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This is for anyone who dreads negotiating.
The secret to being good in high stakes negotiations isn’t talent. It’s reps. And the best place to get them is in situations where the worst that can happen is someone says no.
My personal favorite?
Asking for things that go against “the rules.” The things you’ve convinced yourself you can’t or shouldn’t get.
Case in point: I literally just did that yesterday morning.
Here’s the story. My brother, his wife, and their daughter, are flying from Boston to visit my mom in Coronado, California, an island off of San Diego. (I’m sorry to all of you experiencing snow right now.)
We decided last minute we wanted to drive down from LA to join them. They were able to get a fantastic deal at a nearby hotel through a third-party site, but when we looked it up, there were no discounts to be found. The hotel itself was too far out of our budget. So for about five minutes, we resigned ourselves to staying elsewhere, which would limit the amount of time we would get to hang out. And by hang out, I mean get a drink at the hotel bar 😜
But with any contract, there’s room for negotiation.
So at the urging of my wife (shout out to Ashley!), I simply called the hotel directly and told them the situation: that we wanted to go to their bar and restaurant with my brother, but wouldn’t be able to do that if we stayed at another hotel. I asked if they could price match — and two seconds later, after looking up my brother’s booking, the hotel agreed.
The reason they said yes so quickly? I would be booking directly through them and not a third-party site. So while I might be getting a discount, they were also getting a deal.
I purposely mentioned that we needed to stay at the hotel in order to go to their restaurant bar, because it signaled that we would be spending money — essentially making up the difference for the discount on the room. The personal story didn’t hurt either.
And it wasn’t the only ask I made this week. When I noticed a late fee on my credit card statement, I called my credit card company and told them I’d been late because I’d had trouble logging into their website — all true. Without hesitation, the rep removed the $30 charge. Same principle, different context.
Key Takeaways:
- Ask directly, and make it easy to say yes. I didn’t hint or apologize — I stated clearly what I wanted and why. The easier you make it for someone to understand what you need and what they get in return, the faster you’ll get an answer.
- Find the mutual win. The hotel wasn’t doing me a favor — they were cutting out the middleman and gaining a direct booking. When you can show the other person what’s in it for them, “no” becomes a lot less likely.
- Signal your value. By mentioning the bar and restaurant, I made it clear we’d be spending money beyond the room. Think about what you bring to the table that the other person might not immediately see — and find a natural way to name it.
- Low stakes practice builds high stakes confidence. This wasn’t a salary negotiation or a major business deal. It was a hotel room and a $30 fee. But every time you ask for something you think you can’t have, you prove to yourself that the rules have more flexibility than they appear to.
- The worst they can say is no — and you’re no worse off. We had already resigned ourselves to staying elsewhere. Asking cost me nothing. That’s almost always true.
Your Turn:
If reading this made your skin crawl a little — if the thought of calling a hotel or a credit card company fills you with dread — that’s not a reason to avoid it. That’s precisely the reason to do it.
The goal isn’t the $30 or the discounted room. The goal is building the muscle so that when the stakes actually matter — a salary negotiation, a contract, a difficult conversation with your boss — you’ve already proven to yourself that you can ask.
- Think about a recent situation where you assumed the answer was no before you even asked — a price, a deadline, an exception to a policy. What made you hold back?
- Now flip it: What would it look like to ask anyway? What’s the actual worst case scenario if they say no?
- This week, find one low stakes opportunity to ask for something you think you’re not supposed to get. A discount. A late checkout. A better table. Notice what happens — not just with the outcome, but with how it feels to ask.
The more you practice hearing yes when you expected no, the more natural it becomes to believe that asking is always worth it.
Think of one “rule” you’ve been following that you’ve never actually tested. Hit reply and tell me what it is.
Now go get paid.
x Claire
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