How to Write a Winning Cover Letter: The Dos and Don’ts

Let’s face it. We’ve all been there. This great opportunity. Your résumé is done, redone, buffed and dusted.. Save for this one painful awesome part that keeps holding you back – The winning cover letter!

I must admit that this is my personal worst part of job applications.

It is probably how shiny fruits feel like in the market when they are passed over.

Dejected. Rejected. Despondent.

Reminds of Meredith Grey’s infamous anecdote to McDreamy in the Grey’s Anatomy series: “Pick me. Choose Me. Love Me.” It is not an easy position to be in, when you know you deserve something yet have to go to to great lengths to convince someone that you’re worth it. That’s how I feel every time I have to write a brand new cover letter.


When my recently graduated (YAAAAAY!) younger sister asked me for help with her cover letter, I must honestly admit I died a little bit inside. For years I had kept one template which I unashamedly recycled and lazily reused save for occasionally changing a few lines depending on my mood and the urgency of the application.

But the truth is, I am not who I was last year. We all grow. And so should our cover letters and résumés! Lately I have been trying to revamping my life and after I finished helping the kid sister make a brand new one for herself I decided it was about time I updated  my resume and cover letter as the first steps to my personal overhaul amongst many other things – I choose not bore you with today.

Every time I get to the cover letter I always think to myself that if I was a hiring manager somewhere, I wouldn’t even bother requesting for them! I mean, aren’t they all the same with their self opinionated half truths???  “Focused”. “Work well under pressure” and other similar what-nots.. Honestly, if people (apparently) don’t want to read cover letters and most people do not want to write them.. Why ask for them?!


However, cover letters are not about regurgitated taglines. They are the first chance you have to impress an employer – I have come to learn they are not just a protective jacket for your résumé. I guess the trick is to put yourself into the shoes of someone who receives hundreds of cover letters every day. Ask yourself: if I was in that position, what would inspire me? What would catch my attention?


Like it or not, you’re a commodity, and you’ve got to sell yourself to the employer.

So here are some useful pointers I gathered while begrudgingly researching on this delightful topic:

The absolute Do’s and Don’ts

  1. Do not recap your résumé in prose form: It’s redundant, harder to read than the actual résumé, and provides no additional insight.

    • A cover letter is a personal introduction that accompanies your resume; as such, it should augment your resume in a more personal manner. As a rule, the more personal your cover letter is, the better.
    • Think of your cover letter as an opportunity to distinguish yourself from other job seekers, by highlighting what makes you a unique applicant.
    • Your cover letter also plays a critical role in creating a hiring manager’s sense of you as a person. Use the cover letter to convey more fully who you are than your resume.
    • Go into detail about your background instead of reiterating information on your resume. Remember, your cover letter provides a sample of your writing to a perspective employer.
  2. Do not let it be too long! Please let it not be like listening to your grandmother singing your praises for hours an end. A long cover letter loses the interest of a hiring manager at first glance.

    • Keep the cover letter as short and precise as you possibly can. Rule of thumb is that it should be kept to one page. The shorter the better. It should be brief enough that someone can read it at a glance. You do have to cover a lot of ground—but you should do it succinctly!
    • Personalize your salutation to an individual whenever possible using their name, including his or her title (avoid “ To whom it may concern,” if possible), and always for a specific organization.
    • Your introduction should indicate how you came to apply for the position such as “Responding to a posting on the XXX media”, “Referred to by Jane Doe in Department Y”
  3. Do not write a cover letter as if you are filling in a form: This says, essentially, “Dear Sir or Madam: I saw your ad in the paper and thought you might like me.” And it’s clearly a form letter where maybe you get the hiring manager’s name and company right. However you mention nothing about the work they do and how your qualifications match the job description or requirement.

    • Summarize your qualifications related to the position for which you are
      applying. It is important to address: your qualifications as they relate to the
      requirements of the position, if known, such as with an advertised position.
    • Amplify or augment information contained in your resume, do not merely repeat it.
    • Include a few accomplishments, strengths or personal qualities related to the type of position that you are pursuing.
    • Take the time to think through what is relevant to the hiring manager. Instead of scattering lots of facts in hopes that one will be relevant, offer an opinion as to which experiences the hiring manager should focus on, preferably the ones he has stated he is looking for.
    • Research and highlight the current industry / organization’s challenges and state how your skills and experience counter the specific bottlenecks. It goes a long way in showing the hiring manager that you are not only about showing skills related to the job, but you are the kind of employee who offers up solutions — instead of just laying problems on his / her desk.
  4. End with an action appropriate to the contact.

    • For example, if you are responding to an unadvertised position, indicate you will follow up in a few days. If you are responding to an advertised position, indicate you are looking forward to the opportunity to meet or talk further. If it is an advertised position you should still follow up in a few days unless instructed not to, however, it may be better not to state this in your letter.
    • It is important to balance the tone of your cover letter. You want to be professional, cautiously assertive, but not presumptuous or overconfident.
    • Additionally, while a resume does not conform to standard writing styles, e.g., using personal pronouns, articles, and complete sentences with periods, a cover letter does!

Sample Cover Letter: 


To summarize, there are millions of conflicting advice on what to do and not do with cover letters out here. It is difficult to know where to start. This is worsened by the digital communication age – many might question whether you even need a cover letter anymore. I do not take the title for Cover Letter Writing Expert, however from my personal numerous fails, I can say you definitely advice that the “one-for-all and all-for-one” approach is lazy and self defeating. It is always best to choose a bespoke cover letter for each job and make sure that it suits your individual situation and the job industry the best. It can have a friendly tone if you feel that the hiring manager will not mind the light tone. Or it can be professional sounding if you feel the need to make it “official”. A creative’s cover letter and a banker’s cover letter will have a very different tone.

Don’t start each and every sentence with “I“. It sounds boring. Here are some phrases that you could use to not start your sentences with I: “In my opinion…”, “Working for… has given me excellent insights into…”, “Furthermore…”, “The key question, I like to ask is…”

Whichever the road you choose to take they key things to keep in mind are to:

  • Personalize the letter
  • Be natural (avoid clichés)
  • Be specific and get to the point
  • Have a strong opening statement that makes clear why you want the job and why you’re right for it and to catch the attention of the hiring manager
  • Be succinct — a hiring manager should be able to read it at a glance!
  • Share an accomplishment that shows you can address the challenges the employer faces
  • Be positive
  • Be confident but not arrogant.
  • Be polite and professional.
  • Be efficient
  • Proofread. Proofread again. If you can, have someone else preferably a mentor prooofread it for you
  • Sign it, if possible
  • Package it nicely
  • Always keep a copy of your letter, so you don’t get caught out at interview

For additional reading on this please have a look at the following posts I found very helpful:

  1. Applying for jobs without experience? Here’s how to build and sell your skills by the Guardian magazine
  2. Sell yourself: a cover letter guide for beginners by the Guardian magazine
  3. How to Write a Cover Letter” by the Harvard Business Review

I hope this has given insights, especially to first time cover letter drafters. Stay optimistic. A journey of a thousand miles begins with one step.. In it together!



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