The Great Cover Letter Debate: Why Smart Professionals Still Write Them (And How to Do It Right in 2025)
You're seasoned, accomplished, and frankly, a little tired of jumping through hoops. So when you see "cover letter optional" on a job posting, your first instinct might be to skip it entirely. After all, shouldn't your resume speak for itself?
Here's what I've learned after years of helping mid-to-late career professionals navigate transitions: the cover letter isn't about proving you're qualified—it's about demonstrating you're genuinely interested and strategically aligned with what they need.
Do Cover Letters Still Matter in 2025?
Yes, cover letters still matter in 2025. According to a 2023 Resume Genius survey, 83% of hiring managers prefer candidates who include a cover letter, even when it's not required. More importantly, when qualifications are comparable—which they often are at your level—your cover letter could be the extra edge that gets you an interview.
Here's the part that might surprise you: 45% of recruiters read your cover letter before your resume. Think about that. Your letter is often their first impression of how you think, communicate, and approach challenges.
The numbers get even more interesting when you dig deeper. An analysis by Jobscan found that candidates who submit tailored cover letters are 1.9 times more likely to land interviews, and resume.io reports that 35.8% of successful hires consistently included cover letters compared to just 21.2% who never did.
Connecting the Dots
As someone in the middle-to-late stage of your career, your resume often can't tell your full story, especially when you're:
Changing industries or job functions
Pursuing roles that seem like a stretch
Re-entering the workforce after a career break
Targeting companies where cultural fit matters as much as experience
In all these situations, you could be competing with candidates whose qualifications appear more linear. A well-crafted cover letter, tailored to the employer’s needs, gives you an opportunity to help the reader connect the dots in ways that might not be obvious from your resume alone.
The Four Elements That Actually Matter
Forget the formal letter-writing rules you learned decades ago. The best cover letter structure for experienced professionals today is centered around four functions:
1. Signal Strategic Thinking
Show you understand the business challenge, not just the job requirements. Instead of rehashing your qualifications, demonstrate how you think about their problems and have addressed similar issues in the past.
2. Provide Context for Your Decisions
Maybe you took a lateral move to gain specific experience. Perhaps you stayed at one company longer than typical because you were building something meaningful. Your career choices make sense—help them understand the strategy behind them.
3. Address the Obvious Questions
If you're shifting to a new industry, changing functions, or have a gap in your timeline, address it directly and confidently. Don't ignore the elephant in the room.
4. Demonstrate Effective Communication Style
At your level, how you communicate is as important as what you've accomplished. Your cover letter is a sample of how you'll interact with stakeholders, present to boards, or influence cross-functional teams.
AI Cover Letter Writing: Smart Uses vs. Pitfalls
AI tools like ChatGPT can be incredibly helpful when used the right way—but they can just as easily backfire if you're not careful.
Use AI as a thinking partner, not a ghostwriter. The technology excels at helping you organize ideas, test different approaches, and adjust tone, structure and phrasing. But it can’t express your lived experience, values, or nuanced judgment.
Bottom line: Use AI to help you think better—NOT do the thinking for you.
Using AI Wisely to Write a Cover Letter
Smart Ways to Use AI
1. Kickstart a first draft
Ask the chatbot: “Write a conversational, three-paragraph cover letter for this marketing role based on my resume and these notes. Keep it warm, professional, and specific.” (Remember to upload or paste your resume, job posting, and notes for context)
2. Polish a paragraph you've already written
Ask the chatbot: “Make this paragraph sound more concise and confident without changing the core message: [Insert text].”
3. Adjust the tone for the company culture
Ask the chatbot: “Revise this paragraph to sound more aligned with a startup known for its informal, innovative culture: [Insert text].”
Common Pitfalls to Avoid
Even well-intentioned use of AI can backfire. Here's what to watch out for:
Using content from the chatbot without editing. Recruiters are increasingly able to spot AI-generated language. Always revise it to make it sound like you.
Trusting AI to represent your experience accurately. AI tools may fabricate job titles, misstate outcomes, or inject overused clichés. Always fact-check and carefully proofread.
Not writing in your own voice. The best cover letters reflect your tone, priorities, and perspective, not generic phrasing.
Learn more about using AI for job search materials to enhance your entire application strategy.
How to Write Cover Letter Content That Works
Most advice out there fails to address the specific needs of experienced professionals. For those job seekers, it’s essential that your cover letter reflects strategic thinking and business fluency.
Lead with insight, not enthusiasm.
Instead of "I'm excited about this opportunity," try "Having led (or navigated) through three major industry shifts, I understand what it takes to guide teams through transformation.”Show, don't tell.
Rather than "I’m a strategic leader," describe a decision you made that illustrates strategic thinking: "When I chose to consolidate our three regional offices in 2019, it wasn't just about cost savings—it was about positioning us for the remote-first world we're now living in."Talk about the business, not just the role.
Research the company's recent challenges, strategic initiatives, or market position so you can connect your experience to their priorities.
Cover Letter vs. No Cover Letter: The Bottom Line
The real cover letter debate isn't really about whether hiring managers read them—they do. It's about whether you're willing to make the extra effort to stand out, especially in a competitive job market.
When you’ve built a career on sound decisions, strategic thinking, and excellent results, a tailored cover letter isn’t just an add-on—it’s an effective way to demonstrate the qualities that set you apart.
The question isn't whether cover letters still matter. It's whether you're going to use every tool available to position yourself for the career move you want. In a world where lots of qualified people are vying for the same job, a well-crafted cover letter can often make all the difference.
What to Do Next
If you’ve been skipping the cover letter or relying on a generic version, now’s the time to rethink your approach.
Choose one upcoming opportunity that deserves your attention. Then, take 20–30 minutes to write a tailored letter that connects the dots between your experience and what the employer truly needs.
Ready to position yourself strategically but want to make sure you're hitting the right notes? I’ll help you craft messages that open doors rather than just check boxes. Schedule a complimentary conversation to discuss your specific situation.
Free Download: Cover Letter Checklist
for Experienced Professionals
Want to make sure your cover letter breaks through the clutter?
Start by downloading my one-page cover letter checklist.