Deep Dive: Oren Klaff on How to Write Emails That Get A Response

A Deep Dive is an unsolicited exploration into an individual, service or company that peaks my attention and I feel their message would bring value to our readers. -Michael

oren klaff on how to write emails that get a response logo
In digital years, I’m old. Maybe not grey beard old, but I’m getting close. One of the handicaps that comes with being a part of my generation is that I had some fairly ridged rules grilled into me around writing, presentations, reports and more.

The dreaded GRAMMAR generation!

What was one time consider a “skill” is now too easily detrimental to my goals in the email and text message age.

We’re all familiar with the acronym KISS–Keep It Simple, Stupid. When it comes to composing emails, however, maybe it’s time for an upgrade. KISS 2.0, Keep It Stupid Simple!

Oren Klaff London Real interviewEnter Oren Klaff. I was first introduced to Oren when listening to his interview on the London Real podcast by Brian Rose. I immediately bought the audio version of his book, Pitch Anything and within the first week I had listened to it cover to cover twice.

Oren comes from the world of big finance, which might cause you to ask “What can he teach me that is relevant to web development?”

As web developers we pitch projects and communicate with clients constantly. Whether you’re pitching a billion dollar airport redevelopment or a $5000 website redesign, his lessons in pitching and his methods of frame control are invaluable, but for the purpose of this article, let’s just focus on one small aspect of Oren’s teachings, our emails.

What I’ve learned over time is that the more important it is for me to receive a response to an email I send, the shorter and more concise I need to keep it. Preferably one short question with as little explanation possible.

Here’s how Oren Klaff expressed this same lesson in a recent message:

We all have one customer account that is just out of reach. You know which one I’m talking about. The Big One.

The one account that’s a career maker, and will move us into the spotlight. To land that account, we’ve called them. emailed. Linkedin. Networked.

But still  … crickets.

If we asked why, and they answered truthfully, here’s what they would say:


I recently got a business proposal from two different sources.

One I responded to right away, the other was yours, which I ignored.

Look, I know how frustrating it is to write to someone and not receive the courtesy of a reply. So should I have replied to you? yes, sure. Am I sorry?

Not really. In fact … welcome to The Big Time where only the most concise messages and the most intriguing proposals survive. My inbox is a kill zone. (And pestering me on Twitter and Facebook because you sent an email a few minutes ago does not increase survival rates.)

Here’s the breakdown of why I never got back to you:

1. You included an attachment I never wanted, needed or requested. You’re sending me too much information, too fast.

2. Your emailed required a thoughtful response which would take far longer than 60 seconds to write. See, I don’t type a lot. It creates a papertrail and usually when I lose a lawsuit, it’s because of a papertrial. (I prefer to use the phone.)

3. Your email was excellent. A model of prose. Three neatly written paragraphs. The sentences were well constructed. The ideas well formed. I wish our own sales people could write as well. But this is too obviously a generic sales outreach, and I have too much other stuff to work on right now then dive headfirst into your sales funnel.

4. I previously ignored one of your emails, and now I feel I have the right to ignore ALL of your emails.

5. As a final thought, here’s the email I recieved the same day as yours, it is the one I did respond to.

(the email I received, exactly as written):

Subject: via jeff

Message: John, by way of introduction, the guys at Smith Company thought we should connect about our 27-series products If I send through a 2-page summary, can you spend 3 mins with it, give a quick yes/no. thanks, Oren

To learn more about this kind of email and which messages get through to decision makers, read my book Pitch Anything

In addition to his successful email being short and to the point, it also screams “I’m busy so you’re lucky I took the time to contact YOU!” by how it’s kept to one line and has less than perfect punctuation and capitalization. Here’s something similar I discovered about my own emails.

I always close my emails with either “Thanks,” or “Thank you,” rather than “Sincerely,” or some other valediction. (Grammar generation leaking out again!)

While I do have a signature that’s automatically created in my email client, I intentionally leave out my thank you’s because I don’t want them to ever appear insincere or form-letter-like.

I accidentally discovered once that my thank you’s actually appear more sincere when I leave in my simple mistakes. When I’m typing quickly it’s not unusual for me to type “THanks” or “Thanks you” and while it’s just one small piece to the larger lesson above, these typo’s say “I really mean it because as busy as I am, I just typed Thank You to YOU.”

Take aways:

  • The more important it is to get a response to your email, the shorter and more concise it should be.
  • Keep It Stupid Simple
  • Want to express how busy you are, therefore how important your communication is? Keep the message to one line and don’t obsess over perfect punctuation and capitalization.

1 Comment

  1. on July 5, 2020 at 10:45 AM

    This is a good tip especially to those fresh to the blogosphere.
    Short but very accurate info… Thank you for sharing this one.
    A must read article!

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