I just checked my inbox and there it was. Yet another email that opens with that gawd-awful phrase "I hope you're well."  I get emails like this all the time:

  • "Dear Geoffrey, I hope you're well? Just following up to..."
  • "Geoffrey, I hope you're well. Just a follow-up email to..."
  • "Hi Geoffrey - hope you're well. Wanted to see if you..."
  • "Dear Geoffrey I hope you're well and having a great week so far..."
  • "Dear Geoffrey, Hope you're well? The rise of social enterprise is..."

People use that phrase (and others like it) because they know it's rude to just launch into a request or a sales pitch without showing at least a pro-forma interest in the person they're addressing. However, these phrases annoy rather than ingratiate because:

1. They're trite.

"I hope you're well" says that you couldn't be bothered to think of a real way to connect or to show real interest. Look, you're asking the recipient for a favor--to spend valuable time reading something you've written. If your email is important enough to read, surely it deserves something better than this.

2. They're irrelevant.

Seriously, how is my health germane to any conversation that we might have? Suppose I'm actually not well? Is your email going to self-destruct? Will it miraculously transform itself into a get-well card? Why are you bringing up something that's completely off-topic? Who do you think you are? My GP?

3. They're insincere (at best).

While you might have the abstract hope that everyone (including me) is in excellent health, the truth is that you don't really give a tinker's damn about my health except maybe insofar as it might impede my ability to read your email. You're not my friend (yet), so why are you pretending that you care?

4. They waste space.

Frequently, it's the lead in--the first 10 words or so of the email--that determines whether a recipient will open an email. In terms of open rate, the lead-in is almost as important as the From field and the Subject field. You should therefore craft your lead-in so that it persuades the recipient to open it. "I hope you're well" does the opposite.

5. They're Spammy.

A common Spambot sends email that's spoofed to look like it comes from somebody you know, like so:

From: Jane James
Subject: Re: For Geoffrey James
On Tuesday, April 10, 2019 09:47 AM, Jane wrote: I hope you are well. Just thought you might appreciate this.
[link to some trojan-infected website]

Because I've received dozens of these, I'm immediately suspicious of any email that includes insincere inquiries about my health. Other people undoubtedly are as well.

What Actually Works

So, then, what does work? Genuine curiosity.

Forget what you're trying to pitch for a moment. Do some real research into the person you're writing to. Find something about that person--something relevant--that interests you. Ask about it. Start a conversation. (Email, remember, is a form of conversation.)

Once you're in a conversation (about your recipient), you can bring up what's on your mind. Let it evolve from the conversation. This can be as simple as seguing (in your second email) with "the reason I asked is..." or something that emerges after the trading of several emails.