[PG-13. If you are under 13 in age, this post may be inappropriate for you.]An ice breaking mail is not that easy to write. Yes, you can type it as usual. What I meant is, writing it to fit the purpose and ensuring that it fulfills the requirement needs that bit of extra care.
Why is that so hard?
1) So many fakes out there.
If I get a business email from an unknown person, I usually consider it more of a spam, or even as one of those "enlargement" mails that end up in my spam folder.
2) No clear idea about the knowledge of the reader.
You might assume something reasonable. But it rarely works. The mail shouldn't be too long either.
3) Cultural difference
In foss, we use "Hi {first-name}." But it might be inappropriate to call a professor who is in academia seriously by her name.
Similarly, most businesses try to call the users, "Dear {Salutation.Name}". But that might be considered too intimate in foss communities. [On the flip-side, we have even stopped calling "Dear {first-name}" to even personal mails to our friends. All go with "Hi {first-name}" these days.
Let's break it down.
1) Some research
Before sending the first mail, an initial research on the receiver is mandatory. Google might help to get to know about her background, if you know the receiver's full name or her organization. If the (receiver's) culture permits (for example, a foss-culture), "Hi {first-name}" is much more appropriate than a mere "Hi".
2) No bot in the first mail please
Make sure to send the mail from a real email address. Not from a noreply@mydomain.com. Let the first mail be from a human, than an automated mail from a bot. Give the mail the respect and care that it deserves.
3) Be in the equal rank
For example, if you are sending a mail to someone in an organization, make sure to send it by a person with an equal rank, if possible. Junior executives may send the mail to junior persons, but if the mail is going to a senior person, make sure to send it by a person with an equivalent or an equally senior rank.
4) Introduce yourself
This is your first mail. So give a background of yourself and your organization, and a brief summary for the reason to draw this first mail. If the lede is written impressive, the reader will continue reading. Otherwise he will just ignore or even delete and mark it 'spam'.
5) Give enough background information
Before jumping to the content or the theme of the mail, give a short summary of the background. Keep in mind that your relationship starts now. That means, the first mail should speak for the days up to now. Thus the first mail should include an appealing summary of the stuff that happened up to know which leads to this particular mail.
This is actually common to public speeches and lectures too. Unless you specify a limit for an audience (unless the target-audience is specified clearly beforehand), they may come from different backgrounds. If you suddenly start talking in your technical jargons specific to your product, they will be lost, and also will think you are insane and stupid. [On a related note: It is also believed that someone who used to sleep at the lectures, will make a boring lecture himself.]
Make sure that the mail educates the reader, and not just markets you, your company, or product.
6) I want to learn more
It is always almost impossible to include all the required information in the body of that single mail. If someone is induced by your mail, she would like to know more on that, before responding. Hence it is better to provide links!
Links should lead the reader to the appropriate customized landing page. Make sure that the landing page is not the home page of your company or your personal web site. Rather it is a customized page, specific to this particular mail. Make sure to copywrite the landing page carefully, possibly with the help of a professional copywriter. Other optimizations such as SEO optimizations too can be considered. Landing page may contain links to more pages and third party websites for further research.
7) How to respond back
It is silly to assume that the receiver should simply hit the 'reply' button to get back to you. You should better indicate the preferred communication media, which might include a reply email address, a phone number (office/mobile), or a fax number. An indication of the desire to continue the discussion would help too. Most readers just read, and they do not reply unless they are asked to. "Let me know, if I can get back to you" or "I would like to hear from you on this" might help.
Second mail - If you didn't get a response
If the first mail didn't get a response, it is ok to reply or send a friendly reminder after a reasonable time, without resembling a typical spam. It is safe to assume that the first mail is left unread in this case, and include the reference to the first mail along with a summary of it. However make sure to leave a reasonable time. Most of the people do not read mail over the weekends. Better to mail on an ideal time, such as Thursday 11 am.
Second mail, once you got a positive response
Once the first mail received a positive reply, sending the second mail would be much more easier, as now you know the receiver better, and she knows you well too. Also the need to guess the background knowledge will be eliminated, as you can safely assume the background knowledge of the user to include the information given in the first mail. However this response from you may not be a mail again. It can be a phone call instead, if that is encouraged by the receiver. ;)
I personally don't like a third mail unless at least one of the two initial efforts was positively responded. It is silly to try thrice on anything after being ignored twice consecutively.
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