u/Which-Signature-745

This is going to be a long post, and I will probably break the full story into several posts because there are a lot of lessons I learned throughout this process. Some are about AI, some about interviewing, and others about dealing with rejection and figuring out what you are doing wrong when you keep getting very close but can't get across the finish line. I hope sharing my experience can help someone going through the same thing.

For some background, I am an Engineering Executive with close to 30 years of experience building and leading technical organizations around the world. I've been an expat twice, speak three languages fluently, have managed global organizations, and have been responsible for programs worth up to $3 billion.

I have also been unemployed for the last six months.

I voluntarily decided to leave my previous company, which is a story for a different post. Over the last year, however, I have consistently landed interviews for corporate leadership roles. Getting interviews was never really my problem. I had no issues talking with recruiters, and I successfully interviewed with VPs and SVPs of HR, VPs of Operations, CFOs, Business Unit leaders, and SVPs of Engineering. I would go through four, five, sometimes more interviews and make it all the way to the end.

Then I would meet the CEO.

Five CEO interviews. Five rejections.

That became my curse.

After the second rejection, I hired an HR consultant specifically to help me understand what I was doing wrong and get through that final interview. It didn't help. Actually, I think it made things worse because it drove my frustration even further. Looking back, I consider most of it a waste of time and money. Probably the only really useful thing I got from the experience was having my resume rewritten by a professional HR consultant the agency subcontracted.

A couple of months ago, I started reading about people using AI as a copilot in their job searches, so I decided to give it a shot. I used ChatGPT, but I approached it a little differently than I had seen other people doing. I wasn't particularly interested in having AI write generic interview answers for me. I wanted it to help me understand why I kept failing at exactly the same point.

I started the conversation by telling ChatGPT that I wanted direct, critical feedback. I didn't need encouragement or reassurance. I wanted it to challenge me and tell me what was wrong with my interviewing strategy.

Then I gave it as much information as possible.

I uploaded my resume, but more importantly, I had been taking notes throughout my job search. I had documented the roles I interviewed for, insights recruiters gave me about what companies were looking for, questions I had been asked, and whatever feedback recruiters were willing to give me after a rejection. I also had a log of around 20 interview questions with prepared answers. Every time somebody asked me a new question, I added it to the log.

So instead of asking ChatGPT, "How do I interview better?", I was essentially saying: Here is my career. Here are my answers. Here is what happened in multiple interview processes. Here is the feedback I received. I can consistently pass recruiters, HR, Engineering, Operations and other senior executives, but I have now been rejected by five CEOs. Find the pattern. What am I doing wrong?

The answer was uncomfortable, but it made a lot of sense.

I was presenting myself as a very accomplished technical leader with an extensive background managing projects, programs and engineering organizations around the world. The problem was that, at the CEO level, I was still talking too much like an engineer or project leader. I talked about projects, execution, technical problems, teams, budgets and results. What wasn't coming through strongly enough was my ability to operate as a business partner: understanding the business strategy, allocating capital, managing risk, making tradeoffs, challenging assumptions and aligning the Engineering strategy with what the company was actually trying to accomplish.

That was probably the biggest realization of my entire job search. I thought I was demonstrating executive experience by talking about the scale and complexity of what I had done. The CEOs were looking for something different. They wanted to understand how I thought as a business executive.

So I started going through the questions in my interview log with ChatGPT one by one. I wasn't changing the stories, exaggerating accomplishments or inventing new experiences. The facts remained exactly the same. What changed was how I framed them.

For example, instead of saying, "I executed a project to solve A and achieved X," the answer became closer to, "The business was facing A. I aligned with the leadership team on the business objective and the tradeoffs, developed a technical strategy to address it, and the result was X."

Same story. Same accomplishment. Same person. Completely different message.

We went through dozens of questions this way. Then I practiced them over and over. It probably took me two weeks to retrain my brain because, after almost 30 years as an engineer, my natural instinct is to explain how I solved the problem. I needed to get much better at explaining why the problem mattered to the business, how I made the decision, what tradeoffs were involved, and what changed because of it.

Right around that time, I landed an interview for an SVP-level role. This became the real-world test of whether any of this was actually useful.

I asked the recruiter for the Job Description and uploaded it into the same ChatGPT conversation, along with public information I had collected about the company. I asked ChatGPT to analyze the role against my experience and identify potential gaps, areas I should emphasize, concerns the company might have about me, and questions I was likely to be asked.

I passed the recruiter interview, then the Director of Talent Acquisition, then an SVP of Global HR, and then an SVP from one of the businesses.

Before every interview, I asked the headhunter a very simple question: "What is this person looking for?"

I would take notes on the answer and enter that information into my ChatGPT conversation. Then I would ask how that new information should affect my interview strategy. After each interview, I also added anything new I had learned.

Something interesting started happening as I went deeper into the process. The differences between the answers I had prepared myself and what ChatGPT was recommending became smaller and smaller. I needed to adjust my responses less and less.

That, to me, was actually the point.

I wasn't trying to have AI interview for me. I was using AI to retrain the way I thought about and communicated my own experience.

Eventually I was invited to an onsite interview at the company's corporate office in a large U.S. city. I prepared for it the same way. I wrote down my main talking points in a notebook and practiced the roughly 40 questions I had accumulated by that point.

During the onsite, I met with the VP of HR, two business leaders, the COO and finally the CEO.

And here we go again.

The CEO interview was intense. He asked a flurry of technical questions framed around things like, "How would you solve X?" and "Tell me about a time when you failed on a project and what did you learn from it?" He pressed me particularly hard on the failure question.

There were also a few technical concepts where I didn't think my explanations landed as clearly as I wanted them to. In the past, I probably would have left the interview, replayed everything in my head for the next several days, and waited for the recruiter to call.

This time I did something different.

On the way to the airport, while everything was still fresh in my mind, I wrote down as much as I could remember: questions, reactions, things I thought went well, and things I thought hadn't. I drafted individual follow-up emails for the people I had interviewed with. For the CEO, I spent additional time clarifying some of the technical points we had discussed and included supporting material where I thought it would be useful. I ran the drafts through ChatGPT, edited them myself, and sent them.

Then I waited.

About a week later, I got a call from the recruiter telling me things were "going in the right direction," but that some stakeholders needed further alignment. I put that information into the same ChatGPT conversation and used it to think through what might be happening, what the potential concerns could still be, and how I should handle the next steps.

A few days later, I received a text message telling me they were moving ahead with an offer and were authorizing the role for me.

By the end of the week, I had the offer in my hands.

I start my new role next week.

Looking back at the process, I don't think AI "got me a job." It didn't create my 30 years of experience, lead my teams, execute my projects or sit across the table from the CEO. And no amount of prompting could compensate if I didn't have the experience to back up what I was saying.

What AI did extremely well was help me see a pattern in my own behavior that I wasn't seeing myself.

And I think this is where there is a much bigger opportunity for people using AI in a job search. Don't just upload your resume and ask it to make it better. Don't just ask for "10 questions I might get in an interview." And definitely don't memorize a bunch of AI-generated answers and try to pretend they're yours.

Give it your actual history. Give it your resume. Give it the Job Description. Keep a log of the questions people actually ask you and the answers you actually give. Write down what recruiters tell you about the hiring manager. After an interview, write down what happened while it's still fresh in your head. When you get rejected, get as much feedback as you can and add that too.

Then ask AI to find the patterns.

Ask it what you're not seeing. Challenge its conclusions when they don't make sense. Ask it what a CEO might hear when you give an answer versus what you think you're communicating. Ask it to identify contradictions between how you describe yourself and what the role actually requires.

Most importantly, don't use AI to create a different candidate. Use it to understand how the candidate you already are is being perceived.

Five CEO rejections in a row hurt. When you repeatedly get that close, you start questioning everything. Am I too old? Too expensive? Too specialized? Overqualified? Am I coming from the wrong industry? Or am I simply not as good as I think I am?

In my case, at least part of the problem turned out to be much simpler. I had spent almost 30 years learning how to solve Engineering problems, but I hadn't completely learned how to communicate those same experiences through the eyes of the person running the business.

Changing that changed my interviews.

This time, I got the offer.

If there is interest, I can write separate posts about the five CEO rejections and the feedback I received, my experience hiring an HR consultant, the interview-question log I built, how I prepared for individual interviewers using AI, and maybe the most useful one: actual examples of how I changed my answers from an "Engineering answer" into an "Executive answer."

I really hope some of this helps someone who, like me, is sitting there after another final-round rejection wondering what the hell they're doing wrong.

Definitely hired

Definitely hired

How I used AI to break a streak of 5 final-round rejections and land a mid-six-figure executive role

This will explain all the cancelations we are seeing

I hope this lighten your day.