As long as you're willing to walk if this fails. Also, be aware that your card will be marked and considered somebody who will try this again in the future. I'd expect most companies would reduce the risk of such by making sure what you do has overlap with others. Come the time I expect you'll be managed or re-org'd out the door.
That depends on the situation. Yes, if it was something like "Hey, I know you have this huge project deadline that I am a critical part of, and if you don't pay me a grossly large amount more, I am out" That is hostage taking, and they would not look fondly on you.
But the request of asking for a rate that you are being offered on the open market is not. They have 2 choices there: They can pay you more because you are worth it, or they can wish you the best. If this company had a bunch of employees come in and get take 30% comp less than you and did the same quality of work, do you think they would be "loyal" to you and grossly overpay you? Absolutely not, and they shouldn't. Of course, the company would love to just pay you less, but they realize that your value proposition still exceeds that.
Corporations are completely tone deaf. The way you say things and the details of your situations will not be perceived by the relevant decision managers.
In a small company, it can make a difference. In a large one, it won't.
" card will be marked and considered somebody who will try this again in the future" Not sure this is such a terrible thing. He got far more money than he would have originally if he just said nothing and stayed and if going forward he just gets 3 - 5% it is still a % of a much larger number. Worst case is if for some reason the company gets vindictive they just get a new job and a new raise. Optimally though if the employee is pleasant and up front about a new offer, then the company treats it as strictly business. They decide if the requested salary is worth what the developer delivers, if yes they make the offer, if no they wish the employee well with their new job.
