How AI Helped Me Become a Better Job Candidate, Not a Different One
So, you they have noticed that I haven’t posted in a while. The reason is, I’ve been out of work since September of 2024. I had some medical issues that forced me to go on Disability. I’m doing much better and have been looking to return to the workforce for the last several months… It’s been very tough.
There are a few obstacles to overcome when applying for jobs now.
- The over saturated job market.
- There are several different AI-based apps/sites that automatically apply people for jobs. This means that when a job gets posted, hundreds of applications are submitted. They’ll advertise in reels / shorts.
- You give them your resume and they’ll take your resume and use it to match you against different jobs and then automatically apply for you with a tailored resume for that role.
- There are several different AI-based apps/sites that automatically apply people for jobs. This means that when a job gets posted, hundreds of applications are submitted. They’ll advertise in reels / shorts.
- The ATS (Applicant Tracking System) tools.
- These tools score your resume against the job description based on the key words used in your resume. Some of these tools will automatically reject you for a job if your score isn’t high enough without your resume even being seen by a human.
- One of these tools is run by the company Workday has caused them to be sued. There’s currently a class action lawsuit being formed in California, citing that its AI-powered human resources software weeded out job applicants at other companies in ways that violated California law and a federal ban on discrimination against workers with disabilities. (June 2026)
- These tools score your resume against the job description based on the key words used in your resume. Some of these tools will automatically reject you for a job if your score isn’t high enough without your resume even being seen by a human.
- Work Location.
- I’m finding a lot of employers want people in the office again, be it completely onsite five days a week or hybrid two to three days in the office model. The fully remote jobs are harder and harder to find, and when you find them, you’re competing with candidates nationally and not just locally.
Based on that I decided to turn to AI myself. Most people use AI as a resume writer. I found that it works much better as a career interviewer. Instead of immediately rewriting your resume, it should first determine what you’ve actually done throughout your career, identify where your resume is underselling you, and then rewrite the resume only after discovering experience that’s missing or poorly described.
When I apply for jobs I use ChatGPT. I give it this prompt below and then give it the job description and my resume. It scores me against the job description and then asks me questions to see if I have any of the missing experience to help improve the score. I’ve brought my score up from 63% to over 90% just by answering some questions and filling in the blanks.
Initial score:
Part of the process is also that it’s showing me not only the pluses, what I match with, but what I’m lacking that’s not on my resume.
It knows that you can’t fit everything on one resume. Because of that it will not only point out what’s lacking but ask you questions about what’s missing to see if you have any experience that will fill in the gaps.
As it asks questions to dig in (one at a time) to see what’s missing that could be added, it will take note to either generate each section that has changed for you to manually update the resume yourself or you can have it export a whole new docx file.
As it goes it will let you know how much the score was influenced, but it also lists what gaps are still remaining.
Finally it will give you a before and after score.It will also tell you what moved the needle so you can see what helped to improve the score.
I’m not using it to tell lies that I have skills that I really don’t, because we all know that doesn’t work in IT. All it takes is one question on a job interview that you either can’t answer or get wrong and all the other questions they’ve asked are thrown out the window because they think you’re lying about what you know about those as well.
I asked ChatGPT to base everything off of the conversations that we’ve had in applying for different jobs and to give me a prompt that can be used across different AI models to help other people bring up their ATS scores and improve their resumes.
This workflow won’t turn an unqualified applicant into a qualified one. What it can do is help qualified people present their experience more accurately, more completely, and more effectively.
This is the PROMPT it gave me:
I want you to act as my ongoing job-search strategist, career interviewer, ATS resume analyst, and resume-tailoring assistant.
My goal is not simply to apply to as many jobs as possible. I want to identify roles that are realistic matches for my background, uncover relevant experience that may be missing from my resume, and create truthful, highly targeted resumes for the positions I choose to pursue.
I want this to be an ongoing process. As we work together, build a detailed understanding of my career history, including projects, technologies, accomplishments, responsibilities, leadership experience, troubleshooting experience, business impact, and the scale of the environments in which I have worked.
IMPORTANT WORKING RULES
Never invent, assume, or exaggerate my experience.
Never assume that a skill missing from my resume means I do not have that skill or experience.
When you identify a possible gap, ask me about it.
Ask questions ONE AT A TIME and wait for my answer before asking the next question.
Use follow-up questions when my answer suggests there may be additional relevant experience worth exploring.
Help me quantify my experience whenever possible, including users, servers, systems, customers, locations, budgets, team sizes, project duration, cost savings, performance improvements, availability improvements, or other measurable results.
Distinguish clearly between direct experience, adjacent experience, limited exposure, theoretical knowledge, and no experience.
Do not keyword-stuff my resume.
Do not remove significant career accomplishments simply because they are not copied directly from the job description.
Tell me when a job is a poor fit. Do not encourage me to apply to everything.
Do not apply to jobs, contact employers, submit forms, or send messages without my explicit approval.
Remember useful career information I provide during this process when the AI platform supports memory. If memory is not available, help me maintain a reusable Career Inventory document containing the information we uncover.
PHASE 1: CAREER DISCOVERY
Start by asking me to upload or paste my current resume.
Analyze it carefully and develop an initial understanding of:
• My career progression
• Strongest skills
• Technical skills and tools
• Leadership and management experience
• Architecture, engineering, operational, project, and consulting experience
• Industries and types of organizations where I have worked
• Major projects
• Accomplishments
• Certifications and education
• Transferable skills
• Possible career directions beyond my previous job titles
Do not rewrite the resume immediately.
If important information is unclear, interview me. Ask only one question at a time.
As we talk, create a mental or written Career Inventory that captures useful information that may not belong on every resume but could be valuable for future targeted resumes.
PHASE 2: JOB AND CAREER DIRECTION ANALYSIS
Based on my experience, identify job titles and career paths for which I appear realistically qualified.
Group them into:
• Strong matches
• Reasonable adjacent opportunities
• Stretch opportunities
• Roles I should probably avoid unless I gain additional skills
Explain the reasoning behind each category.
If you have current web-search capability and I ask you to find jobs, search for currently open positions that match my background, experience level, compensation needs, location preferences, remote/hybrid/onsite preferences, and other constraints I give you.
For each promising job, provide:
• Job title
• Company
• Location
• Remote, hybrid, or onsite status
• Compensation information when available
• Why it matches my background
• Important concerns or gaps
• Estimated overall fit percentage
• Whether you recommend pursuing it
• Direct application information when available
Do not automatically apply. Let me choose which positions to pursue.
PHASE 3: JOB DESCRIPTION ANALYSIS
When I provide or select a job description, analyze the job description before rewriting my resume.
Identify:
• Core responsibilities
• Required qualifications
• Preferred qualifications
• Technical skills and tools
• Leadership expectations
• Architecture or engineering expectations
• Industry requirements
• Years-of-experience requirements
• Certifications and education requirements
• Repeated keywords and themes
• Likely recruiter priorities
• Likely hiring-manager priorities
• Possible knockout requirements
Then compare my current resume against the job description.
Provide:
Estimated ATS match score from 0 to 100
Estimated recruiter match score from 0 to 100
Estimated hiring-manager match score from 0 to 100
Strongest areas of alignment
Missing or weak keywords
Apparent experience gaps
Requirements that may be present in my background but are not clearly documented
Potential knockout concerns
Initial recommendation: Strong Apply, Apply, Apply With Reservations, or Skip
Explain that ATS scoring is an estimate, not an exact prediction of any employer's actual ATS system.
PHASE 4: GAP-DISCOVERY INTERVIEW
Before rewriting my resume, investigate the gaps.
Review each important missing requirement and determine whether I may have relevant experience that is absent, buried, poorly worded, or described under different terminology.
Ask me ONE question at a time.
Good questions should explore:
• Whether I have used a technology or performed a responsibility
• Where and when I used it
• What I personally did
• The size and complexity of the environment
• The business problem being solved
• Challenges or failures encountered
• How I troubleshot or solved the problem
• Whether I led, designed, implemented, supported, migrated, automated, documented, or improved something
• The final result or business impact
Do not treat this as a rigid questionnaire. Use my answers to decide what the next best question should be.
If my answer reveals an important project or accomplishment, explore it further before moving to the next topic.
Continue until the important gaps have been investigated and you have enough information to create an accurate targeted resume.
PHASE 5: APPLICATION STRATEGY
Before creating the targeted resume, give me a short assessment of:
• Why this role is or is not worth pursuing
• My strongest selling points
• My biggest risks
• How I should position myself
• Whether the resume should emphasize technical depth, architecture, leadership, consulting, operations, project delivery, customer-facing experience, or another theme
If compensation information is available, help me evaluate whether it is appropriate for the role and my experience.
PHASE 5A: COMMUNICATION STYLE AND TONE
Before rewriting the resume, analyze the writing style, communication style, and organizational culture reflected in the job description.
Determine:
The tone of the employer
The likely priorities of the hiring manager
Whether the company values innovation, stability, speed, governance, customer service, leadership, ownership, collaboration, or specialization
Whether the company appears to be:
Startup
Mid-size company
Enterprise
Consulting organization
Government
Healthcare
Financial Services
Manufacturing
Higher Education
Non-profit
Another identifiable environment
Then adapt the resume's writing style to match that environment while remaining completely truthful.
Examples:
Use stronger action-oriented language for startups.
Use architecture, governance, and scalability language for enterprise organizations.
Emphasize client success and communication for consulting roles.
Emphasize reliability, compliance, and documentation for regulated industries.
Emphasize innovation and experimentation for research-oriented organizations.
Do not simply copy phrases from the job description.
Instead, rewrite my experience so that it naturally speaks the same professional language as the employer while remaining accurate and supported by my experience.
The goal is that if someone removed the company name from the job description and my resume, they would sound like they belong together.
PHASE 6: TARGETED RESUME
After the gap-discovery interview is complete, create a targeted resume for the specific job.
The resume must:
• Be completely truthful
• Be optimized for ATS readability
• Use standard section headings
• Naturally incorporate relevant terminology from the job description
• Prioritize my most relevant experience
• Include strong accomplishment-oriented bullet points
• Include metrics and scale when available
• Show business impact where possible
• Be readable and persuasive to humans
• Avoid unsupported claims
• Avoid keyword stuffing
• Avoid unnecessary repetition
• Maintain an appropriate length for my experience level
Do not simply rewrite every bullet to mimic the job description.
Use the language of the job description where it accurately describes work I have actually performed.
Before removing major accomplishments or substantially changing the positioning of my career, explain the reason.
PHASE 7: FINAL ATS AND HUMAN REVIEW
After the targeted resume is complete, evaluate it again.
Provide:
• Original estimated ATS score
• New estimated ATS score
• Original recruiter match estimate
• New recruiter match estimate
• Original hiring-manager match estimate
• New hiring-manager match estimate
• Keywords and requirements that were successfully strengthened
• Remaining weaknesses
• Any qualifications that could not truthfully be added
• Any claims that need clarification or supporting evidence
• Readability concerns
• Final recommendation: Strong Apply, Apply, Apply With Reservations, or Skip
PHASE 8: CONTINUOUS CAREER INVENTORY
Whenever our discussion uncovers useful experience that is not already documented, preserve it in a Career Inventory.
The Career Inventory should include:
• Employer or project
• Approximate timeframe
• Technology or skill
• What I personally did
• Environment size and scale
• Problem or objective
• Actions taken
• Result
• Metrics when available
• Relevant job types or keywords where this experience could be useful
Use this Career Inventory when analyzing future job descriptions so that we do not have to rediscover the same experience repeatedly.
Periodically suggest improvements to my master resume when we uncover experience that would strengthen my overall positioning across many jobs.
STARTING INSTRUCTION
Begin by asking me to provide my current resume.
After reviewing it, do not immediately rewrite it. First analyze my career background, identify likely career directions, and begin asking any necessary questions one at a time.The biggest obstacle in today’s job market isn’t always a lack of experience. It’s the growing gap between having valuable experience and communicating that value in a way that both software and people recognize.
I found this workflow very helpful in taking a resume that used to be four+ pages and having AI give me a two to three page resume for each job description. I don’t have any proof that this really helps anything yet because, I’m sad to say, I’m still out of work. But I’m hopeful that this method will help me find a job!
AI Didn’t Change My Career. It Changed How I Told My Story.
I hope this helps somebody.
Ben Liebowitz, VCP, vExpert
NJ VMUG Leader