This frequent request comes from users looking for a way to send out meeting requests for training sessions or benefits meetings with HR, where each employee can pick the session that fits their schedule.

I was wondering if anybody can tell me whether or not this is possible, and if it is, how would I do so? We are going to have about six different meetings scheduled soon. We therefore need to send an invitation out to a group of people for those meetings. However, each of them only needs to select one of the six meetings. Is there any way to send a calendar invite that will allow them to choose one of the six meetings and thereby automatically update the sender's calendar AND the responders calendar?

Unfortunately Outlook doesn't have the capability for creating this type of meeting request, but you can do nearly the same thing by creating the meetings in the calendar, then send the invitees a message with each of the meetings attached and instructions to choose the meeting they want to attend.

Create the Request in Outlook 2013 and newer

These are the steps to create the meeting request in Outlook 2013 and newer.

1. Create the invitations and invite required attendees, resources or yourself. The recipients will see original invitees. If you don't want them to see some invitees, add those recipients after you send it (either Forward each meeting individually or update the meeting before anyone accepts).
2. Click Send. This step is important since you need a meeting request that was sent, so the responses can be tracked.
3. Use Ctrl+click to select each meeting item on your calendar.
4. Right-click and choose Forward.
   
5. In your message, tell the recipient to click Copy to Calendar to display a dialog to accept or copy to calendar, if they do not see Accept buttons.
   
6. The recipient may see Copy to Calendar button. Clicking it will give them the option to Accept. They will also see who was invited initially and if they accepted before the meeting was forwarded.
   
7. When the recipients accept the meeting request, they'll send a response and the meeting is added to their calendar. At this point, it will look and act like a "normal" meeting they were invited to.
   
8. The organizer's meeting will update with the recipient's name as an optional attendee.
   

Create the Request in Outlook 2010 and older

The steps are Create the meeting request in older versions of Outlook:

1. Create the invitations and invite required attendees, resources or yourself.
2. Click Send. This step is important since you need a meeting request that was sent, so the responses can be tracked.
3. Open each item on your calendar select File, Save as.
4. Save each item as an ICS on the hard drive.
5. Create the email message and attach the ICS files.
6. When the recipients accept the meeting request, they'll send a response and the meeting is added to their calendar.
7. The sender's copy will update with the recipient's name as an optional attendee.

To avoid confusion, use the meeting date in the subject so the recipient only has to open the meeting they plan to attend.

Save a step in Outlook 2010 and older: create all of the meeting invitations then select the meetings using Ctrl+Click. Use Actions, Forward as iCalendar to send. Don't right click and Forward, do not use Ctrl+F or Forward on the Actions menu.

Pick-A-Meeting Request Video Tutorial

This tutorial shows you how to send multiple meeting requests to someone so they can pick which meeting they will attend. The organizer's calendar will show who has accepted for each meeting. This video uses the long method, where the meetings are saved as icalendar files (*.ics).