Appointments - Do you automate scheduling of meetings?

Last updated by Tom Bui [SSW] 4 months ago.See history

We've all been part of that email chain... "Let's meet to discuss this", "When are you free?", "I can do Friday", "Friday's no good, what about Monday?", "I'm free in the morning", "Penny can't make that, how about Tuesday afternoon after 3?", etc.

AI can make scheduling meetings with multiple attendees much easier.

Note: The following solutions work best when you're dealing with people in your own organization, as they then have access to all calendar data, but with a bit of back and forth, they can still work for externals too. There are some options.

Scheduling Poll in Microsoft Outlook 365

You can do complex scheduling tasks and calendar polls with this built-in Outlook 365 feature.

Video: How to use Scheduling Poll in Microsoft Outlook 365 📆 (3 min)

schedule poll screenshot
Figure: Voting options on Scheduling Poll

Microsoft Cortana Scheduler (formerly known as

Sexy face
Figure: Microsoft Cortana Scheduler

This option is best if you're ok to meet any time that your calendar says is free.

Note: The helpful tool Scheduler has a portal too at

Instructions to use Cortana

Step 1 - Register

Register yourself at Meet Scheduler before you can use this feature.

Step 2 - Send an email

Open an email... not an appointment!

Figure: after your message, add some request to Cortana as you would a PA

Cortana then handles all the back-and-forth emails to find a time when everyone can meet and then she sends out an invite on your behalf.

Figure: Cortana will find a time that suits everyone and send the appointment

More help for Cortana:

  1. FAQ on
  2. Watch the video here

Step 3 - Add Cortana as a contact

To make it easier to add Cortana to your emails, create a Contact.

Figure: Cortana added as a contact

✅ Works great on mobile:

cortana scheduler mobile
Figure: Microsoft Scheduler – Fully works on mobile phone


This option is best if you want to be selective about a few options for when to meet, and send a poll to attendees to choose.

FindTime shows what days and times work the best for you and the attendees when available using free/busy data.

Propose your selected times to all attendees and allow everyone to vote and quickly come to a consensus... and you’re done!

FindTime sends out the meeting invite on your behalf. More on

Note: Findtime’s competitor is

findtime scheduler
Figure: FindTime gives a nice UI for people working in the same org, as you can see times that might be available for all attendees easily (e.g. 8 am above)

Mobile – does not work ❌ As of Dec 2020, FindTime does not work on iOS.

findtime mobile
Figure: FindTime - No mobile support for iOS

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