Cover Letters, Etc.

Go back to Job Search Prep Syllabus.

As a company owner, I occasionally get emails, voicemails, LinkedIn notes, and other forms of inquiries from folks looking for a job.

Based on my own experiences (like this one), as well as experiences shared with me by others, here are 10 tips I can offer for the best way to reach out to others for employment.

  1. Stay in control. If you cold call to ask about open positions, you are completely at the mercy of my mood. If I happen to be thinking about my needs relative to the role you are seeking to play, or if I’m feeling charitable, maybe we’ll talk. If I’m busy, I’m deleting your email before I’ve read the first line, and I’m certainly double 7’ing your voicemail message without calling you back. It’s not that I want to be rude, it’s that I didn’t ask for you to contact me, so I don’t feel obligated to respond.
  2. Play the game. If we meet and, after learning that you’re looking for a job, I ask for a specific piece of information that cannot be found on your résumé , don’t respond with your résumé . Have enough confidence in yourself to play the game! On the dating scene, you don’t move straight from “Hi!” to “Let’s hang out!” There is a space in between that is filled with courtship. Your emails to a prospective employer should demonstrate that you know how to fill that space in a professional context. Don’t get pushy.
  3. KISSASS. When it comes to electronic communications, we go beyond Keep It Simple, Stupid. We go to Keep It Stupid Short And Stupid Simple. Especially if you’re reaching out to an executive, expect your email to be first seen on a PDA. Get to the point, get there fast, and get out.
  4. Be concise. Know what you want, and what I need to say yes to your request. You send me a detailed email, a separate cover letter in an attachment, and your résumé . It’s about four pages of material all told. Hi, have we met? I’m one of the 300 million Americans suffering from information overload. You’re not helping. In fact, what I know about you from your attachment-laden document is that if you worked for me, and I asked you what time it was, you’d give me the time buried in a thick explanation of how a watch works. In other words, I don’t have time for you.
  5. Use LinkedIn wisely. Please, be helpful, creative, and confident. Please. If you just burned a connection to ask me if you can send me your résumé , or worse, if you burned a connection to send me 6 paragraphs about your technical skills and an inquiry as to any open positions I might have or might know about, I’m going to be depressed for you. Don’t make me sad. I want to feel good.
  6. Think for yourself. I’ve heard the story about the person who sent a shoe to a prospective employer along with a clever note about having a foot in the door. I’ve heard about champagne sent in anticipation of a hire worth celebrating about. Don’t copy someone else. Be yourself. Stunts like those are expensive, risky, and better be attached to a highly charismatic individual who can “pull them off.” Frankly, if you were the kind of person who could pull them off, you wouldn’t need to read an article to get the idea.
  7. Stay on top of things. I get lazy, distracted, and forgetful. And it’s your future at stake. So if you’re not sure where you stand, you own the follow up. Don’t be annoying, but if you do it right, I won’t begrudge you managing your own future. In fact, I’ll appreciate it.
  8. Don’t be lazy; mail merge is not your friend. I once got an email to “Dear Recruiter.” It was from a college senior at a great school who wanted an internship. My reply was, in part, “…if you didn’t have the energy to address your email to me—and my name is the name of my firm, you didn’t even have to look it up, for crying out loud—then I don’t have the energy for your application.” Get the message here?
  9. Get comfortable with non-linear communications. I don’t care about you and your job search, I’ve got my own problems. So if you want me to care about you, you have to earn that by first becoming someone I want to care about. And you know who I care about? I care about people who care about me. Who solve my problems. And by problems, I don’t necessarily means what I’m dealing with in my business! It could be choosing a college for my kids. Or dealing with weekly international travel. Or taking care of ailing parents. There is no shortage of ways you can help me—starting with something as simple as sending me an article relevant to my life. What you cannot expect is to be able to come to me expecting to need job, talk about needing a job, moving to an interview, and then getting a job. All that will happen… but with a whole lot of circuitous motion and other “stuff” thrown in.
  10. Match your tone to the medium. Please don’t send me a formal email. I haven’t the time. Don’t be sloppy, don’t skip out on punctuation, don’t tell me I’ll “ROFL when I c yr rez.” But don’t just as you wouldn’t wear a tux to a BBQ, don’t be too formal in your emails, either.


If you are going to use email, LinkedIn, and other forms of communication well, then you need to walk a mile in my shoes first, and understand what I expect of each channel and the people who reach out to me through those channels. You need to put your fears about what to say to rest, and you do that by improving your understanding of the situation.

But how?

You do this by thinking like a recipient rather than a sender. It’s easier than you think… because you ARE a recipient. Don’t you have habits to help you screen emails? What do you do when you get a note from someone you don’t know?

Which ones do you automatically delete? Which do you read? Which do you act on?


Here’s a simple way to start writing better messages:

  1. Set up a second email address if you don’t already have one.
  2. Write your message—whatever it is.
  3. Send your message to your 2nd email address.
  4. ALSO turn on auto-forwarding so that copies of all the messages you receive get sent to your new email address. If that’s too technical for you, just SEND 20-30 other emails from your email inbox. Forward one or two, but for most of them, cut and paste into blank emails. You want the new email inbox to look authentic.
  5. Wait at least 6 hours.
  6. Go check your new email, and ask yourself: (1) Did your note pass the spam filter? (2) Is the subject line compelling?  And (3) When you open message after message, does your message to yourself feel right? Or does it stick out like a sore thumb?
  7. Refine, resend, review until you are happy.
  8. Send the message for real.

Jobs Near You

Restaurant Delivery
DoorDash Potomac, MD
Instacart Delivery Driver - Flexible Hours
Instacart Ashburn, VA
Drive with Lyft - No Experience Needed
Lyft Ashburn, VA
Retail Customer Service Associate- FedEx
FedEx Office Sterling, VA
Sodexo Sterling, VA

2 responses to “Cover Letters, Etc.”

  1. Beverly Lorig says:

    Great suggestion. I get regular emails from someone who marks everything urgent. What do I do? Delete…in an urgent fashion!
    I am going to do this exercise and will let you know what I find! Fear factor!

  2. Emily says:

    Anyone who is having trouble getting interviews should definitely watch Willy and Jason’s video on cover letters and pay attention to Jason’s break-down of Willy’s cover letter. The advice on demonstrating an emotional connection to the company in your letter has been my golden key. I’ve gotten two interviews since I started taking this advice (compared to zero before), and both times the interviewer has mentioned my cover letter as responsible for sparking their interest in me. If you don’t have a personal connection to the company you are applying to, do some research and make one. If you really want to work for the company, then you should probably invest some time in figuring out why you want to work for them beyond getting paid. (Although, I know sometimes that can be easier said than done.)

    Thank you for all of your wonderful advice, guys!

Leave a Reply

Your email address will not be published. Required fields are marked *

Browse ODOJ

Learn about interesting employers with awesome jobs.

Jobs Near You

Popular Locations

Popular Fields

Popular Companies

Get a Job Faster

Check out our job search course and articles.

Copyright © 2007-2015 One Day, One Job. All rights reserved.