She got two sides talking. It saved her $300.
What happened when one reader stopped assuming that every price and every "no" was final.
Hi there, my friend.
Putting my book out into the world has taught me a lot, but perhaps my favorite part has been hearing what readers actually do with it. After all, advice can sound smart in print, but it is something else entirely once someone is on the phone trying it out, when the stakes are real.
I recently talked with one reader named Sara about how she has put what she learned to use, and I wanted to share some of what she told me because it seemed so relatable.
Yes, asking works a lot of the time, maybe even more than you’d expect. However, it doesn’t work every time. Sara’s experience wasn’t a straight line of wins. It was hesitation, trial and error, a couple of real successes, and one case where she did everything right and her attempt at negotiation still fell frustratingly short.
Changing her perspective
Sara works in a role where negotiating on behalf of others is part of the job. She’s comfortable advocating in her job when it is expected and clearly defined. When it comes to advocating for herself, though, it hasn’t always been that simple.
She described herself as a bit of a people pleaser, the kind of person who might hold back rather than risk being seen as “the squeaky wheel.” That instinct is common — I know I can certainly relate to it — and it’s one of the biggest reasons people don’t take advantage of opportunities to save money.
It’s not usually a knowledge problem. It’s a willingness-to-ask problem.
After reading my book, that started to shift. She began to see asking differently. Instead of viewing it as a confrontation, she reframed it as a curiosity. It became more about exploring what was going on and, in some cases, correcting something that might not actually be right.
That change in perspective led to a bigger epiphany:
“I realized how fallible and subjective many different things that I took as objective can be, including price.”
Before that, she approached bills the way most of us do. You get a number, assume someone has a good reason for charging that price, and move on. Afterward, that assumption started to break down.
Putting the new mindset into practice
Once that mindset shifts, the next step is trying it out. That can be a little messy, as Sara discovered.
One of the first times she put it into practice, she was dealing with a set of car repairs. When the shop called with the estimate, she asked if there was any flexibility in the pricing. The answer was a quick no. She didn’t follow up, and that was the end of it.
Looking back, she realized the issue was how she asked. Her approach had been too open-ended.
She said, “I just posed the question, ‘Can we do any better?’ and they were like, ‘No.’”
If she were to do it again, she said she’d get more specific with her request. She’d come prepared with a clearer sense of what the parts should cost and where there might be room to adjust.
That distinction matters. Asking if something can be done often leads to a yes-or-no answer. Suggesting what should be done creates space for a conversation.
Not long after that, she ran into a situation where things played out very differently.
She needed an MRI, and when she arrived for the appointment, the price didn’t look right. In the past, that might have been enough to sign and move on. This time, she paused and asked questions, then called her insurance company on the spot and put them on the phone with the receptionist.
“I actually just called my insurance right then and put them on the phone with the receptionist,” she said. “Having them liaise together did bring down the cost.”
Her decision to get the two sides to talk directly led to a correction and savings of about $300. That’s a big deal.
It all happened because she didn’t assume the number on that bill was final.
Of course, it doesn’t always work out that way.
It is about trusting the process, not about perfection
She also shared a medical billing reimbursement issue where she had done everything right. She had records of whom she spoke to, when the conversations happened, and what she had been told about her insurance’s reimbursement policies. She made a decision based on the information she had been given. Unfortunately, however, what she had been told was inaccurate.
As a result, she got a higher bill than she expected, prompting her to make a series of calls in hopes of reducing what she owed. Ultimately, she was only partly successful. She got a slightly higher reimbursement, but well below what she was aiming for.
That’s frustrating, but it’s part of the process. You’re not going to win every time. It’s about avoiding the default outcome of never asking and always paying what’s presented.
What changed most over time wasn’t just the outcomes, but the approach.
It started with building the habit of asking, getting comfortable raising the question even when it felt a little awkward. From there, she became more precise, doing more homework in advance and making clearer, more targeted requests.
She also started keeping better records, noting names, dates and what was said. That kind of documentation can be surprisingly useful, especially when you need to follow up or push back later.
And she became more intentional in how she approached conversations. Instead of treating them like a confrontation, she focused on creating a sense that she and the other person were working toward the same goal. That shift tends to make interactions more productive and a lot less stressful.
None of this required a personality overhaul. She didn’t have to become more aggressive or more confrontational. She simply started questioning assumptions, asking more often, and refining her approach over time.
That’s where the real advantage comes from.
A few things to keep in mind
Treat prices as starting points, not fixed outcomes. If there’s a number attached to something, there’s often room to question it. Doesn’t mean you’ll always get your way, but it usually can’t hurt to ask.
Don’t worry about getting it perfect right away. Building the habit of asking matters more than how polished the first attempt is. Get your reps in, including role-playing. It may seem kind of goofy, but it can help. Eventually, you’ll get to feel more comfortable and confident.
Be specific when you can. A clear, informed request tends to go further than a vague one. Doing some legwork in advance can make a real difference in helping you frame the conversation. For example, if you can find an offer from a competitor, you can start the conversation there.
Keep track of your conversations. Names, dates, and notes can give you leverage if you need it later. You don’t need to write down every single word everyone says, but keeping some notes of some key details can help immensely.
Until next time!
Matt