So give the impression that you're the love child of a Holy Trinity: the brains of Albert Einstein, the stamina of Optimus Prime, and the persistence of Wile E. Coyote.
Once you get past the opening sentence, let me reiterate a word of advice: Keep it short! People don't have time to read your version of War and Peace. They're too busy four-lettering their way through work so they can get on with life and play.
Ideally, your email will be readable on an iPhone screen in the bathroom. Yes, shocking, but you may not be someone's highest priority and the only time your target might have to scroll through your cover emails is the same place he has a chance to track his Amazon packages—when he's sitting on the can.
In your brief missive, it's also vital to link your skills with the firm's specific needs. This is where your research about the company and job openings will pay enormous dividends. You might even get lucky and what you really want to do is what the company really wants you to do. If you're a golf fanatic, have a degree from Harvard in communications, and don't get an interview for that social media position at Callaway Golf, you might as well pack it in. Even I can't help you.
Personally, I like bullet points, and again, three is usually the magic number. Maybe because I was raised at the altar of PowerPoint, I've found everything in life is generally explained in three short, quick phrases. If you have four really good ones, fine, but anything more than that tends to lose your audience, and anything less feels like you don't have anything to say. So think about the three key points you want to make. Every industry is different, but in banking, for example, here's what matters in order of priority: work experience, grit and hard work, and affinity. Let me explain further, as if I were receiving an email from you.
Work Experience. Show me you've done this work before, ideally at an internship or previous job. Why? Because my time is valuable. I need to make sure I have time for work, watching Netflix, and coitus (that last one takes less time as you age, but I still want the option). Time also means money. I want the highest ROTI on my hires. Remember that ROTI, or return on time invested, is the return on any time expended as valued in dollars. Translation: I want you to do all the work so I can make all the money. The fewer number of hours I need to train you in the basics (i.e., non-revenue generating work), the more time you'll have to make models, pitches, and other grunt work that will allow me to earn the moolah.If you don't have the work experience, you're not exactly out of the running, but it does put you at a huge disadvantage. So be creative. Maybe there's something in your limited resume that can be reinforced in your cover letter. Underscore how you worked hard to get good grades in STEM while at the same time writing about Ponzi schemes for Wharton Magazine. Highlight something creative, even if it's a bit off-the-wall, like creating a PowerPoint presentation where you are the opportunity of a lifetime.To get your juices flowing, I prepared a sample pitch (which you can get if you register on my website2) that highlights a mock candidate, “Mister Perfect,” in the form of a hot IPO. Any resemblance to me is purely coincidental. Feel free to check it out and steal it if you wish.Note that this is a high beta strategy because although there's a chance you appear unique, smart, and innovative, you're more likely to come across as a complete weirdo. But like good ol’ Benny Franks said, “Nothing ventured, nothing gained,” right?One real-life unorthodox approach comes from Michael Henkin, former senior managing director of Guggenheim Securities. Someone who wanted to work for him agreed to work on a single company pitch as a trial run. This allowed Michael to assess him and ultimately “try before you buy.” It worked. Michael eventually hired him. Talk about betting on yourself!
Grit and Hard Work. Show me you'll put up with a lot of crap. A metric ton’s worth. I'm talking about working all hours and not bitching. Expect to get last-minute changes from me on a presentation that you handed me a week ago. Or I'll give you my markup a few hours before the meeting and expect it to be flawless. Remember, crap flows downhill, from the CEO client pissed at me because there were errors in the presentation to you who handed it to me five minutes before the meeting. So it better be perfect!One of the best bankers who worked for me was someone who had been a Mormon missionary. It dawned on me that nothing could take more determination than spending years selling God door-to-door in the farthest-most regions of the Earth facing constant rejection by a bunch of heathens. I knew this person would walk through walls to get the job done. Plus, if he was any good at it, not only would he reserve his place in heaven (and maybe pull a few strings for me), but also chances were high that he was a natural salesman, which would bode well for his future rise in banking. I mean, if you can sell God to the damned, you can sell anything to anyone.Personally, I earned my first grit-wings as a janitor at a Safeway supermarket. I was paid a minimum wage of $3.35 per hour to clean toilets, then got chewed out for failing to double-bag groceries. Nothing is more humiliating than feeling you aren't cut out to neatly stack shopping carts or clean all the piss out of a urinal. That experience put me knee-deep in grit. I worked in college out of pure desperation, but my three jobs while still graduating with honors with a dual degree helped me once I started looking for a job. It showed future employers that if I could put up with real crap, I could certainly stomach their metaphorical shit.
Affinity. Show me that we have something in common. Maybe we're both Houston Rockets fans? Or both watch Pokimane on Twitch? OK, how about being left-handed!? Look for something fun or something you can mock together—school, hobbies, card games, odd habits, anything! But make sure it's not illegal, unethical, or just plain weird. Only your mom will tolerate that you munch on your toenails after cutting them.Sreene Ranganathan, a member of Facebook's Corporate Development team and former Jefferies banker, shared how he first got into banking. When he was in school, by the time he decided he wanted to pursue an investment banking career, he had missed all the on-campus interviews. Undaunted, he did the research and found 107 alumni who worked at various banks and sent customized emails to each one of them. He highlighted recent school activities, figuring it might help him establish common ground with the recipients. It worked! Six answered back and helped him get interviews and, ultimately, a job. Sreene's persistence, coupled with using his noggin to establish some mutual affinity, got him a job.One last point on affinity. Never, ever wade into the shark-infested waters of politics, religion, or race. You might as well bang your head against a landmine in Fallujah. Although it might not be obvious at first blush, you never know if you were dinged from the process because their God told them there were no open positions for Satanists. But if it does happen, look on the bright side. At least you can sue them for asking you an illegal question. Lemon from lemonade!
Go Out with a Bang
Now comes the finale—your signoff. People don't spend enough time on ending an email because they aren't aware of recency bias. It's the tendency of people to place a higher value on recent events than on ones that occurred in the past, which in this case means that the last few words of your email are more important than how you start. This is your last chance to make a final impression before you lose the recipient—potentially forever. So make it stick. Avoid the mundane and the boring. Sure, you can play it safe with something like Sincerely, the most vanilla in this category. No chance of totally screwing up with that one, but I always thought it a little weird—kind of like the written version of “To be honest… .” WTF? You've been dishonest and insincere this whole time and now you're finally going to tell me the truth?
Best or Best Regards has always been my personal go-to. If you're choosing between the two, I prefer Best Regards. It means I was willing to spend at least two words on you and I want only the best for you. Unfortunately, this makes Warm Regards and Regards the equivalent of a limp handshake. I'd avoid those.
Thanks is another one I like, as it can create a subliminal obligation for the recipient to reciprocate, which means you're taking advantage of the celebrated reciprocity bias, which is
