Microsoft Bookings vs. Calendly: Which Scheduling Tool Is the Best?

You’re balancing back-to-back meetings and a growing to-do list. Time is tight, and you need to make scheduling easier.

So you turn to smart scheduling software.

Needless to say, appointment scheduling software is essential for professionals looking to streamline their calendar management.

In this article, we’ll compare two popular calendar apps: Microsoft Bookings vs. Calendly. We’ll also introduce an alternative tool to schedule appointments with ease.

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What Is Microsoft Bookings?

Microsoft Bookings features

If you already use Microsoft Office tools like Outlook, Teams, and OneDrive, Bookings integrates seamlessly with these apps to improve your scheduling experience. Let’s look at the standout features this online calendar offers:

Feature #1: Automated email reminders and follow-ups

Microsoft Bookings simplifies appointment management with customizable email reminders. You can schedule these to be sent anywhere from 15 minutes to two weeks before an appointment, ensuring timely communication with customers.

Once configured, Bookings automatically sends reminders, helping customers stay informed about their upcoming bookings.

Microsoft Bookings also offers automated email follow-ups. You can design these emails to request feedback after an appointment or remind customers to schedule their next session.

Feature #2: Shared Bookings

The Shared Bookings feature in Microsoft Bookings allows multiple team members to manage appointments within a unified system. This feature is ideal for organizations where customer-facing roles require flexibility in scheduling. 

Teams can easily coordinate availability through shared calendars, ensuring customers receive timely service without overlapping schedules.

The system supports real-time availability tracking, which helps avoid double bookings and improves the customer experience​.

Feature #3: Buffer time set-up

Some appointments may require extra time for preparation, cleanup, or travel between customer meetings. To accommodate this, Microsoft Bookings offers a buffer time feature that allows you to set aside time before, after, or both before appointments. 

This ensures a seamless transition between meetings and prevents unnecessary delays for customers. Buffer times can be configured on the Service details page in Bookings.

Microsoft Bookings pricing

• Microsoft 365 Business Basic: $7.20/user per month
• Microsoft 365 Apps for Business: $9.90/user per month
• Microsoft 365 Business Standard: $15/user per month
• Microsoft 365 Business Premium: $26.40/user per month

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What Is Calendly?

Whether you’re a freelancer or small business owner scheduling consultations, a recruiter arranging interviews, or a team leader organizing group events, Calendly simplifies the process.

It’s especially useful when coordinating a shared calendar across multiple participants. 

The meeting scheduling process is intuitive. Calendly helps you set up a personalized booking page, syncing it with your calendar and automatically detecting your time zone. Once configured, you simply add your available time slots and are ready to share your link via email or text. 

Invitees can select the best time for themselves, and Calendly automatically confirms the meeting and adds it to everyone’s calendar. 

Calendly features

Here are some of Calendly’s most popular features:

Feature #1: Customizable event types

Calendly allows you to create different types of events to suit your needs. The free plan supports one-on-one meetings, and paid plans unlock additional features like group, collective, or round-robin meetings.

You can also manage the number of meetings booked daily and set gaps between sessions to prevent back-to-back meetings.

Feature #2: Automated notifications

Calendly sends a confirmation page to you and your invitee when they/you schedule a meeting. It also sends automated reminders via email or text before the meeting, helping reduce no-shows. 

You can tailor the reminders and send follow-up messages after the meeting for a personalized experience.

Feature #3: Time-saving routing forms

Calendly offers customizable routing forms, which, based on customers’ responses, direct them to the right type of meeting or the appropriate person, minimizing the need for manual intervention.

Feature #4: Robust security features

Calendly protects your data with enterprise-level security, including cloud hosting, firewalls, and encryption. It complies with various privacy regulations, ensuring your information stays secure.

Calendly pricing

• Free
• Standard: $12/seat per month 
• Teams: $20/seat per month
• Enterprise: Starts at $15,000/year

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Microsoft Bookings vs. Calendly: Features Compared

Let’s look at a detailed comparison between Calendly and Microsoft Bookings, focusing on key features, capabilities, and pricing:

Now that we know how the two stack up against each other, which tool should you pick for your needs? Depends on what matters most to you.

Feature #1: Ease of use

Microsoft Bookings integrates smoothly with Microsoft 365 products, offering a seamless experience for users who rely on Outlook for email and calendar management.

However, the setup can feel confusing and unintuitive for those outside the Microsoft ecosystem. Navigating the platform can also be tricky due to its heavy reliance on Microsoft-specific processes.

Calendly, in contrast, is known for its clean, modern interface and easy-to-follow setup process. Its intuitive design and customizable settings ensure a smooth user experience, even for those not deeply embedded in a specific ecosystem. 

Connecting multiple calendars across different platforms, such as Google, Microsoft, and Apple, gives Calendly an edge in flexibility.

Feature #2: Integration capabilities

Microsoft Bookings integrates seamlessly with Microsoft’s suite of tools, including Teams, Outlook, and OneDrive, which is ideal for businesses already using Microsoft 365.

However, its integration with third-party apps is more limited than that of other tools.

Calendly, meanwhile, offers over 100 integrations with other online meeting tools, such as Zoom, Google Calendar, and more, making it a versatile choice for businesses using tools beyond Microsoft 365.

Feature #3: Affordability

When it comes to pricing, Microsoft Bookings clearly stands out for its affordability. Starting at just $7.20 per user per month for the Microsoft 365 ecosystem, it offers excellent value, as you also gain access to the suite of apps like Teams, OneDrive, Outlook, Word, Excel, and PowerPoint. 

Calendly starts at $12 per seat per month for standard plans and $20 per seat per month for team plans. While this may be a larger investment for bigger teams, it offers great flexibility and ease of use.

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Microsoft Bookings vs. Calendly on Reddit

We turned to Reddit to see what people thought of the two products and their offerings, and opinions were pretty entrenched in both camps. 

For instance, a Reddit user wrote at length about their positive experience using Calendly: 

However, other Reddit users argued in favor of Microsoft Bookings, with another user about how the platform has helped them immensely:

While both tools had their advocates, everyone agreed that scheduling too many meetings—no matter your tool—was always terrible. 

But for those days when you absolutely can’t avoid scheduling one meeting after another, neither Microsoft Bookings nor Calendly might suit your purposes. But don’t fret—there’s a solution for that, too!

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Meet ClickUp—The Best Alternative to Microsoft Bookings vs. Calendly

When it comes to scheduling appointments, Microsoft Bookings and Calendly are popular choices. 

However, if you’re looking for a scheduling tool that does more than just manage appointments, ClickUp might be the best option. 

ClickUp is a project management tool that can also be used as task-scheduling software. It allows teams to manage tasks, deadlines, and appointments in one place.

Whether managing client meetings, coordinating with your team, or organizing your personal tasks, ClickUp offers a comprehensive solution that is better than Microsoft Bookings and Calendly.

Here are a few extra bonuses that make ClickUp stand out over the competition:

ClickUp’s One Up #1: Calendar View

ClickUp Calendar View allows seamless integration with tools like Google Calendar or Microsoft Outlook. It’s perfect for those looking for a versatile solution to manage tasks, deadlines, and appointments all in one place.

ClickUp Calendar View offers a range of features, including:

• Customizable views: Switch between daily, weekly, monthly, or custom views
• Task timelines: Easily manage and adjust project phases with task timelines
• Easy scheduling: Drag-and-drop scheduling for tasks directly in the calendar
• Public sharing: Share your calendar publicly for transparency and communication
• External calendar sync: Integrate with Google Calendar, Outlook, and other calendars
• Event reminders: Set customizable alerts to never miss important deadlines or meetings

The ClickUp Calendar View feature offers an all-in-one solution for project managers and teams looking to integrate their workflow with their schedules. This means that ClickUp provides an optimized experience that combines task management and calendar planning in a way that neither Microsoft Bookings nor Calendly does.

ClickUp’s One Up #2: ClickUp Meetings

With ClickUp Meetings, you can integrate meetings directly into your workflow with a flexible, cross-platform solution that integrates with various tools, including Google Calendar, Outlook, and even Microsoft Teams.

With ClickUp Meetings, you can:

• Take meeting notes with rich text editing
• Manage agendas using checklists for organization
• Set recurring meetings with automated scheduling
• Assign action items and tasks to team members
• Use slash commands for quick task creation
• Assign comments to team members for follow-up

ClickUp’s meeting feature even converts meeting discussions into tasks automatically. After a meeting, ClickUp creates linked tasks, making tracking progress and managing responsibilities easy without switching platforms.

ClickUp’s One Up #3: Time management

ClickUp’s Time Management tools help track, manage, and optimize your time effectively. You can set time estimates, monitor progress, and receive reminders for upcoming tasks.

Teams can benefit from workload forecasts and customizable alerts to manage deadlines and priorities efficiently.

ClickUp’s Time Management Feature is a big draw for individuals or teams looking to be more productive. Unlike Microsoft Bookings or Calendly, ClickUp integrates time management directly with project schedules and team assignments, helping you meet deadlines and complete tasks on time.

The ClickUp Calendar Planner Template 

Additionally, the ClickUp Calendar Planner Template is perfect for anyone looking to plan out their day easily. It’s fully customizable, whether you want to schedule meetings, set deadlines, or plan events.

Download This Template

With the template, you can:

• Track progress, visualize tasks, and set your calendar easily with different views
• Organize events effectively by setting custom statuses to keep stakeholders informed
• Track tasks and essential details with Custom Fields for maximum productivity
• Leverage tools like time tracking, tags, and dependency warnings to refine event tracking even further

The ability to create a personalized planner is a significant advantage. This feature allows you to create unique workflows specific to your projects. Unlike Microsoft Bookings or Calendly, with this template, ClickUp offers customization at a much deeper level, which makes it ideal for teams looking for tailored solutions.

ClickUp’s One Up #4: Scheduling with ClickUp + Calendly integration

With the Calendly + ClickUp integration, you can map data from Calendly into ClickUp tasks, automatically adding assignees to meetings. This integration ensures tasks are created and updated in ClickUp whenever new meetings are scheduled in Calendly, reducing manual work. 

By linking Calendly’s scheduling features with ClickUp’s powerful task management, businesses can create a seamless workflow where meetings, tasks, and team responsibilities are in sync.

This integration is a big win for teams seeking efficiency without jumping between different tools.

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Simplify Your Meetings with ClickUp

Scheduling apps have become more crucial today than ever. An ever-growing number of meetings clamoring for our attention means that tools like Microsoft Bookings and Calendly are essential.

Each platform has its advantages and disadvantages. Microsoft Bookings is ideal for teams heavily invested in Microsoft 365, offering seamless integration with Outlook, Teams, and other Microsoft tools.

Calendly stands out for its broad integration options and ease of use, making it a great fit for teams using diverse tools. 

However, if you want more than appointment scheduling software, ClickUp is up to the challenge. It combines powerful project management, task tracking, and team collaboration features with automated workflows and AI-driven task management. 

ClickUp can be the go-to daily planner app that allows you to manage your calendar, meetings, and entire project pipeline in one platform.

Get started with ClickUp today and transform how you manage your meetings, projects, and teams!

Everything you need to stay organized and get work done.

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