- Why cover letters are important (and for what jobs they are most important)
- What hiring managers look for in a good cover letter
- Strategies for writing compelling ones
Why is a cover letter important?
All cover letters are important, and some cover letters are more important that others
The cover letter is important to employers because they show the employer
Whether you are capable of formulating sentences into coherent thoughts
Your attention to detail, based on the number of typos and mistakes it contains
How much interest you have in a job based on how much effort you put into writing a decent one
The cover should be important to you because they are:
Your first good opportunity to show genuine, personal interest in a job
A way to put your communication skills on display
And for those of you concerned about masking any communication weaknesses, keep reading
A chance to provide additional color and descriptions to best highlight your previous achievements
For certain jobs, a well-written cover letter is critical! Examples include:
CISOs, Directors, Managers, Team Leads
Anything related to management is a definite; as a manager you have to be able to communicate in writing, often to folks who are non-technical, be it senior leadership or folks in business units
Penetration Testers
What? It’s not all about popping shells and breaking shit? Absolutely not!
Writing skills are vital for respected pen testers, because as much as you’d like to think you are paid just to break into stuff, you are actually paid to deliver a report; and the more people pay for your skills, the more they are expecting a damn good report they can present to leadership
Auditors
Just about everything they do involves writing
Incident Response and Forensic Analysts
They have to document every single activity they perform in case the investigation leads to something that is court admissible
What are hiring managers looking for?
Trust me when I say most hiring managers dread reading cover letters as much if not more than you do writing them
They read an abundance of terribly written ones
They read ones that were clearly written for a different job
Or worse: the person copied it directly from an internet example, slapped in the company name, job title, and maybe the person’s name to whom they are directing it and just called it a day
They can tell right away how much interest you have in the job by how much effort you put into your cover letter; and this is why bad ones are REALLY bad
Here are the things hiring managers want to see
Your ability to write - bottom line, that’s what these are all about
Something unique about you that sets you apart from the other candidates
Whether you paid any attention to the job description and identified points that align to that particular job
A sense that you have genuine interest in the job and/or company
Let’s dig a bit further into each of these
Your ability to write, aka basic grammar and writing skills, which means:
No Typos - proofreading and eliminating misspellings is essential
Particularly, make sure you correctly spell the company’s name, the hiring manager’s name, and the title of the position
Carefully examine words that spell check may not catch such as, its/it’s, they’re/their/there, and two/too/to
Missing or gratuitous punctuation - most common is to overuse commas
Overuse of a thesaurus
If you occasionally have to search for another word for something that you’ve already used a couple times in your letter that’s fine, but don’t pick an terribly obscure word to use, and don’t omit common words in favor of “bigger” words just to sound more impressive - it’s not
Avoid cultural slang and cliches
Americans tend to incorporate informal sayings and cliches into their writing, and you cannot guarantee that everyone who will read your cover letter will be familiar with slang and cliche phrases
Something unique about you that sets you apart
There are various aspects you might include
Your approach to solving problems
How you engage with other company stakeholders
Ways that you have helped instill a culture of security awareness
Programs you’ve written (original code) or applied in innovative ways
You might also consider hobbies or personal interests - particularly if you can show their relevance to this job opportunity
Showing interest in the job and familiarity with the job description
Your cover letter should point to one or more tangible examples of how you align with the job posting
Specific technology experiences
A project your led
Incidents you helped resolve (omit protected info of course)
Your cover should convey tangible interest in the job
Outside of the pay, is there something you can point to as a genuine area of interest?
Will this role permit you opportunities to learn or gain skills of particular interest?
Is there anything attractive about the company as a whole?
What strategies work best in cover letters?
So now that you’ve given thought to the general content, the last step is putting it together into a cohesive unit. In this final section we’ll touch on the following:
Guide to basic formatting
Cover letter pitfalls to avoid
Tips on closing out the cover letter (many people struggle with this)
Guide to basic formatting
I will link to a couple of examples - as mentioned in the previous section though, do not cut and paste these. Use these as guides not templates
The important components are:
Your full name and contact info first
The date you’re submitting the cover letter
Remember to update this if you are starting with a previous one
Address the cover letter to the intended recipient
If you know the recipient’s name, use it with their proper prefixes (absolutely research this)
Mr., Mrs., Ms., Dr., etc.
If you aren’t 100% certain on this, simply “Dear Hiring Manager” works fine
One of the worst mistakes you can make here is using the wrong prefix - it’s potentially as bad as using the wrong pronoun
The body of the cover letter, which should include:
The title of the position to which you’re applying
What interests you in the position
Call out a couple specifics around how your experiences would make you a good fit for the position
Perhaps dedicate two short paragraphs to this
Include something that is uniquely you
A success, experience, interest, hobby - something that another applicant is unlikely to have in common
Close it out with confidence (not arrogance)
More on this below
Sign off
A simple “Sincerely,” and full name is fine
An actual signature is nice but not necessary
Pitfalls to avoid in cover letters
Restatements of your resume
They already have your resume; this is your opportunity to tell them something that either doesn’t fit on your resume, or formats better in writing than as a bullet on a resume
Errors, typos, misspellings, etc.
Yes - I mentioned this above
Yes - it is important enough to be repeated
Sharing your life history
If there is a particular aspect of your history that is relevant and important to this role, by all means mention it, but they don’t want to read a biography
Speaking in negative terms
This isn’t the place to discuss bad experiences in previous employment
The only exception would be maybe touching on why you changing jobs in a short time (anything less than a year tends to raise questions)
Tread carefully with this
Making assumptions about the position or inflating the role
Speak to the elements of the job that are included in the description for sure, but don’t try to impress them with how you’ll turn an entry level job into an executive leader of the company
Embellish the importance of mundane experiences
So you don’t have a “Wow” experience to include - that’s fine; focus more on your approach to the job and your interests then
No one wants to hear how you revolutionized technology at your previous company by enabling a feature in an application
Closing out the cover letter
You don’t need to summarize all the previous points in the closing piece
It’s good to briefly restate your interest in the position/company
The last bit (one sentence, two max) should show confidence - things like:
Look forward to next steps, sharing vision, contributing value, etc
Focus on the future and what you’ll do for them rather than what you’ve done in the past
Best of luck to all of you on your job searches!
