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I have worked at a web dev agency about 5 months and get along with everyone. There is one particular client I do a lot of work for at this shop though contact is usually limited to meetings and the occasional email (just professional stuff).

Me, my team leader and my boss have a meeting with these clients today.

How do I approach them if they have a potential opening on behalf of my friend? The clients own a few medical clinics and I wanted to ask if there was an opening for a medical receptionist or assistant.

Should I even ask at all?

If I did ask, I am guessing it would be near the end of the meeting?

I want to remain professional but also really want to ask on behalf of my friend.

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Do not do this in the meeting.

That would be mixing personal and business. During a meeting you want to remain focussed on the object of the meeting, and on your company's business. You also want to steer very clear of giving the impression that your work for this client and the favour you want to ask are in any way connected.

The best way to do this would be to contact the client entirely outisde of the meetings you have about business. You say you have their email - send them an email rather than bringing up the request at the meeting. If you really want to do it in person, wait until the meeting is very definitely over, or you are clearly on a break from the meeting, and then say "do you mind if I ask you about something different from business". If they are OK with it then ask about jobs.

Also avoid the impression that you are asking for any kind of special treatment. Just ask about available jobs and how your friend should apply.

You might also consider clearing this with your boss before you ask. If I were your boss I would be fine with you asking, but bosses are different, and you really want to avoid your boss accusing you of unprofessionalism.

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Do you know if your friend is good at their job? How do you know this?

Think carefully, as you have two options:

1) Your friend asks personally, leaving you out of the loop

2) You ask the client. Whether you use the words or not, you are sating to the client “I vouch for this person, and their ability to do the job in a professional manner”. If anything goes wrong, then the client will hold you responsible to some extent, and your relationship will change, and it is unlikely to be for the better. In the worst case, the client may complain to your boss, or may even withdraw their custom from your firm.

I know that the latter is probably unlikely, but that’s doesn’t mean that it is impossible.

I have recommended only a few friends in a career of "several" decades.

Generally, I will just tell those who ask the name of the hiring manager and request them not to mention me. So far, no one has been upset about this. – they go the lead after all.

The few whom I have recommended are people with whom I have worked directly, and in who’s technical skills and personality I have faith.

The client may or may not have an opening. It is unlikely that he will create one for you. So, why can’t your friend ask directly?

If you ask, the potential upside is that your fiend may learn about an opening hat the could have learned of themselves. The potential downside is probably something that you would prefer to avoid.

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