How to coordinate meetings across different calendar systems and time zones efficiently?

I’m part of an organization ... our members use a mix of Outlook, Google Calendar, and sometimes nothing at all. Some just keep track of things manually or confirm availability one-off over chat or text.

That is your first source of problems. Even though you are only one organization, you have too many meetings management systems - if any!

The first step of the solution: Decide on exactly one tool for meetings management - and enforce the use of that tool for everyone. Make sure that the tool can automatically handle different users in different time zones - including day-light saving, if applicable.

NOTE: It is OK to use several tools ONLY if they ALL meet the minimum requirements (stated above) and ONLY IF they can operate simultaneously on the same database. Example: It is possible to access the same calendar database both with Outlook and Thunderbird.

The second step of the solution: Agree with the people that occasionally, some sacrifices need to be made. Also, make sure that the rules do not change every week. Also, try to stick with recurring meetings which do not change their start / end times - otherwise you invite chaos.

Several years ago my team had to join meetings with a remote team - the time-zone difference was 9-10 hours (if I remember correctly). It meant that it was not possible to organize meetings inside everybody's work time.

So the solution was simple: our team left the office one hour late (our afternoon), while our counterparts joined their office one hour early (their morning). It was recurrent, one time per week. Everyone knew and accepted the rule, life went on. There was realistically no other reasonable compromise.

Even when a time works for most people, it’s hard to see the full picture: who has too much on their plate and which time slots make sense for the whole team.

And that is the job of a proper scheduling / calendaring tool. Find one that suits all the needs (see above) and then prove by experience that that tool is better than the others - and gradually, everyone will probably switch to it.

However, my instinct tells me that this "organization" also has a people problem - where the said people prefer to not join meetings, and therefore finding excuses, tricks etc. I would not be surprised if some of those people were actually higher-level managers - and that is why nobody can actually dictate any improvement. I hope I am wrong.

Hire an Administrative Assistant

The amount of workload you are describing sounds like it is at the level it could be a full time job, which turns out there are people who do that, namely administrative assistants (or admins for short). These people can do an amazing job when given the right tools and authority and can greatly improve everyone's efficiency by allowing everyone else to focus on their actual work.

Requirements and Needs

For this to work, there are some requirements or expectations that everyone else would need to agree to do:

• The admin would need read access to people's calendars.
• People would be required to keep their work calendar up to date.
• Admin would have authority to move meetings and supersede meetings with ones that leadership deems more important.
• A nice to have is allowing the admin write access to people's calendars.

Handling Different Calendars

Admin are expected to work with external calendars all the time (particularly customers) so they should be able to handle there being a chaotic mix of Outlook, Google Calendars, etc. They should also be able to manage the time zone differences and make sure people know the correct time for a meeting relative to their local time.

How Admins Work

I have seen admins work in various kinds of ways. One way I have seen is if you wanted to schedule a meeting outside your team you send the request to the admin with the length, who needs to attend, the importance or time sensitivity for the meeting, and the agenda. The admin would then coordinate and talk to the various people, check their calendars, move existing lower priority meetings around, and then send out the meeting invite on behalf of the organizer once things have been settled. The admin handles all the headaches while the person requesting it can get back to what they were trying to work on.

Other Responsibilities

Admins do more than just organizing calendars, so it is worth looking up their job description and seeing if any other responsibilities could be delegated to them too thus freeing up others to focus on delivering value to the company.

Establish a recurring time and frequency that everyone agrees to commit to, knowing that this is part of their job responsibilities. It may be at an inconvenient time for some of the participants. It may be at an inconvenient time for all of the participants. Find the best compromise you can. I have been in meetings that required some people to wake up early and others to stay after work in order to I'll be available at the same time. It can be done, if there is a genuine need for it to be done. Obviously, don't put anybody on the meeting who does not genuinely have to be there, to reduce the number of possible conflicts. And keep the meeting short, and focused on the things that genuinely require everyone be present at the same time. Progress reports belong in shared documents or email or slack or similar, not in the meeting; use the meeting strictly to resolve things that cannot be handled quickly enough in other ways.

Then hold to that schedule. People will occasionally have to miss a meeting, and that's okay. If people miss the meeting frequently, have their managers replace them with someone who won't. If their managers don't do so, assume their managers are not interested in the topic either.

First you make a list of convenient meeting times for everyone. Make sure people with extra flexibility get bonus points. For example someone who can leave Work two hours early to have a meeting at 8pm at home.

Then you schedule your meetings. If this is difficult because someone wants meetings at 8am which is 4am for someone else, thats just tough. You tell them to be there at the scheduled time; if they can’t you talk to their manager. Meetings are work, not for your convenience.

If you spend hours scheduling than you made the mistake of spoiling your coworkers. Make clear that rejecting a time will need a very, very good reason and that you will check.

Apps exist that do this

Calendly is a common one, it connects to Outlook, Exchange, and Google. People who want something else need to connect their oddball email to Google. At some point, someone has to take charge and set a standard. On a project, the Steering Committee sets a standard and members are expected to conform. Stop herding cats, give people a couple of choices, and then use an app to connect those choices.

https://calendly.com/ There are other choices.