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How often do our workplace communications open with “I hope you are well” or “I trust you are doing fine”?
These “wellness checks” reflect the fact that everybody has become more conscious of the need to be kind to others. That’s a good thing. Our workplace has become a setting where the best bosses and colleagues take pride in showing sensitivity to the emotional and physical well-being of others.
And for these reasons, beginning a letter or a conversation with “I hope you are well” has some merit. But even if it reflects the best of intentions, this opening should be abandoned for the following five reasons.
1. IT’S A CLICHÉ
First, this opening is a non-starter, because it’s overly general. Of course you want to begin an email or conversation with something that warms up the relationship. I call this the “grabber.” But people who use “I hope you are well” or a similar phrase are simply making a pro forma statement that could be made to anyone. The words sound good but have no deeper personal or individual meaning.
Instead, ask yourself what you can say to show that you do care about the person you are writing to or talking with. You might begin: “You have been on my mind lately,” and then explain why. Or say: “We were so enthralled with the event you hosted last month.” In short, find something in the relationship to draw out.
If it’s a new contact, show you’ve done your research and say something positive about that person. For example: “I’m so impressed with your HR organization,” or “I am looking forward to meeting you and being part of your product launch.” Being specific gets the relationship off on good footing.
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James' World 2 
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