How to Use AI to Improve or Streamline Your Applications

Thank you for reading the EdSkipper, Skip’s newsletter about skipping from education to education-aligned careers. Every Saturday, I send out a list of curated remote jobs. Premium subscribers receive two additional emails a month with industry insights and advice to help you apply more competitively to the jobs you’re passionate about.

This has been a whirlwind year for AI — it’s hard to believe that it’s not even been a full year since Meta, OpenAI, and Microsoft announced consumer-facing AI platforms in the same month.

Unsurprisingly, I’ve gotten tons of questions from my coaching clients about whether they should use AI and how they can use it to get good results. And, I’ll be honest, I’ve seen a lot of bad AI resumes or resume bullet points. But it can also be helpful — generating even a bad bullet point can help you brainstorm a better one as you ask, ‘why isn’t that working for me?’ And a generic cover letter can save you a lot of time staring at a blank page.

Spoiler alert for rest of this newsletter: AI can be useful as you apply to jobs but it still relies a lot on you to guide the prompt and/or to revise the results. And, if you’ve used AI a lot already, you know about the dangers of hallucinations or the frustrations when the same prompt elicits different results the next time you use it.

My goal today is to walk through some of the downsides I regularly see in AI-generated resume content and offer some prompts to help you generate better content.

This is an area where I’m still learning the ins and outs too — and the technology changes so rapidly that we always have to innovate and experiment. One example of where the technology has outpaced me? I’ve barely even tried Google’s new AI model, Gemini.

I primarily rely on OpenAI’s ChatGPT (both 3.5 and 4, including a bunch of plug-ins) as well as Strut, which bills itself as an AI workspace for writers. I’ve tested out a bunch of others too — Claude, Bard, Jasper.ai, Copy.ai, and probably more!

I’ve yet to find one that replaces me or automates tasks sufficiently to adopt it fully. That said, I think this is a promising technology that can help us do tasks more efficiently and with greater precision or clarity. (Once they get over the hallucinations!)

You may even have more experience using AI than I do because educators have been quick not just to adopt AI to manage their workload but also to work with students to explore its benefits and limits for learning.

What’s in this issue:

• Is it Ethical to Use AI When I Apply to Jobs?

• What are the Downsides to Using AI in my Applications?

• Pros & Cons of the Major AI Platforms Transitioning Teachers Use (premium subscribers only)

• AI Prompts You Can Use with Your Application Materials (premium subscribers only)

  • For Job Descriptions

  • For Resume Bullet Points

  • For Cover Letters

  • For Interview Prep

Is it Ethical to Use AI in Job Applications?

I don’t think there’s an easy answer to this question. It’s such a new technology that it’s hard to know how companies or individual recruiters and hiring managers will react to it. Some indeed might frown if they knew your cover letter was AI generated. Others might applaud your efficiency (assuming the cover letter helped them understand your skills more).

And, of course, ATS (Applicant Tracking Systems) are certainly not worrying overly much about ethics (or potentially the law) as they roll out AI feature after AI feature to sort through candidates. Linkedin Recruiter, for example, is working to integrate AI fully into their job searching and recruiting platforms. A lot of recruiters are still skeptical of these features and many do not use them. But that appears to be more because the tools don’t seem reliable than because they want to avoid them in general.

For applicants, using AI is fair game in my mind. It can help you refine your application documents and — where I think it shines — prep for interviews. The application process just gets you in the door so if you’re using it to refine your resume and/or cover letter, I wouldn’t worry about it too much. After all, these are just informational documents.

I would definitely not submit a writing sample generated by ChatGPT. Writing samples are used to evaluate your skills rather than outline your experience so using an AI version feels disingenuous.

Ultimately, understanding the limits and promises of AI may even help you in your job search because it is such a new field and an unfamiliar one. But it’s going to transform the workforce once we all collectively figure out how to use it!

What are the downsides to using AI in applications?

The obvious downsides are the heavily reported limits of AI: hallucinations or inaccurate information. These are easy enough to avoid if you’re editing your documents but can sometimes make using AI more of a pain than a collaborator.

The biggest weaknesses I’ve seen with AI-generated application content are when it:

1. mirrors parts of your inputs without synthesizing the information completely, or when it

2. summarizes content in an obvious way so the response is generic

An example of mirroring is when you copy your professional summary alongside a job description and ask ChatGPT “Is this a good professional summary for this job?” Its response typically is some version of “yes, here’s why” followed by a rewording of the job description. 

I’ve also seen this type of result when people type in their resume and the job description and ask ChatGPT to write bullet points for that role. It tends to reword the job description and say, ‘You have this experience!” 

In other words, ChatGPT isn’t actually analyzing your content – it’s just repackaging it. 

An example of bland (and even banal!) summarizing is when you copy your resume into ChatGPT and ask it to write your professional summary for a learning and development role. The response opens with “Dedicated and results-driven educational professional with a strong background in secondary English Language Arts instruction.” The rest of the response is generally a list of key responsibilities, without any of the high-level synthesis or personality that makes a professional summary really shine. With the exception of your SME, this summary doesn’t provide a recruiter with compelling evidence of your L&D skills.

Again, ChatGPT isn’t doing a great job here of analyzing what skills you need in L&D and then aligning your skills with it. 

Of course, ChatGPT’s core functionality is impacted by the prompts you give it. Garbage in, garbage out. You can create stronger prompts that will elicit better results. And, when you combine what you as a human do well and what ChatGPT as a robot does well, you can create some decent drafts to revise and submit.

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