Any business operating in today’s world needs a scheduling tool.
Automated scheduling improves your productivity and time management and gives customers a better experience when dealing with your business.
Like any industry, though, there are a bunch to choose from. Today, we’ll zoom in on two popular options: Calendly and Microsoft (MS) Bookings.
Whether you're a professional looking for a no-frills scheduling app or a business needing a robust booking system, we’ll walk through everything you need to know to pick the best solution for your team.
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Calendly |
MS Bookings |
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Best for |
Businesses and individuals needing a versatile scheduling tool that integrates with apps outside the Microsoft ecosystem. |
Businesses and individuals looking for a scheduling solution that deeply integrates with Microsoft’s apps. |
| Free trial available | ✅ | ✅ |
| Free plan | ✅ | ❌ |
| Pricing | Starting at $10/month/user (when billed annually) | Starting at $6/month/user (when billed annually) |
Calendly is a user-centric scheduling tool that makes booking super easy. Its user-friendly interface and various advanced features have made it a top choice for professionals and businesses.
Calendly's not-so-secret recipe is its personalized booking link. Users can share it with invitees, who can view availability and select a time slot that works for them. The seamless integration with popular calendars, including Office 365, Outlook, and Google Calendar doesn’t hurt either, ensuring your booking link is always up-to-date.
Calendly key features include:
Goh X., a small business manager, explains the pros and cons of using Calendly:
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“Pros: I like how it completely automates the booking part so I don't have to go back and forth with clients just to nail down an appointment date and time. Also, it is a good filter to find out which prospects are serious about the project and which ones aren't. Cons: Sometimes because it's too easy to book an appointment via Calendly, people don't show up. So now I didn't integrate it into the website directly. Instead, I send the Calendly link to them manually (after they opt-in with their phone number) so they are aware of all my available time slots and can make a decision accordingly.” |
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4.7/5 (2,400+ reviews) |
4.7/5 (4,000+ reviews) |
9.1/10 (600+ reviews) |
Curious how Calendly compares to other popular booking platforms? We’ve got the details: |
MS Bookings delivers functions well beyond scheduling. MS Bookings offers a seamless experience for those using the suite—integrated into every part of the Microsoft ecosystem.
Bookings is your all-in-one scheduling solution, letting you create events, set reminders, and invite attendees, all within the familiar Microsoft environment. Advanced integration with other Microsoft tools, such as MSTeams, brings your scheduling to the next level.
MS Bookings key features include:
Rosie H., CEO of a marketing and advertising company, delves into the benefits and drawbacks of Microsoft’s scheduling solution:
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“Pros: The convenience of being able to sync calendars, create recurring appointments and send and get confirmation through the booking systems connection to our Outlook makes Microsoft Booking a highly effective and very necessary part of our tools and systems. Clients can confirm within the email and we get that confirmation as well as regular reminders on the appointed day. Fewer missed appointments by our clients because they also get SMS reminders making it really convenient for us. I also like that it integrates with Zoom and Teams to have additional functionality to what appears to be a "simple" scheduler Cons: I don't like that getting paid for appointments is still not as simple as some of their competitors who have their standalone booking systems that also allow for payment within their software.” |
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3.8/5 (30+ reviews) |
4.4/5 (150+ reviews) |
8.6/10 (500+ reviews) |
If you’re looking for a scheduling app that’s user-friendly and versatile, and integrates with many different tools, Calendly will be your best bet.
Calendly’s advanced features and flexibility will let you smoothly manage different kinds of meetings, regardless of your business type. Additionally, its ability to sync with over 150 diverse tools lets Calendly plug into your existing workflow easily.
If you faithfully use apps in the Microsoft ecosystem, MS Bookings might be the tool for you. It’s a scheduling solution that’ll streamline your booking process and intuitively connect with other Microsoft tools.
As it’s included in a Microsoft 365 Business subscription (not available to those on individual plans) along with apps like Word, Excel, and Outlook, Bookings will also be a good choice for individuals and businesses looking for solutions outside of only scheduling.
Calendly offers a user-friendly experience. Potential clients just click on the appointment link, select the desired meeting/event type and time, and provide their contact details. Once they’ve booked a slot, they’ll get a confirmation email.
Calendly can support communication with any number of invitees (and different time zones) and gives the option for individual or group bookings. Its mobile functionality also guarantees compatibility across devices.
Designed for Microsoft 365 users, Bookings provides a simple scheduling process. Invitees can choose from available time slots and book appointments with precision and confidence. Multiple staff members can use this system, while clients and colleagues can access other team members’ schedules.
Compared to Calendly, MS Bookings will likely be a bit more complicated and time-consuming to set up, but the platform still offers an intuitive design and handy booking options. However, you might find that MS Bookings has fewer integrations compared to Calendly, which can be a pain for some users.
The two online schedulers share a few features typically found in the top scheduling apps, including:
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✨ Looking for smarter scheduling? Explore 16 new YouCanBookMe features requested by business owners just like you! |
Calendly offers quite a few features that MS Bookings lacks, including:
As it’s a standalone app, you only get access to a booking tool when you opt for Calendly. If you’re looking for a package deal with other apps, MS Bookings comes as part of a more extensive suite of Microsoft tools, so if you work within the Microsoft sphere, MS Bookings is the better choice.
MS Bookings is a simple scheduling tool that shines because it's part of the broader suite of Microsoft apps. However, when it comes to scheduling features alone, it doesn't bring anything to the table that Calendly doesn't already offer.
Aside from the somewhat limited scheduling features, MS Bookings’ main drawback lies in its inability to connect with apps outside the Microsoft suite. This can make it an inconvenient tool to work with if you aren’t an avid Microsoft user.
In the battle of integrations, Calendly comes out on top with over 150 tools in its scheduling arsenal, while Bookings only integrates with apps within the Microsoft suite.
Here are a few of Calendly’s standout integrations:
MS Bookings’ only native integrations are the apps available in Microsoft 365, including:
Although Calendly also integrates with a few of those apps, Bookings offers a deeper sync with the tools.
For example, while Calendly integrates with Microsoft Teams, the capabilities are limited to automatically generating unique Teams video conference links, while MS Booking has a more nuanced integration. You can add MS Bookings directly to MS Teams, allowing you to book and edit meetings without leaving the conferencing app.
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💡 Pro tip: If you want to connect MS Bookings to a select few apps outside of the Microsoft Suite (such as Zoom or Stripe), it’s possible but a tad complex. The integration will run via the Bookings Connector in Power Automate, and you’ll need to create triggers based on different appointments manually. If you just want an automated, uncomplicated connection to third-party apps, Calendly will be the better choice. |
Calendly’s plans (billed annually) include:
Calendly offers a 14-day free trial of its Teams plan.
Unlike Calendly, MS Bookings isn’t a standalone tool—it’s only one of many apps included in a Microsoft 365 subscription. Therefore, choosing between the following plans won’t be based on the scheduling features you’re looking for, but rather on the Microsoft capabilities at your disposal.
The plans (billed annually) include:
Although Microsoft doesn’t offer a free plan, you can opt for a one-month trial of the plan of your choosing.
Need more perspective on both scheduling tools? It’s time to turn to real-life users who can offer deeper insights into the pros and cons of Calendly and Microsoft Bookings.
What do you like best about Calendly?
No more back and forth with customers. It always felt like I was berating them just to get the meeting set up. Now I can focus on the agenda and what is important content for that meeting!
What do you dislike about Calendly?
There are not many downsides. I don't like that I get 2 emails in reply to new appts getting set. Clogs my inbox. Also, I would like for the name and emails to be visible in the invite when I have multiple spots available in a session.
With Calendly's group scheduling feature, several users can reserve timeslots at once. By setting buffer times between meetings, users of the platform can allocate time for preparation or breaks. Calendly makes it simple for participants to reschedule meetings, preserving flexibility for all involved.
What do you dislike about Calendly?
More comprehensive analysis of scheduling patterns and participant behaviour would be helpful. Only the premium plans offer more sophisticated branding and customization options.
What do you like best about Microsoft Bookings?
I love that Microsoft Bookings makes it easy for me to set up interviews, appointments, and meetings with minimal effort on my part. I like that bookings show up directly in my calendar after they’re created.
What do you dislike about Microsoft Bookings?
The one thing I dislike about Bookings is the fact that you can't set multiple weeks at a time. For example, my availability changes every week. I don't always work the same days or times. When I set up a booking option for an interview with me, I need to create an option for each week which can occasionally be confusing for my interviewees when they attempt to book with me.
What do you like best about Microsoft Bookings?
I love how easy it was to setup! It is one of the main reasons we switched over to Microsoft! Bookings allowed us to maximize our license and move to Microsoft from Calendly.
What do you dislike about Microsoft Bookings?
It would be nice to receive a notification when someone cancels a meeting, or be notified in the calendar when they cancel. Right now the only way we are aware of for clients to cancel a meeting is to go into the invite and cancel on the web page.
👉 Calendly is the go-to solution for professionals and businesses seeking a UX-enhanced, dedicated scheduling tool. Its advanced features, user-friendly interface, and flexibility in handling various meeting types make it a great choice. It’ll also be a better option if you use tools that aren’t part of the Microsoft suite, as Calendly offers integrations with over 150 different work apps.
👉 MS Bookings instead offers a broader set of functions within the Microsoft ecosystem. It's perfect for individuals and businesses deeply rooted in the Microsoft universe. It’s a feasible option with seamless MS integration and comprehensive scheduling capabilities. If you’re already paying for a Microsoft 365 subscription, give MS Bookings a shot to see if it fits your business well.
Ultimately, your choice between Calendly and Microsoft Bookings should align with your unique scheduling requirements. Whether you prefer the simplicity of Calendly or the comprehensive MS integration of Bookings, your schedules will become easier to create, edit, and manage. Both tools aim to simplify scheduling, freeing up your time to make the most of other business needs.
If neither Calendly nor Microsoft Bookings quite fits your scheduling needs, YouCanBookMe (YCBM) provides a more flexible middle ground. It’s built for individuals and teams who want greater control over customization and booking workflows without being tied to a single software ecosystem.
Where Calendly focuses on speed and simplicity, and Microsoft Bookings prioritizes deep Microsoft 365 integration, YouCanBookMe is built for small businesses and professionals who care about first impressions and flexibility just as much as efficiency. Here are the key features that put YouCanBookMe above other scheduling tools on the market:
"YouCanBookMe is an amazing tool for businesses, every type of business... From somebody that's a freelancer, because I know you have this amazing integration where you can actually take payments, up to really large businesses where they need more value and more flexibility and more in-depth features or integrations."
– Georgie Ionescu, Passion.io
YouCanBookMe's superiority is not a singular trait but a triad of features that redefine the scheduling landscape. From its powerful notifications workflow to personalized availability views and unique booking controls, YCBM offers an unmatched scheduling experience.
Elevate your booking process, try YouCanBookMe today, and embrace the difference in scheduling efficiency.