Following simple steps with a generative AI LLM can speed up your job fishing.

In a previous post, I mentioned that job fishing might be a better phrase than job hunting. This post is more step-by-step as I wanted to show you how you might job fish with generative artificial intelligence large language models (AI LLM) available today. You can use the free versions of the models, but you will notice better results with the paid models (for example, ChatGPT and run $20USD/month at this time).

Why use AI for Job Fishing?

As mentioned in earlier posts, anyone seeking a job must get past the dreaded Applicant Tracking System (ATS), which typically works on keyword matching. (Yes, some new AI-based ATS exist, but I've not heard of widespread adoption yet.). Customizing your resume and cover letter to match the job offer is a great way to avoid being screened out by an ATS.

I don't know about you, but constantly rewriting your life history can be a soul-sucking exercise. If you feel this way, you may be interested in saving yourself time in writing customized cover letters and resumes.

Customizing Your Resume with
(or any generative AI LLM)

First, prep your resume by including all relevant work information for the last 10 or 15 years. Generate a PDF version of the resume so you can easily feed it into the LLM. Also, have the web page of the full job description available.

Enter the following prompt in the LLM prompt field: Can you rewrite the attached resume to fit the job description below?

Before hitting the "enter" key, paste the job description in the prompt field and attach the PDF resume.

Screen capture for entering the prompt, job description, and your resume in the current paid version of (Claude 3 Opus)
Screen capture for entering the prompt, job description, and your resume in the current paid version of (Claude 3 Opus)

You will get a modified version of your resume as text.

Text output of modified resume from prompt to v3 Opus
Text output of modified resume from prompt to v3 Opus

There are two reasons I prefer for resume re-writing. First, it rarely hallucinates. For instance, notice the last bullet that mentions "Proponent of metrics..." My resume doesn't mention metrics, but metrics were mentioned in the original job description. I'm okay with leaving that in, as it's not an exaggeration. However, you should carefully review what any LLM writes to check for accuracy and tone. If it sounds boring when you read it, there is a good chance no one will read it.

Second, the format of the output translates more easily back into a resume document. You will still spend time cutting and pasting results into your resume and cleaning up the formatting regardless of which LLM you use. This may change as generative AI improves or custom applications are created based on generative AI.

You can do something similar with ChatGPT and leverage some custom GPTs. For instance, Tim Robinson told me about his Resume Review GPT he's made available through the ChatGPT app store. While there is no additional charge to use the app, you need the ChatGPT monthly subscription mentioned earlier. Tim tells me he may make this available elsewhere. I'll update this article if he does.

Generating Your Cover Letter with
(or any generative AI LLM)

Your cover letter should not regurgitate what is on your resume. Instead, you want to highlight relevant experience and anything not on your resume that amplifies that you have the requested skills. This can be very helpful if the job description lists "nice to have" skills.

One simple prompt to the LLM can help with this: What do you see missing from my experience shown in my resume that is requested through the job description?

A screen capture of the input with the prompt: What do you see missing from my experience shown in my resume that is requested through the job description?
A prompt for to point out gaps between the resume and the job description.

Again, provides clearer and more informative responses. See the example below from what suggested.

Screenshot of multiple numbered suggestions from
Some of the output from based on the prior prompt.

After reviewing suggestions from, I could amplify my experience with numerous agile project management tools, flow diagramming tools, and product roadmaps. So, I can emphasize that in my cover letter. I can even ask the LLM to write that for me by providing additional information.

A detailed prompt to as follows: Can you write a cover letter based on my resume, aligning with the job description, and emphasizing my experience with project management tools like Rally, VersionOne, and Jira, with flow diagramming tools such as Miro, Mural, Excalidraw, and OmniGraffle, and coaching product managers on various styles of product roadmaps?
A prompt to requesting it write a cover letter based on the information sought in the job description but not specifically called out in my resume.

The first draft went over a page. You want to quickly highlight things for the human who reviews your cover letter and resume. Keep it short and to the point.

A prompt reading: Can you make that letter a little shorter? Perhaps 375 words or less?
Another prompt to to make the cover letter shorter.

Again, review what the generative AI wrote for accuracy and tone. If the cover letter sounds dry and boring, you will likely get filtered even if you do get past the ATS.

How much time can this save?

The resume writing step can be completed in less than 10 minutes. Customizing a resume for a specific job used to take me an hour. You can verify your resume with other tools, such as (I'm not an affiliate. I have found Jobscan useful for jobs I was very interested in.). That could add a few 10-15 minute iterations.

Once you have the customized resume and ask the LLM about gaps between it and the requested skills, you might have a cover letter in another 5-10 minutes. Again, read through everything the LLM writes to check for accuracy and tone.

A process that used to take me 1.5 to 2 hours per application can now take 15-20 minutes. This can allow you to apply to many more jobs in a day or allow you to do other things than job fish.

Hope this helps.

P.S. Other Notable News

  • AI technology changes quickly. I'll write new articles as I learn about new job fishing capabilities. I've already rewritten this article once and tried to film it once in the last week. This technology moves hyper-fast and there are pitfalls. More later.
  • If you are in Orlando on March 27, 2024, you might want to attend the event: How AI is Changing Jobs! presented by my friend Heidi Araya.
  • Thanks to Om Patel for letting me know about this April 9 online event: The Impact of AI on Job Searching Strategies
  • For something completely different, Jim Benson and I will provide an online mini-workshop on Building the Best Distributed Team on April 4, 2024.