I wanted to share thoughts on how to email someone “important” — and maximize your chance for a response. This could be a key email to win a customer, a cold email to an investor or reaching out to a potential mentor.
When To Use Email vs. Social Media or In-Person
My experience has been that nothing substitutes for meeting someone face-to-face; that is the tipping point for most relationships. However, email is generally the next best option.
Twitter is a good place to get someone’s attention via a DM or tweet, but few people want to have a conversation over DM. Linkedin now seems a waste of time – I rarely bother checking messages as 95% are SPAM.
How To Approach Outreach
First, “important” people are generally very busy and have lots of people competing for their attention. As such you need to:
- Standout From the Crowd: use a clear short subject line
- Provide Context: Hyperlink to anything relevant like a document or Linkedin profile
- Provide Social Proof: When possible mention something you have in-common: a person, university, etc
- Make an Ask: Clearly articulate an ask, ideally something they can reply to immediately without needing to put a lot of thought into.
- KISS: Keep it short (or simple) stupid!
The worst thing you can do (at least on cold outreach) is ask to “pick someone’s brain”. Why would someone who doesn’t know be willing to make the time?
Warm Introductions Are The Way To Go
Social leverage is your friend. If at all possible get an email introduction from someone who knows the person. Having a mutual acquaintance makes a huge difference because it establishes immediate trust and validates you.
Where Emails Go Wrong
Outreach tends to take a bad turn when:
- You end up writing an essay: no one has time for that. 1-2 paragprahs max.
- “I’m friends with…” Don’t say you are friends with someone unless you truly believe it. The last thing you want is a back channel “I barely know that dude!”
- It’s Formulaic: This isn’t so much the case anymore but Gmail used to clearly show when a name has been copy-pasted
- You Didn’t Do Your Homework: There is nothing more annoying than getting an email where its clear the person did no research. Also check for spelling and grammar.
- Using Calendly: It’s my opinion that if you email someone you consider important, you should manage the scheduling. Don’t send them a third-party link.
The Art of Email Follow-Ups
Important people truly are super busy so it’s okay to follow-up. Limit yourself to respectful intervals of 1-2 follow-ups. If there is no response after that, let it go. It’s not worth the potential of annoying someone and maybe you can network your way to meeting them later.
And when you do land that next communication: in-person, video chat, or otherwise make sure you are taking the initiative to schedule it and send the calendar invites. Work around their schedule and acknowledge multiple times your appreciation for them making the time.
It’s also completely possible to have an introductory call in 20 minutes.
Like this post? Also see: How to make email introductions
