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Meet her for a coffee. (If you're a guy, mention that it's to talk about her career and meet her in a totally non-romantic setting, otherwise she might get scared you are interested in her romantically).

During a 1:1 conversation there are plenty of ways you can say something without saying anything that could cost you your job:

• ask her about her plans - when she says she's applying, stress that you will be happy to provide references


• mention that a job in your company is also an option, that you were happy with her, but imply that many changes are coming... The culture is something that not everybody likes and her new boss has a management style very different to yours.


• stress that she should think it over and that you won't take offense if she rejects the offer.

It's a lot about your tone.

You shouldn't say too much but if she's smart she will understand.

Referring to the previous answer: yes, you need to stay loyal to your company. But if the company is really so bad, the woman would quit quickly anyways. So it is in the interest of the company for you to let her know what she can expect.

Sounds to me like you don't owe this company any particular allegience -- the key to being ethical with this is separate your business responsibilities from your personal obligation not to harm this person.

Send the intern the offer from your corporate email with no comment on its desirability one way or the other.

Then phone the intern/meet in person on your own time and give her your thoughts on the company as an impartial human being.

She is then free to make up her own mind about what to do.

I'm considering making the offer while privately advising her to
decline it. Are there any ethical, legal, etc. implications that I
should be aware of? Or any reason not to do this?

Your boss told you to make the offer, and you acknowledge that she deserves the offer. Thus, you have to do it.

If she asks you about the offer or company, you can carefully disclose some of your feelings while still making it clear that this is solely her decision to make. And you can offer to be a great reference for her if this offer isn't what she is looking for.

Remember, she may not share your feelings about the company and manager. And while it's not what you want, it may still be what she wants.

One major reason not to do this is: what if she accepts the offer, despite your warnings?

You are now in a very awkward position: your junior is now in a position to blackmail you. This is especially important as you are considering jumping ship: your reputation capital gained at your current firm is at its most valuable. (In fact, you are vulnerable to blackmail or the consequences of inadvertent disclosure whether or not she accepts the offer.)

Regardless of whether the moral thing to do is telling the excellent former intern that your company is toxic and destined for the corporate dustbin, you are now putting your own career in jeopardy.

A missed opportunity is a relatively minor thing early on in your career. Later on, being seen to act against your employer's interests and in a matter that is entirely work related... well, that's a line on your CV that you don't want.

Regarding the decision itself and its potential consequences, let's look at its moral, legal and financial aspects, examining each separately.

Morally - telling her the lay of the land is absolutely the correct thing to do. (Companies' personalities are a legal fiction and you owe them no moral loyalty - pay them no heed when considering right and wrong.) However, no one should presume to tell you that you must put the interests of others before your own.

Legally - Presuming a common-law jurisdiction, there's multiple potential heads of claim your company might pursue against you, if they were to find out about your thwarting their attempt to recruit the intern. The most relevant tort is tortious interference with business relations. There might be a case to answer for defamation or possibly malicious falsehood, depending on exactly what is said. (Truth is always a defence in defamation actions, but - roughly - if you say something that would make someone think less of another, they can establish a prima facie case.)

Actions in contract are also very possible, even if your employment contract doesn't appear to cover this explicitly: good faith and fair dealing is an implied term in all contracts (in the US, at least). The duplicity involved in paying lip service to your duties to your employer while secretly undermining them demonstrates clear bad faith on your part, and would be a breach of contract. (Some other answers seem to suggest that your duty to your employer stops when you clock off: this isn't true.)

If all this seems unfair to you, consider if you interfered with a potential client for your firm similarly, submitting a tender to satisfy your boss while privately advising the new client not to accept it. From a legal perspective, this situation is pretty much the same, although in this example we don't have the emotive factor of a deserving young person potentially being harmed by your inaction, so it is perhaps easier to see why the law works the way it does. (Regardless, the legal system is largely indifferent to whether we might think it is fair or not.)

In addition, regardless of whether or not you are doing the company damage in legal terms, if your current company were to sue you on any grounds, it wouldn't be hard for a good attorney to find some pretext to get this situation into evidence to (correctly) portray you as disloyal. (This is particularly bad if you are in a jurisdiction where a jury is the trier of fact in civil cases.)

Now, all of this is contingent on the company finding out about you telling the intern and being able to prove it. This is, in itself, unlikely, if you are careful, so while nothing will probably come of this, legally, you're doing yourself no favours at all by telling the intern how things are - you are creating potential liability on several fronts, as well as giving your firm an excellent reason to fire you.

Financially, there's no upside. Only potential downside. You're risking getting fired and getting sued, as well as your future employability, and, grim as it is to say, you are gaining nothing quantifiable - nothing that will put bread on the table - by telling the intern how things are.

No attorney would tell you it was in your best interest to do this. Probably, you'd get away with it, and nothing would happen, other than you would get a warm glow from having gained the gratitude of the former intern. However, if this whole thing went wrong, it would probably go wrong very badly for you.

To repeat: only downside.

By telling the intern how things are you aren't just being honest: you're asking her for her confidence, and that is by no means a given. A particularly mercenary and ambitious personality might even smell an opportunity in your indiscretion.

I can completely understand how someone might nevertheless want to go ahead and warn the intern despite this advice; however, doing so is not the sensible and considered thing to do. It's your life you're talking about, more than hers, and prudence and discretion should be your watchwords.

If this does go wrong for you, it will come from either lack of caution on your part or from the indiscretion - deliberate or otherwise - of the former intern herself regarding your actions here (perhaps more likely if she takes the job, but the legal consequences are such that you are vulnerable either way). So, if you do choose to tell her, consider putting as much distance as you can between yourself and the advice, to minimise evidence and to ensure that there is nothing that can be traced back to you or that otherwise identifies you. An anonymous note, for instance, would probably be taken much less seriously by the former intern than advice not to accept coming directly from you, but it would be rather less likely to come back and bite you as well.

Advice could be problematic; informed consent is not. Present her with the offer, as well as the relevant information that she needs to make an informed decision. The offer is not only for a position with a particular compensation package, it is for an employment relationship with the company. Like any relationship, there are not only benefits, but liabilities and responsibilities. She needs to be made aware of the reasons that underlie your desire to recommend against taking the position, and then leave her to make her own decision. As part of this, highlight things that she may otherwise overlook, such as the fact that in her role as an intern, she has been insulated from some of the less palatable aspects of working there, as well as the fact that her work experience and her exemplary performance would qualify her to work at any number of other employers, and that it’s always wise to assess multiple offers rather than accepting the first opportunity that presents itself. Also stress that you’d be happy to serve as a reference not only for this role, but for any role outside of the company.

Once you have laid all of your cards on the table, the decision to accept or reject the offer will truly be her decision, which she will be able to make with eyes wide open. She may choose to take the job and regret it. But if she does, it will be her choice and her learning experience. Unless you give her the relevant information, you’re depriving her of that opportunity to decide for herself. I appreciate your desire to go to bat for her. You just need to do so in a way that is equitable for all parties concerned. As long as you stick to the facts, you should be fine.

If this other Manager is as bad as you make them out to be, I recommend that you:

1. Make sure she is aware that this other Manager is going to be managing her and that their style may be different to yours.


2. Try to arrange for her to meet with this other Manager in person, before deciding whether to accept.

If she meets with the other Manager, then it may help her to get a better feel for what they are like, and whether they are someone that she can work with. If it was me, I would definitely want to meet with a prospective new Manager first, to make sure the 'personality fit' is right, because the relationship you have with your direct Manager is so important.

Otherwise, I agree with the other answers that recommend meeting her informally to discuss the situation. Don't advise her not to take it, but try to make sure she has enough information to be able to make an informed decision. The decision has to be hers. Even if that other Manager is difficult to work with, she might decide it would be good to work there for 6 months to a year, just to get their name on her resume, which is fair enough.

Helping her to make an informed decision is not, in my opinion, contrary to the interests of the company. It would not be in the interests of the company, if she leaves after 2 months because she didn't realize what she was getting herself into.

You know this is somehow wrong, and you're looking for a way to do it anyway.

Since you haven't marked one of the other answers as accepted, here's mine.

I'm considering making the offer while privately advising her to decline it

Write up the offer and print it out on company stationary.

As you said, she deserves it.

You can't actually advise her to decline it - you know that or you would have done it already.

You can do other things like work to eliminate any guilt she may feel about declining it. If that happens to nudge her in the direction of declining it, well... you already think that's best for her right?

Use the company email to inform her that [company] is so pleased with the job she did that [we] are prepared to discuss an offer. As her former supervisor it is your privilege to discuss be the person make the offer to her. Say that you'd like to do this off site so there is less pressure. (Seriously there's nothing more awkward than someone asking, "So, did you take it?" as you're walking to the parking lot)

Suggest some well-lit coffee shop (anything not a bar, residence or restaurant). Tell her you expect it to take 30 minutes, but you're available for questions immediately or over the next few days.

Explicitly say that she will receive a written job offer when you sit down with her (reinforces that you're meeting for business reasons).

Explain that she WILL NOT be expected to accept or decline the offer at the meeting.

(This expectation gives her time to think about the subtle things you will be saying and discuss those with a parent/friend/etc.)

When you sit down with her:

First explain that she did such a wonderful job for you that you would be available as a reference not just for this job, but for any other job she might have applied for recently or will apply for in the future.

Be clear that your offer to be a reference is valid regardless of whether she accepts this offer.

Second explain that she would be reporting to [the jerk], and not to you if she accepts. Mention that you won't have much interaction going forward (if this is appropriate).

Then you can explain that internships 'are a sheltered experience'. Accepting this job means that she will be a regular employee and have to deal with all the junk that you have to (smile while saying it).

Then you give her the written offer.

As you hand it to her, tell her she can take it with her.

After that she's on her own.

This is her decision - you cannot in good conscience make this decision for her - which is why you can't tell her not to take it.

For all you know, that person who you think is a nightmare to work with might have a totally different relationship with her. There's less than twenty people in the company, she has to at least be aware of that person, right?

Finally, let it go.

She's an adult now and needs to start reaping the rewards of her decisions - the good and the bad.

Your only responsibility is to make sure she gets enough information to make an informed decision.

We are talking here about a person who has already worked an internship at your company. She's not some walk-up candidate that doesn't know what it's like. She didn't work for Manager X but it's a 12-person company, I find it hard to believe that she knows nothing about him. At the maximum, try to broker a meeting between her and her prospective new manager prior to the offer. You seem to have an assumption here that you know better than she does, which is borderline offensive given the facts.

You need to realize that:

1. You may be burned out and being overly bitter. Apparently a bunch of other folks work at the company and haven't fled screaming. You are likely projecting your own dissatisfaction about random "inside baseball" decisions on a new grad that just wants some good experience coding and a good-looking resume line item of working for a startup. There is nothing "ethical" about spreading your negativity to someone else.




2. Anything beyond openly discussing with the team that you think the role might not be a good fit for her is direct sabotage of your company. You seem to feel that no one should come work there because it's so bad. You should be looking for other opportunities instead of sabotaging them. As a hiring manager, if I found someone on my team had told a candidate "don't come here this company is dysfunctional," they would immediately be fired for cause. If you are unable to support your company any more, leave.

You should not do this.

As long as you work for the company, your allegiance and responsibility is to the company and not a potential future employee. You are free to decide for yourself whether to stay or go, but you should not be trying to keep the intern from joining the company. From your own review, she is a potentially valuable employee for the company and you would be actively trying to harm the company.

While I can't speak to specific legal concerns, I would expect in any country that actively trying to damage the future of the company is a fire-able offense at a minimum.

I'm personally in the midst of looking for other opportunities. And the person she would report to (even if I were to stay) is an absolute nightmare to work with (I was able to keep him at a distance during the internship).

Only you know the extent of this would-be manager's abusiveness, but given that you deliberately shielded your intern from him, my instincts suggest he is quite bad indeed.

If giving her direct advice to reject the offer would spare her months or even years of abuse and would not constitute a worse roadblock in her career (perhaps offer her your recommendation to another job), then it is the company's problem that they keep so toxic a person in their employ. It might even save the company a lawsuit down the line, depending again on the manager's misbehavior.

Do, then, what the other answers suggest: give her the offer as is required by your job duties, and then (on your own time) give her all the objective, legal-to-divulge information she would need to make an informed decision. In particular, it sounds like you will need to tell her about this manager since she doesn't have any information about him already.

I think the ethical thing would be to resign or at the very least ask somebody else to handle the hiring negotiations and process. You should not be in a position of trust while actively considering what is essentially sabotage, as much as I commend your protectiveness.

I don't know the legal ramifications but I don't think you should name names - either of the company or the manager.

If there is a way you can direct the intern to this thread, you could say something like "Of course interviews should work both ways so be aware of that. Have a look at this cautionary tale that I happened across."

I repeat, I am no expert but this is probably what I would do.

There's probably something in your contract that expressly forbids this sort of thing; even if there isn't, this probably wouldn't look great for you to be doing.

That said, there is a difference between making an offer and recommending the offer, and that's in presentation. You could go into the meeting and say "hey, you got the offer! Good job! Here's the contents of the offer. I think it's really great because XYZ". You could also go into the meeting and say "We have decided to present you an offer. The contents of the offer are XYZ. Please let us know your decision." One statement of the offer obviously plays up the offer and makes it more attractive to take. The other one doesn't. (IANAL) You are probably obligated only to present the offer, but not to be energetic about it, so just don't.

I do think it's appropriate to talk to her, but you need to do so in the right context.

I have a practice when I interview candidates, work with interns, or extend job offers. I always set the stage by saying something along the lines of,

I want to make sure this process is a two way street. In representing the company, I am going to be evaluating your skills and making a decision on your fitness for this position. But, I also want to make sure that you have the opportunity to decide for yourself if this company and this offer is a good fit for you. Do you have any questions about the responsibilities, the work culture, or other aspects of the job that are important to you?

With very junior employees, or others who may not be well positioned to evaluate this via their own questioning (such as the employee you're considering), it's totally legitimate to plant some suggestions or leading questions.

In other words, I don't think it's appropriate to tell her, "you don't want to work here" but I do think it's completely appropriate, and in everyone's best interest, to help her ask some questions that will lead her to making the best decision for her, with a full understanding of the employment environment.

Also, to fully answer your question, I think it's important to ask yourself a few things in terms of the conclusion you've arrived at. Would be actually be a bad thing for her to work there? Or are you just assuming that?

• 
  working with a difficult manager can be a great learning experience for the employee. It's not something you'd wish on someone of course, but it can be a good opportunity for her to understand how to deal with difficult coworkers or superiors (which is a critically important skill that everyone should have)


• 
  working for a failing company can help her understand what makes companies fail, which may put her in a position to contribute some other employer in the future who may be starting to head down that path. I've worked for failing companies and while it's stressful, it's also incredibly eye opening


• 
  someone freshly out of college may simply need a job no matter how bad you think it is!

Would it be possible for you to write a review about the company on “GlassDoor”, and then ask her to write a review about her experience as an intern?
However, this may be hard in a small company, as your boss may work out who wrote the GlassDoor review.

Clearly details of who she would report do, and how that will be different from when she was an intern should be included in the job offer, so she knows it will not be your she reports to.

Since you're asking, an ethical thing to do might be to tell you boss what your concerns are -- explain that you don't want to recruit while such dysfunction exists -- and/or that you don't want to recruit for that other nightmare-to-work-with person

Having said that to (having been honest to) your boss -- and having refused the role of recruiter -- perhaps you can then (ethically) also be honest to your intern.

Obviously I also agree with an answer like this one that there's a potential downside to you -- telling your boss, and refusing an assigned role (as recruiter) -- i.e. your boss might not like that.

On the other hand maybe your concealing the truth-as-you-see-it-now is not in your employer's best interests.

Let's take a step back and look at the facts:

1. 
   She's good, deserves the job, is inexperienced in the workplace but seems all-round capable and able to handle herself.


2. 
   Her expected new boss is difficult to work with, especially for someone less experienced


3. He's someone you personally dislike


4. 
   The company politics are difficult to navigate, especially for someone less experienced


5. 
   You dislike working at the company, and you're already making plans to leave

3 and 5 - your personal feelings - are irrelevant, and likely influenced by things like frustration.

2 and 4 - the challenges she'd face in the new job - are absolutely things a manager can and should talk to a junior colleague about. Diplomatically and professionally, obviously.

Just give her practical advice about the challenges, then let her decide

So have a meeting with her to discuss the offer. You don't need to do anything clandestine or awkward like meet in secret in a coffee shop (though maybe it's the kind of work environment where that is a natural place for this kind of chat). Then just say something like:

I'm recommending that [Boss] gives you a full time offer. I think you definitely deserve it, assuming you don't have something better lined up already

(It's important to be positive about her up front like this because if you're saying potentially off-putting things, you don't want to risk looking like you're trying to intimidate her or squeeze her out)

The thing is, you'd be working with [Bob]. He's good at [honest example here], but a lot of people find him difficult to work with. If you do work with him, I'd suggest a good strategy would be...

(then give honest, practical advice, and be careful not to let your personal dislike of Bob taint or exaggerate this. Be professional. You're sharing information with a less experienced colleague on how to be productive when working with someone you know better than she does. It's a 100% legit workplace conversation to have. There was also a very good suggestion in another answer of proactively introducing her to Bob - this would be good for everyone: she'd be better informed in her decision, Bob would be better prepared; and of course, if she did decide to decline, it'd look like Bob put her off, not you!)

How do you find working here?

(then have an honest but professional conversation where you share advice on how to navigate aspects of the company you find dysfunctional. Again, you need to keep it professional and untarnished by your personal feelings of frustration, and be open to the possibility she has no problem with the things you find frustrating. And again, there's nothing clandestine here - you're sharing what you've learned with a colleague, so she can be more productive. It's a 100% legit workplace conversation to have).

After this, she knows all the relevant facts, and she's in a position to make an informed decision. She's probably guessed that you aren't a big fan of the company, but that's not particularly important, so long as you were professional about it.

If she does stay, she's in a stronger position to make it work, she'll be more effective and productive thanks to your advice (so the company benefits and you've 100% done nothing wrong), she knows you're someone she can turn to for advice, and you personally have maybe earned the trust of a talented potential ally whose future career looks promising.

Also, you might learn a thing or two in return from her fresher, less jaded perspective on the company.