Cover Letter Flowchart
23 Feb 2022
Table of Contents
Heaven help me, I hope I don’t regret publishing this next time I apply for a job – I’m practically handing over the secret decoder ring to my inner thoughts. 😅
One of my hobbies is giving people cover letter makeovers. Having been blessed with the opportunity to screen resumes many times in my career, I’ve had a chance to pick up tricks from the best of the best, and I think I’m pretty decent at helping people make themselves look good in a way that’s completely honest and upstanding.
The answers to two questions guide the tone and structure in any cover letter I help write:
- Q: What’s your motivation for applying?
- A: Desperation: “I need a job fast.”
- A: Specifics: “I want this job because of what’s written in the advertisement.”
- A: Unenthusiastic: “I probably don’t even want this job, but never say never.”
- Q: Do you have any special skills from the job ad?
- A: Yes.
- A: No.
Tone guides
You can borrow concepts from all six “tone guides” below – sometimes, as you think about what to write, you might realize your answer to the questions has changed, or that it’s some combination of several answers, depending on which part of the job ad you’re thinking about.
TL;DR
| Skills - No | Skills - Yes | |
|---|---|---|
| Desperation | Wow, we’re both awesome! I love you! | Wow, we both XYZ! 💪💪💪 And I have other skills, too! 💃 |
| Specifics | Wow, we both *ahem* “XYZ”! 😅😅😅 And we’re both awesome! | Wow, we both XYZ! 💪💪💪 I love you! |
| Unenthusiastic | (Seriously?) | Wow, we both XYZ! 💪💪💪 Let’s talk. |
Motivation - Desperation. Skills - No.
- Enthusiastically fire their own words back to them about their business needs and/or mission (as expressed in the ad and/or on their web site), slipping in mentions of your soft skills & transferable experience & past successes.
- Need filler to hit a long enough letter? You’d be surprised what can sound professional. Just make sure it has both what they can do for you and what you can do for them in it.
- Want a shorter commute in a brick-and-mortar business-to-customer environment? “… blah blah blah … serve my community … blah blah blah …”
- Seriously, mirror their corporate mission statement. But make sure something about you is in the sentence so you don’t come off as a meaningless copy-paster, but instead sound like a match made in heaven for the company’s mission.
Motivation - Desperation. Skills - Yes.
- Highlight your experience with the special skills.
- Need more words? Highlight what a flexible team player and fast learner you are. Maybe a little story about saving the day or earning revenue by taking initiative to perform a drudge-work task (preferably one that sounds vaguely related to the day-to-day boring tasks of someone doing the job you’re applying to) or learning a new skill (preferably that requires the same type of transferable/soft skill – such as attention to detail or clear writing – as one from the job ad).
- Need more words? Enthusiastically fire their own words back to them about their business needs and/or mission (as expressed in the ad and/or on their web site), slipping in mentions of your soft skills & transferable experience & past successes.
Motivation - Specifics. Skills - No.
This is when you really wish you had a job doing XYZ, but you haven’t yet had a job doing XYZ.
- Enthusiastically fire their own words back to them about their business needs and/or mission (as expressed in the ad and/or on their web site), slipping in mentions of your soft skills & transferable experience & past successes.
- “Wow, (insert your soft skills & transferable experience) is just like skill XYZ that you need help with!”
- Make a mountain out of a molehill about a small experience you had that had something to do with skill XYZ.
- (Be ready to elaborate in the interview about all the transferable skills you used during this experience, and to share some insight in the interview about the connection between XYZ and the business purpose it was used to accomplish – e.g. why it was right for the job or wrong for the job.)
- “I’m so enthusiastic to do XYZ all the time. I saw how useful it was for (business purpose A from your past), which it just like (business purpose B from the job ad or the company’s mission statement), so we’re going to get so much done together with me helping you do XYZ.”
Motivation - Specifics. Skills - Yes.
This is the kind of cover letter you’ll likely find easiest to write.
You’re going in with confidence about at least part of the job ad, so your task is simply to craft good business English that lets the company know what a rockstar you would be for them.
- Highlight your experience with the special skills, and do it with enthusiasm and mirroring
- “Oh my gosh!!! YOU’RE looking for XYZ? I’M awesome at XYZ. And I love doing XYZ! What are the odds? We should totally work together, I could help you (insert their business needs and/or mission) so much.”
- Afraid you’ll be rejected because can’t do certain specific skills in the listing very well? Just don’t mention them (you can figure out what to do about that in the interview), or borrow from the “mountain out of a molehill” approach in “Motivation - Specifics. Skills - No.”
- Need more words? Enthusiastically fire their own words back to them about their business needs and/or mission (as expressed in the ad and/or on their web site), slipping in mentions of your soft skills & transferable experience & past successes.
Motivation - Unenthusiastic. Skills - No.
Wait, why are you even applying to this job?
But if you insist, follow the principles under “Motivation - Desperation. Skills - No.”
Motivation - Unenthusiastic. Skills - Yes.
- Highlight your experience with the special skills, and do it with enthusiasm and mirroring
- “Oh my gosh!!! YOU’RE looking for XYZ? I’M awesome at XYZ. What are the odds? I could help you (insert their business needs and/or mission) so much. Let’s talk.”
Miscellaneous tips
Length
4 paragraphs. Maybe 3 or 5. Definitely not more than 1 page in a font size that’s at least 10-point, preferably larger.
The first sentence/paragraph is to get someone to want to keep reading. If I have a clever sentence, a referring name to drop, etc. that goes here. So does a very concise mention of which job ad this is about. If I have nothing interesting to say, I just try to write something catchy that name-drops my most relevant specialized skill or enthusiasm along the lines of a first interview question asking, “So why do you want this job?” Only way more concise than I’d answer it in an interview.
The last paragraph is, “Call me!” Not “Please call me” or “I’d love to speak with you” but “I’m looking forward to hearing from you.” Firm handshake! E-mail address and phone number right in the paragraph.
That leaves about 2 paragraphs of 2 sentences apiece to do everything that fits the spirit of the letter I chose with my flowchart above.
Editing
Not a great business writer?
Here’s a tip: write an unprofessional but enthusiastic letter that conveys everything you wish you feel – perhaps it’s even a little bit too long (like a page and a half, not an essay). Then give it to a friend who is a good business writer and let them help you edit it.
Eventually, you’ll get the hang of what kinds of adjustments your friends make and learn to do it yourself. Or, at least, you’ll have learned enough from your friend to make better use of “sample cover letters” you find on the internet as a compare-and-contrast tool to your own writing to help you self-edit. And you can always go back to your friend for a final edit!
Imagine an interview
Seeking inspiration? Look at “sample interview questions” – all those “tell me about a time…” types of question.
Things that make great interview stories are great cover letter stories – you just don’t get to use as many words telling them.
Quiz yourself
More inspiration: have a friend take notes as you answer the following questions:
- Q: What about past work, personal or professional, has made you feel creative?
- Q: What about past work, personal or professional, has made you feel talented? / What are your professional and interpersonal and organizational superpowers?
- Q: What about past work, personal or professional, has made you feel helpful?
- Q: What about past work, personal or professional, have you enjoyed doing? (Even if you don’t anymore.) Why?
- Q: What skills do you lean on to “fake it ‘till you make it” or “overcompensate” when you’re in over your head or have impostor syndrome? (Hint: these are probably superpowers, and considering you’ve been able to use them successfully multiple times, likely quite useful traits that a future employer would love to learn that you have.)
