• Hillary Hufford-Tucker

How to Write a Strategic Cover Letter

Why do people think cover letters are passé? Because they aren’t using them strategically, and therefore, don’t get the job.

Cover letters are a practical part of the job search process when used with intention, particularly for people making a functional or industry change. The poorly constructed cover letter has developed a bad reputation because it:

  • Is not addressed to a person

  • Has noticeable typos or grammatical errors

  • Repeats the job posting or resume verbatim

  • Lacks personality or a creative pitch

  • Misses the opportunity to communicate value

Think of the cover letter as the bow on the bottle of wine that you bring as a party gift. You can offer the wine to the host without wrapping, but by simply putting a bow on it, you lift its value. A cover letter can elevate your value as well by:

  • Detailing career successes – value-added achievements

  • Providing specific experience links to the job – make the connection for the reader

  • Highlighting your personality – think cultural fit

  • Displaying a passion for the new company – how you’re driven to succeed

  • Promoting job-related soft skills – examples of being a team player, leader, or communicator

Many applicant tracking systems do not have a place to upload a cover letter. Not having the option to upload doesn’t mean you’re wasting time developing your tailored pitch to a particular company. After any application upload, you should use LinkedIn or other professional resources to find the hiring manager, recruiter, or a company connection. Use the main points from the cover letter to make the outreach more pointed.


Cover letters can be a letter or an email. The only requirement is that you address the letter to a person and don’t use “To Whom It May Concern.” It’s critical to quickly grab the reader’s attention with unique details specific to the job. Everyone appreciates brevity, so an e-cover letter should be only three to five sentences (read: one screen), while a standard cover letter can run three to five paragraphs. There are many approaches to getting the attention of your reader, including:

  • Detailing an Exciting Project: Identify an interesting company goal or project and suggest how your expertise applies to the situation

  • Highlighting a Quirky Tie-In: Find a unique detail of the job description or company that applies to your skillsets - this can be difficult, so tread lightly and maintain appropriate humor

  • Sharing Your Origin Story: Describe your career path and how it adds value to the company

  • Celebrating an Accomplishment: Share your achievements, awards, or superior performance in previous roles and how they add value to the new role

  • Highlighting Your Transferable Skills: Identify the skills that align with the job and how they apply to a particular project or process at the company

  • Expressing Your Excitement About the Company: Link a past success to the mission or vision of the company

  • Showing How You Hit the Ground Running: Show how enthusiastic you are about the prospect and how you can contribute on day one


The ultimate purpose of a cover letter is to connect with the reader. While resumes are a place to list skills and experience, the cover letter provides an opportunity to build rapport, show cultural fit, and highlight your skillsets by connecting your character, goals, and accomplishments. After researching the role and company, list out the key ways you add value. Create headlines and bold the typeface for paragraphs two, three, and four. Remember to use, but not overdo, relevant keywords. In detail, the structure for the cover letter is:

  1. Header: Use a standard letter-style format. Include the date, the contact’s name and mailing information, the job title, and the job number (if applicable).

  2. Opening Salutation: Be friendly but formal. In today’s more relaxed workplace, it’s easy to be casual. The best greeting is “Dear” followed by their name. The intro, “To whom it may concern,” is considered archaic; so, if after searching for the right contact on company websites and LinkedIn, you still can’t find anyone, use “Dear Hiring Manager.”

  3. Paragraph 1: Grab the reader’s attention and show expert status. Use job-specific keywords to grab the reader’s attention and briefly summarize your approach, methods, and why you would be a good fit. Action words for this section might include: award-winning, leading, proven, or accomplished.

  4. Paragraph 2: Define a connection. Scour company information for an item or two that piques your interest. After a headline highlighting an achievement, explain how your goals and past achievements blend with the company’s mission and culture. Action words could include: promoted, achieved, strategic, executed, or proven.

  5. Paragraph 3: Show enthusiasm. Write a statement about your excitement followed by how your current role connects to past successes and future achievements. Suggest how a previous process or project would benefit one of the company’s initiatives. You can also discuss how a specific achievement is relevant to the role. Action words may include: passionate, enthusiastic, excited, captivated, or avid.

  6. Paragraph 4: Prove achievement and value. Building persuasively on the other paragraphs, write a headline that defines the benefit you’ll bring to the employer. Support that statement with a past success that reiterates your value proposition. Action words may include: challenge, managed, increased, strategy, oversight, and responsibility.

  7. Call to Action: Convey fit and make your ask. The closing paragraph should seal the deal by showing fit, gratitude, and including a request to connect or for an interview.

  8. Closing: Be nice, not informal. Select a close, like “kindest regards,” “best regards,” or “thank you.”

  9. Postscript: Pique interest. Use the postscript, or P.S., to briefly sample something fascinating about a past role or something relevant outside of jobs, and tell them you’re eager to share more.


The cover letter email, or e-cover letter, gets to the point fast. It should introduce you and your experience and show how you solve pain points for the reader. When developing the email, remove unnecessary words from your standard cover letter template until it’s tight without losing relevant details. At the end of the email, be sure to provide a call to action like, “Please let me know when we can talk further.”

  • Sentence 1: The reason for the contact. Explain why you’re emailing and how you’re an expert in the field.

  • Sentence 2: What you’ll do for them. Apply your background to a specific pain point.

  • Sentence 3: What you want to do. Discuss how you’ll fit into the organization.

  • Sentence 4: Call to action. Indicate your eagerness to talk more.

Remember that the time spent creating a cover letter is applicable for other parts of your search. Researching a company and knowing your value proposition is relevant to screening calls and interviews and as a template for outreach to other companies – just don’t forget to remove previously used names and companies.


As a certified career coach, Hillary guides extraordinary people and their personal brands. She's a career solutionista that helps clients discover their unique worth to find new employment, pivot industries, or move toward cause-oriented work. When Hillary's not busy coaching amazing people, she rides bikes, learns about wine, cooks for friends, and travels globally with her family. Find out more and sign up for her newsletter at www.careersolutionista.com.

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