How to Safely Use ChatGPT and Other AI for Your Executive Resume and Job Search

If you’re like a lot of people, you’re using ChatGPT or other Artificial Intelligence platforms for many purposes.

Maybe you have Alexa in your home and you ask it a barrage of questions and give it tasks throughout the day.

Or maybe you’re using using AI for things like this:

• Planning workouts and meals
• Organizing a messy computer desktop
• Organizing research for a thesis
• Skimming dozens of academic articles
• Sorting through an archive of pictures
• Learning and playing with language
• Designing parts for spaceships
• Creating an app and fixing bugs in code
• Playing Pong and 3D games
• Making a Spotify playlist

And it’s being used to help people write all kinds of content like:

• Wedding speeches and vows
• Online dating profiles
• Homework
• Email messages
• An appeal on an insurance denial
• Excel formulas
• Getting feedback on fiction
• Resumes, LinkedIn profiles, cover letters and other job search materials

Engaging with AI can be seductive. After all, it’s designed to rope you in, compel you to hang around maybe longer than you’d planned, and then come back more often.

In fact, it’s the rare person who doesn’t come into contact with AI on a daily basis.

Maybe you’re not on board yet with AI for resume writing, but many other job seekers are.

This article will help you decide whether it’s right for you, and learn how to use it to your best advantage. I’ve included plenty of AI prompts to get you going.

With so many people using AI for so many purposes, it should come as no surprise that AI has heavily infiltrated the job search landscape.

Although Artificial Intelligence (AI) has been around since the 1950’s, the launch of OpenAI’s ChatGPT in November 2022, and it’s rapid and meteoric rise in usage, have pushed the conversation about AI in job search into the forefront.

Those of us in the careers profession (resume writers, coaches, recruiters, etc.) constantly talk about the ins and outs of using AI.

Executive Job Search and AI

Job seekers turn to AI to help them with their resumes, LinkedIn profiles, job interviews and more. Some of this is good, some is not so good, as you’ll see below.

And more and more recruiters and other hiring professionals rely on AI-assisted systems to source and recruit candidates.

To illustrate, here’s a case study from a job search coach:

Recently, a client I had been advising for just three months was invited to interview with a healthcare organization for a fractional program manager role. He hadn’t applied. No recruiter had reached out. There was no warm introduction or referral.

When he asked how they found him, the answer was shocking: “ChatGPT recommended you.”

What surfaced his name wasn’t a résumé refresh or a job search strategy. It was the fact that he had been consistently posting thoughtful, specific content on LinkedIn about a narrow operational challenge. Over time, that content created a clear signal of expertise.

In just three months of posting regularly, he received seven inbound opportunities, none of them tied to traditional job search activity.

What made the difference wasn’t his background on paper. It was the unique insights for his industry and expertise that he had made visible.

AI is changing what counts as professional signal.

Hiring managers still hire the way they always have, relying on résumés, references and reputation. But the tools they use are evolving. AI-assisted systems pay attention to what’s visible. Public profiles, posts and commentary become inputs that can be compared, grouped and surfaced.

AI is not a recruiter and isn’t recommending the best possible candidate. It’s surfacing candidates based on signal, not suitability.

The people who found this job seeker through AI used prompts that featured the areas of expertise he had been posting regularly about, and positioning himself around.

AI is plagued by controversy

With the proliferation and high demand for AI-based products and services these days, exercising caution when using these platforms is a very good idea.

According to Ezra Klein, opinion writer at the New York Times, who has read numerous policy papers and spoken with AI engineers:

What they tell me is obvious to anyone watching. Competition is forcing them to go too fast and cut too many corners. This technology is too important to be left to a race between Microsoft, Google, Meta and a few other firms. But no one company can slow down to a safe pace without risking irrelevancy. That’s where the government comes in — or so they hope.

He prioritized the following categories for regulation:

Interpretability, which may not be achievable. But without it, we will be turning more and more of our society over to algorithms we do not understand.

Security. Any firm building A.I. systems above a certain scale should be operating with hardened cybersecurity.

Evaluations and audits. Right now, the testing done to make sure large models are safe is voluntary, opaque and inconsistent. No best practices have been accepted across the industry.

Liability. The way to make A.I. systems safe is to give the companies that design the models a good reason to make them safe. Making them bear at least some liability for what their models do would encourage a lot more caution.

Humanness. A.I. systems can be tuned to return dull and caveat-filled answers, or they can be built to show off sparkling personalities and become enmeshed in the emotional lives of human beings.

What are ChatGPT and other AI platforms, and how do they work?

ChatGPT (Chat Generative Pre-Trained Transformer) is a natural language AI chatbot developed by OpenAI, an AI research and deployment company that interacts in a human-like conversational way.

As with other AI platforms, ChatGPT can answer questions about most any topic and help you compose emails and other content. And it will answer followup questions, admit its mistakes, challenge incorrect premises, and reject inappropriate requests.

The technology goes well beyond the data you’ll get with a Google search of keywords, leading to web pages that provide the information you seek:

AI’s power is the ability to parse queries and produce fully-fleshed out answers and results based on most of the world’s digitally-accessible text-based information – at least information that existed as of its time of training.

But, like Google and other search engines, the content AI provides is based only on what information already exists online or what you feed it.

AI is not a panacea

As the ChatGPT website stresses, the platform does have limitations:

• ChatGPT sometimes writes plausible-sounding but incorrect or nonsensical answers.
• ChatGPT is sensitive to tweaks to the input phrasing or attempting the same prompt multiple times. For example, given one phrasing of a question, the model can claim to not know the answer, but given a slight rephrase, can answer correctly.
• The model is often excessively verbose and overuses certain phrases, such as restating that it’s a language model trained by OpenAI.
• Ideally, the model would ask clarifying questions when the user provided an ambiguous query. Instead, our current models usually guess what the user intended.
• While we’ve made efforts to make the model refuse inappropriate requests, it will sometimes respond to harmful instructions or exhibit biased behavior.

The dark side of this technology

With all the accolades and excitement about ChatGPT, some people have noticed serious downsides.

The technology comes with issues challenging other chatbots:

It reflects society and all the incorrect biases society has. Computational scientist Steven T. Piantadosi, who heads the computation and language lab at UC Berkeley, has highlighted in an X thread a number of issues with ChatGPT, where the AI turns up results that suggest “good scientists” are those who are white or Asian men, and that African American men’s lives should not be saved. Another query prompted ChatGPT to indulge in the idea that brain sizes differ and, as such, are more or less valuable as people.

The reason is the same that nobbles every chatbot: The data it uses to generate its responses are sourced from the internet, and folks online are plenty hostile.

How good is AI for resume writing and job search?

Resume writer and career coach Gillian Kelly noted some of the things job seekers and hiring professionals can do with this technology:

• Review a jobseeker’s resume and provide general input on grammar, spelling, layout, readability, content, and keywords (when compared with a job advertisement). You can even ask it to pick up any red flags or weak spots that a recruiter may identify.
• Help candidates identify their skills and strengths from their outlined work experience or past activities.
• Suggest potential jobs or careers suited to a specified set of skills or offer similar alternative paths to a specific job.
• Identify skills sought for a particular job title.
• Find recruiters in a particular sector or geographical area.
• Research an organisation; its employee reviews, values, competitors, or core products.
• Generate conversation starters for networking.
• Assist in creating a cover letter, e-note or thank you note.
• Assist in salary research.
• Support interview practice by prompting common questions or helping a job seeker summarize or refine their answer.
• Help a jobseeker create an elevator pitch, their LinkedIn summary, and LinkedIn posts or assist with writing other online profiles or career biographies.

The smart and safe ways to use AI for resume writing and job search

AI can be extremely helpful, and a major time-saver, for building your target company list and then researching those companies.

AI will also be helpful for job interview prep, using the targeting and research information-mining you did initially, augmented by specific prompts related to interviewing.

Popular AI platforms include ChatGPT, Claude, Perplexity, Gemini, and Copilot, but there are many others.

In particular, Crunchbase can be very helpful because it provides in depth information across industries such as company size, funding details, leadership, and recent news, as well as other similar companies.

You’ll get the best results with AI using prompts that are specific, such as these to build your target company list:

“Create a list of (X number) companies in or near (city, state) that have hired (role you’re seeking).”

or

“What are the top companies located in (city, state) in the (X) industry that are expanding their focus into [your areas of expertise that you want the job to focus on]?”

or

“My dream job is a [job title or type of job] role at [company name], located in [location]. What other companies in this geographical location offer the same role?”

Here are some tips and excellent prompts from Diana Vasileva, a job seeker herself who used ChatGPT to great advantage for research and job interview prep:

I build my understanding of the company’s business, ecosystem, and top 3 competitors by directly engaging with their available platforms: website, app, social media, LinkedIn page, etc. Additionally, I sign up for their emails, follow their social mages, read their blogs (if available) and skim their latest press releases or knowledge center.

To further this preparation, I use AI to generate a comprehensive knowledge arsenal:

“Research [Company Name]’s current market position and future goals. Extract their major achievements and challenges. Create talking points about industry trends. Build engagement hooks from company news. Format this as my company knowledge arsenal.”

“Compare [Company Name]’s marketing strategy with its top three competitors. Highlight major differentiators, areas where they lag behind, and opportunities to gain a competitive edge. Provide actionable insights on how they can refine their positioning.”

“Analyze [Company Name]’s marketing funnel based on available information. Identify strengths, weaknesses, and opportunities for improvement. Provide a strategic breakdown of how they acquire, convert, and retain customers. Offer data-backed insights on potential gaps in their approach.”

“Map out the ideal customer journey for [Company Name]. Identify potential friction points in the current experience and recommend optimizations to improve conversion and retention. Include strategies that leverage content, automation, and personalization.”

Start with meaty prompts like these, then have a conversation with AI.

Ask specific questions and follow up with more probing prompts, and/or ask for more options based on what you’ve already asked.

Using AI for interview prep, cover letters and thank you letters

Harvard University offers this advice:

Conduct background research. You can use generative AI to do initial research about an industry, market, etc. Keep in mind that generative AI can generate factually incorrect information, so it’s important to double-check your research with trusted sources.

Brainstorm answers to likely questions. You can also ask follow-up questions in response to prompt responses. For example, how might an answer change if you incorporate the company mission statement, or information about their culture?

Evaluate your proposed answers. Type up your answers to behavioral questions in STAR (Situation Task Action Result) format, and ask the AI to provide feedback on your answer.

Do not memorize answers! You want to generate ideas but not a word-for-word script, as you will need to be able to adapt in the moment during your interview. Also, make sure to put your responses in your own voice, not the voice of the AI. Remember that the response you get from a generative AI model may not be accurate.

An article on The Muse suggests keeping these things in mind before getting started:

Add context: Feed AI a lot of information in the first message or first couple of messages.

This can be anything from your background or working style to background on the company or role—the more details you provide, the better it can work in your favor. And remember that you can continue the conversation to get a more specific answer, and ChatGPT will learn as you go and build its answers off of everything you’ve said previously.

The same Muse article offers up a long list of AI prompts for interviews, resume, cover letters and thank you notes, including the following (check it out for lots more):

• I’m interviewing for [job title] with [company/type of company]. What skills, attributes, or previous experiences are useful to talk about in my interview?
• Here’s my resume: [resume text]. What should I bring up in a job interview for a position as [job title] at [company/type of company]?
• Here’s my cover letter: [cover letter text]. What should I bring up in a job interview for a position as [job title] at [company/type of company]?
• You’re the interviewer for this role: [job description]. Can you come up with 3-5 interview questions based on this job description?
• You’re the interviewer for this role: [job description]. What are you looking for in a hire when interviewing them?
• You’re the interviewer for this role: [job description]. Conduct a mock job interview for me.
• Ask me [interview question you want to prep for], and I’m going to provide an answer. Give me feedback on my answer as if you’re the hiring manager: What elements of my story stood out? What pieces were missing? Given interview best practices, what did I do well, and what could I do differently?

For thank you notes and follow-up after the interview, they offered these AI prompts:

• I interviewed for [job title] at [company/type of company]. We talked about [describe what you talked about in the interview]. What should I write in my thank-you note to my interviewer who is [role of interviewer]?
• I interviewed for [job title] at [company/type of company], and I’m planning to send a thank-you note to [role of interviewer]. Here’s what I’ve written: [thank-you note draft]. Do you have feedback on how I could write this better?
• I don’t want to move forward in the interview process for [job title] at [company/type of company]. What’s the best way to send a rejection/What should the email look like?
• I interviewed for [job title] at [company/type of company], and I have a follow-up question for my interviewer. How can I ask it in a follow-up email?

Going a little deeper, here are some AI prompts to use when you have a specific job description in hand, from Hannah Morgan, the Career Sherpa:

Prompt 1: Identify the top qualifications and skills in the job posting

Acting as a [recruiter/hiring manager] in the [industry] industry, identify the 5 most important qualifications for the role listed below and list the 5 most important skills [paste job posting here].

Prompt 2: Generate a list of questions you should prepare for

Acting as the [recruiter/hiring manager] create a list of questions you would ask a candidate to evaluate skills, fit, and experience for the following role [paste job posting].

Prompt 3: Determine which accomplishments align with the job

Acting as an experienced career coach, use the attached resume to identify how this candidate’s resume aligns and where it does not align with the requirements in the job posting pasted below. [paste resume and job posting].

Prompt 4: Generate a list of questions YOU should ask

You are an experienced job seeker looking for [job title interviewing for]. What 10 questions would you ask the [recruiter, hiring manager] based on this job posting to better understand the role and company culture [paste job posting]?

When you don’t have a job description to work from, and are networking your way into a company, some of the prompts above will apply.

But to gain deeper insights than AI will probably be able to offer, rely on informational interviews (the old fashioned strategy).

Overall, think of AI as a starting point to mine the kind of information you’ll use in your resume, cover letters, thank you notes, etc. Then customize and personalize it as much as possible.

Take the time to craft vibrant content for your job search materials that will truly differentiate you and resonate with recruiters and other hiring professionals.

But be careful how you use AI

AI can be helpful in the ways I’ve noted.

But I strongly advise against using it to entirely write your resume, LinkedIn profile, cover letters, or other job search materials.

It could be risky to feed it any sensitive, personal information or confidential company information.

We just don’t know how that information may be used.

So it’s best to anonymize whatever you input into AI. Don’t give it anything you wouldn’t want to land online for all to see, because that could happen.

And don’t count on AI to do your personal branding work

Also, AI typically writes in a generic way that won’t do much to give a feel for your personality and differentiate you from other candidates like you.

Don’t expect that the content provided will be entirely useful as it is. It may be fairly generic in nature, and could apply to others competing for the same jobs.

In other words, it won’t do a good job with personal branding. You’ll need to work on that yourself. My Personal Branding Worksheet will help you.

In order to differentiate yourself, you’ll need to edit, augment, personalize and customize the content AI provides for your specific target employer(s) and personal brand.

More to think about before using AI for resume writing

There are other considerations when using AI for resume writing, from job search strategist and former hiring manager Matt Tooker:

Myth vs Reality: Using AI to write your resume is the best way to create a compelling document that catches the attention of a recruiter.

AI is a powerful tool. But handing it the keys to your entire resume? That’s where many job seekers go wrong.

Myth: AI knows how recruiters think.
Reality: AI predicts language. Recruiters assess risk, impact, and fit. Those are human judgments shaped by context AI does not fully understand.

Myth: AI creates differentiation.
Reality: AI creates averages. If your resume sounds like everyone else’s, you disappear into the pile. Differentiation requires lived experience and strategic positioning.

Myth: Keywords are all that matter.
Reality: Keywords get you scanned. Humans decide who gets interviewed. AI often over optimizes for systems and under delivers for decision makers.

Myth: AI captures leadership and complexity.
Reality: AI struggles with nuance. Managing change, influencing stakeholders, navigating ambiguity. Those stories need human framing to land correctly.

He ends by advising: Use AI as a collaborator, not a ghostwriter.

My advice: Take the time to craft vibrant content for your job search materials that will truly differentiate you and resonate with recruiters and other hiring professionals.

In summary, the technology may help you bring out at least some of the information you need to include in your resume, etc.

But instead of piecing it together yourself and hoping you’re doing a good job, consider working with a career professional, who knows what should and shouldn’t be in your job search materials.

Hiring professionals can spot an AI-written resume, and they don’t like it

Another potential problem with using this software for resume writing and job search. AI-generated content tends to read like AI-generated content.

Recruiters and other hiring professionals are attuned to it, can easily spot it, and can be turned off to people who use it.

Especially at the executive level, you’ll be expected to have a good handle on written communications and be able to write a cover letter yourself, and provide a well-written resume.

According to career expert Amanda Augustine, AI’s influence on resumes and hiring will only grow further over the years to come. Job seekers must adopt a better balance in using AI to write their resumes:

Over the past year, employers have increasingly pushed back against fully AI-generated résumés. Recent research shows that 74% of hiring managers say they can spot AI-generated résumés, and 57% are significantly less likely to hire candidates whose applications appear entirely AI-driven. Their main concern is that AI-generated documents often feel generic, overly repetitive, inauthentic, and—at times—a misrepresentation of a candidate’s qualifications.

To stand out in what is likely to remain a competitive job market, job seekers should use AI thoughtfully to ensure their résumés retain the crucial human touch. If you decide to use AI for drafting your résumé, review and revise its content carefully to tailor it to the specific role, accurately reflect your qualifications, and showcase elements of your personality. Highlight specific accomplishments and contributions, and avoid repetitive phrases when describing your work experience. The most effective résumés will be those that are AI-optimized, yet maintain the authenticity and human element that hiring professionals crave.

Experts weigh in on ChatGPT for resume writing and job search

Executive recruiter Jack Kelly noted some statistics of interest about the platform:

✅ By January 2023, it became the fastest-growing platform with 100 million users, reaching 1 billion visits in February alone. By contrast, Twitter took five years to reach 100 million users, while Instagram took 2 ½ years after its launch, and TikTok nine months.

✅ OpenAI’s technology platform managed to score in the 90th percentile on both the college-entry SATs and the attorney bar exam.

✅ According to a February survey from ResumeBuilder.com of 1,000 current and recent job hunters, nearly half (46%) of job seekers are using the chatbot to craft their résumés or cover letters.

✅ Seventy percent of respondents saw a higher response rate from companies when using ChatGPT.

✅ Seventy-eight percent of candidates who used the chatbot scored interviews, while nearly six in 10 job hunters were hired after using the AI tool during their application process.

All that sounds great, right? But he also noted the following:

11% of job seekers were rejected once it was learned from the hiring company that the candidate used ChatGPT.

Career professionals mostly like ChatGPT for resume writing and job search

He spoke with several job search and career experts about the value of ChatGPT

Hannah Morgan, Job Search Strategist

ChatGPT is empowering job seekers. It can provide answers to their specific questions beyond what a basic Google search will find (articles and videos). For example, ChatGPT can help develop a list of questions a job seeker can ask during an informational meeting. It can help job seekers identify alternative job titles in a new industry. It can even help them make a career shift to something totally different. Plus, it helps get rid of writer’s block. It can craft a rough draft of a cover letter, thank you note or even a follow-up email.

Sweta Regmi, Career And Résumé Strategist / Interview and Branding Coach

Job seekers have the power to use AI just the way employers have been using it for years for recruiting.

I tested ChatGPT as a job seeker by providing the prompt. I asked ChatGPT to identify core competencies based on the targeted role and added four job postings. Now, I have the resources with soft skills and hard skills to create a résumé. It helped me understand my strength, weakness, opportunities and threat (SWOT) to self-reflect.

As an employer, I created job descriptions to test out. It saved me time on productivity. I still have to have knowledge of HR and employment laws in my country and city. AI can only help if you have the skills or knowledge.

Ruth Sternberg, Job Search and Résumé Writer

When you feed it your résumé, you can ask to see jobs that seem to align with it. ChatGPT can give you a list of what’s important for a particular role, based on descriptions and other developed material, so you can compare your own job history to see if you match up. You also can ask the software to suggest ways you could improve what you’ve written based on a particular job. It can help you determine what types of jobs match a particular college major.

It also could translate résumés into other languages; add keywords from a particular industry and help you spot incongruities or flag unusual claims in your narrative to prompt a fact check.

I’ll add a caveat to Ruth’s suggestion:

It’s not a good idea to upload your resume, as is, to this platform. We don’t know what they may do with any confidential, sensitive or identifying information about you or your career. To be safe, only upload or prompt with non-identifying info or data about yourself or your career.

More About Resume Writing and Executive Job Search

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