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How to Write the 7 Most Awkward Job-Related Emails

Writing Emails

It’s not what you say but how you say it.

In Boston this spring, the Massachusetts Department of Transportation proved that statement when it turned a mundane road sign into a viral sensation.

Rather than tell motorists to “Use Your Turn Signals,” the department took a more familiar approach with locals:

Now go “Pahk the Cah in Hahvahd Yahd.”

MassDOT officials realize to catch the attention of drivers, they need to connect with their audience in a thick Boston accent.

The takeaway for our careers? People will listen to — and act on — what we ask of them, but we need to use the right language in the right ways. Frankly, that’s a huge reason young professionals struggle to land jobs.

Below are instructions for how to write the seven most awkward job-related emails. You know, the kind of emails where you think “Umm, how do I say this exactly?”

1. How to respond when you don’t get the job but still want to stay on the company’s radar

“Hi _____

Thanks a lot for the response. I’m sorry I did not land the job but appreciate your email to let me know.

All the best,


Note: Then, when they least suspect it, you also send a handwritten note and thank the person for the opportunity to interview. Why? Check out this comment from an NTLB post republished on Ragan, a communications resource: “I sent a thank you note after I bombed a technical interview where I was clearly not qualified for the job, and a couple weeks later they called me with an opening that was a perfect fit because my note had made them remember me.”

2. How to network with someone who’s really important

“Hi _____

My name is _______, and I am [how you know this person]. I saw [your connecting person] the other day, mentioned what I’m up to and she suggested I connect with you.

[2-3 sentences on "what you're up to" and in this section, clearly explain why you'd like to network with this person. What do you want from him/her? Be direct.]

I know you’re busy, and I would really appreciate a few minutes of your time. If you have a few minutes, we can meet in person somewhere convenient for you or talk over the phone.

Thanks in advance, and please let me know what works.

- You”

Notes: It’s important to tell the person 1) your connection to him/her 2) what you need/want and 3) you understand he/she is super busy and you want to be respectful and not take a lot of time. Important people move fast, especially in big cities.

3. Networking email to someone you sorta kinda know at a company where you want to work

“Hi _____,

My name is _______. A while back, you and I [give the reason you two know each other; be as descriptive as possible so the person will know right away]. I hope you’re doing well!

I was on your company website and see your team is hiring for [specific name of the position]. I am well qualified for the job and have a good deal of experience. [Give one solid example to back up your claim; no longer than 1-2 sentences.]

If I send along my resume, do you think you can pass it to the right person? If you need me to provide any other information that would help, I’m happy to do so.

Thanks so much, and I hope to hear from you.

- You”

Notes: Details. Details. Details. Be clear who you are, how you know the person and what you need that person to do. And don’t make this mistake with your job application.

4. Email two weeks after a job interview and you’ve heard nothing

“Hi ______,

My name is _______, and two weeks ago I interviewed at your office for the position of _______. I want to follow up and check on the status of the job opening. If you need more information from me, please let me know.

Thanks so much,

- You”

5. Bothering someone important who said he/she would pass along your resume but hasn’t yet

“Hi _____,

I hope you’re doing well!

I am ______, and I [remind the person how you two became acquainted]. I want to follow up about my resume as you mentioned you could pass it along to [the person who you want to see it]. Again, it would be great if you’re still able to do that.

And if you can send along the resume, please remind [the person who you want to see it] that [1-2 lines on why you are the best person for the position; give your networker a bit of ammo he/she can use].

Again, I know you’re busy so I appreciate your willingness to help me.

Please let me know if you have any questions.


- You

Notes: Always overcommunicate the small details. Never assume people remember you or what you need from them.

6. How to ask for a letter of recommendation from someone you haven’t talked to in five years

“Hi _____,

This is [your name], your student from [names the class(es), the year(s) and the school]. I know it’s been a while since we last spoke, and I hope you’re doing great.

[If you feel comfortable enough, ask a question or two about the person. For example: "How's college life still treating you?" or "How's your family?"]

I am [the reason you need the letter of recommendation]. I would appreciate a recommendation from you if you have the time. If you need me to send along any biographical information or remind you of the work I did in your classes, I am happy to do that.

Thanks so much, and I hope to hear from you soon.

- You

Notes: Offer to provide additional information, make absolutely sure the person will remember who you are and, in general, be accommodating. You have 17 other challenges to worry about in the real world. Avoid a snag here.

7. How to write an email to set up the “I’m leaving” conversation with your boss

“Hi _____,

Do you have a few minutes at the end of the day? I’d like to talk with you about something.


- You”

Notes: No easy way to start this conversation, but it’s best to leave the details to the in-person meeting.

(This content was originally posted at News to Live By.)

Read the original blog entry...

More Stories By Shelly Palmer

Shelly Palmer is the host of Fox Television’s "Shelly Palmer Digital Living" television show about living and working in a digital world. He is Fox 5′s (WNYW-TV New York) Tech Expert and the host of United Stations Radio Network’s, MediaBytes, a daily syndicated radio report that features insightful commentary and a unique insiders take on the biggest stories in technology, media, and entertainment.

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