I am a proud extrovert.
I might not own the best approach or game on how to talk to people, nor I consider myself a "super-connector" but I do think I'm reasonably decent when it comes to reach out to people and build relationships.
Like most things in life I truly think that initiating conversations (in real life or email) is a skill that you can train and improve, just like building muscle or writing.
That leads to relationship building (business development) which is some of the things I do for a living and enjoy quite a lot.
I truly think that you are the average of the 5 people that you spent the most time with. That said, It’s not unnatural for all of us to actually try to reach out to people that are better, smarter, richer or stronger than us.
In an effort to NOT be the smartest person in the room 90% of the time, here are some tips on cold email:
1# Do your homework
Before reaching out to anybody do as much research as possible on that person. Google them, read all their tweets and try to understand how they operate. Is the person you are trying to reach driven by ego? How passionate he/she is about their work? Do they have kids? Can you find the answer that you are looking for on your own or are you just being lazy? Can you also help them in a totally different matter? People are on so many social media channels that it’s not hard to understand the best way & time of the day to approach them.
bonus-tip: when I write an email feeling prepared, it’s as if there is a special energy or karma that flows with the message. It always works better than purely copy+past of a [Insert Name] type of message.
2# Use the subject line appropriately
The magic of Twitter or the old days of SMS are the character imitations. Scarcity generates value. The same applies to subject lines and emails, but on this case people tend to do the opposite and end up writing subject lines that are short, make no sense like “getting in touch” “email to Pedro” or “Partnership”. Lots of people tend to scroll trough their inbox, before actually opening the messages, so if you write a clear, well-done subject line you’ll certainly find better results in response rates and time.
bonus-tip: don’t be afraid of actually inserting your ask inside the subject line. Experiment with it. Something like “5 reasons why it will be awesome for us if you become my mentor for 20 min” or “Partnership between [your company] and [their company] on [feature/platform/placement]. Another suggestions is a more personable approach where you mention something specific that just happened such as “listening to you talk about XXXX right now on SXSW panel. Great talk! Quick question…” (also on this one, go there, say hello and shake their hand and introduce yourself - mention you just emailed them but don’t expect them to respond)
3# Be short, concise and have your ask as one of the first things
It’s natural for us to try to explain ourselves or make an extra effort on generating perceived value right from the get go. What happens? You end up with an extremely boring, ego-centric long email about you and leave your ask (which is usually what you are trying to achieve) for the last lines of the email. I tend to re-read cold emails and often copy-past the last paragraph as the first one. Read your email again, make edits if necessary. Remember you are a stranger to that person, so it’s important for them to have some sort of validation followed by the immediate reason on why you are getting in touch.
bonus-tip: if you can, try to be introduced to the person by somebody that they trust even if they are just a simple LinkedIn connection. That not only instantly puts you in a circle of trust, but generates a sense of urgency. Make the job of your acquaintance easy by writing the introduction email yourself.
4# Don’t send attachments, ton of links or possibilities on the first contact
This is probably the equivalent of mailing a physical object to somebody that you’ve never met. It’s just plain weird. Don’t do that. Sometimes it’s perfectly fine to add additional information (link to 1 or 2 things at most) on your first message. If your goal is to get feedback on a pitch deck, for instance, mention that (on the subject line and first few sentences) and then ASK, if you can send them more details in case they have the time and are interested. I am assuming you are messaging people that are more knowledgeable/busy than you so don’t worry, if they are interested and if this is a good opportunity, it will happen.
bonus-tip: providing more context on the reason you are reaching out is a great thing. The more specific (without sounding creepy) you can be, the better. Things like: Hey [human] I recently watched an You Tube video where you talked about “[insert something related to your ask”] and since we are working on something similar, we would love your feedback. I know you don’t have a lot of time, so if you could just talk to the [specific part of the book / presentation] that would be amazing! To make it easier for you, I’ve highlighted the places where [reinforce your ask here]
5# Have additional triggers to follow up with that person and don’t be a stranger
What I mean by that is that usually you can use extra resources to “skip” the traditional line. Most people that are truly busy, generally have a presence on the internet and have preferential channel for interaction. Email is probably not one of them. Find that other channel, where instead of being message 5000 you can just be message 5. But please be advised, follow up on your original request a couple of times, before messaging somebody on their Facebook
bonus-tip: when taking this approach never email multiple addresses at the same time or follow up on different inboxes. That just make you look unorganized and desperate. Adapt your message to the media. A tweet or DM is not the same as a Facebook message or a LinkedIn request.
6# Provide an out to the person
A lot of the times the most clear way to say no is to never reply. That said, is just much much better when you are polite and prepared enough to provide the person you are reaching out the ability not to help you and pass on the request. It improves your perceived value and who knows, they might even refer you to the right person that could actually be better for your specific situation (has happened a couple of times). Be polite with things like: “please, if this does not make sense to you I would love some sort of guidance or assistance on how to actually improve. Or if you are not the right person, who would be the most appropriate contact?”
bonus-tip: approach this tip like a humble-genius. It’s extremely important to be a likable person in the first place, so by providing an out to the person, you are also demonstrating that you are humble, but intelligent at the same time. It also works well when you are reaching our to C-level people. You can always ping the big guy and ask: "who is the right person inside your company I should be talking to?"
7# Use some sort of non-trivial hook, but don’t be a freak
The line between personal and professional lives does not really exists for most of the people that I usually want to get in touch with. Of course that it does exist to a certain degree (please respect people’s privacy!). What I mean is that is totally fine to reach out to a VC that happen to also be a triathlete (or something unusual) and use that as an excuse to talk about other things, even thought the primary reason people get in touch with him in the first place is to get funding. It's just a matter of being able to add value at any cost.
bonus-tip: only take this approach if you can actually help and provide a tangible, measurable perceived value to the other party. For instance I can usually speak to a lot of Brazilian or Latin American things, but I would never venture talking about any Chinese related stuff.
8# Add more value than what you can capture
It must feel good to the other person for anything to work in the first place. I this approach from email all the way to my sex life. You must provide value (or pleasure) before actually getting something in return. Suck it up and be proactive with a smile. If you are just not feeling like doing it today, wait until the next day.
Lots of times people will help excepting something in return or ask too much without providing compelling reasons why the other party should even care in the first place. Expect nothing and help as much as possible, until it makes sense.
bonus-tip: don’t be afraid of connecting people that you think could learn from each other. Do random acts of kindness once in a while with total strangers. Send articles that can be helpful for the people you work with. Listen and understand their pain. Just focus on solving that first, if you can of course.
9# Do more and get better at it.
Don’t be afraid of failure or rejection. It’s going to happen in your professional and dating life. It always will be a numbers game. After a certain numbers of attempts it will start working, but you must act. Don’t suffer by anticipation. Don’t overthink and work on procrastinating as little as possible to send the messages out. The more you practice, the better you will get at it.
bonus tip: If nothing is working try some kamikaze approaches but be careful. There could me hundreds of reasons behind why that person didn’t actually responded to your message. That said a lot of the times I've realized that using smart emails tools like followup.cc that remind you when to follow up can help quite a lot.