Cover Letter Checklist

Written By Sharla Taylor

Stand Out, Connect, and Land the Interview

Stop sending cover letters into the void. Most cover letters sound like everyone else's, generic, forgettable, and destined for the "no" pile. This checklist will help you write one that actually gets you noticed (and called in for an interview).

Before You Write

  • [ ] Research the company's mission, values, culture, and recent news. What products and services does the company make or sell? Who are their biggest competitors? What is their market share? Study their annual reports. Set news alerts for the C-suite executives.

  • [ ] Analyze the job description and highlight 3-5 key qualifications they're seeking

  • [ ] Identify specific problems this role is meant to solve for the company

  • [ ] Prepare 2-3 quantifiable achievements that align with their needs

  • [ ] Find the hiring manager's name (check LinkedIn, company website, or call)

  • [ ] For Executives: Review investor relations materials, recent earnings calls, board composition, and strategic priorities

Format & Structure

  • [ ] Keep it to ONE page (250-400 words max)

  • [ ] Use an 11-12 pt sans serif font (Aptos, Calibri, Arial)

  • [ ] Match font style to your resume for consistency

  • [ ] Use 1.15 or single line spacing

  • [ ] The header of your cover letter should match your resume and include your name, phone, email, LinkedIn profile URL, and the URL of your online career portfolio, if applicable.

  • [ ] Address to specific person: "Dear [Name]" (not "To Whom It May Concern")

  • [ ] Save file as: YourName_CoverLetter_CompanyName.pdf

  • [ ] For Executives: Consider addressing your cover letter to the CEO or Search Committee as appropriate

Opening Paragraph: Show You Get Them

Goal: Prove this isn't a generic application

  • [ ] Hook them with a specific connection to their company

  • [ ] Reference their mission, values, recent project, or culture

  • [ ] Show genuine enthusiasm for THIS specific opportunity

  • [ ] Make it clear why you chose them (not just any employer)

  • [ ] For Executives: Demonstrate strategic awareness of market position, competitive landscape, or board priorities

Example Framework (Professional/Mid-Level): "Your company's focus on [specific value/initiative] aligns perfectly with my experience [achieving specific outcome] at [previous company]."

Example Framework (Executive): "Scaling [specific business function] from [X to Y metric] taught me that [specific insight]—which is why [Company's] ambition to [specific goal] is precisely where I can drive impact."

Middle Paragraph(s): Prove You're the Solution

Goal: Match your skills to their specific problems

  • [ ] Pull directly from the job description's "wishlist"

  • [ ] Use hard numbers and metrics to quantify your achievements

  • [ ] Show how you meet or exceed each major qualification

  • [ ] Tell a brief story that demonstrates problem-solving ability

  • [ ] Use the problem-solution-outcome approach: identify their challenge, then show how you've solved similar issues and the business outcomes you've achieved

  • [ ] Focus on what you'll contribute to them (not what you'll gain)

  • [ ] Include relevant technical skills, soft skills, or certifications

  • [ ] For Executives: Emphasize strategic outcomes (revenue growth, market share, organizational transformation, P&L results, stakeholder management)

Power Words to Use:

  • Professional/Mid-Level: Increased, decreased, improved, generated, launched, streamlined, transformed, led, collaborated, achieved

  • Executive: Scaled, transformed, orchestrated, delivered, drove, repositioned, accelerated, navigated, optimized, captured

Avoid:

  • Repeating information already on your resume word-for-word

  • Vague statements without proof ("I'm a hard worker")

  • Bullet points (use narrative prose instead)

  • For Executives: Avoid overly humble language; be confident but not arrogant

Closing Paragraph: Ask for the Interview

Goal: End with confidence and clarity

  • [ ] Reaffirm your enthusiasm for the specific role

  • [ ] Include a confident call-to-action

  • [ ] Reference your resume/attached materials

  • [ ] Use professional sign-off ("Sincerely," "Best regards," "Thank you")

  • [ ] Leave space for signature (if physical copy)

  • [ ] For Executives: Signal readiness for board presentations or stakeholder discussions

Example Framework (Professional/Mid-Level): "I'd welcome the opportunity to discuss how my experience in [specific skill/achievement] can contribute to [their specific goal/challenge]. I look forward to speaking with you about how I can add value to [Team/Department]."

Example Framework (Executive): "I welcome the opportunity to discuss how my track record of [specific executive achievement] can accelerate [Company's] [strategic priority]. I'm prepared to share detailed strategies for [specific challenge] with you and the [board/leadership team]."

Quality Control: The Final Check

  • [ ] Spell-check AND read aloud for flow

  • [ ] Verify all company and contact names are spelled correctly

  • [ ] Remove any placeholder text ([Company Name], [Your Experience], etc.)

  • [ ] Confirm you're not using clichés or generic phrases

  • [ ] Check that each sentence adds unique value (not filler content)

  • [ ] Ensure you've used first person ("I," not third person)

  • [ ] Verify no grammatical errors or typos

  • [ ] Confirm it's written in conversational, authentic language

  • [ ] Make sure it sounds like YOU (not AI or a template)

  • [ ] Test that any included links work properly

  • [ ] For Executives: Ensure tone is peer-to-peer, not aspirational or deferential

Customization Checklist

Remember: 75% of your cover letter should be unique to each job⁴

  • [ ] Company-specific research integrated throughout

  • [ ] Job description keywords naturally included

  • [ ] Addressed to the correct department/hiring manager

  • [ ] References specific role requirements

  • [ ] Tailored examples that match their needs

  • [ ] For Executives: Alignment with stated strategic priorities from annual reports or investor communications

What NOT to Include

  • [ ] Personal details (age, marital status, unrelated hobbies)

  • [ ] Salary requirements (unless requested)

  • [ ] Negative comments about current/past employers

  • [ ] Desperate language ("I really need this job")

  • [ ] Multiple pages or excessive length

  • [ ] Exact text from your resume copied over

  • [ ] Quotes or emojis (unless culturally appropriate)

  • [ ] For Executives: Avoid overly detailed tactical descriptions; focus on strategic impact

Pro Tips from 2025 Hiring Trends

  • [ ] Remember: 94% of hiring managers say cover letters influence interview decisions¹

  • [ ] Stories are 22x more memorable than facts—weave in brief narratives²

  • [ ] Demonstrate digital proficiency and adaptability for modern roles

  • [ ] Show understanding of remote work skills if relevant

  • [ ] Position yourself as a solution provider, not just a job seeker³

  • [ ] Prioritize authenticity over corporate jargon

  • [ ] Use AI tools to refine (but never replace your unique voice)

  • [ ] For Executives: Lead with strategic vision and demonstrate board-level thinking

Executive-Level Specific Considerations

Tone & Language:

  • [ ] Write as a peer to the CEO/Board, not as a supplicant

  • [ ] Use confident language that reflects your seniority

  • [ ] Demonstrate industry expertise and market awareness

  • [ ] Reference strategic frameworks or methodologies you've deployed

Content Focus:

  • [ ] Emphasize P&L responsibility, budget size, team scale

  • [ ] Highlight board interactions, investor relations, or stakeholder management

  • [ ] Include market context (competitive positioning, industry trends, disruption)

  • [ ] Show change management and organizational transformation experience

  • [ ] Demonstrate cross-functional leadership and enterprise-wide impact

Research Depth:

  • [ ] Understand the company's competitive threats and opportunities

  • [ ] Know the leadership team's backgrounds and previous company performance

  • [ ] Reference recent strategic moves (M&A, partnerships, market expansion)

  • [ ] Acknowledge regulatory, market, or industry challenges they face

Credibility Markers:

  • [ ] Mention work with comparable company sizes/scales

  • [ ] Reference relevant industry recognition or thought leadership

  • [ ] Include experience managing similar revenue, team size, or market cap

  • [ ] Note any relevant board service or advisory roles

Final Question: Would this cover letter make ME want to interview this candidate?

If yes, you're ready to submit. If no, revise until the answer is a confident yes.

Remember: A great cover letter doesn't beg for a job; it demonstrates exactly why you're the most compelling candidate for the position.

As Steve Martin said, "Be so good they can't ignore you."

Want a cover letter written by a professional writer and career coach who knows what hiring managers want? Book a call today using the button at the top right of your screen.

Bibliography

¹ ResumeLab Cover Letter Statistics 2025: https://resumelab.com/resume-statistics/cover-letter

² Stanford Graduate School of Business, "Stories are 22 Times More Memorable": https://www.gsb.stanford.edu/insights/why-stories-sell

³ Harvard Business Review, "Position Yourself as a Problem Solver": https://hbr.org/2023/01/how-to-write-a-cover-letter

⁴ Career Research on Cover Letter Customization: https://www.themuse.com/advice/cover-letter-tips

Sharla Taylor
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