How to Send Effective Emails

Jason Advice

This is the real deal on sending effective emails to people with power and influence– who will not normally email you back unless they know you. Forget all of the other crap you hear about sending good emails, this is down and dirty way to ensure you get a reply every single time.

  1. Drop a name. Being referred by someone they know increases reply rates dramatically. If at all possible you want this. This does not mean the referrer must make the introduction, but that you just need permission from the referrer to use their name so that you can reach out.
  2. Rule of Reciprocity. Mastering this rule will nearly guarantee a reply to your email. Here’s how it works: Do someone a favor without any heads up (don’t ask, just do) and be sure they know what you did. Whether they actually needed or wanted that favor is irrelevant. Personalized gifts can work, but not generic ones. It’s better to give them something of real value. Once you do, the rule of reciprocity is triggered and a return favor will be forthcoming (i.e. an answered email, a meeting, a referral, etc.). See full example at bottom of this list.* Read all about the Rule of Reciprocity here.
  3. Personalized subject line. Reference a person, event, or product that they are familiar with as part of the subject. Good Examples = “Following up on…” , “Referred by…” and “Quick question about…”. Bad Examples= “Hello”, “Potential partnership” , “Meeting”, etc.
  4. Keep it short. 1-2 paragraphs, 500 words max. Shorter = better.
  5. Get straight to the point. No small talk. Forget the weather, the family, and holiday crap.
  6. Only touch on ONE idea. If you have 5 great ideas or things to discuss, choose one. You can talk about the others in future emails, which gives you 4 good reasons to follow up later.
  7. Clarify and position your ask. Make it clear what it is you want, they should not have to decode your message. Never send an email without a clearly defined ask at the end of it.
  8. Do an effort analysis. What you’re asking for should require little to no effort on their part. The more they have to do, the more likely it is they won’t do it. Frame it so that you will do the majority of the work required if possible.
  9. Design for one word reply. This critical piece is often missed. Do not make open-ended asks that require actual thought to reply. Design your ask in a way that allows for a one word reply like “Sure” or “OK” or “Absolutely!” The wording is everything and differences can be subtle, but costly. Bad Ask Example: “That’s my proposal, so what do you think?” Instead, use this Good Ask Example: “I’d love to talk with about it. Would it be okay if I reach out to your assistant to schedule a 15 minute phone conversation?” Now you’ve hit #6, #7, #8, and #9. Talkative big shots may still choose to reply in more detail.
  10. What’s in it for them? Never send an email without being able to answer this question. Don’t send “need advice” or “can you help” emailsuntil the rule of reciprocity has previously been triggered. If it hasn’t then delete the email and rethink what you can do for them. You want to limit the word “I” as much as possible through editing. For example, “I created a new app and I think I know a way you could use it. I would love to talk to you about it sometime.” should become, “My new HotShot app could save your organization millions of dollars with very little risk. Does this sound like something you would be interested in hearing more about?” Two sentences hit #5, #6, #7, #8, #9, and #10. Of course your HotShot app must be of value to them for this to work.

*Rule of Reciprocity Example:

  1. I want to meet Bob, CEO of Acme, Inc., but I have no connection.
  2. I learn that Acme is looking to expand their sales of widgets into China.
  3. I find out that Dr. Kim, a professor at a prestigious university, specializes in breaking into Chinese markets. Dr. Kim is quite valuable to Bob.
  4. I read Dr. Kim’s research on the topic and then email him, framing his research in terms of Acme. I suggest that Bob could be a great resource for Dr. Kim and ask if he’d like to meet him.
  5. I re-read the 10 email commandments to ensure that Dr. Kim replies to me.
  6. I write a one page summary of Dr. Kim’s research and propose ways it could impact Acme.
  7. I finally email Bob, informing him that I’m a fan of Acme and I’m familiar with their desire to get into China. I include my one page summary and mention that I’ve spoken with Dr. Kim about Acme and that he’s interested in chatting.
  8. I connect Bob’s assistant to Dr. Kim’s T.A. to set the meeting.
  9. The RoR has already been triggered at this point, but becomes more powerful if I postpone my request until after Bob and Dr. Kim have spoken.
  10. I have now triggered the RoR in both Bob and Dr. Kim. I will likely ask for just one thing from both of them in return, “Do you know someone I could speak with that..”  (See Commandment #1)

Read in-depth chapter on the Rule of Reciprocity.