3 strategies that help this job seeker stand out and land interviews

Kaleah Mcilwain has been on the job market for eight months, and in that time, she’s learned a few hard truths about the application process.

Chief among them? Submit a cover letter every time.

Her best trick to write an effective cover letter quickly is to focus on one prompt: Directly solve a problem in the job description.

The company is “hiring for a reason,” says Mcilwain, 28, a digital editor in Philadelphia, “and they just want the best person who can solve that reason for them.”

Identify one or two pain points in the job description and use your cover letter to tell the hiring manager exactly why you’re the best person to solve that for them, she says. Provide examples of your skills or prior experience that show how you can solve the problem, and also include why you want to do it for that company.

In Mcilwain’s line of work, for example, she may be looking at a job where a business wants to improve their social media strategy. Mcilwain can then give examples of how she’s run Instagram, TikTok, YouTube and other platform handles for a previous employer, giving specific growth and engagement metrics from her tenure.

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The key is to stay focused on how you can solve their business need, Mcilwain says.

“While people love telling their full career history [in a cover letter], don’t talk about anything else besides the one thing that they mentioned they need someone to do,” she says.

Mcilwain says putting effort into the cover letter is worthwhile when many others rely on AI to write theirs, don’t spend much time and attention on it, or skip it altogether. Some 2 in 3 job-seekers say they don’t consistently submit a cover letter when applying, according to a 2024 Jobscan survey.

She’s a fan of AI tools but says it’s better to use them when reviewing your content, rather than by generating it.

“I write all my own things, and then I will just tell AI, can you analyze this against a job description to tell me the likelihood that it matches up with it that way?” Mcilwain says. The analysis allows her to check that she’s hit all the job description’s bullet points and used keywords in meaningful ways.

She cautions against using AI to generate the substance of your resume or cover letter, otherwise it may look too similar to other AI-generated applications.

A generative AI tool “isn’t going magically write like you will,” Mcilwain says. She used the tool to generate a few items and noticed “they all look exactly the same: They follow the same exact type of opening followed by a chronological order of what you’ve done in your job history, followed by a closing.”

Hiring experts agree that it’s not a great practice to have AI generate a resume or cover letter, since it can lead to errors and over-used (read: boring) phrases and statements.

Mcilwain say she’s being intentional in her job search, so far applying to roughly three or four dozen openings. It’s her third time on the job market since graduating from college, and the most competitive against other job-seekers.

One new strategy that’s led to results: “I’m very big on cold-emailing the CEO of the company, which has worked for me multiple times to get an interview,” Mcilwain says.

She keeps things brief with an introduction, a statement that she applied to the opening, and three bullet points about why she’s qualified for it.

Then she’ll finish with a polite request that her application gets to the right person. After sending off her email, she’ll also request to connect on LinkedIn, but says that sending another message on the platform is “overkill.”

“I’m never asking these people to look at my resume or anything like that, just simply [that] I applied” with the hopes the message will be passed on to the hiring manager, she says. “I did this, and literally, I got an interview like the next day.”

So far, the method has secured her at least three job interviews. The point is to put in the effort to make contact with the hiring manager directly, which boosts your chances of a human response.

“You never know how people are reviewing their applications. It may be a human, it may be a computer system, it may be AI,” Mcilwain says. “So instead of trying to make sure your application can get around all of those things, I just go [straight] to people.”

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