual level and also to deal out meetings to a sales team, helping busy organizations focus on running meetings, not scheduling them.

Once you set up your account, keep the scheduler@scheduler.ai email at hand whenever you need to find a time to meet. To begin scheduling, CC that email, and add the following sentence: “Scheduler, find us a time next week”.

Scheduler will take a look at your calendar and fire a reply to you and your contact suggesting the best time, pre-reserving that slot until the meeting is confirmed, so you don’t get double-booked. If the other half of the 1-on-1 has to reschedule, Scheduler can handle the email interaction until it finds a new slot.

If your sales process involves group meetings to get the buy-in of all the decision makers, finding the time to make it happen can be terrible. Like when handling 1-on-1s, Scheduler will take care of suggesting times based on the data it finds on your calendar. Better yet, when your leads connect their own calendar, Scheduler can read both and find the best option. If it doesn’t, it’ll notify you of the conflict, so you can start troubleshooting the meeting manually.

One cool feature here is how you can create meeting types and attach them to keywords. For example, if you frequently have coffee and chat with people, you can set up that meeting type in the dashboard, set the typical duration and whether you need to have some buffer time before and after. Then, all you have to do is mention coffee during the scheduling process: “Scheduler, find us a time to have coffee next week.” You can add as many as you’d like and set up whichever keywords make sense for the event type.

This flexibility to interpret intent and convert it into scheduling actions sets Scheduler AI apart from the competition. You can use it with your Gmail account, on Slack, integrate it into your website or web forms, and even use it in text messages.

Scheduler AI price: Basic plan starts at $25/user/month.

How to find the best AI meeting scheduler

AI calendar management is the future—and I’m not sad about it. As I was researching each AI scheduling app, I started paying attention to how much time I spend on scheduling every day: it added up to about 45 minutes. That’s 10% of my day (and maybe yours) spent on scheduling.

If you’re in the same boat—or in rougher waters—pick up the AI calendar app that speaks to your pain the most. Try it out for a few weeks and see if it helps you spend your time more productively. I’d be surprised if you didn’t notice the difference after even a few days.

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