Cover letters

[guinnessguzzler]

I've been job seeking for about a year, currently in a job but looking for my next move. I am finding the whole process so disheartening and very time consuming. For the type of jobs I'm looking at (senior voluntary sector) everyone wants a CV and covering letter and the covering letter usually has to explain, with examples, how you meet between 15 - 30 points on a person spec in two sides of A4! I genuinely struggle to believe that is actually possible and I usually end up with at least four pages. Has anyone had any luck with using AI, or other methods, to cut it down? If so, what would you recommend?

Not AI but I’ve recently got to interview stage where the process was exactly that.
I did my CV first then c&p’ed the person specification into a new document.
I deleted the requirements which were covered in the CV leaving me a table of fewer requirements. There were a couple of requirements I’d evidenced in the CV but could write interestingly and impressively about, so I left them in the table. I wrote paragraphs for each and then turned them into a nice piece of prose. Bullet points/ lists/ tone are all very personal and industry specific so no advice there. It is a time consuming process. How far are you getting? How many applications have you done?

You can't send a 4 page cover letter!
Just ensure your cv is brief but covers all the main points and then in the cover letter highlight some key things you've done which match the job description and maybe explain the main reason you'd like the job.

Thanks for the reply. I've had one job where I made it to the final two and was beaten by the internal candidate. Feedback was I was appointable and there was nothing they could tell me to improve, which is obviously less than helpful. I've only applied for around 8 or so jobs at this point because suitable ones are pretty few and far between and only had a couple of interviews. I've been told by one of the agencies I've worked with that the market is just really competitive at the moment but it is so frustrating.

Your approach sounds similar to mine, so it sounds like I'm not way off, although I have tended to repeat stuff in the covering letter that is on my CV so as not to miss anything so I'll try at least cutting those bits out which will save a few paras, thanks. Whenever I've sought out feedback it has been along the lines of level of competition rather than where I'm going wrong. However I'm not convinced you can always (ever?!) trust that they will give honest feedback and it is often very generic.

Last time I took almost four years, off and on, so I keep trying to tell myself it is early days, but voluntary sector pay is so low that I feel my life is on hold until I can make my next move. And I've been in my current role for five years, done everything I set out to do and am ready for something new.

Thanks @bestbefore I know, it's just really difficult to know how to approach when they are telling you you need to cover every point in a really long spec for shortlisting. Perhaps it's more describing what I've done and leaving them to grasp how that connects with the person spec, that sounds like what you're suggesting? Earlier in my career it was generally application forms requiring a personal statement to cover each point of the person spec so I've likely got into bad habits with that too.