I use different email accounts to manage my business vs. family and friends vs. other "buckets" in my life. Many of my clients do the same.
For those of us who use Gmail, the "sticky wicket" is when we are in a hurry and just let Gmail auto-complete the "To" address from the top of its preview list.
Is there a way to get a prompt or some kind of reminder when there is more than one address to choose among for a specific person?
Notes
I assume this is a Gmail function, but maybe it's tied to the browser or the operating system? (I'm using Chrome and Windows 10).
My interest is in the "To" fields for email addresses; i.e., To, CC, and BCC (not the Subject or email message fields).
Best Answer
It seems to me Gmail already offers a "Which address?" prompt because as long as there is ambiguity it will show the options:
Indicating what it would default to (with shading) seems helpful as that is the one that would autocomplete (with Enter). Given that you have presumably chosen not to autoreply (because that would go to the 'wrong' address) the pop up showing the choice would be sufficient warning for me, as a rare sight. If the automatically chosen selection is not correct, just click on an/the other.