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.
| Feature | Calendly | Microsoft Bookings | Impact |
|---|---|---|---|
| Calendar invites | Automatic calendar invites sent to both parties. | Confirmation email with attached .ics file only. | Reduced risk of missed meetings and confusion for clients. |
| SMS reminders | Built-in, native SMS support (AU included). | Limited to US/Canada (AU requires an additional integration or manual workaround). | Fewer no‑shows and last‑minute cancellations. |
| Round robin for teams | Fully supported, auto‑assigns by availability and can be tailored to your priorities. | Not supported. | Makes it easier to share workload across advisers, improving booking efficiency. |
| Website integration | Clean, modern, and customisable embeds. | Less polished, clunky user experience. | A smoother, branded booking experience that leaves a better first impression. |
| Login experience | No user account required, simple to book. | Clunky; may force login if a Microsoft account is detected. | Clients can book faster and with less frustration, especially when using personal emails. |
| Client usability | Intuitive, mobile‑friendly interface. | Functional but more complex for non‑tech users. | More bookings completed without manual assistance from your team. |
| Brand control | Cleaner design, better impression for clients. | More generic, harder to customise. | Presents a professional, consistent brand experience from the first interaction. |
| Pricing | Free or ~$16/month for Teams plan. | Included with Microsoft 365. | Calendly offers stronger ROI when considering saved admin time and improved client experience. |
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.
Calendly FAQs
An .ics file is a calendar data file in a standardised format that most calendar applications can read. When Microsoft Bookings sends a booking confirmation, it attaches an .ics file to the email. The client then has to open the attachment and confirm they want to add the event to their calendar, which is an extra manual step. Many clients, particularly those who are not especially tech-comfortable or who are reading emails on their phone, will skip this step and simply assume the appointment is saved. It is not.
A proper calendar invite, which is what Calendly sends, bypasses this entirely. The event lands directly in the recipient’s calendar without any action on their part, in the same way a meeting invite from a colleague would. For advice firms where missed or confused appointments carry a real cost in adviser time and client experience, this distinction is more consequential than it might appear.
Round-robin scheduling is a method of automatically distributing incoming bookings among multiple team members based on their availability. Rather than a client choosing a specific adviser, they simply pick a time that suits them, and Calendly assigns the booking to whichever team member is available at that time. In Calendly, you set this up by creating a “Round Robin” event type under a team.
You add the relevant team members, sync their calendars, and configure any weighting to ensure certain advisers receive a higher proportion of bookings. For example, a senior adviser might be set to receive 30 per cent of initial enquiry calls while two associate advisers share the remaining 70 per cent. Calendly checks each person’s live calendar availability before offering time slots, so double-bookings are avoided automatically. This is particularly useful for initial discovery calls where any qualified team member can handle the first conversation, freeing up the firm’s senior advisers for later-stage meetings.
This is a question worth asking before you embed any third-party booking tool on your website. Calendly is a US-based company, which means client data collected through the platform is processed and stored on servers outside Australia. Under the Australian Privacy Principles, if your firm transfers personal information to an overseas recipient, you are generally required to take reasonable steps to ensure the recipient handles that information in a way that is consistent with the APPs. In practice, this means reviewing Calendly’s data processing agreements and privacy policy to understand where data is stored, how long it is retained, and what security standards apply.
Calendly does offer a Data Processing Agreement for business users, which is particularly relevant if your firm is subject to stricter data handling requirements, such as those that apply when working with government employees or other regulated client segments. You should also ensure your own privacy policy discloses that booking data is handled by a third-party platform. The OAIC publishes guidance on overseas disclosures at oaic.gov.au. This article does not constitute legal or compliance advice, and you should seek your own guidance on your specific obligations.
Yes, Calendly lets you add custom questions to the booking form that clients complete before confirming their appointment. On paid plans, you can add multiple question types, including short text, long text, single select, and multiple choice. This is useful for advice firms that want to capture basic qualifying information before an initial meeting, such as what the client hopes to achieve, whether they were referred by someone, and their approximate life stage. The practical limit is not a technical one but a behavioural one.
The more questions you ask, the higher the drop-off rate before a booking is completed. For an initial discovery call where trust is still being established, two to four short questions is generally the upper limit before friction starts to cost you bookings. Keep questions simple and frame them as being in the client’s interest, for example, “So we can make the most of our time together”, rather than “We need this information before proceeding.” Reserve detailed fact-find questions for a separate form sent after the booking is confirmed.
That being said, while you can add questions and triage within Calendly, the experience often presents more smoothly when the questions are integrated directly into your website, with the relevant Calendly booking displaying conditionally.
Calendly draws its availability directly from your connected calendar, typically Outlook or Google Calendar. Any time marked as busy on your calendar will not appear as available in Calendly, so the most reliable way to block time is to create calendar events for the periods you do not want booked. If you want to protect Friday afternoons for file work or planning, add a recurring “Focus time” or “Unavailable” event to your Outlook calendar covering those hours each week. Calendly will treat that time as blocked.
You can also configure working hours directly within Calendly under each event type’s availability settings, which allows you to set different availability windows for different meeting types. For example, your initial discovery calls might only be available on Tuesday and Thursday mornings, while your client review meetings are available across a broader range of times. This gives you meaningful control over your diary without requiring manual management each week.
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