In today’s cutthroat job market, a subpar cover letter can mean the difference between landing an interview and being overlooked.

In this context, leveraging AI in your cover letter is no longer optional. Everyone is going to start doing it, and you better get on with the program…

If you’re not using AI, you risk falling behind competitors who are more tech-savvy, missing out on opportunities, and being relegated to the bottom of the resume pile.

The Importance of a Strong Cover Letter

A compelling cover letter:

  1. Introduces You: Offers a brief but powerful introduction.
  2. Showcases Your Fit: Aligns your skills with job requirements.
  3. Highlights Unique Qualities: Reflects your individuality.
  4. Uses The Language of Value: You must use this everywhere, in every single instance of your professional communications. (If you don’t already know what The Language of Value is, see this.)

However, even with these tips, crafting an effective cover letter is challenging. Fortunately, AI-powered tools can not only help, but even revolutionize this process.

We’ve already discussed how to use ChatGPT to write cover letters where we gone over the basic process, and outlined how to structure your prompts. You should read that article, if you haven’t already done so.

Here, we’re going to take things up a notch…

Benefits of AI in Cover Letter Writing

Precision and Personalization

AI tailors your cover letter to match specific job requirements and language with very little effort, increasing your chances of both passing ATS (Applicant Tracking Systems) and impressing hiring managers.

Efficiency

AI tools drastically reduce the time needed to draft a cover letter by providing templates and suggesting content based on your resume and the job description.

Error Reduction

AI-powered grammar and style checkers ensure your cover letter is polished and error-free, reflecting professionalism and attention to detail.

Warning: While AI will save you time, it won’t give you a great cover letter IF you don’t already know how to write a great cover letter yourself. You need to learn how to write a great cover letter first, no shortcuts! This is because, the default cover letter AI tools generate are extremely unremarkable and mind-numbingly unpalatable. You need to guide AI with the right prompts and give it constructive feedback to get to a great cover letter. Just instructing AI “write me a cover letter for X job” is a great way to generate the same lazy letter all those other applicants are generating, and end up together with them in the trash pile.

Assuming, at the very least, you know the basics of cover letters that we teach on our free platform, here’s how you can leverage AI to get jobs above your paygrade.

How to Use AI Tools for Cover Letter Enhancements

Step 1: Analyze the Job Description

Use AI tools like Textio or Jobscan to analyze the job description. Highlight key skills and keywords to incorporate into your cover letter.

Step 2: Generate Content

Leverage AI writing assistants such as OpenAI’s GPT-4 or Google Gemini to generate personalized content based on your resume and the job description.

Step 3: Refine and Customize

Refine the AI-generated content to add your personal voice and unique anecdotes, making your cover letter more engaging and authentic.

This part is crucially important!

If you simply use AI to generate every word of your cover letters, the employer’s AI can detect that your cover letters were generated by AI, and instantly trash it before a human gets to read it. Furthermore, a purely AI written cover letter will be obviously AI generated to any human reader – and this flaw of AI generated content will persist for the foreseeable future.

As a rule of thumb, you must have at least one part your original content, for two parts of AI generated content to pass the AI filter tests. In the context of your cover letter, this means removing some sentences written by AI, and adding a few of your own.

Step 4: Proofread and Edit

Once you’ve made your adjustments, submit your entire cover letter back into the generative AI software you’re using, and ask it to edit/proofread your work.

You may also want to utilize AI grammar and style checkers like Grammarly or Hemingway to further proofread and edit your cover letter for clarity and conciseness.

Radically Empowering AI Cover Letter Hacks

Hack #1: Hyper-Personalization with AI-Driven Data Mining

AI tools can scan publicly available data about the hiring manager and the company. And they can do so a lot more efficiently and effectively than you can.

This information allows you to craft a cover letter that speaks directly to the reader’s interests and priorities. Mention a recent company achievement, or align your skills with a current project the company is working on. This level of personalization shows you’ve done your homework and are genuinely interested in the company.

Example

If you find out the hiring manager recently spoke at a conference, mention how their insights resonated with you and how your skills can contribute to the initiatives they discussed.

Hack #2: Predictive Analysis for Skill Matching

Using predictive analysis, AI can identify which skills and experiences are most valued by the employer. It analyzes past job postings and employee profiles to predict what the company is looking for in candidates. By tailoring your cover letter to emphasize these predicted skills, you increase your chances of catching the hiring manager’s eye.

Example

If the predictive analysis indicates a high demand for project management skills, ensure your cover letter prominently features your project management experiences and accomplishments.

Hack #3: Sentiment Analysis for Tone Adjustment

AI can perform sentiment analysis on your cover letter to ensure the tone matches what is likely to resonate with the hiring manager. Whether the company culture is formal or laid-back, AI can help you adjust your writing style accordingly, making your cover letter more appealing and aligned with the company ethos.

Example

For a startup with a casual culture, the AI might suggest a more conversational tone. For a traditional firm, a professional and formal tone might be recommended. You need to, of course, feed AI all the required information about the company through prompts. (If you don’t know how, ask AI!)

Hack #4: AI-Powered Competitor Analysis

Use AI to perform a deep dive into the profiles and likely applications of other candidates. This involves using tools that analyze public data to predict the qualifications and experiences of your competition. Adjust your cover letter to highlight your unique strengths and directly address gaps that other candidates might leave.

Example

AI analysis of typical applicant profiles for one role might highlight a lack of experience in cross-functional team leadership. You can prioritize your experience in cross-functional team leadership to stand apart. (Basically, give the employer what they are lacking from other candidates; lower supply = higher value)

Hack #4: Test for Cognitive Load Optimization

Use AI to ensure your cover letter is easy to read and process. Tools like Hemingway can help you optimize sentence structure and complexity, reducing cognitive load and making your cover letter more digestible.

A well-structured, clear, and concise cover letter will keep the reader engaged and reduce the likelihood of them tossing your application to trash.

Example

Once your cover letter is written, feed it to AI and ask for multiple rewrites, with each re-write specifically asking for a reduction of cognitive load.

(Pro Tip: You can further leverage AI in order to use some powerful cognitive biases to make your letters significantly more persuasive. These include but are not limited to The Primacy Effect, Recency Effect, Illusory Truth Effect, Confirmation Bias, Social Proof and Authority Bias. See Launch Your Career to learn about “getting their brain on your side”.)

Recommended AI Tools for Cover Letter Writing

  1. Textio: Enhances your writing by analyzing job descriptions and suggesting improvements.
  2. Jobscan: Compares your cover letter and resume against job descriptions to optimize keyword usage.
  3. OpenAI GPT-4: Generates personalized content based on your input.
  4. Grammarly: Provides advanced grammar and style checking.
  5. Hemingway: Improves readability and conciseness.

Conclusion

Incorporating AI into your cover letter writing process can give you a significant edge.

In today’s job market, precision, efficiency, and error-free content are expected. And AI tools can not only provide these for you, but they can also help you craft a compelling narrative that resonates with employers. (See career narrative for details)

The bottom line is, you need to embrace these technologies to enhance your cover letters and increase your chances of landing high-value jobs.

Make no mistake, the difference between an ordinary job and a high-value job is not just limited to the 50% to 500% greater pay. It’s also about the lifestyle benefits, the opportunity ecosystem, and the thrill of working on projects and working with people you care about.

Of course, you don’t need to obsess over every word on your cover letters and pass it through multiple AI systems if you’re simply applying to “whatever job you find on job boards” so that you can find “something to pay the bills”.

But… We’re not about those types of jobs…

And for the types of jobs we are talking about, yes, absolutely – you do need to obsess over every word on your cover letters; for when it’s all said and done, each individual word may actually be worth thousands, and perhaps even tens of thousands of dollars to you.

For more insights on optimizing your career strategy, and getting high-value jobs, explore our Courses and Publications.