Send the letter or not?

None of the above. I would look for a new job and secure a good offer, and then begin the discussion with leverage.

Even if you were essentially happy with the job you had, just hoping for a bit more money?

Yes. In my short experience of asking for raises, my boss (who I got on well with) would agree with everything I said and would say he will think about it, and then that was the end of that conversation. Then again, in all the jobs I’ve worked so far the managers seem to be there to keep employees happy rather than to actually address their problems. If your company is not like that, maybe you’ll get more consideration from your boss than I have from mine.

The question isn’t really about a job or money. It’s sort of an allegorical, metaphorical, possibly rhetorical, question. But your answer still applies so I thank you for it.

Ah, I did not notice your topics. Interesting to think of this as a metaphor. Glad I could help, even with off-the-mark answers.

Don’t send the email. Set up an appointment, meet with the boss in person, and make the case for being deserving of a raise. Metaphorically of course.

I wouldn’t be working for and happy with a place where 3 was an even remotely possible option. That’s just not rational behavior, and I value rationality very highly.

As a boss, I would much rather get this type of communication in person rather than via e-mail. It’s good that you’ve (metaphorically) written everything out, and that helps you prepare and “practice” your presentation. If number three is a real possibility, then I would make sure the presentation speaks directly to the extra value that you’ll deliver rather than why it is you’re deserving of more pay for the same value.

A shortened version of this may be written as so:

Would you gamble on a situation that you were generally happy with if there was a chance you could lose it all?

I agree with @SuperMouse. This is a conversation you have in person. There’s no room for misunderstanding your tone; you can explain yourself and adjust your pitch in real time according to the reaction from your boss.

If you know the company is in no position to offer a raise, then you don’t ask.

I am not sure what kind of allegory you are trying to make, but I’m going to add that you’ve set up a very specific kind of dynamic by calling this a “boss-worker” situtation. One person has all the power, the other has none. That will affect people’s responses.

Regarding the gambling situation – obviously it depends on the stakes and the odds. What do you stand to gain? What do you stand to lose? How likely is that chance?

No. The risk is too great if you’re generally happy with the situation.

For all intents and purposes, it is a boss-employee relationship; one person has the power to change everything—good, bad, or indifferent. That’s all fine and I’m not unhappy with the answers so far. I’m just refining as I go along.

Send the email. You are unlikely to get fired. Most likely nothing will happen. But you might get a raise.

What is this an allegory for? I’m afraid I don’t get it.

Mr. Entropy, while you’re technically correct about the boss having all the power, there are work environments where employees are highly engaged, highly valued and, frankly, quite powerful. I work in such an environment. As you’ve laid out the landscape in your question, the balance of power does seem one-sided.

Of course, I can’t know the answer to this . . . I can only offer my opinon based on your statements about the “metephorical” situation . . . but I think the employee can project confidence, value, credibility and power.

I’m top dog now (if we can ignore the Board of Directors for a minute); but for most of my career, I’ve been subordinate, sometimes to multiple powers. But I always relied on my superior knowledge in certain situations, my ability to communicate and sell an idea and my ability to paint a different vision of the future to empower me. It never failed. But if you don’t have those feelings, then it will be different.

Face to face. Don’t send the email.

Outcome Number three seems to me unlikely especially if you do good work. You won’t get what you don’t ask for. What is the harm in asking?

I wouldn’t send the e-mail: I’d talk to them. You can parcel out what you say and judge by your boss’s facial expressions how he/she is taking it and keep going or stop. It’s very hard to do that in an e-mail without superpowers.

You shouldn’t ask for a raise or promotion by email. Some things need to be done in person.

Metaphorically speaking:

If you know they can’t give you what you want, don’t ask at all.

If that’s not the case, ask in person. Very rarely would this result in losing your current situation (happy enough), but you might not get what you’re asking for. Think about how that would make you feel…will you come to resent it? Will it sour your good feelings about your current situation? If so, probably better not to ask.

I would ask for the raise (in person). My boss’s (a man in this case) response, verbal and non-verbal, would tell me a lot about his perspective of my place in the organisation. That would help me to consider whether I had a future there or not. Being happy in your work involves more than a large pay packet. If I was otherwise very content, but I felt I deserved more pay and knew the company could afford more, and I was told no. I would weigh up whether I felt valued enough to stay anyway or I felt I was being taken for granted and would be better off somewhere else.

If he said no and I knew the company was strained economically – I would bide my time and see how things progressed. I think it’s important to let my boss know I feel I am being underpaid though.

If he said no and fired me. It might take a while but I would be thankful for not working for such a company. That shows a distinct lack of care for their employees. If a member of staff is feeling unsatisfied with their pay or otherwise, that is something to discuss and work with them to resolve not just brush the problem under the carpet by firing them. If they had tried already to improve my work conditions but I was still not satisfied – then they were right to let me go.

I disagree with the idea of manipulatively looking for another position before asking for a raise. It is tantamount to holding your employer to ransom. “Pay me more or I leave”. That might work once but it has the strong potential for leaving your employer as seeing you as being money-hungry and not committed to the organisation. It would also be disappointed with a member of staff who did that because it would suggest they don’t feel they can approach me to discuss their unhappiness with their pay. I would rather have happy, content employees and will do what I can to achieve that goal.

If you have asked for a pay rise and been refused and feel dissatisfied by this, sure look for another job. I personally wouldn’t make that my first step though.

He might of course say yes – and then I will be happy.

I wouldn’t think of doing this by e-mail. For one thing, in a personal conversation you can feel your way, gauge reactions, and decide how to proceed. For another, writing is so easily misconstrued. And for a third, with an e-mail you have no assurance of privacy. Some things are your own business and ought to be kept that way.