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Hey — it’s Jeffrey, back again!
Negotiating a raise is always uncomfortable.
You want to be confident and clear, but not arrogant. You need to show your value, without sounding defensive. And you definitely don’t want to say the wrong thing and hurt your relationship and reputation.
So this week, I turned to ChatGPT to help me prepare.
It turns out, it’s kind of the perfect tool for this.
In just a few prompts, it helped me:
Write a raise request script in a professional, respectful tone
Figure out how much to ask for, with data to back it up
Identify the results I should highlight
Anticipate and prepare for the most common objections
Whether you’re planning to ask for a raise soon, or just want to be ready when the time’s right, here’s how to use AI to make your case and walk in with confidence.
📬 Table of Contents:
In today’s Money Meets AI edition, we look at:
🤖 ChatGPT Prompt 1: Create your raise request script
📊 Prompt 2: Gather salary and contribution data
💬 Prompt 3: Prep your rebuttals (and boost your confidence)
🔁 What to do next
🛠️ Other tools to check out
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THIS WEEK’S TESTED TOOLS
🔧 Prompt 1: “Help me ask for a raise like a pro”
Here’s where I started: asking ChatGPT how to actually make the ask:
“I’m a [job title] at [company]. I’ve been here for [X years], and I’m preparing to ask for a raise. Can you write a confident, professional script for this conversation?”
ChatGPT took this a bit literally and gave me a full script to recite, which wasn’t ideal. But when I followed up and shared more details (like my role, salary, and recent wins), it gave me useful talking points I could actually use.
Another thing I’ve wondered about when asking for a raise: when is the best time to ask for a raise, and what conversation is most appropriate to bring it up?
I asked ChatGPT:
How should I set myself up with my boss to have this discussion? When is the right time?
Here's the response:
Overall, this would’ve helped boost my confidence as this is a pretty intimidating situation.
📊 Prompt 2: “How much of a raise should I ask for and what data can I use to support this?”
Next, I wanted to see how ChatGPT could help me decide how much of a raise I can ask for and if it could back that up with some real data. I was thrilled with what it delivered!
I asked:
How much of a raise should I ask for and what data can I use to support this?
The number it suggested felt reasonable, and sure enough, the research it pulled from sites like Glassdoor and Levels backed it up.
This saved me some time from searching on each website to get the data.
💬 Prompt 3: “How should I respond if they push back or say no?”
Last, I wondered what I should do if my manager pushed back or rejected my raise proposal, which is totally realistic despite how much I believe in ChatGPT to get the job done.
I asked ChatGPT (within the same conversation, so it had all the context):
How should I respond if they push back or say no?
ChatGPT presented several scenarios and what to do:
I really liked the suggestion to ask for a timeline and next steps. Most managers will be receptive to this, and even if you can’t get the raise you want now, you’ve started the conversation and planted the seeds for future talks.
What Didn’t Work So Well
Each week, I try many tactics, and some don't work out well. I mostly want to focus on things that do work because that's probably most helpful for you.
Other things I tried but didn’t find as useful:
In Prompt #1, ChatGPT initially made an awkward suggestion by saying I should I go in with a script to recite to my boss. Obviously, that could come across as unnatural and awkward.
However, when I followed up to point this out, ChatGPT suggested going by talking points and even suggested techniques to practice.
All in all, the conversation with ChatGPT was quite efficient. Just remember that you’ll almost always need to ask follow-up questions after using these prompts I’ve outlined. That’s the beauty of these tools: it’s a conversation.
🛠️ Other Tools to Check Out
Other tools I came across but didn’t do a deep dive into for this newsletter:
Wonsulting AI - AI career tools, like resumes, cover letters, interview help, and more.
Levels.fyi - Salary transparency by role and company. I played around with it, and there’s a bit of learning curve. Over 1.5 million professionals use Levels.fyi each month.
What to Do Now
🔍 Try Prompt #1 with your actual role and experience
📊 Use Prompt #2 to list your wins + get market comps
💬 Run Prompt #3 to rehearse for a “not right now” answer
📅 Bonus: Ask GPT to roleplay your manager and practice the conversation
PS—I’d love to hear your other feedback or suggestions. Just hit reply — I read every email!
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One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I’m not a financial advisor — just someone sharing ideas and tools I’ve found useful. Use what works for you, skip what doesn’t, and always do your own research before making financial decisions and using the tools shared in this newsletter.