The Best Cover Letter Tips Ever

Letter from Lyman Spencer

Nothing says “Hire me now!” like super-curly handwriting. (Or, in this case, “please send me some rulers!”)

When you’re approaching a company for employment, your cover letter is your opportunity to make a great first impression. These tips will guarantee that you get the attention you deserve.

Provide concrete examples of your qualifications for the job. By “concrete,” I mean “specific,” unless the job involves actual concrete, in which case I mean “concrete.”

Be brief and to the point. Cover letters longer than one page are suitable only for direct mail solicitation positions. For those, cover letters should be no shorter than five pages, with multiple inserts, sent to the hiring manager several times a week in differently colored envelopes to test open rates.

Specify the position for which you are applying. “Whatever you’ve got” is not specific enough.

Mention where you learned about the position. This is especially important for companies with many openings. It would be awfully embarrassing to be interviewed for a position with slightly different requirements!

Use LinkedIn and other websites to research the hiring manager and personalize your greeting. For example, “What up, Joe! How’s that hawt wife of yours?” would be suitable only if you can verify that his wife is indeed “hawt.”

If you have been referred by someone known to the hiring manager, mention his or her name. Be careful, though, because you don’t want to seen as a name-dropper.

Here’s an example of name-dropping:

Last night, at LeBron’s house, Kim Kardashian said I would be perfect for this job. Philip Roth and that little girl from Beasts of the Southern Wild agreed.

Here’s an example of using references well:

Dear Dad, Mom said you need to give me a job.

Don’t go into details about why you’re looking for work or how long you have been looking. That’s what your blog is for.

If you include URLs to online portfolios or resumes, make sure you have created a custom, personalized URL. Instead of a random string of letters and numbers, use something like “”

Cast yourself in the best possible light. Use words like “awesome,” “rocking,” and “superstar” multiple times in your letter.

Consider hand delivering your cover letter. Almost no one does that, mainly because it’s creepy. If you go this route, consider taping your cover letter to a rocking box of homemade chocolate chip cookies. Consider sending me a box, too, as thanks for this awesome advice. Then you’ll be a superstar.

Use a professional-looking font. Comic Sans is not professional, unless you’re applying to every freaking business in my town. What is up with these people?

A little dab of perfume never hurts.

Save Time in Your Job Search with TextExpander

TextExpander from Smile Software

TextExpander from Smile Software

When you’re applying for jobs, you find yourself entering the same information into online forms over and over again: work history, contact information, names, etc. A few forms allow you to import information from an uploaded resume or from your LinkedIn profile, but even these don’t always get all of your details correct. It isn’t easy to stay motivated during the job search, and entering the name and phone number of your supervisor from seven years ago for the 50th time doesn’t help any.

This is where I use TextExpander to save time and stay focused.

What is TextExpander?

TextExpander does what its name says: expands text. At the simplest level, the program allows you to create custom shortcuts — called snippets — for text that you have to type repeatedly. For example, I have a snippet for my cell phone number. I can type:


anywhere I need to type my cell phone number, and TextExpander changes the string into my number. Not only is “ccell” shorter than my 10-digit number, but it also takes less time to type on my non-number pad-equipped Macbook.

There are more advanced features — I’ll cover one of them below — but you can read more at the TextExpander website.

Note: TextExpander is a Mac-only program, though there is an iOS version for iPhone and iPad. There are similar programs for Windows, and if you use one that you recommend, tell me about in the comments.

Basic Examples: Work History

How does this work in practice? Let me share a couple of actual examples that I use for entering my work history. Perhaps this is more helpful to me than to other people, because I have a history of long job titles at organizations with long names. Let’s take one of my former positions as an example: Director of Foundation Services at the Cincinnati Better Business Bureau.

When I type:


TextExpander expands it to “Cincinnati Better Business Bureau.” (The period at the beginning is a trigger that distinguishes the Snippet from the initialism CBBB.)

A couple more common snippets related to my CBBB position. The following two:


expand to “Director of Foundation Services” and the CBBB’s main phone number, respectively. You get the picture. Snippets can expand to much longer text, too, so I could create Snippets for the CBBB’s address, my job description there, or even my full resume.

Advanced TextExpander: Cover Letter Templates

Now for a more advanced example. One of my deep dark shames is that I hate writing cover letters. Actually, that’s not quite accurate. I really don’t mind writing one cover letter, but by the third or fourth or twentieth, I’m a bit weary of the procedure. So I’ve created a cover letter snippet that saves me a great deal of time and mental energy. All I have to do is type:


and a small pop-up window appears.

TextExpander Window

Click for a clearer image.

Notice the blanks in the text. This is a generic cover letter, with spaces for the address, salutation, and some custom language about my experience and expertise. (Today’s date is automatically generated by TextExpander.) When I’ve filled in the blanks, I click “OK,” and the new text is inserted into whatever program I’m using.

I’m still not done with the cover letter, as this is only a template to help get me started. But the hard work of getting to a first draft is done. Now I can revise, reword, and craft the cover letter to fit the specific position, much faster and much more easily that if I were starting from scratch each time.

TextExpander is one of the three apps I immediately install on a new Mac. It syncs with Dropbox, too, so that my snippets travel with me from computer to computer. TextExpander offers several pre-defined snippets (e.g. special characters, HTML coding), and smart people like Brett Terpstra and David Sparks have created bundles of TextExpander snippets that are much better than anything I could come up with. TextExpander also allows scripting within snippets, enabling even more powerful shortcuts. One of my current favorites is a script snippet from Brett Terpstra that pastes in the current URL from Safari.

Do you have any tips for speeding up job applications? If you use TextExpander, do you have any favorite tricks?