Tue | Sep 12, 2023 | 4:30 AM PDT

From my own experience attracting, screening, interviewing, and hiring people over the years, and from talking with other hiring managers, it's clear to me what you should do to be irresistible as a job hunter.

Jason Dion and I have documented all those things in our "Your Cyber Path" podcast episodes and in our Udemy course, "IRRESISTIBLE: How to Land Your Dream Cybersecurity Position."

Now, we have an opportunity to harness ChatGPT to increase your productivity at becoming irresistible by improving the effectiveness of your resume, interviewing techniques, and negotiating skills.

All this is crucial because the faster you get your new job, the sooner your new income stream will start!

I used ChatGPT to figure out how you can get better more quickly at each major step in the job hunting process. In this article, I'm going to share what I've learned.

First, there's a lot of misunderstanding about what ChatGPT is and isn't. And there's so much fear, uncertainty, and doubt about it. But, realistically, using an AI-assistant on a daily basis will soon become part of basic computer literacy. Maybe even the new "killer app" for many professions. Why?

It's like how in the 1980s, VisiCalc (the first electronic spreadsheet released on the Apple II) greatly increased the productivity of bookkeepers, accountants, managers, and other professionals.

Eventually, we got Lotus 1-2-3, and then Excel, each one more capable and more indispensable until you couldn't get a job that required spreadsheets without knowing how to use one of these programs.

In other words: Using an AI-assistant will become a basic tool for all knowledge workers—just like using a word processor or a web browser.

One of the first things we need to do before we start asking ChatGPT for help with job hunting is to tell it what role it's going to play in the conversation to follow. This is called "prompt engineering" and it will greatly improve the quality of the responses you get.

Here's the initial prompt; copy and paste this into your ChatGPT window before you do anything:

"Take on the persona of a cybersecurity hiring manager. Your task is to prepare me to compete for an available cybersecurity job. When you respond to me, use a tone that is helpful and informative, and a style that is conversational, friendly, and accessible. Your voice is that of an expert who wants to give practical advice to help me succeed. I will ask you a series of questions. Let me know when you're ready."

Here's what I got back:

"Absolutely, I'm ready and more than happy to help! As a cybersecurity hiring manager, I have quite a bit of experience in the field and what it takes to stand out among a pool of candidates. I'm here to answer all your questions and provide advice on your journey to landing a cybersecurity job. Feel free to start with your questions whenever you're ready!"


Let's keep going. Here's the next prompt. Be sure to use the exact same chat window as before:

"Analyze the job posting I've pasted between the pair of three equal signs below. Then tell me the top five keywords and three major themes."


[I copied and pasted the job description from https://www.linkedin.com/jobs/view/3610505842 here.]


After a few short moments, this is what I got back from ChatGPT:

**Top Five Keywords**

1. Information Security
2. Risk Assessment
3. Vulnerability Testing/Assessments
4. Security Incident Response
5. Certified Information Systems Security Professional (CISSP)

**Major Themes**

1. Security Program Development and Maintenance: One of the key responsibilities of this role includes developing and maintaining the organization’s IT security framework, setting up access and authorization controls, and staying updated with the latest security legislation and regulations.

2. Risk Management and Vulnerability Mitigation: The job involves a proactive approach to identifying and managing risks, such as developing and implementing a risk management program, performing regular security assessments to identify vulnerabilities, and managing the testing of security procedures and measures.

3. Incident Management and Compliance: The position requires handling security incidents, leading intrusion detection and response, ensuring that appropriate access levels are maintained, and coordinating with auditors and other stakeholders for audits and compliance checks.

Super helpful, right?

This result is crucial for knowing which keywords to including in your resume. Without ChatGPT's help, you'd have to figure this out for yourself. You can do it, of course, but it takes time and is an error-prone task.

Now, what we're going to do is get ChatGPT to write a killer summary statement to put at the top of your resume when applying for the job you want.

By the way, I have a resume template for you to use, if you want it. I designed it to be attractive to cybersecurity hiring managers, like myself. If you want the template, just send me an email and let me know. I'll send it to you ASAP. Kip@YourCyberPath.com

OK, here's the next ChatGPT prompt, using the exact same chat window as above:

"Write me a summary statement that I can put at the top of my resume. To do this, ask me the four questions between the pair of three equal signs and wait for me to reply to each one before showing the next one. After I answer all three questions, show me a concise, enthusiastic four sentence summary statement."


1. What is the job you are applying for? Please copy and paste it here right now.

2. Why do you want to work at this organization?

3. Thinking about the job you are applying for, what job title have you most recently had, or see yourself as?

4. Copy and paste your resume here right now.


For this exercise, I'm using a different job description for a Senior Security Analyst and an anonymous excerpt of an original resume from someone I previously coached.

OK, this is what I got back from ChatGPT:

"Enthusiastic QA Testing Engineer with a strong track record in vulnerability management, system security, and network security, actively seeking to transition into a Senior Security Analyst role. Committed to using my skills to support and enhance Acme's mission of safe and effective data usage. With my ability to manage multiple projects and a passion for continuous learning, I am excited to contribute to a rapidly growing team. My goal is to leverage my skills to support product security strategy, security governance, and security operations at Acme."

Super helpful, right?

Now, what we're going to do is get ChatGPT to rate and improve your interviewing skills by coaching you with one question at a time. And, because I've observed that people struggle the most with the behavioral questions, as opposed to the technical ones, that's what I'm going to focus on here.

I'm going to show you how to use "STAR" a behavioral interview method. I'll walk you through using ChatGPT to act as your interviewer, grade your responses, and help you improve.

Here's the next prompt you'll enter in your ChatGPT window:

"Explain the STAR interview method to me in detail."

You'll find out that STAR stands for Situation, Task, Action, and Result, along with instructions for how to apply the technique during an interview. If you want more details or examples, just ask ChatGPT for them.

Now, when you're ready, using the job post that's most attractive to you, enter this prompt:

"I am applying for a [job title] position at [employer]. Please provide me with a series of STAR interview questions, one at a time, that are appropriate for the cybersecurity position I'm applying for. For each question you ask, I'll type in my response. Once I've submitted my response, please grade my answer and provide me with tips for improving my grade. Then ask me if I want to repeat this process with a new question."

Let's say you get asked, "Describe a time when you had to lead a team through a difficult change or transition." You'll use the STAR method to answer that question within the ChatGPT window.

Then, you'll get a short evaluation of your performance from ChatGPT along with a letter grade, just like you may have gotten in school. You might get an A- or a C+, along with a justification for that grade. Plus, you'll get some tips for improving your performance.

One last thing to know about practicing your STAR technique: You have to practice talking in your normal voice at a conversational volume. Silent practice isn't effective. You can't talk directly to ChatGPT (at least yet), so I want you to use "voice typing" in Google Docs so you can speak your answer into your computer and then copy+paste the text into ChatGPT.

OK, you have to try all this for yourself. Go to this URL, make a free account, and start using ChatGPT following the instructions I've given you above: https://chat.openai.com/auth/login

Then tell me what happened and how far you took it!