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The Surprise Personal Email

I want to show you a neat little email you could start sending today. You could call it the “surprise personal email”. It usually comes from someone high-up in an organization. Someone you wouldn’t expect to take the time to email you.

To see this email in action, you could sign up for a trial at Optimizely – an A/B testing tool, or Olark – an on-site chat tool.

Here’s the twist. Zach didn’t see I just signed up. In fact, this is just an automatic email / lifecycle email / drip email / triggered email. You pick your term.

And here’s the same type of thing from optimizely. They send two emails.

Lets be honest folks, it wouldn’t fool any of you savvy marketers. And even if a recipient did suspect that it was automated, they probably don’t mind. There’s nothing shady about a friendly email offering help.

Here are a few tips and tricks for you to send a surprise personal email.

1. Delay the email

Olark’s email came 2 hours after I signed up. You may want to experiment with the delay.

I’m currently running an email like this 7 days after signup.

2. Have your replies go to a team

Sometimes I email you from the address colin.n at If you click reply it goes to everyone on the team.

Olark used “zachs” rather than “zach” to accomplish the same thing.

What’s great about this is you avoid having a “single point of failure” so if I’m in a 2 hour meeting, you’ll still get help quickly.

3. Make it open ended

The beauty of this email is that it is open ended. If you waffle on about all the things the person might be wondering it would be a difficult email to write.

So a simple “hey, I just wanted to check in to see if you need any help” works wonders.

4. Don’t use formatting

It should go without saying that you want the recipient to perceive this as personal outreach. Take it out of your template and just send text.

I’m going to duck under a table while I say this… but I’d recommend you don’t have an unsubscribe link. This is a one-time email. This type of email straddles the line between transactional / marketing and the unsubscribe link kills perception of it being personal.

And as a final idea, you could always add “Sent from my iPhone” to the signature if you really want to go for the “CEO in a rush” style email.

Do you send any emails like this already? Want some more ideas for emails you can send?

Share your thoughts in the comments below