1. Open Regedit
2. HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Identity
Create REG_DWORD named: EnableADAL set as 0
Under the same registry key, create a DWORD value named DisableADALatopWAMOverride and set it to 1
Links:
https://techcommunity.microsoft.com/t5/outlook/outlook-password-prompt-disappears-quickly/m-p/793317
If this doesn't work, go to Windows > Settings > Accounts --> Access work or School (list on left side) to delete this account, then restart your Outlook, it will pop up the prompt for Password, enter your password and to see the result.(if Outlook is going to ask you if you want to join it to your Windows account in the process. Please skip for now.