how to approach a LinkedIn Contact I worked years ago for a job

[needsomeadv]

I have a 6 years break now - to care for a family member and then tried to set up a business. Business didn't work out. I have been trying and don't get interview calls.

This contact is in senior position. There are several junior level roles in his company in my location (where he is also based).

I want to ask him if has any positions under him/ own his department. Also want to tell him that I am finding job search difficult because of long gap and reasons for gap. Is it too much to write to him? On the other hand just a plain CV and a note that I interested in a role won't get the same level of interest.

He was happy with my work when we worked together and come across as very kind and understanding person.

I would really appreciate your suggestions.

I would definitely contact him with a short note. Don't say job search difficult, but announce you are back after a caring role, enjoyed working for him before and interested in working for new place, for x reason. Has he any advice or know of any opportunities.

I'm approached from time to time and even if I don't know someone all that well, met at conference etc, I do my best to help. If it's someone I know well then I do a lot - recently helped an old uni friend with advice on roles in my org, she got offered the job.

Can you message to tell him you will Be in the area and would he like a coffee and a catch up?

Thank you @Pollaidh and user147

He is from my country so I feel I can talk a little less formally.
Truth is my CV is so bad that I won't be given a chance unless company needs a person desperately and have no choice.
I took break more than once - all for valid reasons but CV looks very bad.

He is very senior and still very humble. Is there a reason you think I should avoid saying I am finding job search difficult? I was told by a recruiter that on an average 400 plus candidates (young) apply for those roles. I am in 40s.

user he is in the same city I live in and in a job very high up, not sure I can suggest a coffee meet up. We were never friends. I worked for a project indirectly for him.

I just wouldn't put it quite like "I'm finding the job search difficult" as it (1) suggests he is way down your list, and (2) might make him wonder how many rejections you've had, and why. I just try to avoid provoking negative thoughts, however inaccurate.

Instead I'd say "I took 2 career breaks for x reason and y reason and am keen to return to my career now, but I'm concerned that those gaps in my CV are putting/might put people off. What do you think, and is there any chance there are opportunities at your company, I really enjoyed working in your team previously..."

Even if you could get him to help you towards a maternity cover or temp cover it will mean a more recent reference and a recent job on your CV.

Pollaidh, really appreciate your suggestion.

Also, I have seen there are 2 jobs in his company (one maternity cover) in his company. LinkedIn shows him being able to refer me to those.

Should I mention being interested in those roles? Or else, he might think why didn't I do a simple linkedIn job search.

Thanks a lot for your help.

Yes, I'd mention it.

@Pollaidh thank you

@Pollaidh, I sent him a message and didn't hear back. It's been almost a week. Perhaps he is busy.

Can I dm you with my CV? Would be able to have a look and give your honest views on what I can do to get back to work? I am happy too retrain. Just want to make sure that's the right decision. Thank you.