I always feel a little awkward bringing up salary again after an offer comes in, even though I know that’s the time to do it. Does that feeling ever go away?

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It did for me, somewhere about 10 years in. You stop caring so much and treat it like the business conversation it is. Nothing to feel awkward about. The people you're countering to expect it and have had similar conversations 100000x already. They expect it.

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Never

Don't let anxiety grab you by the balls ⛹️‍♂️⛹️‍♀️
This is when your ego is supposed to stand up for your right to have access to a livable wage; with confidence, couth and in a respectful manner; of course. 😉
If it was the other way around do you think they'd feel awkward letting you know that they know their worth..

Having negotiated with executives for compensation - some of which were very tough negotiators, ALWAYS negotiate and ask for the most you can. Don’t be outlandish, but push for all you can get.

The company doesn’t cry when they fire you, cut the benefits program, pass you up for a promotion or sell the company without asking you first.

This is business, if you’re not advocating for yourself and asking for more - you won’t get it. I constantly push for more, recording and documenting my wins so I can show I bring value. The worst thing they can say is No.

Advocate for yourself

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