In past articles, I explained the basics of writing resumes for law students and lawyers (here) and Bay Street business professionals (here). But any competent job application package needs more than a resume. That’s where the cover letter comes into play. But what, exactly, should your Bay Street cover letter look like?

My hope is that this article will cover the basics of writing a fool-proof cover letter to get you hired on Toronto’s Bay Street. Frankly, you could use these tips to write a cover letter to impress most any employer. But for now, let’s stick to Bay Street.

In a separate article, I’ll provide some high-quality Bay Street cover letter templates. Stay tuned for when those become available.

Don’t Underestimate the Power of Cover Letters

Whether you believe it or not, employers can a lot about your cover letter—especially Bay Street employers. Cover letters are often the first thing that employers look at when they review your job application. They set the tone for the rest of the recruitment process.

The Bay Street norm is that job applications include a cover letter. You don’t want to be the person who breaks this norm; it sets a bad first impression. No cover letter also makes it more likely that your resume will be tossed aside.

Think of a good cover letter like your first introduction to a prospective employer. You want to come across as polished, friendly, smart and competent—the same attributes you would want to convey if you met your prospective employer in person.

How to Write the Perfect Cover Letter

1. Write a Short Story

Your cover letter should be a short story about why you are the perfect candidate for the job. Let me unpack what this mean.

By “short”, I mean one page. Hard stop. Your cover letter should not be any more than one page, using the same font size and margins as your resume (i.e. 11 or 12 point font, and 1 inch margins). You should use short, concise and to-the-point paragraphs. Leave lots of white space.

By “story”, I mean that you should use your cover letter to explain what you want the job you’re applying for and why you are the best fit for that job. I recommend that you start by briefly introducing who you are, stating why you why the job, and then going into some detail explaining why you are the best candidate for the job. Typically, a cover letter has the following format:

  • Paragraph 1: Introduce yourself. State who you are, what job you are applying for, and set out the two or three points you want to get across. Treat this last part a bit like a thesis statement.
  • Paragraphs 2 to 4: This is the body of your cover letter. Go into some detail on the two or three points you want to get across. Each point should be its own paragraph. I like when candidates focus on specific skills or experiences that are useful for and connected to the job at hand.
  • Paragraph 5: Conclude your letter. In a sentence or two, wrap up why you are the best candidate for the job.

2. Individualize Your Cover Letter

No two cover letters should be identical. Each cover letter you send out should be unique and individualized to the recipient.

At a basic level, you need to individualize your cover letter by adding the recipient’s name. Do your absolute best to figure out the name of the person reading your cover letter. Avoid using “To Whom It May Concern”. If you cannot find the recipient’s name, then considering addressing the letter to the intended recipient’s position (e.g. “Dear Hiring Manager”).

It should be clear, based on your cover letter, that you have some knowledge of your prospective employer’s business. At a minimum, show that you read their website. Don’t mention skills and experiences that have no usefulness to your prospective employer; focus on what is relevant and applicable to them and how you can help them grow their business.

I get it, you’re probably applying to multiple jobs and want to use the same cover letter for each job. And it’s fine if you re-use the bulk of your cover letter in each application. But there still needs to be some level of individualization. Show that you at least put in some effort to tailor your cover letter for the intended recipient.

3. Pay Attention to Spelling, Grammar and Names

Many employers use cover letters as a way of filtering out bad candidates. How? They look for the cover letters that have spelling errors, grammar mistakes, and/or incorrect names and then toss them. After all, if you can’t even write a proper cover letter without mistakes, how can you write a legal brief as a lawyer, compile accurate financial statements as an accountant, etc.?

It goes without saying that your cover letter should be error-free. It is, after all, a one-page document with around 250 words. Your spelling should be perfect, your grammar should follow conventional rules, and you should double-check every name in your cover letter.

As easy as it may sound to make an error-free cover letter, I can’t emphasize how often I’ve come across cover letters full of mistakes. These mistakes can be minor—such as incorrect punctuation—but they can also be serious, such as misspelling the employer’s name or using the wrong company name altogether. Both minor and major errors can be fatal to your application.

To avoid making these basic cover letter mistakes, I recommend that you not wait until the last minute to draft your cover letters. Start them in advance. Edit them. Then edit them some more. Have a friend (or two) review them. Your job application should not be tossed aside over something as preventable as a grammar error or mistaken name.


Don’t brush off the importance of the cover letter. When applying to a job on Bay Street, you need to submit a cover letter along with your resume. Your cover letter should be a short story. Keep it at one page in length, individualize it for each specific job application, and proofread your cover letter until every mistake is gone.

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