Some Things I Have Learned About Email

A non trivial part of my time is spent reading and writing a lot of email. Here are some things that I have learned and that work for me.

There are only two legitimate uses for bcc. First, explicitly moving someone to bcc who no longer needs to be part of the ongoing exchange. Second, to send email to a large group of people by putting all of them on bcc. I strongly recommend never using bcc any other way. If you want someone to know about an email you sent, send it and then forward it …

Avoid attachments when you can. For instance if you want someone to look at one or two charts, just paste them right into the email. Use text to summarize the key point of the charts in addition to that. So much email is read on mobile devices today and opening up an attachment is a big extra step, especially if it is massive in size. If the recipient needs more detail, ideally just link to a cloud resource. This cuts down on all the “I couldn’t open the attachment can you please resend” emails.

Try to answer obvious follow on questions in your initial email. Email is not chat and that’s a good thing. For instance, if you are sending an email inquiring about a job write why you are interested and how you are qualified. These can be a few sentences each but a recipient definitely needs both. If you don’t do that, the other person will have to immediately get back to you with a question and you wind up with a lot of unnecessary back and forth. Before I hit send on an email I always ask myself if I got this what would be my obvious first question and then try to answer that before I hit send.

Much has been said about double opt-in intros and yes, I try to do this pretty much always. To help with this I usually ask people to send me an email that I can forward. By that I mean an email written in their own voice. Sometimes people seem to think this means a draft of what I will write, but I simply will add a sentence or two of my own as a “wrapper” to their email. If their email is well written this is very efficient (see point immediately above about answering obvious follow up questions).

Whatever methodology you use to cope with email, understand that ultimately your email traffic is somewhat of a reflection of what you are spending time on. So ultimately the only thing that I have found works whenever I feel overwhelmed by a certain type or category of email is to change how I approach that particular topic of my work. For instance if I am constantly on email with an entrepreneur in our portfolio it probably means that we are in a phase of their company where we should check in more over the phone or in person.

I do think there is still some interesting room for innovation in inbox management and email tools. I am not expecting something that writes well thought out replies, but something that’s better at understanding priority and can send an auto-responder selectively to lower priority emails to help manage senders’ expectations.

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