Forum Discussion
Calendars of multiple accounts in Outlook scheduling assistant possible?
Basically you need to use one of the methods here to configure calendar sharing between the two orgs: https://technet.microsoft.com/en-us/library/jj916670(v=exchg.150).aspx
Then just add both his accounts as participants, and you should be able to see availability.
1) Generally speaking yes, but it depends on what exactly you mean by "both companies" - if those are two different tenants, some admin configuration is needed
2) Yes, as long as they add both his accounts to the request (they can remove the "unneeded" one later)
VasilMichev, thank you for your answer.
1. Yes, two accounts on two different tenants. Could you point me to more info on changing those settings?
2. Fair enough you'd have to add both accounts for them to appear in the scheduling assistant. I fear this will be confusing for some as not all employees are very digi-literate, and not everybody is aware of who has second accounts.