5 Months 100 Job Applications and a Crash Course in AI. How can I help?

Originally published on LinkedIn in November 2025. Republished here for completeness.

I’m in a new role and loving what I’m doing. But after 5 months on the job search, I’m still a little shell shocked from the whole experience.

My network has some great people here. Seriously, some of the best recruitment talent not only in Brisbane but further afield. I know a lot of them took the time to call and see how I was doing, gave me some of the best feedback I’ve ever had, and sat and shared my sense of woe at the job market that is.

Add to that mix, some of the nicest people I know, that are current job seekers, recent new hires, and some peeps that have been in their roles forever and probably will never leave.

I know Phil Kan has all the stats from his job hunt and can probably reshare these in the comments, but I know that I applied for about 100 roles in those 5 months. I’m a data engineer and data modeller with experience across a broad range of toolsets, so all of these roles were roles that I felt I was suitable for.

That breaks down to on average of an application a day. But we all know those ads don’t all come neatly packaged each day – they’re more like a tidal surge that comes in hard then nothing for a few days.

During that time I continued to upgrade my skills and keep my brain somewhat active. So I decided to learn a lot about AI. I wrote and built an AI RAG powered chatbot application from the ground up. It’s cool – it worked well, but I don’t trust it enough to put it to market given the amount of hallucinations it still had. One day LLMs might fix the issue - I’m not holding my breath.

I’ll get somewhere closer to my point.

I hear and see so many posts and comments decrying the use of AI on job applications. I get it, seeing the same auto generated, spray and pray drivel will get tiresome if you’re a recruiter or a hiring manager.

I also see all the posts and comments from recruiters, job seekers and a whole range of people who suggest doing a custom, specifically written cover letter and resume for every job you apply for. A standout idea, but it’s got warts too in so much that this takes time, and you want to get in early and you probably only have a couple of days to apply in some cases.

So yeah, I’ll freely admit that I used AI help a lot during my search. My contacts that I applied through – anyone pick up on that? If you did – that’s great. If you didn’t - that’s better.

But what I did learn through everything is that the key to using AI wisely is in the prompts, and feeding it the correct context, and giving it the right instructions, so the LLM you’re using, be it ChatGPT, Claude, or CoPilot, can learn to write like you.

Will it be perfect? Hell No!

Will you need to refine it? Hell Yes!

So what do I want to get out of this post I hear you ask?

I want to build a guide or even a series of posts to support job seekers out there in the right way to use AI in a job hunt. Is there one out there? There’s a few, mostly in the spray and pray space.

Did I find one that made sense to me, in the market that I was in? Sadly, no.

So if you’re a recruiter and you have some ideas, let’s catch up and have a chat. If you’re a job searcher, and you’ve tried some things that you found helped or worked, let’s catch up and have a chat. Virtually, by phone, or over a coffee. I’m always keen for a coffee though and I’m in the city 3 out of 5 days.

What’s in it for me I hear you cry? Paying it forward. Like I said, I got helped by a whole bunch of people along the way. I’m just hoping I can help someone else get back into the workforce one day.

Oh - and the cover image is AI generated.