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Microsoft Bookings vs. Calendly vs. Clockwise Scheduling Links

Microsoft Bookings vs. Calendly vs. Clockwise Scheduling Links

Judy Tsuei
April 2, 2024
Updated on:

Microsoft Bookings vs. Calendly vs. Clockwise Scheduling Links
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Time is everyone’s most valuable asset — and the SaaS industry knows it. Scheduling software is quickly becoming a must-have tool in just about every line of work, from healthcare to hair salons to freelance talent.

In this guide, we’re going to compare three of the most popular online scheduling tools: Microsoft Bookings, Calendly, and Clockwise Scheduling Links. These tools simplify the scheduling process with personalized booking pages that share your availability and allow people to book a time slot with you. It’s a powerful alternative to calendar invites (sharing your entire calendar with someone) or trying to find a time that works for both parties in an endless email thread.

Despite working in similar ways, there are some key differences between Microsoft Bookings, Calendly, and Clockwise Scheduling Links. To discover which one is right for you, keep reading!

Microsoft Bookings

Image: Microsoft


Microsoft Bookings is a scheduling tool that’s included with your subscription to either Office 365 or Microsoft 365 (previously Microsoft Office). It allows you to create and customize booking pages that you can send to your clients for easy scheduling.

When comparing Bookings to Calendly and Clockwise Scheduling Links, we noticed that Bookings is more focused on small businesses as its target audience. Alongside using more language tailored toward business owners, such as “services” and “appointments,” the scheduling app also includes:

  • The ability to manage appointments for multiple staff members
  • The ability to add multiple service types
  • A Business Information page, which you can populate with details like a relevant name, address, phone number, web site URL, privacy policy URL, logo, and business hours

You can access it via its fully-fledged web app or Microsoft Teams with limited features.


Microsoft Bookings is available in two ways: as a web app and as a lightweight app within Microsoft Teams. The Microsoft Teams app offers a simple way to schedule meetings, but for full functionality, we recommend using the web app.


Microsoft Bookings isn’t available as a standalone app. To access it, you need one of the following Microsoft subscriptions:

  • Office 365: A3, A5, E1, E3, E5, F1, F3, Office 365 operated by 21Vianet.
  • Microsoft 365: A3, A5, E3, E5, F1, F3, Business Basic, Business Standard, Business Premium.

Ultimately, Microsoft Bookings is a paid service. However, if you’re a student or an employee of an organization that already pays for a Microsoft license for one of the above plans, you can take advantage of Bookings at no extra cost to you!


  • Great for small businesses, especially those with multiple staff members and different types of services


  • Only available with a paid Microsoft account
  • Requires a steeper learning curve when compared to Calendly and Clockwise Scheduling Links
  • Doesn’t integrate with calendars and video conferencing tools outside of the Microsoft suite


Image: Calendly


Calendly is a scheduling automation platform that’s easy to set up and easy to use. Just like Microsoft Bookings and Clockwise Scheduling Links, Calendly lets you share your available times via a scheduling link, eliminating the hassle of back-and-forth communication.

What makes Calendly unique from Microsoft Bookings is its workflow automation features. While Bookings and Calendly both offer automatic email reminders, Calendly takes it one step further with automatic follow-up emails and other messages for your events.

Calendly is also more flexible than Microsoft Bookings. Whether you’re a business owner who wants to simplify the way clients book appointments with you, or you're a corporate employee who wants to share available meeting times with fellow team members, Calendly is a great solution. It’s even useful for scheduling group events like webinars.


Calendly is available as a web app, iOS app, Android app, Chrome extension, and Firefox extension. To start using Calendly, all you need to do is create a free account, connect your calendar and video conferencing tool (see compatible software below), and set up your event type and availability.

Compatible calendars:

  • Google Calendar
  • Microsoft 365
  • Outlook
  • iCloud

Compatible video conferencing tools:

  • Zoom
  • Google Meet
  • Microsoft Teams
  • Webex
  • GoTo Meeting


Calendly offers four different plans:

  • Free: 
  • Standard: $10/seat/month (billed annually) or $12/seat/month (billed monthly)
  • Teams: $16/seat/month (billed annually) or $20/seat/month (billed monthly)
  • Enterprise: Contact sales for quote


  • Free version is available
  • Offers plenty of integrations, including Slack, HubSpot, Salesforce, Stripe, and Paypal. See the full integrations list here.
  • Lets you automate your scheduling workflow with automatic event notifications (via email and SMS/text messages), follow-up emails, and more
  • Automatically detects your time zone and invitees’ time zones and adjusts accordingly
  • Offers round robin scheduling
  • Syncs with your calendar, helping to prevent double booking


  • The free version gives you access to one event type only — for multiple event types (e.g. 15-minute discovery call and 1-hour strategy call), you’ll need to upgrade to a paid plan starting at $10/seat/month

Clockwise Scheduling Links

With Clockwise you can book the best time, not just the next time.


Like Microsoft Bookings and Calendly, Clockwise Scheduling Links lets you share your availability instantly by creating a booking page to send to whomever you’re meeting with. But that’s not the best part.

What sets Clockwise Scheduling Links apart from similar scheduling software is that it proactively protects your schedule in whatever way is most important to you. Using AI, Clockwise Scheduling Links factors in a unique set of scheduling considerations — from Focus Time to the number of back-to-back meetings — to surface the best times for the invitee to schedule.

Simply put, Clockwise Scheduling Links helps you find the best time, while competing tools help you find the next available time. Rather than trying to squeeze everything in, Clockwise Scheduling Links empowers you to manage your time more thoughtfully — just one way Clockwise helps you create a more sustainable schedule.


You can access Clockwise Scheduling Links via the Clockwise web app. It’s free to sign up; all you need is a professional Google account. That’s because Clockwise works on top of Google Calendar, rather than as a standalone calendar app.

While you’re there, take advantage of all of Clockwise’s amazing AI-powered scheduling features, like Focus Time, which creates and protects uninterrupted blocks for deep work. Or Flexible Meetings, which automates your schedule and minimizes conflicts. Clockwise has everything you need to create your ideal day, however that looks for you.


Clockwise Scheduling Links is available with all Clockwise plans, including the free version! If you have a Teams plan or above, which starts at $6.75/user/month, you unlock extra features like unlimited links, group scheduling, and more!

Click here to claim your free scheduling link.


  • Helps you find the best time — not just the next available time — by taking into account factors like: preferred meeting hours, Focus Time, avoiding consecutive meetings, preserving your Travel Time, and preserving your Lunch Time
  • You can customize the branding of your booking page with your company logo and a URL of your choosing
  • Works for internal and external attendees; an attendee doesn’t need to be part of your organization nor do they need a Clockwise account to use your scheduling link
  • Available with Clockwise’s free plan
  • Syncs with your calendar, helping to prevent double booking


  • The free plan gives you access to one scheduling link; upgrade to a paid version for advanced features like unlimited scheduling links, group scheduling, and single-use links

Going forward

To recap, Microsoft Bookings, Calendly, and Clockwise all work in a similar manner — they let you create a booking page from which people can easily see your availability and schedule a meeting with you in just a few clicks. Here are the key differences to keep in mind as make your decision:

  • Microsoft Bookings is convenient if you already have a Microsoft subscription. Because it’s part of Microsoft 365, it integrates seamlessly with other Microsoft products like Outlook Calendar and Microsoft Teams. It’s also more of an appointment scheduling software than a general scheduling tool, making it ideal for small businesses looking to book clients (rather than corporate employees looking to book meetings).
  • Calendly is free (and easy) to use. Users love that it offers plenty of integrations and is able to connect with various calendar providers (Google Calendar, Microsoft 365, Outlook, and iCloud). It also lets you automate many of your scheduling workflows (event reminders, follow-ups, etc.).
  • Clockwise Scheduling Links is free to use, and it’s the only tool that helps you find the best time, not just the next available time. For example, if you want to protect your Focus Time, Clockwise Scheduling Links will surface times for your invitee that don’t compromise your deep work. Clockwise Scheduling Links understands your preferences and proactively protects them.

About the author

Judy Tsuei

Judy Tsuei is a Simon & Schuster author, speaker, and podcast host. She has been writing for Clockwise for several years while also being featured in MindBodyGreen, BBC Travel, Fast Company, Hello Giggles, and more. As the founder of Wild Hearted Words, a creative marketing agency for global brands, Judy is also a mentor with the Founder Institute, the world's largest pre-seed accelerator. Judy advocates for mental and emotional health on her popular podcast, F*ck Saving Face. Follow along her journey at

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