Calendly vs. Microsoft Bookings: Which scheduling tool is right for your team?

Your team needs a scheduling tool that makes managing meetings easier — whether you’re booking sales calls, product demos, partner meetings, candidate interviews, customer onboarding, or all of the above. 

If you’re already using Microsoft 365, you might consider sticking with Microsoft Bookings, the built-in scheduling app. While Bookings can handle basic scheduling, a dedicated scheduling platform like Calendly offers more advanced features and integrations that large teams need to tackle complex scheduling.

Let’s walk through the key differences between Microsoft Bookings and Calendly, and help you decide if adding Calendly to your Microsoft 365 tech stack is the right fit for your team.

What is Calendly? 

Calendly is a user-friendly, cloud-based scheduling platform. Calendly simplifies the scheduling process for teams of all sizes across industries.

Here’s how it works:

1. You connect your work and/or personal calendar(s) to Calendly and set your available hours, so you never have to worry about accidental double bookings.

2. Calendly uses this info to show your available meeting times on your booking page. (No one can see the details of your whole calendar — Calendly only shows your open time slots.)

3. When you share your Calendly scheduling link, invitees can quickly see your availability. Available times are automatically shown in invitees’ time zones.

4. Invitees choose their preferred time and, in less than a minute, your meeting is booked! Calendly adds the meeting to your connected calendar.

For professional teams, Calendly is much more than a scheduling link. Calendly lets you automate the time-consuming activities before and after meetings, so you can spend less time on busy work and more time collaborating with customers, prospects, candidates, and teammates.

Calendly is intuitive enough for individual users, scalable enough for SMBs, and powerful enough to meet the needs of enterprise organizations — including four out of five Fortune 500 companies. Calendly is the only provider that’s created specific solutions for departments across your organization, including sales, marketing, recruiting, customer success, and more.

What is Microsoft Bookings?

Microsoft Bookings is the appointment scheduling software built into the Microsoft 365 suite of business tools.

Microsoft Bookings is best suited for organizations with straightforward scheduling needs who are already deeply invested in the Microsoft 365 ecosystem. If your company already pays for Microsoft 365, your IT department may see Microsoft Bookings as more bang for their buck.

Despite its potential, Microsoft Bookings has faced criticism for glitches and bugs, a lack of scheduling features for complex meetings, and its steeper learning curve.

Features shared by Calendly and Microsoft Bookings 

Both Calendly and Microsoft Bookings let teams:

• Provide links to schedule meetings, making it easier to find a time that works for everyone

• Book multi-person meetings

• Build in buffer time between meetings

• Create unlimited appointments and meetings

• Automatically show available times in invitees' time zones

• Sync with Outlook, Exchange, and Office 365 calendars

• Gather information from meeting invitees at booking with custom questions

• Automate text and email reminders

Top differences between Calendly and Microsoft Bookings 

Calendly and Microsoft Bookings share some basic online scheduling features. But when it comes to integrations, user experience, admin management, and complex scheduling, they begin to look a lot different.

Calendly integrations go beyond the Microsoft suite

Because Microsoft Bookings is part of the Office 365 suite, it only integrates with other Microsoft software, like your Outlook calendar and Microsoft Teams. This works well for teams who exclusively use Microsoft apps — but can be limiting for everyone else.

For example, Bookings only lets you connect to one calendar, and its default conferencing system is Microsoft Teams. You can use Microsoft Power Automate to connect Bookings to Zoom and Webex, but Automate costs extra and requires complex manual setup and management.

Calendly integrates with many of the tools you use every day, so you can add scheduling to your processes without reinventing the wheel. Some of the 100+ native Calendly integrations include:

• Multiple calendars (Google Calendar, Outlook, Exchange, Office 365)

• Video conferencing (Zoom, GoToMeeting, Webex, Google Meet, Microsoft Teams) — automatically add meeting links to your calendar invites

• Sales and marketing tools (Salesforce, HubSpot, Microsoft Dynamics 365 Marketo, Gong)

• Recruiting software and ATSs (Greenhouse and JazzHR)

• Collaboration and project management (Slack, Notion, Asana)

• Payment processing (Stripe and PayPal)

• Workflow automation (Microsoft Power Automate, Zapier, Outfunnel)

Calendly is easier to set up and use for users, admins, and invitees

Calendly makes scheduling easy for users, admins, and invitees, so you can create a better experience for your team and your prospects, clients, or candidates. G2 ranks Calendly as one of the easiest-to-use scheduling software platforms.

Calendly’s browser extension lets you manage your schedule and book meetings without switching tabs, while the mobile app simplifies scheduling on the go. Bookings doesn’t offer any browser extensions and no longer has a mobile app.

“There is so much to love! The ease of use for you and your customers, the integrations … these tools will absolutely save you time and help you become more efficient in how you operationalize your calls and meetings across the board.”

Tiffany Keel

Head of Customer Advocacy, Product Marketing at ClickUp

For admins, team leads, and IT teams, Calendly’s admin management features and dashboard make it easy to manage, standardize, and scale scheduling across the organization. Admins can create a consistent meeting experience across the team with lockable templates for meeting types and automated reminders and follow-ups. 

On the other hand, Microsoft Bookings doesn’t offer an admin console, making team management complex and time-consuming. Bookings creates a new booking mailbox for every event type created, making it hard to manage and standardize branding across meetings and users.

Calendly can handle more complex scheduling scenarios

Calendly’s team scheduling features make it easy to schedule multi-person meetings with any combination of attendees — whether you’re booking client consultations, sales calls with inbound leads, group interviews, product demos, vendor and partner meetings, or all of the above. Microsoft Bookings also offers group scheduling features, but the options are more limited.

Here are a few complex scheduling situations where Calendly has the edge:

Round-robin scheduling: With Calendly’s Round Robin meeting distribution, you can automatically assign new meetings to team members based on availability, team member priorities, or equal meeting distribution. This feature lets you respond to customers faster and offer them more available meeting times. Microsoft Bookings also offers round-robin scheduling, but there's no way to ensure equal distribution or cap the number of appointments a team member is assigned.

Meeting polls: Use Calendly Meeting Polls to find the best time for one-off meetings with up to 40 people. Invitees vote on preferred times. Once everyone votes, you choose a meeting time, and Calendly sends calendar invites and meeting details to everyone who voted. Microsoft Bookings doesn’t include any meeting poll features.

Meeting reminders and follow-ups: Calendly Workflows let you automate and pre- and post-meeting communications, including customizable templates for reminder texts, thank-you emails, follow-up meeting requests, and more. Microsoft Bookings’ automatic email and text notifications are more limited, and SMS messages are only available on higher-tier plans.

Lead routing: Instantly qualify, route, and book leads through your HubSpot, Marketo, Pardot, or Calendly forms with Calendly Routing. Automatically route known leads or customers to their account rep’s booking page with Salesforce and HubSpot CRM account matching. Leads can book appointments with the right team member, on the spot, at the height of their buying interest. Microsoft Bookings offers no routing features or native routing integrations, and manual integrations are complex to set up.

“Now that we’ve implemented Calendly’s routing feature with Salesforce integration, demos are always booked with the correct AE, reducing friction for both our team and the customer.”

Abbie Deaver

Director of Marketing at RCReports

How does Calendly work with Microsoft apps?

While Bookings is already built into your Microsoft tech stack, Calendly offers a full suite of native integrations with the Microsoft apps and tools your team uses every day:

• Outlook and Office 365 calendar connections: Keep your availability up to date and avoid double booking by connecting your calendar to Calendly

• Microsoft Teams video conferencing: Automatically add Teams video conferencing links to Calendly meetings

• Microsoft Teams chat: Get real-time updates on your Calendly meetings right in Teams

• Outlook add-in: Schedule Calendly meetings right from your inbox

• Edge browser extension: Share your availability and schedule meetings without switching tabs

• Microsoft Dynamics 365 integration: Sync lead and meeting details to your CRM (Enterprise Calendly users only)

• Azure SSO: Add a simple and secure way for your team to access Calendly (Enterprise Calendly admins only)

Many of these integrations are included in the free version of Calendly. For a full tour of the Calendly + Microsoft ecosystem, check out our webinar: How Calendly Integrates with Microsoft. It’s the best way to learn all about the features built specifically for Microsoft users like you.

Webinar: How Calendly Integrates with Microsoft

Take a tour of the Calendly x Microsoft ecosystem and learn more about the features we’ve built for Microsoft users like you.

Watch now

Calendly vs. Microsoft Bookings pricing

This is a bit of an apples vs. oranges situation — Calendly is a standalone product and Microsoft Bookings is included in Office 365. 

Calendly pricing

Calendly has four pricing plans:

• Free forever: Includes one calendar integration and one type of meeting

• Standard: $10 per user per month (billed annually)

• Teams: $16 per user per month (billed annually)

• Enterprise: Custom pricing starting at $15k/year

Want to try out Calendly’s advanced features? Sign up for a 14-day free trial of the Teams plan.

Microsoft Bookings pricing

Microsoft Bookings doesn’t offer a free plan. Bookings is included in all pricing tiers of Microsoft 365 Business.

Calendly + Microsoft = better scheduling for teams and enterprises

When your team is already using Microsoft 365, sticking with Microsoft Bookings for scheduling might seem like the easiest choice. But for large teams looking to make scheduling as easy and efficient as possible, adding Calendly to your tech stack is a smart move. Here’s why:

• Bookings only integrates with other Microsoft tools. Calendly connects natively with 100+ tools and apps, from Google Calendar and Zoom to Salesforce and HubSpot — plus Microsoft products like Outlook, Teams, and Dynamics.

• Calendly is designed to simplify complex scheduling scenarios across teams and industries while still being easy to use. In contrast, Microsoft Bookings isn’t Microsoft’s primary offering or priority. Bookings doesn’t have a dedicated support team, and its limited features are best suited for more basic scheduling.

• Calendly offers enterprise-grade security features like domain control, SAML SSO, and communications archiving, so you can rest easy knowing your data (and your customers’ data) is safe and sound.

See how more than 100,000 companies simplify scheduling and delight their customers. Request a Calendly demo.