Chris Fralic, First Round Capital
By Chris Fralic, Partner at First Round Capital in New York.
Email is broken.   Do you know anyone who loves email?  I don’t - it can be frustrating and it doesn’t scale well, and there aren’t enough hours in the day to process it all.  But for many executives it’s the reality of how a lot of business gets done, and everyone has to deal with it and make the best of it. Here’s an example (chart below) of the email volume problem I have as a venture capitalist. This is the number of emails I have SENT each year for the past 6 years.
This is my work-only, outbound-only email volume, and it seemed like a lot when it was around 10,000 a year, and in 2012 it hit around 17,000. That means I’m spending multiple hours sending an average of 76 emails every workday, and reading, processing, filing and deleting a whole lot more. And a large part of what I do involves introducing people by email. Over the years, consistently about 20% of these emails contain the word “introduction” or “intro.” So that’s why I’m passionate about sharing some of the best practices I’ve learned along the way.

The Higher Order Goals:
Before we get into the details and specifics, at a higher level I think there are several overarching themes and goals that business professionals should be striving for that certainly apply to email introductions:
1)   Help everyone involved
2)   Make it easy to help you
3)   Build relationships and reputation along the way
This means you are doing your best to make introductions and connections that you think makes sense for all parties, you’re doing all the work to make it really easy for people to respond and help you, and that with each interaction you’re building relationships and trust along with your reputation.  At the end of the day, these tips can help, but a big part of the equation is who is sending the email and the expectations from all previous interactions with your personal and/or company brand. Your reputation and relationships are big drivers of your email response rates, and you should be looking to build them both along the way.
1) The ASK
Sometimes it makes sense to just make the introduction when asked, but in most cases I think it’s a best practice to ask for and receive permission before an introduction is made. This makes it a choice for the recipient and doesn’t create an obligation. And if you’re the person asking for the introduction, you should ask the person making the introduction how they’d like to have it made, and how you can help them make it. Some people like the double opt-in approach, but I prefer the Self Contained Forwardable Email.
2) The SCFE – Self Contained Forwardable Email
This is a brand new email that is self-contained with a custom/relevant subject line and opening paragraph and a specific call to action that can be easily forwarded.  Whew...  That sounds like a lot and is, so why am I suggesting all that?

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First, doing this makes it something that can be forwarded along in minutes from a mobile device along with a sentence or two about why the recipient should care/engage. And being in that category of “easy to forward” is where you want to be. You don’t want to make the person have to think about crafting an email from scratch when they’re back at their computer, or cutting and pasting from your email – many in that category never get done.  And it makes it easy for the recipient to respond or not, and they have all the information they need to make that decision.
3) Make it PERSONAL
Do some work and research on the recipient, and have the email come from your voice.   I’m talking about a sentence or two up front that shows you’ve done at least a Google search on the target/recipient, and have a sentence or two in there about why they should care and what’s in it for them. And if you’re asking for 3 introductions from someone, you should be sending them 3 separate emails.
4) Getting them to Read and Act on your Email
By and large, less Is more – spend the time to boil it down into as few sentences as possible to get your point across. Bold the ask – make it easy for them know what you’re looking for. It can make a big impact to underline or strikethrough words, and it looks clean and saves space to put links in words.
Beware of multiple fonts, especially when copying and pasting – it can make your email look lazy at best and at worst, it can look like a ransom note. And it’s really important to have a clean signature block that is on every single email and response you send, with all your relevant contact info and preferably from your work email. And DON’T add in a graphic file to your signature – those can really confuse people because every email from you looks like it has an attachment.
5) Target Individually
“If you send an email to everyone, you send it to no-one.” This one is especially notorious as introductions to VC firms often come to multiple or all of the partners.  This can make it hard to know who should respond, and everyone might assume someone else has it covered. It’s best to send the email to one single person, and to copy the others if necessary.
6) The Response
Once you have permission, don’t send an email introduction to two people and have the originator/requestor immediately respond - that can sometimes feel overwhelming to the recipient. I’ve found it’s best to give the target/recipient some time to respond. But when they do, it’s important for the originator/requestor to "lean in" to the response quickly, and one best practice I’ve seen is suggesting multiple potential times to meet/connect in that first response.
7) BCC and ACK
BCC (blind carbon copy) might be the three most powerful and underused letters in all of email. It’s really nice on the first reply to see something like “thanks for the intro – moving you to BCC to save your inbox…” so that the loop is closed and you’re saving an unnecessary party from being copied on every one of the next 10 emails trying to find a time for a meeting. But beware the blind “FYI” type of BCC – I’ve seen too many unintended “Reply All’s” where the recipient had no idea who else was copied until that happened – it’s best to forward the email you sent to someone else as an FYI instead.
And I'm calling this one ACK because of the old SMS/Modem technical term for “acknowledge” – I’ve been really impressed lately by seeing some people give quick email responses like “On it” and “Got it” or “Will do” as quick messages to know something was received and understood.
8) Close the loop
A best practice is a quick note to let people know the results of an introduction after the fact – the good, the bad, or whatever happened.  It’s really helpful for feedback and learning, and a Twitter sized 140-character email update can make a lot of difference and really stand out.
9) Follow Up, Don’t Pester
Your email was sent but you didn’t hear back yet – should you send a follow up every single day for seven days in a row? No – I find the best approach is to follow up once (usually) or at most twice (sometimes) in a reasonable period of time (a few days to a few weeks). Some good ways to do that include resending the original email with a “bumping this up to the top of your email...” or “the deadline is on Monday and I wanted to be sure you saw this…” or “making sure this wasn’t stuck in your spam folder…”
10) The Presumptive Negative
This is a more advanced form of follow up designed to elicit a response, for important emails where you haven’t heard back in a while. Some good examples I’ve used and received include “I assume this isn’t a fit since I didn’t hear back from you, but just wanted to make sure…” or “it seems like First Round doesn’t want to invest in my company...” I don’t use it often, but when I do I’ve found it has at least a 50% chance of a response, and more than half the time it’s positive. It’s harder for people to acknowledge something they’re missing than it is just to ignore it, and even if you confirm that they’re not interested, at least you know.
So there you have it: some my best advice and best practices I’ve gleaned from dealing with lots of emails since I’ve been at First Round, and going all the way back to my first email account around 1985. Here are some other resources worth checking out – How to email busy people by Jason Freedman and Tips on approaching a VC by Charlie O’Donnell. May you have many fruitful introductions and an uncluttered inbox.
Chris Fralic joined First Round Capital in 2006 and has focused on a number of the firm's investments in areas such as Advertising Technology, Social Media, eCommerce, Gaming, Mobile and more.  Chris has over 25 years of technology industry experience, with significant Internet business development roles since 1996 including VP of Business Development at both Del.icio.us (acquired by Yahoo!) and Half.com (acquired by eBay).  He can also be found @chrisfralic and nothingtosay.com.
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