Cover Letters: Stop Writing Snooze Notes!

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Let’s be honest — most cover letters put hiring managers to sleep. “I am writing to express my interest…” blah blah blah. If your letter reads like that, you’re already in the discard pile.

✍️A good cover letter doesn’t rehash your entire resume. It connects the dots between you and their problem. Think of it as your 30-second elevator pitch in written form.

⚠️I want to caveat something here: This post is aimed at that early to mid-career professional. Or even a recent college graduate. It may not be applicable to someone just looking for that first job that will often be in a high turnover industry. Or for executive positions, which will be covered in a future posting.

🔎There Are Two Main Types of Cover Letters

In my experience there are two types that I have seen.

• The cover letter attached with a resume in response to a job announcement.

  
  

• The cold call letter that is sent unsolicited with a resume.

⚠️"Cold calling with a generic cover letter and resume may feel like blasting a shotgun. Don’t do that." 

✍️If you have marketable skills, education, and training, you should take the time to focus on quality outreach, not quantity. Focused time will almost always net you a position that you want, not just any job where they need a body now.

🔎Why Cover Letters Still Matter

Yes, some managers barely glance at them. Others read them after shortlisting resumes.

Either way, a cover letter is a chance at bat. Done well, it tips the scales in your favor. Done poorly, it just wastes space.

💡Pro Tip: From a hiring manager perspective, I would give a cover letter about 5 seconds worth of time. Unless it immediately struck me and kept me reading, I was moving on.

⚠️When I say struck me, "I mean, I saw something quickly that made me want to look deeper into the resume". Normally that was a fact, or skill that I was looking for and I could see it immediately.

🔎The #1 Mistake

⚠️Generic, one-size-fits-all letters. “Dear Sir/Madam, I would like to apply…” "I am seeking a position that". That’s not a cover letter, that’s spam. If I can swap a company name with any other company, you’ve missed the mark.

💡Pro Tip: Think of this as your first introduction, that first, handshake, that "tell me about you moment" (in 5 seconds or less).

🔎Who Do You Address It To?

“Dear Hiring Manager” Screams copy-paste. "To Whom it may concern": is "in my opinion" a nonstarter, period! A little digging goes a long way:

• Read the announcement carefully. Often the point of contact (POC) is buried in the job posting. (If you reach out, they may not know a name, but they may know some details that will put you into a path to finding out)

• Google the company. The structure/org charts may lead you to a name, a contact, or at least the office, or team you would be working for.

  
  

💡Pro Tip: You should already be doing this just to ensure you are targeting your resume correctly and understanding what experiences you have, that align with what this company needs. True for both your resume build and prepping for interview questions.

• Check LinkedIn. Search the agency or company + job title. Often the team lead is right there. (Using the team, or department name shows you at least did some research)

  
  

• Call HR. A quick call asking, “Who should I address my application to?” takes 30 seconds and shows initiative.

  
  

• Last resort. If you truly can’t find a name, or even the name of the team or department that has the opening, then “Dear Hiring Manager” works — but make it the exception, not the rule.

  
  

💡Pro Tip: Addressing it to a real person instantly lifts you out of the “generic” pile. It shows you did your homework.

⚠️(I can say from experience, out of thousands of resumes received over the decades. I can count on one hand the times I received a cover letter addressed to me personally as a hiring manager. Yes, I read those)

🔎A Structure That Works

Three short paragraphs (Or less). That’s it.

1. The Hook: Show why you want this job.

   “As someone who has led federal acquisition teams for over a decade, I was excited to see DHS’s posting for a Program Manager. This is exactly where my background fits.”

   
   

2. The Value Match: Connect your skills to their need.

   “In my last role, I managed a $2B acquisition portfolio and built the process playbook now used across multiple agencies. I’d bring the same discipline and results to your team.”

   
   

3. The Close: Tell them what you want.

   “I’d welcome the chance to discuss how I can help deliver results for DHS. Thank you for your time and consideration.”

   
   

🔎Tailor Without Rewriting from Scratch Each Time!

✍️Don’t reinvent the wheel for every job. Build a framework letter with blanks you can fill in:

⚠️(We have covered much of this in previous posts: "Interview like a pro", "Narratives vs Bullets", "Questions you will always be asked"). This is about building out your story and having it at the ready.

• Company/agency name.

  
  

• Job title.

  
  

• Space for 1–2 specific examples that align with the posting.

  
  

• Ending and signature block.

  
  

✍️Swap those out, and you’re tailored in under 15 minutes.

🔎⚠️Common Pitfalls

• Rehashing your resume. If you’re just copying bullets, why send it?

  
  

• Too formal. Nobody talks like a 19th-century butler.

  
  

• Too casual. This isn’t a text message. Find the middle ground.

  
  

💡Pro Tips:

• Keep it under one page (3–4 short paragraphs max).

  
  

• Often the tone of the announcement will give you clues as to how to match the tone with your cover letter.

  
  

• Use plain language. If I need a dictionary, you’ve already lost me. (This includes acronyms, never assume the person reading a cover letter knows anything about your previous world of work, if you make me have to think about what something means, I am moving on).

  
  

• Always write to the reader. What problem do they need solved? (It is always in the announcement) How are you the solution? (Come right out with it: I am level III certified in______: Current security clearance of_______: Decade of specific experience with_____ at the $_____ level). You will see from the announcement what they are looking for.

  
  

• ✍️If you see something repeated in the job announcement a few times, (even if re-worded a few different ways) you know that skill is a key one, and important to highlight.

  
  

🎯The Bottom Line

A cover letter won’t get you hired. But it can get you noticed.

And that’s the whole point — to move you from paper to interview.

Don’t write a snooze note. Write something that makes the hiring manager think,

✍️“This one’s worth a closer look.”

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