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by Cathy Vandewater | January 13, 2012


Joe Maddalone wasn't exactly "cold" contacting Morgan Stanley when he sent the CEO an email at 3:02pm the day after New Years.

He'd already interviewed with the company for a sales position, and was contacting James Gorman, whom he hadn't met yet, to introduce himself.

Here's the email:

"Mr. Gorman,

Hope you had a great holiday. My name is Joe Maddalone, and purpose of this email is to see it you received a letter of recommendation on my behalf from Mr. T Boone Pickens. It was FedExed last week, and should have arrived last Friday.

I am currently waiting for my final interview to be scheduled, and wanted to email you to introduce myself. I graduated from college in 3 years, and currently run my own company in NYC.

I just thought I would email you to introduce myself. I hope to join the Morgan Stanley team, and meet you soon.

Thank you,

Joe Maddalone" [sic]

What sort of response do you think he got?

Let's preface this by noting that Joe Maddalone has had luck reaching out to people in high places before. He famously called T. Boone Pickens for a month straight before securing an internship, as chronicled by Business Insider.

But the response he got from Mr. Gorman was less warm:

"You need to call our recruiting team not me. That is why we have a recruiting team! Friday was the last day before New Years. if you want to work in this industry use some judgment and don't contact CEOS over the New Years weekend." [sic]


So what went wrong?

As Gorman writes, timing, for one thing. But it's likely the tone of the email that didn't go over well. As Maddalone notes in his interview with Business Insider, he sent the email on January 2nd because he figured his would be one of very few messages in Gorman's inbox, making it more likely to be seen.

That strategy worked—but considering the holiday, the note could have probably been shorter and less demanding. Several references to time, urgency, and "waiting" are made, with Maddalone doing some metaphorical foot tapping by mentioning a FedExed-delivered letter of recommendation.

Putting pressure on an senior person that you don't know is rather inappropriate at any time, as a job candidate. But especially over a holiday, it reads as inconsiderate and self important.

Speaking of self important, what part of "I graduated from college in 3 years, and currently run my own company in NYC" expresses interest in Morgan Stanley? Where in the email does he demonstrate the ability to work on a "team," as he mentions he'd like to do?

Rather than convincing Gorman he could do the job or is interested in the work, Maddalone comes across thinking he's entitled to a spot at the company because of his accomplishments.

The bottom line: tenacity in job searching is good—as well as a healthy appetite for rejection—but it should be tempered with a little humility. CEOs are people, too. They don't want to be annoyed over the holiday, or treated as a stepping stone for someone else's objectives.

Cold calling does work sometimes; getting your name on company's radar can make all the difference a job opens up. And if you're already interviewing, having several points of contact at the company can help.

But if you mess it up, you can ruin your chances at the company and damage your reputation.

Here are few ways you can—carefully, intelligently—reach out:

1. Be humble

Yes, you are your own advocate, but know the time and place for self-promotion. Reaching out to someone you don't know is a good time to tone it down. Instead of your laundry list of achievements, emphasize your interest in the company, and the opportunity you see to specifically do great work with them.

2. Be polite

If you were visiting your target in person, would you feel comfortable asking them point blank if they received your letter of recommendation/resume/bouquet of flowers? Probably not, and for good reason—it's rude!

Instead, resist the urge to guilt trip. Mention that you sent the materials and wanted to make sure they received it. Then let it drop.

3. Be pleasant

Again, in person, would you launch into an elevator pitch before saying hello? Maddalone gets one thing right—wishing Gorman happy holidays. Greetings are very important, especially when asking for something (which is really what you're doing when introducing yourself regarding a job).

A nice touch is mentioning something going on with the company—that you heard about the merger and hope it went smoothly, that your HR contact mentioned the holiday party had karaoke, etc.

4. Be professional

This is less about "sounding" professional (ie. using jargon, formal letter structure), than it is about respecting corporate culture by:

1. Keeping your email concise and as short as possible, and

2. Using proper grammar, capitalization, and spelling.

The trick is sending a pitch-perfect note that reads as uncalculating, but shows flawless judgment and consideration for the reader.

Notice that Maddalone's email feels sort of stiff and buttoned up, but nonetheless has a few missing words and repeated phrases. Being able to communicate well off the cuff is a huge skill—make sure your email proves that you "get it."

Read More:
How to Build a Network Before You Need It
Joe Maddalone and T. Boone Pickens
Joe Maddalone and James Gorman

--Cathy Vandewater,