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Craig Kerstiens

How I hack email

In a conversation with @alexbaldwin yesterday the topic of email came up, with each of us quickly diving into various observations, how its both awesome and a great form of communication/engagement, how most people still do it really bad. Alex has some good experience with it with hack design having over 100,000 subscribers. A tangent in an entirely unrelated meeting with @mschoening and others it was suggested instead of emailing a list to send out a ton of individual emails instead. Both of these reminded me that email is incredibly powerful, but taking advantage of its power has to be intentional.

This is not about ways to get to inbox 0 or better manage your inflow of emails. Rather its about how to get the maximum output out of emails that you send, or minimum output depending on what you prefer.

1 email to 100 vs. 100 emails to 1

This is perhaps my favorite approach to get more efficient feedback and also know how broad an impact something has. Most smaller companies or groups within a company have a mailing list thats or When people want to communicate out to the entire list its a great mechanism, however when you want feedback from the entire company its not a great mechanism.

The reason being is that most people will know how many are on that list and assume that someone else will pick it up. This concept is fairly common in physical settings known as the bystander effect, stating that individuals often do not offer up help to a victim when there are other bystanders preset.

Finally in certain situations you’ll want to hear the same thing 100 times. Hearing something once doesn’t represent how much others echo that. You’ll only see so many +1s on a thread, getting 100 individual responses ensure you get not only the breadth of responses but amplitude of them.

FWIW, I ran a test of this sending an email to essentially all@heroku, then an individualized email in a similar form. The one directly addressed to people received 5x response as well as more thorough responses in the same time frame

Scaling requests for input

The issue that typically exists with the above is that you don’t want 100 responses from 100 people most of the time. Most of the time you want feedback from 2 or 3, then feedback from 4 or 5, then smaller feedback or revision from the rest of that 100. This is actually how I craft blog posts, I start with broad messaging/theming. At that level there’s truly 100 different directions it could go, that kind of input it not helpful when I have to narrow it down to a single one. When collecting product/roadmap input it can be helpful. Knowing which of the two I’m aiming for is critical in deciding a method.

Being explicit about the before and the ask

On the note of crafting a blog post I do usually start with a request from 2 or 3 to get general direction. This takes the effect of, is this interesting? From here though theres still further refinement. The next phase is, does this flow, does it make sense? Here having a broader list is helpful so usually it’ll hit around 4 to 5 people. Finally I’ll revert to the 1 email to 100 people on a mailing list asking for grammar input because mine is crap. Here I don’t mind the bystander effect because I want people to intentionally filter so it works well.

The key at each step of the process is being extremely clear of whats already been done. With a blog post as an example… If I don’t explain the process of people having reviewed and set the goals and some consensus that it meets them, that several have been over it for flow, and that what I’m looking for now which is grammar feedback.

Circulating through people

Email and requests are a time burden on people. I commonly diversify and circle through a set of people. Much in the same way I reach out to people to have drinks or coffee every so often I am to not do the same person every week and only that person with the exception of my wife.

Having more of a rotating basis of getting through people increases their excited-ness to provide input. If I’m always going back to the same people they may feel slightly drained by my constant requests, and quite rightfully so. At the same time the input is good, but diversifying where you receive it gives a broader perspective.

Delayed sending

This is one that may be a little more obvious to people. But sending an email to slow down a thread, not seem over eager, or for whatever other reason you may have is hugely useful. There’s really two tools I look to here: 1. Boomerang and 2. Yesware. Both have slightly different benefits. Boomerang with a much simpler interface, Yesware better integration with Salesforce. Regardless of which you choose, if you ever want to type and email but send it at some point later one of these is critical.


While this list is less of a defined process and more of a collection of random processes, several of these I’d be much less effective without, and the collection of all makes getting appropriate reactions from email incredibly useful. I’d love to hear what hacks you use to elicit positive impact from the emails you receive, as always if you have feedback please drop me a note.