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I have a meeting that needs to be attended by 10 individuals. Each of these individuals is either a manager, director, or member of executive leadership. There is very little overlapping availability, so I pick the time slot with the most availability.

Inevitably I hear from user A and B that they cannot attend so I schedule for the next most available time, and hear from user C and D that they cannot attend.

I then reach out to each individual person and confirm their availability, and which meetings they can punt if they absolutely need to. Then create a matrix that at the end of all of this absurdity reveals the most likely time that everyone might meet.

Is there a tool or plugin or methodology that attempts to solve this perhaps within Outlook?

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    I’m voting to close this question because tool requests are out of scope
    – MCW
    Commented Feb 16, 2021 at 17:33

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If the executives have assistants, get in touch with them and make a telephone conference with them. Very often they know what meetings in the calender can be cancelled for your meeting. Once you have a meeting slot with the most senior managers the others will follow... not always, but it's a possible solution. Good luck!

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The real-world reality of this situation is that you might simply have to have "more than one meeting." Everyone is busy, each in their own way, and schedules don't coincide. "Plan accordingly."

Carefully document exactly what was said in each meeting – quite literally, "appoint a scribe," and "keep minutes" – then distribute it both to the attendees of the present meeting and those who will attend the next one. Be certain that everyone knows the entire list of "interested parties," and their appropriate contact-persons.

If any "out-of-band contact" occurs, e.g. through privately-sent emails, be sure to stress the importance of the idea that "the scribe" should always be cc'd on everything, so that an ongoing record can be made of it. Such contacts are normal and are to be expected, but they need to be captured "for the record."

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A lot of calendar systems have "first available" for all resources functionality. My firm uses Outlook and it has this functionality.

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  • Thank you for that recommendation. I just tried that. The auto-generated Outlook selection put the meeting that needs to take place tomorrow for early March. I think there still needs to be a manual intervention step on the behalf of the meeting attendee. I've used Calendly in the past for private engagements, but I'm really looking for the attendees hashing out when they're going to meet, not a project manager spending an entire morning coordinating schedules.
    – Mark Saluta
    Commented Feb 16, 2021 at 17:22
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    Yes, it solves the problem for first availability. Manually, you just have to hunt but you'll like end up with the same selection. The only other solution is for the sponsor to mandate the meeting and tell them to reschedule their conflicts.
    – David Espina
    Commented Feb 16, 2021 at 17:54

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