I asked ChatGPT to interview me for a Pentester position and this how it went.


3 min read

As part of my role I regularly interview people and have a pool of questions that I ask during technical interviews, so trying to diversify a little I thought it was a good idea to ask ChatGPT to give me some scenario-based questions and then ask follow up questions based on my answers. In a couple of cases, I asked it to provide its answer as well and the results were pretty interesting. Here is an extract from our conversation:

I gave it my answer and then it came back with some follow-up questions:

I did that one more time:

And one more:

Now this time, I told it that I didn't have an answer for question #4, and asked how it would respond to that question. Here's the answer:

Which sounds like a reasonable answer to me.

I then asked it to provide answers to its questions so I could compare them with my answers (so far I was Acing the interview or so I thought, read until the end...)

One thing that went wrong the first time I asked this was that the AI tried to use my answers as part of its answers. I asked a second time and asked specifically not to do this:

I was satisfied with the results so far, so I asked to restart the exercise with another scenario. This is how it went this time:

Once again, I kept on getting follow up questions as I answered its questions:

And since I wasn't very sure about #2, I asked it to explain that one to me:

We had a few more interactions and then I finally asked ChatGPT how I did and if it would hire me as a Pentester ๐Ÿ˜ฌ ?

I guess that "some basic understanding of the process and techniques involved in penetration testing" would have to do for me. I hope my current employer would not let a machine influence their past decision of hiring me as pentester... #toolate

The Lesson Learned here is that ChatGTP might be a good partner when preparing for interviews, certification exams and to pretty much test your knowledge in every major field out there.

Also, we all know that AIs or at least some type of automation already play a role when it comes to hiring. Do you see yourself being interviewed by an AI in the near future? Let me know your thoughts in the comments section below.

As a bonus, here is an AI-generated picture of ChatGTP interviewing me (this image was generated by Midjourney, an art creation AI which you might wanna check if you haven't done it already). I have to accept that I look a little different (better of course) but that's just because this AI hasn't had the pleasure to meet me in person ๐Ÿ˜…

Have fun.