This is a good question. My answer: As many times as it takes to produce the result you want produced.
Communication is a very complex phenomenon. However, we rarely think about it that way. What’s more common is to think, I spoke, he/she/they heard. That’s it. Communication complete.
That’s insufficient for effective communication.
Consider we each come to every communication with a file cabinet filled with our past experiences. This file cabinet is our reference point for everything, how things should be, how things shouldn’t be, what things mean, etc. And the biggest barrier to effective communication is that we all think that we have the same things in our file cabinets.
In fact, no two people have the same stuff in their file cabinets because we all have different past experiences, and more importantly, we all have interpreted those past experiences through our own unique point of view.
What does that mean? Here is an example:
Mom: Kids, I want you to clean the garage today
Kids: Ok, mom, we will. (Hey, they are good kids, what can I say)
Mom goes off to work and the kids go outside to clean the garage.
Mom returns home from work to find the outside of the garage sparkling clean but the inside still a mess.
The mom in this scenario thinks she was clear because she knew what she meant and ASSUMED the kids knew what she meant. This is such a common problem. The worst part is we then assign meaning to the kids failure to produce the desired result, i.e., “They were being… defiant, smart asses, difficult, etc.” By blaming the “listener” (the kids in this case) we don’t recognize that it was a communication breakdown. Instead we think we have to motivate the kids, or teach them teamwork or something else to fix them.
To rectify virtually every situation when you asked someone to do something and they either failed to do it or they failed to do it they way you wanted, consider it is an opportunity to be responsible for your failure to be clear.
All that’s needed is to inquire into what they heard, what was the meaning they added to what they heard and then to clarify your request/message. It’s really simple when you understand it as a communication breakdown rather than attribute the failure to another cause.