Struggling to land an entry-level IT job after 7 years. What am I doing wrong?

Forums › Jobs › Struggling to land an entry-level IT job after 7 years. What am I doing wrong?

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CtrlAltKiwi

37 posts

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#3529516 20-Sep-2026 14:24

kiwi_64:

Have you tried getting AI to assess your application compared to the job advert (and suggest improvements for weak fit areas)

Given that (for better or worse) recruiters are leaving AI to run the first pass and produce a shortlist, the actual company may never be seeing your application.

I often give AI the job advert and then work history from my CV to tailor a cover letter. However I have recently not bothered with cover letter given how long it takes me to tailor each one

for the job and not having any luck. I normally get it to write the cover letter for me and I just use the command ''Don't make it sound like AI''

Sometimes I change words or get it to change certain words if they are not words I use.

CtrlAltKiwi

37 posts

Geek
+1 received by user: 12

#3529518 20-Sep-2026 14:29

Last year I was in the running for the Internship at Datacom I actually got a scam on LinkedIn (Fake recruiter and the job paying way more then datacom do for a starting out position and using Datacoms name) Didn't loose any money from it - they tried to get me to go to this site to ''fix my LinkedIn profile'' This was while my application was in progress and I actually

Gave the recruitment person a heads up to the scam which she was so thankful of (A lot of people likely wouldn't have bothered) This didn't even help my application I thought maybe she would put in a good word but nope unsuccessful and when I called asking for feedback they said ''The other candidates we decided to progress had on their CVs that they used chatgpt''' Well she could have asked me that before deciding not to progress me further. It's now listed on my CV.

Nate001

694 posts

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+1 received by user: 502

#3529522 20-Sep-2026 14:40

CtrlAltKiwi:

I often give AI the job advert and then work history from my CV to tailor a cover letter. However I have recently not bothered with cover letter given how long it takes me to tailor each one

for the job and not having any luck. I normally get it to write the cover letter for me and I just use the command ''Don't make it sound like AI''

Sometimes I change words or get it to change certain words if they are not words I use.

I'm not in the IT field, but having been on the side of reviewing CVs I can say without a cover letter most people will pass over you. A cover letter does not need to be fancy or over the top, just a bit about why you want to work at XYZ and 1-2 points about how your experience or skills are applicable to the job. If you are applying for similar jobs then the cover letter should be adaptable without needing a complete rewrite.

enserf

enserf
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#3529523 20-Sep-2026 14:48

Nate001:

CtrlAltKiwi:

I often give AI the job advert and then work history from my CV to tailor a cover letter. However I have recently not bothered with cover letter given how long it takes me to tailor each one

for the job and not having any luck. I normally get it to write the cover letter for me and I just use the command ''Don't make it sound like AI''

Sometimes I change words or get it to change certain words if they are not words I use.

I'm not in the IT field, but having been on the side of reviewing CVs I can say without a cover letter most people will pass over you. A cover letter does not need to be fancy or over the top, just a bit about why you want to work at XYZ and 1-2 points about how your experience or skills are applicable to the job. If you are applying for similar jobs then the cover letter should be adaptable without needing a complete rewrite.

Yes you certainly need a cover letter with each application. As suggested above, I just edit mine for each role to highlight how my experience matches with the listed requirements and let AI do the rest.

roobarb

803 posts

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#3529533 20-Sep-2026 17:46

I certainly sympathise.

The current recruitment AI systems are literally engaged in an arms race with applicants and the goal of the AI system is to prevent most applicants succeeding. ( eg choose the best out of many also means discard the other 99.99% ).

From the recruiters side it is great because "the great filtering" is happening and they only have to consider "the best applicants", hence they have achieved an increase in their efficiency.

I have seen the stories where the only way to get a cover letter past AI is to use AI to write your cover letter.

I think of the applicant strategies as

forlorn hope - only apply for the most suitable positions hoping to stand out
frontal assault - use AI to defeat the AI and apply on mass
outflanking manœuvre - find a real person to talk to and bypass the AI completely

I suggest focus on a few organisations that you would like to work for, understand who they are and their history and do whatever you need to do (legally) to talk to someone at that organisation and ask them how to get in contact personally with HR. You will be pleased to know the Germans have a word for that, Initiativbewerbung.

Good luck

PS - or a recruitment agency - their job is to get you a role.

dfnt

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#3529538 20-Sep-2026 19:01

The IT market is pretty bad at the moment so you’ve picked a pretty bad time unfortunately

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CtrlAltKiwi

37 posts

Geek
+1 received by user: 12

#3529541 20-Sep-2026 19:11

roobarb:

I certainly sympathise.

The current recruitment AI systems are literally engaged in an arms race with applicants and the goal of the AI system is to prevent most applicants succeeding. ( eg choose the best out of many also means discard the other 99.99% ).

From the recruiters side it is great because "the great filtering" is happening and they only have to consider "the best applicants", hence they have achieved an increase in their efficiency.

I have seen the stories where the only way to get a cover letter past AI is to use AI to write your cover letter.

I think of the applicant strategies as

forlorn hope - only apply for the most suitable positions hoping to stand out
frontal assault - use AI to defeat the AI and apply on mass
outflanking manœuvre - find a real person to talk to and bypass the AI completely
I suggest focus on a few organisations that you would like to work for, understand who they are and their history and do whatever you need to do (legally) to talk to someone at that organisation and ask them how to get in contact personally with HR. You will be pleased to know the Germans have a word for that, Initiativbewerbung.

Good luck

PS - or a recruitment agency - their job is to get you a role.

I picked one organization which was One NZ and I thought that a Customer Service role with them would be quite easy to get given my 6 years Volunteering for them and the previous interview though that was about 10 years ago.

I also reached out to the CEO asking if the staff that were on their forum would remember me and be able to offer me a reference. He put me onto someone that seemed to have no knowledge of a Vodafone Community Forum ever existing....

I've always had a keen interest in Mobile Network Build & Design since I was young.

I think I've pretty much given up on One NZ now.

CtrlAltKiwi

37 posts

Geek
+1 received by user: 12

#3529542 20-Sep-2026 19:14

@Nate001

@enserf

Yes I will certainly get back into sending cover letters I just heard that recruiters don't bother reading them and that most people don't submit one.

CtrlAltKiwi

37 posts

Geek
+1 received by user: 12

#3529543 20-Sep-2026 19:19

Is it getting harder now because soon there wont be jobs and everyone will just be getting an Automation payment?

lxsw20

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#3529544 20-Sep-2026 19:28

You mentioned a Mitre 10 job - did you take that job? Are you currently employed?

CtrlAltKiwi

37 posts

Geek
+1 received by user: 12

#3529547 20-Sep-2026 19:39

lxsw20:

You mentioned a Mitre 10 job - did you take that job? Are you currently employed?

I did not take that Job as I thought and the manager agreed that the Volunteer role I took instead of Mitre 10 would lead to better jobs in the future a better skillset for the type of job I actually wanted.

Im now thinking perhaps that choice was a mistake.

I work one day per week gardening and office work for an elderly lady my Mum worked for. Also I drive her around using her car.

That may be the reason Mitre 10 picked me out of 500 Applicants due to my experience gardening.

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gokiwi64

47 posts

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+1 received by user: 35

#3529551 20-Sep-2026 19:55

Cover letters are important - its the thing that we use to gauge how interesting you are to us, but not full of waffle, target the role you are applying for, research the organisation and make a paragragh demonstrating some knowledge of that organisation. Be honest and truthful, most important be humble and be respectful.

I will look on a cover letter that has all the above in it long before a cover letter full of waffle and acronyms/'sales" talk.

For my sins (and a bit of background) I am 62 years old with 47 years in I.T (specifically networking) - I have enough knowledge of operationg systems/applications etc to be dangerous, I am currently wearing multiple hats as a Team Leader/Senior Network Engineer and a Technical Lead.

Once a cover letter has got my interest , it will go into a follow up pile, I will then go over that pile and reduce that to no more than 6 or 7 , I will then send out invites for either an online type interview or possibly an in person interview , this would typically be no more than 30 minutes (but if I like what I am hearing and seeing it could go longer).

Questions not to ask me at the first interview.

How much holiday do I get ?.
When will I get my first pay rise ?.
Tell me what you wont do.
Tell me what hours you will work.

Any of those will terminate the interview there and then.

Ask me questions - the interview is a two way process , show interest , ask questions about the role, the potential team or environment you might working in , I might at that point ask you a question such as "Tell me something about yourself that other people may not know - its not a trick its about me trying to understand what makes you tick.

Also your physical demenour is important , be presentable - dress according to the role and organisation, ask the question (if you are being invited for an interview but also applies to an online meeting) - What is the expected dress code ? - But researching the organistion may give you valuable clues. Dont use arrogant or couldnt care less body language 9If you are sitting opposite me and have your arms folded and are leaning back in your chair - thats not a good sign, shows either arrogance or boredom or even both.

Full disclosure - I have a tendancy to look for experience over qualifications and someone who is a little bit older, someone who demonstrates stability and a willingness to take instructions but also someone who will actively look for work.

Once you get to the 2nd and usually last interview (in my employers case this could include a senior manager and an HR representitive - so you could end up in another face to face with 3 or more people) we will talk about the technical aspects of the role , what we expect from the candidate and that is where we expect almost as many questions from the candidate as we will ask,the organisations expectations and usually a bit more chit chat about yourself.

I dont know if this has helped you at all but thought a little snippet into the employers side might help in some way.

CtrlAltKiwi

37 posts

Geek
+1 received by user: 12

#3529552 20-Sep-2026 20:12

What do people think of my use of AI to answer personality tests and also to ask questions asked of me in recorded 3 question interviews?

I've got tired of answering truthfully and with the personality test I was advised that there are no right or wrong answers. One that stands out was Ricoh where I got to the second interview then they got me to do a personality test which I answered truthfully.

After I didn't hear back for a bit I called the manager that interviewed me and she said that the test came back as there were signs that I may get stressed so I asked her ''what type of person are you looking for are you wanting a robot someone that doesn't feel emotions''

They said that they would talk to HR about me going into the office to see how I find it for like a day or 2, This never happened the manager ended up getting covid and I called her mobile to see if she was alright and get an update on my application and I was ghosted didn't even have the decency to return my call I had genuine concern for her health.

2 interviews and a personality test reference check stage (they never called those references) It was very upsetting. I actually produced an Invoice for my time that they wasted and sent to their Accounts team with a cover letter explaining why.

I obviously didn't follow it up I was just very upset.

gokiwi64

47 posts

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+1 received by user: 35

#3529553 20-Sep-2026 20:19

If I was aware that you were using AI , I would not proceed any further with an interview. I am not employing a robot, a rocket scientist or a ghost. I am employing a human being , a two legged (mostly) creature that has feelings, emotions, technical capabilities and must demonstrate that they are better than anyone else for the role they have applied for.

Nothing in life is easy , it never has nor will it ever be a walk in the park , be yourself, be honest more than that cannot be expected of anyone.

gzt

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#3529558 20-Sep-2026 21:20

CtrlAltKiwi: After I didn't hear back for a bit I called the manager that interviewed me and she said that the test came back as there were signs that I may get stressed so I asked her ''what type of person are you looking for are you wanting a robot someone that doesn't feel emotions'' They said that they would talk to HR about me going into the office to see how I find it for like a day or 2, This never happened the manager ended up getting covid and I called her mobile to see if she was alright and get an update on my application and I was ghosted didn't even have the decency to return my call I had genuine concern for her health.

That's good dialog. The HR clearly went to bat for you there in a marginal situation. It's something you can be genuinely thankful for. The 'ghosting' part, well yeah you just have to accept that part it comes with this territory, part of life in that phase and situation. In a sense it is the standard behaviour. You will see it multiple times. Just expect it then anything else is a bonus. Be thankful for the opportunity and move on with the learning.

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