it's only a email, not going to be published anywhere

they will understand it's meaning

just all those "to" seemed strange

Yes, too many.

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@polksaladallie wrote:

Tell us what Brad's problem is.  Lots of experts here.  

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brad's biggest problem is that he doesn't listen.

and the other problem is with a custom built software program. s i be thinking the "experts" here won't be able to help

Hi the way to put it is

Who does Brad need to talk to, to solve the problem. 

No 'toos'

No 'to whoms'   too outdated. 

Or as Message 13 says -    talk with.

Both are fine. 

Would love to know more about Brad   

To whom does Brad need to talk to solve a problem.

Correct grammar is never outdated.

With whom does Brad need to speak to solve the problem?

To whom should Brad speak in order to solve the problem?

Oh, FGS.

Just get Brad to come to this thread and we'll help him to solve his problem.