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I have a younger sibling that has been out of high school a year. He's had one short term temp job and is now looking for another job. In my free time I browse jobs that I think he'd do well at, but there is always a problem with them. These are usually something like him not fitting every requirement in the job posting. I then try to explain that as long as you fit the general description of what they're looking for, there's no harm in applying.

Ultimately, he wants to start his own business down the road, but would like a source of income first. After he rejected several jobs I had told him about, I asked him what he's looking for. All he says is that he wants something that doesn't make him tired and miserable after getting off work.

How can I communicate with him to find out exactly what he's looking for so that I can help?

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    Have you asked your brother if he wants your help? – Andrew Aug 31 '18 at 16:14
  • Has he talked to you at all about what he's looking for in general? What's he interested in? What type of business is he thinking of starting? – DaveG Sep 1 '18 at 13:21
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Before answering the question

First of all, you can't help someone who doesn't want it. If he's always rejected your suggestions, doesn't elaborate on what he's looking for or how you can help him, or has never shown being grateful for your help, this might mean he's not interested in your help. If he didn't ask for it in the first place, that's also a good clue. Reflect on those things (or ask him) before putting more effort in his job hunt.

Than there's the fact that he might have unrealistic expectations, or is lazy, about his job hunt. First, he says he doesn't fit all job requirements when he rejects the postings you found, then later tells you he just didn't like the jobs themselves. Someone who lies about why they don't pursue a job, then tell you the reason is because they're picky, is not someone who seems very serious or invested in his quest.

Answering your question

But let's say he wants your help and you still want to give it to him. Maybe it's hard for him to think of specifics, so I'd ask about job posting he has been interested in and wanted to pursue. Maybe also look over a couple of job posting you thought would be great for him, and ask what particularly he didn't like. I'd go back to him and say something like : "I want to help you in your job search, but up until now you've rejected many job openings I forwarded to you. If you'd like me to still help you, I'll need to know more about what you're looking for. Could we maybe look over some job postings you've liked ? I'd like to know more about what kind of jobs and what aspects of a job you're interested in."

If he doesn't seem interested and continues to give you vague responses, I would stop helping him, at least for a while. You can ask questions and offer your help, but in the end it's his job search and up to him to accept your help or not, you can't force him.

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Since your sibling does not have much experience with previous jobs, maybe the best approach is to convince him about finding a job only to help him to realize what he likes. Is quite hard to know what one likes or dislikes is you have barely experienced a job.
He does not need to see the job as the ending of something, but as a milestone in the way. By having different jobs he'll discover for sure what he really likes.
By talking to him about having a job only with the purpose of getting experience, you'll force him to describe at least what he does not like about certain jobs available.
Fortunately, he's brief description (avoiding feeling tired and miserable) is quite wise, because is a feeling, not an idea. To feel something means that you must experience it first.

So, once you have convinced him about that concept. The next step is to ask him to describe what he dislike about a specific job offer.

What about this job, do you think you'll enjoy it or dislike it?

Maybe his answer will describe his expectations, if he does not seem to sure. Your next move might be:

Since you don't seem to hate that job, give a try for some time, to let you gain some insight about how you feel in that kind of work.

If he declines the idea, he has to give you an argument, otherwise your previous sentence still apply. But, if he describes what he dislike about that job, you'll have some information you need to find out what he is looking for.

By repeating the cycle with other jobs, each rejection will carry a description of the job he expects.

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