Calendly vs. Microsoft Bookings: Which is right for you?


Steph Knapp, July 21, 2022

When you work with a large team or company, you need a scheduling tool that everyone can get on board with easily. Calendly and Microsoft Bookings are both popular appointment scheduling choices for teams. But beyond some shared functionalities, they fit into your workflow very differently. 

Let’s compare Calendly vs Microsoft Bookings to help you decide which is right for your team and business scheduling needs. 

Calendly overview - who is it for?

Calendly is a hub for scheduling and managing meetings efficiently. It has the essential features your meeting scheduling software needs, like one-click booking. There are also integrations and workflows, making it a solid choice for cross-functional teams.

There is a free plan and small business options for Calendly, but if you’re considering it alongside Microsoft Bookings, chances are you work on a team. That’s good news: Calendly integrates with Microsoft products, so if you’re a 365 user, Calendly is still on the table. Calendly’s platform security and compliance are designed specifically for large teams. 

Calendly is great for teams that:

  1. Use a variety of tools. We’ll explore Calendly integrations later in the post. For now, just know you can use Calendly alongside a wide variety of tools, including Zoom, Salesforce, Hubspot, and Slack.

  2. Need a solution that’s easy to spin up. According to G2, Calendly is the #1 easiest to use online appointment scheduling software because of its intuitive design. 

  3. Want to create automated meeting workflows. Most meetings require more work than just setting a date and time. Automate tasks like meeting reminders and follow-up emails using Calendly’s Workflows to help you save time and accomplish more.


Microsoft Bookings overview - who is it for?

Microsoft Bookings is the online scheduling arm of Microsoft 365, previously called Microsoft Office. If your team already has a paid version of 365, you may already have access. Bookings only works in the Microsoft  ecosystem, so if you don’t have a higher-tier plan already and don’t want to pay for one, this won’t be the best option. 

Microsoft Bookings is an option for teams that:

  1. Already pay for business or enterprise Microsoft 365. If you’re in one of those camps, you can begin using Bookings immediately. 

  2. Want simple scheduling software. Microsoft Bookings integrates with the Outlook calendar and Office suite for simple booking. It won’t automate your meeting workflow, but you can schedule appointments one at a time. 

Scheduling usability and features for Calendly vs Microsoft Bookings 

Now that we’ve reviewed Calendly and Microsoft Bookings from a high-level, let’s compare them feature-to-feature starting with the meeting scheduling process. 

Manage calendars

Microsoft Bookings only works with your Office calendar, though you can create and manage multiple businesses or booking calendars. For example, you could create a calendar for each team member. Your booking page only shows available times based on your linked calendar. You can also customize appointment duration and how far in advance customers can book appointments.

If you or your team wants to work across calendar apps like Microsoft, Google, and Apple, Calendly is the easier choice. You can connect multiple calendars to manage availability. This way, your sales meeting on your work calendar can’t interfere with the doctor appointment on your personal Apple calendar. You can also add meeting buffers with Calendly, which automatically builds breathing room before and after events to avoid back-to-back bookings. 

Create meetings

Calendly offers a few ways for invitees to choose an available time from your calendar. You can share your scheduling page link or use the Calendly Outlook Add-in to embed available meeting times directly into an email from your inbox. Calendly uses time-zone detection, so your invitees will automatically see your available times translated to their time zone. You’ll also have the option to route invitees to the correct team member automatically. 


With Calendly you’ll never forget to include a videoconferencing link again, because it integrates with Zoom, Webex, GoToMeeting, Google Meet, and Microsoft Teams. With Microsoft Bookings, well, hopefully you like using Teams’ video conferencing because that’s your only option. 

How you interact with meetings set up through Microsoft Bookings depends on your role and access level. If you set up appointments, you’ll use the Bookings app to create events and share the scheduling link with attendees. If you only need to see your scheduled meetings and not make them, you’ll view and join them from your calendar. If you work internationally, beware that the booking page uses the host’s time zone and language. 

There seems to be a steep learning curve for using Microsoft Bookings. Cindy L., a director of marketing, noted on G2 that “after setting it up, the link did not always work. Often got "bad request" errors when embedding it in a button or text link. Thus, it's too unreliable to work for us right now.” There are also limited features for customizing your appointment web pages.

Send reminders

Nobody wants to waste time with no-show appointments, so Calendly and Microsoft Bookings have meeting confirmation and email reminders. U.S. and Canada bookings users can also enable SMS text notifications. Unfortunately, users have reported issues with double booking and faulty reminders. 

Calendly’s follow-up settings are highly customizable, allowing you to choose who receives what email or text message minutes, hours, or days before and after an event. There are also confirmations if someone cancels an event. 

Teamwork usability and features for Calendly versus Microsoft Bookings

Both Calendly and Microsoft Bookings share some essential features, like scheduling pages that prevent double booking. They begin to diverge when you consider workflows and collaboration. Here’s how both tools stack up for teams. 

Team member management

Calendly knows there are many ways your staff members work together, so various types of team scheduling exist. You can create a Round Robin event for product demos that any sales team member can pick up. Or perhaps you need an all-hands collective event with multiple team members in attendance. You can also create group appointments like webinars or trainings, where multiple invitees can book the same time slot with your staff. 

Calendly offers several ways to align schedules between team members.

Microsoft Bookings also allows you to distribute appointments to a group, but there's no way to ensure equal distribution or cap the number of appointments a single team member is assigned. 


Automated workflows are another area where Calendly and Microsoft Bookings are at odds. Calendly allows you to design a meeting process from front to back one time and use it over and over. 

For example, you can send every sales prospect a recording of the demo after an event automatically. Or, you can send the same branded follow-up reminders at consistent intervals before events. There’s also a Calendly and Zapier integration you can use to create tasks from new events, send Slack messages with new calendar invites, and more.  


These workflows ensure your organization delivers a consistent experience across the board and frees up time and mental energy for your team. 

Unfortunately, Microsoft Bookings doesn’t have workflow automations at this time. You can create consistent event types to choose from, though. 


If you want insights into your teams’ meetings, you’re in luck, because both Calendly and Microsoft Bookings have reporting. 

Microsoft Bookings reports only include four months of data at a time. Still, you can download information like event type, duration, and price in a .tsv file. 

Calendly also has event reporting in a dashboard, with information like meetings booked, average event duration, and popular event types. Calendly users also like to connect their Google Analytics or Facebook Pixel accounts to track conversions


Integrations for Calendly vs. Microsoft Bookings 

Chances are you aren’t starting from scratch with your tech stack, so you need a scheduling app that works with your other tools. 

Since Microsoft Bookings is part of the Office 365 suite, it only integrates with other Microsoft tools. While it plays nice with Microsoft Outlook Calendar and Microsoft Teams, your options pretty much end there. 

If you want to make appointment scheduling a seamless part of your workflow, Calendly integrations offer way more options. Some of the tools with native Calendly integrations include:

Related reading: Get actionable feedback from Calendly + Typeform integration

Calendly vs Microsoft bookings: Choose scheduling software based on your priorities

Microsoft Bookings is a built-in, pared-down appointment scheduling option for teams that want basic functions where they already work. However, organizations that want to scale the impact and effectiveness of their meetings, or work across tools, will feel stifled by the software. It also isn’t a viable option for teams that aren’t already paying for a higher-tier Microsoft 365 subscription. 

Calendly, on the other hand, has tools for everyone, from small businesses to enterprise organizations. Meeting workflows and collaboration are customizable, and integrations with top apps like Zoom, Salesforce, and Microsoft products make it a seamless fit.  

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Steph Knapp biography
Steph Knapp

Steph Knapp is a freelance B2B + SaaS content marketer that loves educating and empowering curious humans. When she's not typing away, you'll find her volunteering at the animal shelter and obsessing over a new hobby every week. 

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