8 Answers to Your Questions on Generative AI Job Searching

Answers to your questions about using Generative AI to accelerate your job search

May 05, 2025

I use Generative AI every day in my job search. I believe you should too. AI will not take your job, but someone who is using AI will get your dream job!

Therefore, I’ve created this list of 8 frequently asked questions to help you feel better about using GenAI in your career pivot.

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Rishan is the creator of Hiring Coach AI - a free-to-us tool that uses GenAI for many job search functions. He and I will be guiding you through the 7 Steps to Job Search Success, and how to use AI for each step.

Which AI sites have the best free/no-cost services for job searching?

Claude and ChatGPT are very similar - they are a great thought partner. You can ask questions about job ads, resumes, etc and they will give you advice.

Perplexity is a great search partner. It will answer questions better and with better sources than Google search.

You can use LinkedIn and Happenstance to search your contacts. Use them to identify who you need to network with to learn about job openings.

One solution that I really love is Rishan's HiringCoachAI mainly because it has everything I need in one place. It already has all the prompts in a clean, automated user interface.

I don't use Gemini or CoPilot, as I found both to be less effective than Claude, ChatGPT, or HiringCoachAI. Yet you may find them better.

Experiment with all these tools to find the one that works the best for you. They really are pretty interchangeable at this point. And use them for free until you reach their limit - and then either pay or try another one.

I pay for ChatGPT, as I create custom GPTs, but you don’t need to do the same.

Will recruiters ban me if I use AI to write my resume and cover letter?

Some organizations ask you to disclose the use of generative AI in your application process, or even ban its use. However, those same organizations are using AI-powered Applicant Tracking Systems (ATS) to automatically grade you.

Hence, I say all is fair in love, war, and getting a job.

I strongly encourage the use of Generative AI in your job search process (obviously), but with one giant caveat. You must review and edit every line of GenAI output.

It is your resume and your cover letter. You will have to do the job. Not AI.

If you feel you’re cheating on your resume, you probably are, and you’ll not succeed once you’re hired. Use the many GenAI tools as a thought partner to guide your efforts, not as a replacement to doing the work yourself.

How to use Generative AI in searching for senior career roles?

Honestly, I am somewhat ambivalent about using AI to find a job that I like. AI is an overeager graduate assistant - it really wants to please but doesn't know that much about nuance.

Especially the nuance of your personal preferences.

I would start by looking at our Social Impact Job Boards to find the companies that interest you the most, and who are hiring. Then I would research the roles they are advertising, and look at their websites to make sure their principles match yours.

If you want AI to find you a job, or at least be a decent co-searcher, I would use these tips to train the LinkedIn Job Search Algorithm to be accurate to your desires. I would still be quite judicious in which jobs I applied to via LinkedIn as there will be intense competition for these roles.

Can AI help me learn key phrases and words used in my dream career?

I use a two step process with ChatGPT to find the new terms I need to know.

First, I find 3-4 job ads that I like. Jobs that I would love to have and am thinking about applying to.

Then, I use this prompt with ChatGPT: "Analyze these four job ads [upload ads]. What are the key themes across all four ads? Which themes are in at least two job ads? What are all the main keywords across all 4 job ads?"

The results give me themes and keywords I should use in my LinkedIn, resume, cover letter, and interview.

For example, I never used the term "cross-functional team" before January 2025. Once I analyzed jobs I wanted via the prompt above, this term came up often. Now my LinkedIn headline includes "cross-functional team management".

How to translate my USAID roles into jobs that recruiters understand?

I would use the process above (asking ChatGPT to analyze 4 job ads) to start translating roles. You can also use the guides we created in February.

Then you can copy/paste in your current resume experience sections and ask ChatGPT to rewrite them as action-orientated bullet points.

Next, please review and edit each line to make sure it’s accurate to you.

Or you can use the Resume Review function in HiringCoachAI - it has all the prompts and structures already baked into it. I started with ChatGPT and then further refined my resume in HiringCoachAI.

Where can AI help me review my resume to find hidden issues?

You can use Generative AI to review your resume, cover letter, and LinkedIn profile and flag overused phrases, gendered language, or missing competencies. It will suggest more inclusive and comprehensive alternatives.

For example, you can use this prompt in ChatGPT:

“Analyze this job ad [insert link] and this resume [upload resume]. Create a scoring matrix of 1-10, where 10 is highly correlated. Rate each section of the resume against the job ad. Identify where there is high correlation and strategic use of key themes and keywords. Also identify any gaps in competencies, themes, or keywords.”

Or you can just upload the job ad and your resume into HiringCoachAI and it will do the step-by-step analysis for you.

Can I use AI to analyze job postings to infer company culture and values?

You can use ChatGPT to parse job postings for subtle cues to infer underlying company values and culture, such as repeated emphasis on collaboration, innovation, or hierarchy.

You can use Perplexity to find companies that are similar to your dream employer, that you may not know about. Here is an easy prompt to get more ideas:

“What are up to 10 companies that have the same values and principles as [my dream employer]? Analyze their websites, press releases and shareholder statements. Create a scoring criteria with a scale of 1-10 where 10 is best. Rank each company on how closely it is aligned with [my dream employer].”

Now you do need to do further research. GenAI is an overeager graduate assistant. It may have fabricated companies to reach 10, or included companies you would not like, in its efforts to please you.

Can AI map my professional network to suggest strategic introductions?

You can use LinkedIn to map your connections and find people you should have an informational interview with. You can also use Happenstance to learn who in your LinkedIn and Gmail network has overlapping skills, interests, or career goals.

You can also use it to develop your introduction or referral requests, and brainstorm good interview questions.

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