Calendly or Microsoft Booking: Which should your advice firm use?

Since you’re likely already committed to Microsoft 365, it’s natural to consider Microsoft Bookings for your client scheduling rather than Calendly. Microsoft Bookings is included in your subscription, integrates with your Microsoft environment, and might feel like the “default” option.

But for most advice businesses, our answer is clear: Calendly offers a smoother, more reliable experience, saving your team time and enhancing client experience.

In this article, we explain why Calendly is generally the better fit for financial advisers, and highlight the few exceptions where Microsoft Bookings might make sense.

Quick comparison

Here’s a side-by-side summary of how Calendly and Microsoft Bookings compare on the factors that matter most to advice practices.

In the next section, we break down these key components.

Why Calendly wins for most advice businesses

Calendly is largely considered the best in its class. Compared to Microsoft Bookings specifically, it provides a much more polished experience that’s easier for clients and advisers alike.

Here’s where it stands out:

1. Seamless calendar integration

Calendly automatically sends both you and your client a proper calendar invite. It appears directly in both calendars, no extra steps required.

Microsoft Bookings, on the other hand, sends a confirmation email with an .ics file attached. The client must download and open the file to add the appointment to their calendar. Many won’t, and that increases the risk of confusion, missed meetings, or frustrating no-shows. This can be especially frustrating for busy clients who assume an invite has already landed in their calendar when it hasn’t.

2. Built-in SMS reminders

Reducing no-shows matters, especially for businesses that rely on booked consults or review meetings.

Calendly includes native SMS reminders for clients, helping ensure they show up on time. Microsoft Bookings only supports SMS functionality in the US and Canada – if you’re in Australia, you’d need to connect a separate SMS provider such as Twilio and build a workaround. That adds friction and risk.

3. Round robin scheduling for teams

Have multiple advisers or team members available for certain meeting types? Calendly allows you to set up round robin scheduling so meetings are auto-assigned based on availability, and can even be weighted based on adviser priority for that meeting type.

Microsoft Bookings doesn’t currently support this. If you’ve ever wished a client could “just pick a time with whoever’s free,” this feature alone may justify Calendly’s price.

4. Better website embeds

Calendly’s embed options are more customisable and generally look better on your website. The interface feels native, smooth, and modern.

Microsoft Bookings can feel clunky or disconnected from your brand, and the user experience is more dated, something that can impact a client’s impression from the very start.

5. More intuitive for clients

Calendly is designed to be simple. Whether your clients are tech-savvy or not, most people find it easy to use, even the first time.

Microsoft Bookings, while functional, can confuse users with its less streamlined interface. If your clients aren’t particularly comfortable with digital tools, this becomes a real barrier.

When Microsoft Bookings might make sense

That said, there are a few situations where Microsoft Bookings may still be suitable:

You work with highly security-conscious clients, such as government employees or IT professionals, who prefer staying within the Microsoft ecosystem.

You need a zero-cost solution and aren’t ready to pay for a tool like Calendly.

You’re only handling internal bookings, and don’t rely on external client scheduling.

Even in these cases, you’ll need to weigh the trade-offs in client experience, flexibility, and supportability.

Is Calendly worth the cost?

Calendly’s paid Teams plan costs about $16 USD per user, per month, a cost we believe is justified for most advice businesses.

We use it ourselves, even though our team is technically proficient and fully invested in Microsoft 365. The difference in usability, especially from a client’s perspective, is hard to overstate.

If cost is a concern and you’re a single practice adviser, Calendly’s free package supports a standard initial chat, though Calendly branding will be visible.

This is a classic case of what we call “Best in Class versus Best in Microsoft”. The Calendly team specialise in this space exclusively, making scheduling easy their sole focus, and you can see the results.

When weighing up the costs, at this price point, considering the cost (let alone opportunity cost) of time when this process isn’t as smooth as possible can quickly tip the scales in Calendly’s favour.

Even without considering the user experience, with Calendly you’re likely to see:

• Fewer clients just calling because they couldn’t be bothered,
• Fewer calling because something went wrong,
• Fewer missed appointments, or
• More opportunities to use your scheduling tool due to its multi-adviser (aka Round Robin) functionality.

It probably doesn’t take more than one of these every couple of months for Calendly to make sense on costs alone.

Need help making it work?

If you’re unsure how to integrate Calendly into your existing workflow, or want to get more out of it, we’ve got a detailed guide to help you in our blog here.

It covers how to sync Calendly with your Outlook calendar, manage appointment types, avoid double-bookings, and more.

Final thoughts

For most financial advisers, Calendly just works better. It reduces friction, enhances your brand presentation, and helps ensure clients show up on time. Even if Microsoft Bookings is “included,” it may cost you more in lost time and missed opportunities.

Still, the right tool is the one that fits your business. If you’re committed to using Microsoft Bookings, we’ll support you in getting the most out of it. But if you’re open to a switch, or still weighing your options, Calendly is well worth a closer look.