If you haven't yet read Part One of this post ("While I Was in the Ambulance Last Night, I Decided to Share My Most Valuable Sales Secret") I recommend you do so now, because this is a continuation of that post.

In Part One, I explained why I haven't written about this emailing technique in detail in the past, provide some background, and (IMPORTANT) provide the basic structure of a well-crafted cold email.

Please note that, in this series of posts, I am NOT writing about email-marketing but about writing a customized, one-off, email that will has a very highly likelihood of being opened and answered by a specific C-level executive.

Here's how it's done:

1. Consider the company's entire top management team.

While you may want to speak with, say, the CFO, you might have better luck starting with a different C-level exec, say, the CIO. Once you successfully start a conversation that exec, you can probably get an introduction to the C-level exec you're targeting. 

How do you know which C-level executive to start with? Well, you start by looking at their portrait shots on the corporate websites. Which of the C-level execs look the most approachable? It's a gut feeling thing.

Rank them all from "most approachable" to "least approachable" and work down the list during the next step.

2. Do deep research on your target C-level executive.

Obviously, read the exec's LinkedIn profile carefully, but that's only the start. Google the exec's name (in quotes) with the company name (also in quotes if necessary.) Example:

  • "John Doe" "Acme Widgets"

Chances are the search results will just be some corporate stuff but look for anything unusual--anything that might separate that exec from the pack, either personally or professionally. Read anything that piques your interest.

Now do the same search but with additional terms. I generally do these three:

  1. "John Doe" "Acme Widgets" charity
  2. "John Doe" "Acme Widgets" hobby
  3. "John Doe" "Acme Widgets" wife

Nine times out of ten, those queries will tell you the town or part of the city where the exec lives, as well as a glimpse into his or her personal life. You're looking for 1) a better understanding of the person you're trying to get into a conversation with and/or 2) a personal "hook" that might allow you to open a conversation.

Here's a quick example of the latter. Back when I was a reporter, I wanted to write for a certain, very prestigious magazine. Rather than leaving voice mails for the editor-in-chief (which never worked even back when important people still listened to voice mails), I did "deep research."

I discovered that, in addition to all his business stuff, the editor was wicked into large-scale model rocketry. He was building, like 6-foot models with composite engines that were lofting them up several miles. Hard-core stuff, if you're into that kind of thing.

Well, as it happened, like many unrepentant dweebs, I'd done some model rocketry (on a much smaller scale) in the past, so rather than emailing the editor about my story idea, I emailed him a question about his most recent launch.

Sure enough, he gets back to me in less than an hour and we start corresponding about model rocketry. I segue the conversation to an article idea about how microprocessors are making large-scale model rocketry more scientific. Bingo. Sale.

As it happens, I never wrote that article due to changes of direction at the magazine but it's a great example of how to use a non-traditional "hook" to get a bigwig into a conversation.

3. Find "triggers" that might lead the exec to want to speak with you.

Look over the press releases on the corporate website and search the latest news reports on the company for anything that might make the exec want to have a conversation with you. The "magic list" is:

  1. Mergers
  2. Acquisitions
  3. Top management changes
  4. Big new customers
  5. Indictments
  6. Layoffs

As you find these triggers, don't limit yourself to "business thinking"; consider how those changes will affect the exec personally.

Here's a real-life example from one of my clients. The product was an ERP system; the target exec was the CFO. In the specific case, the big company in which the CFO worked had just been acquired by an even larger company.

A "business thinking" approach would be to address, in the cold email, the fact that a merger usually means a re-examination of the computing infrastructure, which might lead to a desire to start afresh with a new ERP.

But a "personal thinking" approach takes the politics into account. When a large company acquires another, not-so-large company there is always a turf war to see which C-level execs will control the merged entity.

Therefore, there are four possible career outcomes for the CFO from the not-so-large company:

  1. He gains power and takes control. If this is the case, then the CFO will want ways to consolidate power. In this case, the best cold email "hook" is "changing to a new ERP system will strengthen your position."
  2. He loses power and gets fired or is put into a "holding pattern" position until he resigns. In this case, the best cold email hook is "I have industry contacts that I'm willing to put at your disposal."
  3. He's already about to jump ship to another company. If so, he'll be looking to consolidate power by quickly putting his stamp on the new company.  In this case, the best cold email hook is (again) "changing to a new ERP system will strengthen your position."
  4. He takes a golden parachute or buyout and plans to spend a few years on the beach. If so, he really doesn't give a flying rat's behind about ERP systems... but might, just might, be willing to put you in touch with whomever in the new company is now responsible for computing infrastructure.

Of all these outcomes, the least likely is #1, because in merger turf wars the execs from the smaller company almost always lose, which is why so many of them work hard during merger negotiations to ensure they're "taken care of" after the change (i.e. #4).

The most likely (IMHO) is #2 but that's just guesswork. To find out what's really happening, continue to whatever news is available until you can make the most educated guess possible.

What's important here isn't the specific example but the thought process, which is to imagine the likely political situation and extract the likely position that the C-exec is now in, as the result of a change in the corporate environment.

5. Decide on the most likely "hook" for the cold email.

Let's recap. When you started this process, you essentially knew two things about your target exec: name and title. (Or maybe even just the title!) By now, however, you should have a strong picture in your mind of who the C-level exec is as a person and where they are, at this point of their career and this state of their company. 

Can you see how this is powerful? Your deep research has probably provided you with at least one and probably several angles or "hooks" that you can use to get into a conversation. Just as important, when you DO get into a conversation, you'll be starting with an understanding about what this person is all about.

That will make it easier to reach rapport, even if the bulk of what you've learned never comes up in the conversation!

If you really want to get good at this, spend some quiet time visualizing yourself as the person you want to reach. Imagine that you look like that person, that you had that person's experience, that you're sitting in what you think that person's office would look like, etc., etc.

Yes, that all sounds a bit crunchy, but the better and more deeply, you understand that C-level exec, the easier it will be to craft an email that will intrigue them and convince them to respond!

6. Craft a cold-email based upon the most-likely "hook."

Zounds! Once again, this post is running a bit long, so I I'll give specific examples of how this is done in part 3, "3 Cold Emails that Big-Company, C-Level Execs Will Open and Answer."