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Tech Insight: Calendly Vs Microsoft Bookings

In this insight, we take a brief look at Calendy contrasted against Microsoft Bookings and highlight some of the pros and cons of each.


Founded in 2013, Calendy is a SaaS meeting and event scheduling app for website, Chrome extension or mobile app, which has 100+ partner integrations, and has 10 million users worldwide. Users can send their availability with a Calendly link so that the invitees can book a time that suits them, and Calendly will round robin the meeting by availability or priority automatically.

Users can choose event-types that will suit their individual or multi-person scheduling needs. For example, meetings or events can be scheduled one-on-one, for a group (e.g. training sessions or webinars), collectively by schedule across a team’s calendars for events the organiser co-hosts with others, or round-robin balancing hosting responsibilities for the team automatically.

Microsoft Bookings 

Microsoft Bookings is the meetings and appointments scheduling tool that’s integrated with the Microsoft 365 or Office 365 calendar. With Microsoft Bookings in Teams, users can track, manage, and organise the team’s appointments and calendars all in one place. Also, users can create a Bookings calendar and add team members to it, build new appointment types, and create and manage in-person and virtual visits for staff and attendees.


There are many different features and aspects of each app that could be compared, but here are a few of the main popular areas of comparison:

– A big plus for Microsoft Bookings is that it integrates with the hugely popular Outlook calendar and Office suite which enables simple booking, and users can schedule appointments one at a time.

– Microsoft Bookings comes free with your license whereas with Calendy costs $8, $12, 16$ /seat /month  for Essentials, Professional, and Teams. There is also an Enterprise price that is not advertised. A basic version of Calendly is free, with rather limited features.

– Calendly uses time-zone detection, so invitees can automatically see a user’s available times translated to their time zone whereas the booking page on Microsoft Bookings uses the host’s time zone and language.

– Calendy is intuitive and user-friendly, and Microsoft Bookings is easy to implement with step-by-step guides.

– Calendy works across many different calendar apps like Microsoft, Google, and Apple, and allows meeting buffers to be added. Microsoft Bookings only works with the Office calendar.

– Microsoft Bookings works with Teams video conferencing whereas Calendy integrates with Zoom, Webex, GoToMeeting, Google Meet, and Microsoft Teams. On the general subject of integration, Microsoft Bookings only integrates with other Microsoft tools whereas Calendy integrates with many different tools. However, Microsoft Bookings integrates seamlessly with Microsoft products, and with Microsoft 365 being used by more than one million companies worldwide and widely regarded as the best online collaboration tool, and with Teams being the most popular business communications tool in the world, seamless integration with Microsoft’s products is a big bonus and advantage in itself.

– Calendly and Microsoft Bookings both have meeting confirmation and email reminders, and both offer reporting to gain insights into meetings.

– Both Calendly and Microsoft Bookings share notable features like scheduling pages that prevent double booking.

– Calendly allows new users to register without entering credit card or proof of identification which has led to criticism that it may be leaving the platform open to abuse. This could be one of the reasons why phishing actors were found to be actively abusing Calendly back in March this year.

– Microsoft Bookings won’t automate the meeting workflow in the same way that Calendy will. Calendy enables automated workflow such as automatically sending messages to invitees before or after booked and automatically performing tasks specified in condition the users sets. It also has a Zapier integration to allow the creation of tasks from new events, sending Slack messages with new calendar invites, and more.

– Some commentators have said that Bookings involves a learning curve, although many would disagree by saying that Microsoft products are familiar, lots of instructions are available, and with the wide usage of Teams, fuelled by remote and hybrid working, most users are well able to operate Bookings.

What Does This Mean For Your Business? 

Calendy’s growth, like other platforms, was hugely accelerated and boosted by the pandemic and the move to home and hybrid working, bringing it half the scheduling apps market share in the US, and turning it into a $3+ billion business. Users like its minimalist design, its simple focus on solving the problem of identifying and matching availability between two people, and its breadth of integrations. Microsoft Bookings, however, integrates and syncs seamlessly with other Microsoft products and tools, it already comes as part of a user’s subscription thereby saving costs, and it has the backing of the Microsoft brand and their market dominating OS and collaborative working tools. Reports vary about how user-friendly Calendy is, depending on the needs of the user, but for many people the convenience and compatibility of Bookings with their existing use of Microsoft products across their wider team is likely to retain their loyalty and discourage serious thoughts of switching.