Emailing someone to ask for a favor, or a meeting, or an introduction, can be uncomfortable, especially if you haven’t spoken to that person for a long time.

People often try to overcome this awkwardness by beginning their email request with something personal or by recalling a shared experience, such as a school they attended together or a company they both worked for. By beginning with something positive, they hope to soften the dreaded “ask.”

I’ve received plenty of these kinds of email requests, and most of them felt icky and salesy and fake. You’ve probably gotten a few yourself. And like me, you felt like you were being “buttered up.” I hate getting them and I hate sending them.

Fortunately, I came across a great piece of advice for turning uncomfortable “asks” into opportunities for real connection. It is so simple, yet very effective:

Reverse the order of your email content.

In other words, be direct and up front with your request, then follow up with the personal parts. Let’s compare two samples:

The Typical Method

Hi Sally,

How are things going? I hope Harry and the kids are doing well. Are you enjoying living in Seattle?

Anyway, the reason I’m writing is because I have an amazing business opportunity I’d like to run past you. I think it has great potential. Let me know if you’re interested.

Thanks, –David

Yuck. I know, right? This version comes across as insincere (although that may not actually be true) and a little manipulative — like David is using his relationship with Sally to pressure her into listening to his sales pitch.

Let’s try it again, but this time reversing the order of the content:

A Better Method

Hi Sally,

I have an amazing business opportunity I’d like to run past you. I think it has great potential. Let me know if you’re interested.

So, how are things going? I hope Harry and the kids are doing well. Are you enjoying living in Seattle? The next time I’m in town, I’d love to get together for coffee.

Thanks, –David

Much better, right? Same basic wording, totally different feel. By ending on a personal note, this version feels more genuine, more real — whether or not David is sincere, which we hope he is. It goes without saying that all our communications should be authentic and truthful. Trust me, if you use this method as a tactic or a sales tool, it will backfire on you. People are pretty good at sniffing out shady proposals disguised as friendly hellos.

I’ve personally been using this format in my email requests for a few years now. And I can vouch for its effectiveness. I always get a better, happier response using this writing style of request first, personal second — but only when I truly mean it.

NOTE: I can’t remember where I first read about this better way to structure email requests, but when I do, I will update this article and give credit where credit is due.