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How to negotiate a raise when on a trial period

I currently make $38 per hour but I want to make at least $48.50 per hour. My HR has a history of never giving raises, but I'm currently on a trial period for the company. The mental issue is that it's a company that I love so it's easy for my brain to rationalize a lower salary even though I want to make at least $100,000

    1. Get a raise at work #1

    I currently make $38 per hour but I want to make at least $48.50 per hour. My HR has a history of never giving raises, but I'm currently on a trial period for the company. The mental issue is that it's a company that I love so it's easy for my brain to rationalize a lower salary even though I want to make at least $100,

    2. Get a raise at work #2

    I was brought in as interim CTO for three months. When the guy came back, he offered me $40k more than my old job (which was about the same pay as this one). He said he would "pay whatever it takes" to keep me there. But I left anyway because of reasons unrelated to money. This makes me feel like maybe I should have taken that money and stayed there instead of leaving for another job with less pay

    3. Negotiate

    I am going to negotiate my way up from $38 to at least $48.50 (a 22% increase).

    There are two ways to look at this:

    A) If they say no then you will know they don't value you and you can leave if you want or...

    B) If they say yes, then you will know they do value you and were just waiting for an excuse (i.e., your trial period) before giving you what you want. Either way, this is an opportunity to find out how much they value you and either get exactly what you want or decide if it's worth it or not by weighing your options elsewhere if they don't give what you want.

    Also, when someone says "no", that means nothing unless they follow up with actions proving their "no". So even if they say no here, still ask again later after having some further discussions about why your contribution is so valuable and why now is the best time ever for them to give raises given all the recent successes the company has had since your arrival there.

    And also realize that people who do compensation LOVE talking about compensation because it's such a fun thing for them to think about and plan out . So some of these conversations might go on forever but that's ok because chances are good that once they start talking about compensation then suddenly everything else becomes much easier in negotiations because now THEY'RE thinking about all the other things related to compensation such as benefits, titles, etc . And once those things are settled then the money part becomes easy since everyone knows where everyone stands in relation To each other and what everyone wants out of their career within the company. It's like peeling layers off an onion until eventually we get down to just one layer left which is...the money!
    
    So I'll ask twice over next few weeks and see what happens but this is an opportunity given my current situation where I can either get exactly what I want or decide if it's worth it or not by weighing my options elsewhere if they don't give what i want
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